Amphiphilic Esters of Pyromellitic Acid: Synthesis and Prospects of Applications

dc.citation.epage90
dc.citation.issue1
dc.citation.journalTitleХімія та хімічна технологія
dc.citation.spage79
dc.contributor.affiliationLviv Polytechnic National University
dc.contributor.affiliationNorth Dakota State University
dc.contributor.authorDonchak, Volodymyr
dc.contributor.authorVoronov, Andriy
dc.contributor.authorBudishevska, Olha
dc.contributor.authorKohut, Ananiy
dc.contributor.authorStetsyshyn, Yuriy
dc.coverage.placenameЛьвів
dc.coverage.placenameLviv
dc.date.accessioned2026-03-30T09:18:36Z
dc.date.created2025-02-27
dc.date.issued2025-02-27
dc.description.abstractЦей огляд стосується амфіфільних діестерів і поверхнево-активних “геміні”-речовин, синтезованих із піромелітової кислоти, поліетиленгліколів, аліфатичних спиртів і холестеролу. Обговорення охоплює їхні унікальні колоїдні та хімічні властивості, з акцентом на взаємозв’язку між критичною концентрацією міцелоутворення (ККМ) і гідрофільно-ліпофільним балансом. Структурні фактори, зокрема довжина ліпофільних замісників, істотно впливають на значення ККМ у водних системах. Крім того, наявність карбоксильних груп у фрагменті піромелітинової кислоти дає змогу здійснювати рН-залежну модуляцію поверхневої активності. Описані амфіфільні речовини мають винятковий потенціал для формування міцелярних структур, здатних солюбілізувати гідрофобні речовини, зокрема барвники, олії, холестерол і біологічно активну речовину куркумін. Окрім підвищення стабільності цих речовин, вони забезпечують механізми контрольованого вивільнення, які імітують взаємодію із клітинною мембраною. Така універсальність дає змогу розглядати ці матеріали як перспективні кандидати для інноваційного застосування у цільових системах доставки ліків і як нанореактори для синтезу наночастинок срібла. Цей огляд підкреслює їхній потенціал у розвитку нанотехнологій і біомедичної інженерії.
dc.description.abstractThis review focuses on amphiphilic diesters and “gemini” surfactants synthesized from pyromellitic acid, polyethylene glycols, aliphatic alcohols, and cholesterol. The discussion encompasses their unique colloidal and chemical properties, with an emphasis on the relationship between critical micelle concentration and hydrophilic-lipophilic balance. Structural factors, particularly the length of the lipophilic substituents, significantly influence CMC values in aqueous systems. Additionally, the presence of carboxyl groups in the pyromellitic acid core allows for pH-dependent modulation of surface activity. The amphiphiles exhibit exceptional potential in forming micellar structures capable of solubilizing hydrophobic substances, including dyes, oils, cholesterol, and the bioactive compound curcumin. Beyond enhancing the stability of these substances, they enable controlled release mechanisms that mimic cellular membrane interactions. Such versatility positions the materials from amphiphilic diesters of pyromellitic acid as promising candidates for innovative applications in targeted drug delivery systems and as nanoreactors for synthesizing silver nanoparticles. This review underscores their potential in advancing nanotechnology and biomedical engineering.
dc.format.extent79-90
dc.format.pages12
dc.identifier.citationAmphiphilic Esters of Pyromellitic Acid: Synthesis and Prospects of Applications / Volodymyr Donchak, Andriy Voronov, Olha Budishevska, Ananiy Kohut, Yuriy Stetsyshyn // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2025. — Vol 19. — No 1. — P. 79–90.
dc.identifier.citationenAmphiphilic Esters of Pyromellitic Acid: Synthesis and Prospects of Applications / Volodymyr Donchak, Andriy Voronov, Olha Budishevska, Ananiy Kohut, Yuriy Stetsyshyn // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2025. — Vol 19. — No 1. — P. 79–90.
dc.identifier.doidoi.org/10.23939/chcht19.01.079
dc.identifier.urihttps://ena.lpnu.ua/handle/ntb/124840
dc.language.isoen
dc.publisherВидавництво Львівської політехніки
dc.publisherLviv Politechnic Publishing House
dc.relation.ispartofХімія та хімічна технологія, 1 (19), 2024
dc.relation.ispartofChemistry & Chemical Technology, 1 (19), 2024
dc.relation.references[1] Alkan, B.; Daglar, O.; Luleburgaz, S.; Gungor, B.; Gunay, U.S.; Hizal, G.; Tunca, U.; Durmaz, H. One-Pot Cascade Polycondensation and Passerini Three-Component Reactions for the Synthesis of Functional Polyesters. Polym. Chem. 2022, 13, 258–266. https://doi.org/10.1039/D1PY01528A
dc.relation.references[2] Koziel, K.; Lagiewka, J.; Girek, B.; Folentarska, A.; Girek, T.; Ciesielski, W. Synthesis of New Amino-β-Cyclodextrin Polymer, Cross-Linked with Pyromellitic Dianhydride and Their Use for the Synthesis of Polymeric Cyclodextrin Based Nanoparticles.Polymers 2021, 13, 1332. https://doi.org/10.3390/polym13081332
dc.relation.references[3] Afinjuomo, F.; Barclay, T.; Song, Y.; Parikh, A.; Petrovsky, N.; Garg, S. Synthesis and Characterization of a Novel Inulin Hydrogel Crosslinked with Pyromellitic Dianhydride. React. Funct. Polym. 2019, 134, 104–111. https://doi.org/10.1016/j.reactfunctpolym.2018.10.014
dc.relation.references[4] Arkas, M.; Vardavoulias, M.; Kythreoti, G.; Giannakoudakis, D.A. Dendritic Polymers in Tissue Engineering: Contributions of PAMAM, PPI PEG and PEI to Injury Restoration and Bioactive Scaffold Evolution. Pharmaceutics 2023, 15, 524. https://doi.org/10.3390/pharmaceutics15020524
dc.relation.references[5] Polotti, G. Perspectives from Industry. Adv. Chem. Eng. 2020,56, 259–330. https://doi.org/10.1016/bs.ache.2020.07.003
dc.relation.references[6] Ciesielska, A.; Ciesielski, W.; Girek, B.; Girek, T.; Koziel, K.; Kulawik, D.; Lagiewka, J. Biomedical Application of Cyclodextrin Polymers Cross-Linked via Dianhydrides of Carboxylic Acids. Appl. Sci. 2020, 10, 8463. https://doi.org/10.3390/app10238463
dc.relation.references[7] Peimanfard, S.; Zarrabi, A.; Trotta, F.; Matencio, A.; Cecone, C.; Caldera, F. Developing Novel Hydroxypropyl-β-Cyclodextrin- Based Nanosponges as Carriers for Anticancer Hydrophobic Agents: Overcoming Limitations of Host–Guest Complexes in a Comparative Evaluation Pharmaceutics 2022, 14, 1059. https://doi.org/10.3390/pharmaceutics14051059
dc.relation.references[8] Monfared, Y.K.; Mahmoudian M.; Cecone, C.; Caldera, F.; Zakeri-Milani, P.; Matencio, A.; Trotta, F. Stabilization and Anticancer Enhancing Activity of the Peptide Nisin by Cyclodextrin-Based Nanosponges against Colon and Breast Cancer Cells. Polymers 2022, 14, 594. https://doi.org/10.3390/polym14030594
dc.relation.references[9] Girek, T.; Koziel, K.; Girek, B.; Ciesielski, W. CD Oxyanions as a Tool for Synthesis of Highly Anionic Cyclodextrin Polymers. Polymers 2020, 12, 2845. https://doi.org/10.3390/polym12122845
dc.relation.references[10] Demasi, S.; Caser, M.; Caldera, F.; Dhakar, N.K.; Vidotto, F.; Trotta, F.; Scariot, V. Functionalized Dextrin-Based Nanosponges as Effective Carriers for the Herbicide Ailanthone. Ind. Crops Prod. 2021, 164, 113346. https://doi.org/10.1016/j.indcrop.2021.113346
dc.relation.references[11] Qi, H.; Meng, L.; Lin, X.; Xu, W.; Chen, Y.; Zhang, C.; Qiu, Y. Anti-Wrinkle Finishing of Cotton Fabrics with Pyromellitic Acid Enhanced by Polyol Extenders. J. Donghua Univ. (Engl. Ed.) 2022, 39, 533–541. https://doi.org/10.19884/j.1672-5220.202209006
dc.relation.references[12] Tarnavchyk, I.; Voronov, A.; Donchak, V.; Budishevska, O.; Kudina, O.; Khomenko, O.; Harhay, K.; Samaryk, V.; Voronov, S. Synthesis and Selfassambling of Amphiphilic Oligoesters Based on Pyromellitic Acid. Chem. Chem. Technol. 2016, 10, 159–172. https://doi.org/10.23939/chcht10.02.159
dc.relation.references[13] Müller, R.H. Colloidal Carriers for Controlled Drug delivery and Targeting: Modification, Characterization and in Vivo Distribution; CRC Press, 1991.
dc.relation.references[14] Mishra, P.; Nayak, B.; Dey, R.K. PEGylation in Anti-Cancer Therapy: An Overview. Asian J. Pharm. Sci. 2016, 11, 337–348. https://doi.org/10.1016/j.ajps.2015.08.011
dc.relation.references[15] Kudina, О.; Tarnavchyk, I.; Khomenko, О.; Budishevska, O.; Voronov, S.; Voronov, A. PEG and Cholesterol-Containing Pyromellitates: Synthesis and Self-Assembly. Macromol. Chem. Phys. 2013, 214, 2761–2767. https://doi.org/10.1002/macp.201300488
dc.relation.references[16] Klok, H.-A.; Hwang, J.J.; Iyer, S.N.; Stupp, S.I. Cholesteryl-(L- Lactic Acid)n Building Blocks for Self-Assembling Biomaterials. Macromolecules 2002,35,746–759. https://doi.org/10.1021/ma010907x
dc.relation.references[17] Heino, S.; Lusa, S.; Somerharju, P.; Ehnholm, C.; Olkkonen, V.M.; Ikonen, E. Dissecting the Role of the Golgi Complex and Lipid Rafts in Biosynthetic Transport of Cholesterol to the Cell Surface. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 8375–8380. https://doi.org/10.1073/pnas.140218797
dc.relation.references[18] Klausen, T.K.; Hougaard, C.; Hoffmann, E.K.; Pedersen, S.F. Cholesterol Modulates the Molume-Regulated Anion Current in Ehrlich-Lettre Ascites Cells via Effects on Rho and F-Actin. Am. J. Physiol. Cell Physiol. 2006, 291, C757–C771. https://doi.org/10.1152/ajpcell.00029.2006
dc.relation.references[19] Levitan, I.; Christian, A.E.; Tulenko, T.N.; Rothblat, G.H. Membrane Cholesterol Content Modulates Activation of Volume- Regulated Anion Current in Bovine Endothelial Cells. J. Gen.Physiol. 2000, 115, 405–416. https://doi.org/10.1085/jgp.115.4.405
dc.relation.references[20] Maxfield, F.R.; Tabas, I. Role of Cholesterol and Lipid Organization in Disease. Nature 2005, 438, 612–621. https://doi.org/10.1038/nature04399
dc.relation.references[21] Yusa, S. Self-Assembly of Cholesterol-Containing Water- Soluble Polymers. Int. J. Polym. Sci. 2012, 609767. https://doi.org/10.1155/2012/609767
dc.relation.references[22] Ringsdorf, H.; Schlarb, B.; Venzmer, J. Molecular Architecture and Function of Polymeric Oriented Systems: Models for the Study of Organization, Surface Recognition, and Dynamics of Biomembranes. Angew. Chem. Int. Ed. 1988, 27, 113–158. https://doi.org/10.1002/anie.198801131
dc.relation.references[23] Zhou, Y.; Briand, V.A.; Sharma, N.; Ahn, S.; Kasi, R.M. Polymers Comprising Cholesterol: Synthesis, Self-Assembly, and Applications. Materials 2009, 2, 636–660. https://doi.org/10.3390/ma2020636
dc.relation.references[24] Shibaev, V.P.; Platé, N.A.; Freidzon, Ya.S. Thermotropic Liquid Crystalline Polymers. I. Cholesterol-Containing Polymers and Copolymers. J. Polym. Sci. Pol. Chem. 1979, 17, 1655–1670. https://doi.org/10.1002/pol.1979.170170609
dc.relation.references[25] Shibaev, V.P.; Tal’roze, R.V.; Karakhanova, F.I.; Platé, N.A. Thermotropic Liquid Crystalline Polymers. II. Polymers with Amino Acid Fragments in the Side Chains. J. Polym. Sci. Pol.Chem. 1979, 17, 1671–1684. https://doi.org/10.1002/pol.1979.170170610
dc.relation.references[26] Yamaguchi, T.; Asada, T.; Hayashi, H.; Nakamura, N. Dependence of the Packing Structure of Mesogenic Groups on the Flexible Spacer Length of Liquid-Crystalline Side-Chain Polymers. Macromolecules 1989, 22, 1141–1144. https://doi.org/10.1021/ma00193a024
dc.relation.references[27] Knop, K.; Hoogenboom, R.; Fischer, D.; Schubert, U.S. Poly(ethylene glycol) in Drug Delivery: Pros and Cons as Well as Potential Alternatives. Angew. Chem. Int. Ed. 2010, 49, 6288–6308. https://doi.org/10.1002/anie.200902672
dc.relation.references[28] Menger, F.M.; Littau, C.A. Gemini Surfactants: Synthesis and Properties. J. Am. Chem. Soc. 1991, 113, 1451–1452. https://doi.org/10.1021/ja00004a077
dc.relation.references[29] Menger, F.; Littau, C. Gemini Surfactants: A New Class of Self-Assembling Molecules. J. Am. Chem. Soc. 1993, 115, 10083–10090. https://doi.org/10.1021/ja00075a025
dc.relation.references[30] Zana, R.; Xia, J. Gemini Surfactants: Synthesis, Interfacial and Solution-Phase Behavior, and Applications; Marcel Dekker, 2004.
dc.relation.references[31] Sakai, K. Development of Commercially Available Gemini Surfactants. J. Oleo Sci. 2012, 12, 627–633. https://doi.org/10.5650/oleoscience.12.627
dc.relation.references[32] Rosen, M.J. Geminis: A New Generation of Surfactants.Chemtech 1993, 23, 30–33.
dc.relation.references[33] Villa, C.; Baldassari, S.; Martino, D.F.C.; Spinella, A.; Caponetti, E. Green Synthesis, Molecular Characterization and Associative Behavior of Some Gemini Surfactants without a Spacer Group. Materials 2013, 6, 1506–1519. https://doi.org/10.3390/ma6041506
dc.relation.references[34] Zana, R. Gemini (Dimeric) Surfactants. Curr. Opin. Colloid Interface Sci. 1996, 1, 566–571. https://doi.org/10.1016/S1359-0294(96)80093-8
dc.relation.references[35] Brycki, B.E.; Kowalczyk, I.H; Szulc, A.; Kaczerewska, O.; Pakiet, M. Multifunctional Gemini Surfactants: Structure, Synthesis, Properties, and Applications. In Application and Characterization of Surfactants; Intech World's Largest Science, Technology & Medicine Open Access Book Publisher, 2017.
dc.relation.references[36] Song, B.; Hu, Y.; Song, Y.; Zhao, J. Alkyl Chain Length- Dependent Viscoelastic Properties in Aqueous Wormlike Micellar Solutions of Anionic Gemini Surfactants with an Azobenzene Spacer. J. Colloid Interface Sci. 2010, 341, 94–100. https://doi.org/10.1016/j.jcis.2009.09.023
dc.relation.references[37] Ahmady, A. R.; Hosseinzadeh, P.; Solouk, A.; Akbari, S.; Szulc, A.M.; Brycki, B.E. Cationic Gemini Surfactant Properties, Its Potential as a Promising Bioapplication Candidate, and Strategies for Improving Its Biocompatibility: A Review. Adv. Colloid Interface Sci. 2022, 299, 102581. https://doi.org/10.1016/j.cis.2021.102581
dc.relation.references[38] Pei, X.; Zhao, J.; Ye, Y.; You, Y; Wei, X. Wormlike Micelles and Gels Reinforced by Hydrogen Bonding in Aqueous Cationic Gemini Surfactant Systems. Soft Matter 2011, 7, 2953–2960. https://doi.org/10.1039/C0SM01071E
dc.relation.references[39] Degiorgio, V.; Corti, M. Physics of Amphiphiles: Micelles, Vesicles and Microemulsion; North Holland Physics Publishing, 1985.
dc.relation.references[40] Shrestha, R.G.; Shrestha, L.K.; Matsunaga, T.; Shibayama, M.; Aramaki, K. Lipophilic Tail Architecture and Molecular Structure of Neutralizing Agent for the Controlled Rheology of Viscoelastic Fluid in Amino Acid-Based Anionic Surfactant System. Langmuir 2011, 27, 2229–2236. https://doi.org/10.1021/la1048248
dc.relation.references[41] Shrestha, R.G.; Abezgauz, L.; Danino, D.; Sakai, K.; Sakai, H.; Abe, M. Structure and Dynamics of Poly(oxyethylene) Cholesteryl Ether Wormlike Micelles: Rheometry, SAXS, and Cryo-TEM Studies. Langmuir 2011, 27, 12877–12883. https://doi.org/10.1021/la202879f
dc.relation.references[42] Bhadani, A.; Shrestha, R.G.; Koura, S.; Endo, T.; Sakai, K.; Abe, M.; Sakai, H. Self-Aggregation Properties of New Ester-Based Gemini Surfactants and Their Rheological Behavior in the Presence of Cosurfactant – Monolaurin. Colloids Surf. A: Physicochem. Eng. Asp. 2014, 461, 258–266. https://doi.org/10.1016/j.colsurfa.2014.08.001
dc.relation.references[43] Pei, X.; Xu, Z.; Song, B.; Cui, Z.; Zhao, J. Wormlike Micelles Formed in Catanionic Systems Dominated by Cationic Gemini Surfactant: Synergistic Effect with High Efficiency. Colloids Surf. A: Physicochem. Eng. Asp. 2014, 443, 508–514. https://doi.org/10.1016/j.colsurfa.2013.12.007
dc.relation.references[44] Lin, Z.; Scriven, L.E.; Davis, H.T. Cryogenic Electron Microscopy of Rodlike or Wormlike Micelles in Aqueous Solutions of Nonionic Surfactant Hexaethylene Glycol Monohexadecyl Ether. Langmuir 1992, 8, 2200–2205. https://doi.org/10.1021/la00045a021
dc.relation.references[45] Vinson, P.K.; Talmon, Y. Comments on “Electron Diffraction Observed in the Gigantic Micelle-Producing System of CTAB- Aromatic Additives,” by Hirata, Sakaiguchi, and Akai. J. Colloid Interface Sci. 1989, 133, 288–289. https://doi.org/10.1016/0021-9797(89)90305-6
dc.relation.references[46] Jerke, G.; Pedersen, J.S.; Egelhaaf, S.U.; Schurtenberger, P. Flexibility of Charged and Uncharged Polymer-Like Micelles. Langmuir 1998, 14, 6013–6024. https://doi.org/10.1021/la980390r
dc.relation.references[47] Groth, C.; Nydén, M.; Holmberg, K.; Kanicky, J.R.; Shah, D.O. Kinetics of the Self-Assembly of Gemini Surfactants. J. Surfactants Deterg. 2004, 7, 247–255. https://doi.org/10.1007/s11743-004-0308-8
dc.relation.references[48] Rosen, M.J.; Tracy, D.J. Gemini Surfactants. J. Surfactants Deterg. 1998, 1, 547–554. https://doi.org/10.1007/s11743-998-0057-8
dc.relation.references[49] Micich, T.J.; Linfield, W.M. Wetting Properties of Nonionics from Branched Fatty Diamides. J. Am. Oil Chem. Soc. 1988, 65, 820–825. https://doi.org/10.1007/BF02542540
dc.relation.references[50] Quencer, L.B.; Kokke-Hall, S.; Loughney, T. Proceedings of CESIO 4th World Surfactant Congress. 1996, 2, 66.
dc.relation.references[51] Kumar, N.; Tyagi, R. Industrial Applications of Dimeric Surfactants: A Review. J. Dispers. Sci. Technol. 2014, 35, 205–214. https://doi.org/10.1080/01932691.2013.780243
dc.relation.references[52] Rosen, M.J. Gemini Surfactants. Industrial Applications of Surfactants IV 1999, 151–161. https://doi.org/10.1533/9781845698614.151
dc.relation.references[53] Li, J.; Dahanayake, M.; Reierson, R.L.; Tracy, D.J. Amphoteric Surfactants Having Multiple Hydrophobic and Hydrophilic Groups. US patent 5,914,310, June 22, 1999.
dc.relation.references[54] Choi, T.-S.; Shimizu, Y.; Shirai, H.; Hamada, K. Disperse Dyeing of Nylon 6 Fiber Using Gemini Surfactants Containing Ammonium Cations as Auxililiaries. Dyes Pigments 2001, 48, 217–226. https://doi.org/10.1016/S0143-7208(00)00105-4
dc.relation.references[55] Choi, T.-S.; Shimizu, Y.; Shirai, H.; Hamada, K. Disperse Dyeing of Polyester Fiber Using Gemini Surfactants Containing Ammonium Cations as Auxililiaries. Dyes Pigments 2001, 50, 55–65. https://doi.org/10.1016/S0143-7208(01)00033-X
dc.relation.references[56] Choi, T.-S.; Shimizu, Y.; Shirai, H.; Hamada, K. Solubilization of Disperse Dyes in Cationic Gemini Surfactant Micelles. Dyes Pigments 2000, 45, 145–152. https://doi.org/10.1016/S0143-7208(00)00015-2
dc.relation.references[57] Dreja, M.; Tieke, B. Polymerization of Styrene in Ternary Microemulsion Using Cationic Gemini Surfactants Langmuir 1998, 14, 800–807. https://doi.org/10.1021/la9710738
dc.relation.references[58] El-Sadek, B.M. Synthesis of Selected Gemini Surfactants: Surface, Biological Activity and Corrosion Efficiency against Hydrochloric Acid Medium. Der Chemica Sinica 2011, 2, 125–137.
dc.relation.references[59] Mobin, M.; Masroor, S. Cationic Gemini Surfactants as Novel Corrosion Inhibitor for Mild Steel in 1M HCl. Int. J. Electrochem. Sci. 2012, 7, 6920–6940. https://doi.org/10.1016/S1452-3981(23)15758-0
dc.relation.references[60] Chen, X.; Wang, J.; Shen, N.; Luo, Y.; Li, L.; Liu, M.; Thomas, R.K. Gemini Surfactant/DNA Complex Monolayers at the Air−Water Interface: Effect of Surfactant Structure on the Assembly, Stability and Topography of Monolayers. Langmuir 2002, 18, 6222–6228. https://doi.org/10.1021/la025600l
dc.relation.references[61] Yan, X.; Janout, V.; Regen, S.L. Hydrophobic Sponges: Resin- Bound Surfactants as Organic Scavengers. Macromolecules 2002, 35, 8243–8246. https://doi.org/10.1021/ma020568n
dc.relation.references[62] Fielden, M.L.; Perrin, C.; Kremer, A.; Bergsma, M.; Stuart, M.C.; Camilleri, P.; Engberts, J.B.F.N. Sugar-Based Tertiary Amino Gemini Surfactants with a Vesicle-to-Micelle Transition in the Endosomal pH Range Mediate Efficient Transfection in vitro. Eur. J. Biochem. 2001, 268, 1269–1279. https://doi.org/10.1046/j.1432-1327.2001.01995.x
dc.relation.references[63] Buijnsters, P.J.J.A.; Rodriguez, C.L.G.; Willighagen, E.L.; Sommerdijk, N.A.J.M.; Kremer, A.; Camilleri, P.; Feiters, M.C.; Nolte, R.J.M.; Zwanenburg, B. Cationic Gemini Surfactants Based on Tartaric Acid: Synthesis, Aggregation, Monolayer Behaviour, and Interaction with DNA. Eur. J. Org. Chem. 2002, 2002, 1397– 1406. https://doi.org/10.1002/1099-0690(200204)2002:8<1397::AID-EJOC1397>3.0.CO;2-6
dc.relation.references[64] Wilhelm, M.; Zhao, C.L.; Wang, Y.; Xu, R.; Winnik, M.A.; Mura, J.L.; Riess, G.; Croucher, M.D. Poly(Styrene-Ethylene Oxide) Block Copolymer Micelle Formation in Water: A Fluorescence Probe Study. Macromoleules 1991, 24, 1033–1040. https://doi.org/10.1021/ma00005a010
dc.relation.references[65] Schmitz, C.; Mourran, A.; Keul, H.; Möller, M. Synthesis and Association Behaviour of Linear Block Copolymers with Different Microstructures but the Same Composition. Macromol. Chem. Phys. 2008, 209, 1859–1971. https://doi.org/10.1002/macp.200800205
dc.relation.references[66] Matsuoka, H.; Matsutani, M.; Mouri, E.; Matsumoto, K. Polymer Micelle Formation without Gibbs Monolayer Formation: Synthesis and Characteritics of Amphiphilic Diblock Copolymer Having Strong Acid Groups. Macromolecules 2003, 36, 5321–5330. https://doi.org/10.1021/ma0215161
dc.relation.references[67] Khomenko, О.; Budishevska, O.; Voronov, A.; Varvarenko, S.; Kudina, O.; Tarnavchyk, I.; Voronov, S. Amphiphilic Diesters of Pyromellitic Acid with Cholesterol Fragments for Solubilization of Lipophilic Substances. Reports of the National Academy of Sciences of Ukraine 2013, 7, 123–129. http://dspace.nbuv.gov.ua/handle/123456789/85809
dc.relation.references[68] Suckling, K.E.; Benson, G.M.; Bond, B.; Gee, A.; Glen, A.; Haynes, C.; Jackson, B. Cholesterol Lowering and Bile Acid Excretion in the Hamster with Cholestyramine Treatment. Atherosclerosis 1991, 89, 183–190. https://doi.org/10.1016/0021-9150(91)90059-C
dc.relation.references[69] Mol, M.J.T.M.; Erkelens, D.W.; Leuven, J.A.G.; Schouten, J.A.; Stalenhoef, A.F.H. Simvastatin (MK-733): A Potent Cholesterol Synthesis Inhibitor in Heterozygous Familial Hypercholesterolaemia. Atherosclerosis 1988, 69, 131–137. https://doi.org/10.1016/0021-9150(88)90006-8
dc.relation.references[70] Rosenson, R. Patient education: High Cholesterol and Lipids (Beyond the Basics). UpToDate. 2024, Sep 27. UpToDate Inc. www.uptodate.com.
dc.relation.references[71] Molecular probes. Amplex® RedCholesterolAssayKitCatalogno. A12216.
dc.relation.references[72] Okada, H.; Toguchi, H. Biodegradable Microspheres in Drug Delivery. Crit. Rev. Ther. Drug Carrier Syst. 1995, 12, 1–99. https://doi.org/10.1615/CritRevTherDrugCarrierSyst.v12.i1.10
dc.relation.references[73] Scott, G.; Gilead, D. Degradable Polymers, Principles and Applications; Chapman & Hall, 1995.
dc.relation.references[74] Anderson, J.M.; Shive, M.S. Biodegradation and Biocompatibility of PLA and PLGA Microspheres. Adv. Drug Deliv. Rev. 2002, 64, 72–82. https://doi.org/10.1016/j.addr.2012.09.004
dc.relation.references[75] Grizzi, I.; Garreau, H.; Li, S.; Vert, M. Hydrolytic Degradation of Devices Based on Poly(DL-Lactic Acid) Size-Dependence. Biomaterials 1995, 16, 305–311. https://doi.org/10.1016/0142- 9612(95)93258-F
dc.relation.references[76] Vert, M.; Li, S.M.; Garreau, H. Attempts to Map the Structure and Degradation Characteristics of Aliphatic Polyesters Derived from Lactic and Glycolic Acids. J. Biomater. Sci. Polym. Ed. 1995, 6, 639–649. https://doi.org/10.1163/156856294X00581
dc.relation.references[77] Vert, M.; Li, S. M.; Garreau, H. Recent Advances in the Field of Lactic Acid/Glycolic Acid Polymer-Based Therapeutic Systems. Macromol.Symp.1995,98,633–642. https://doi.org/10.1002/masy.19950980154
dc.relation.references[78] Huh, K.M.; Min, H.S.; Lee, S.C.; Lee, H.J.; Kim, S.; Park, K. A New Hydrotropic Block Copolymer Micelle System for Aqueous Solubilization of Paclitaxel. J. Control. Release 2008, 126, 122–129. https://doi.org/10.1016/j.jconrel.2007.11.008
dc.relation.references[79] Konno, T.; Junji, W.; Ishihara, K. Enhanced Solubility of Paclitaxel Using Water-Soluble and Biocompatible 2- Methacryloyloxyethyl Phosphorylcholine Polymers. J. Biomed. Mater. Res. - A 2003, 65A, 209–214. https://doi.org/10.1002/jbm.a.10481
dc.relation.references[80] Kim, S.C.; Kim, D.W.; Shim, Y.H.; Bang, J.S.; Oh, H.S.; Kim, S.W.; Seo, M.H. In Vivo Evaluation of Polymeric Micellar Paclitaxel Formulation: Toxicity and Efficacy. J. Control. Release 2001, 72, 191–202. https://doi.org/10.1016/S0168-3659(01)00275-9
dc.relation.references[81] Desai, N.P.; Trieu, V.; Hwang, L.Y.; Wu, R.; Soon-Shiong, P.; Gradishar, W.J. Improved Effectiveness of Nanoparticle Albumin- Bound (NAB) Paclitaxel Versus Polysorbate-Based Docetaxel in Multiple Xenografts as a Function of HER2 and SPARC Status.Anti-Cancer Drugs 2008, 19, 899–909. https://doi.org/10.1097/CAD.0b013e32830f9046
dc.relation.references[82] Wu, J.; Liu, Q.; Lee, R.J. A Folate Receptor-Targeted Liposomal Formulation for Paclitaxel. Int. J. Pharm. 2006, 316, 148–153. https://doi.org/10.1016/j.ijpharm.2006.02.027
dc.relation.references[83] Litzinger, D.C.; Huang, L. Phosphatodylethanolamine Liposomes: Drug Delivery, Gene Transfer and Immunodiagnostic Applications. Biochim. Biophys. Acta, Rev. Biomembr. 1992, 1113, 201–227. https://doi.org/10.1016/0304-4157(92)90039-D
dc.relation.references[84] Sinha, R.; Kim, G.J.; Nie, S.; Shin, D.M. Nanotechnology in Cancer Therapeutics: Bioconjugated Nanoparticles for Drug Delivery. Mol. Cancer Ther. 2006, 5, 1909–1917. https://doi.org/10.1158/1535-7163.MCT-06-0141
dc.relation.references[85] Sakamoto, J.H.; van de Ven, A.L.; Godin, B.; Blanco, E.; Serda, R.E.; Grattoni, A.; Ziemys, A.; Bouamrani, A.; Hu, T.; Ranganathan, S.I. et al. Enabling Individualized Therapy through Nanotechnology. Pharmacol. Res. 2010, 62, 57–89. https://doi.org/10.1016/j.phrs.2009.12.011
dc.relation.references[86] Lo, C.-L.; Lin, K.-M.; Huang, C.-K.; Hsiue, G.-H. Self-Assembly of a Micelle Structure from Graft and Diblock Copolymers: An Example of Overcoming the Limitations of Polyions in Drug Delivery. Adv. Funct. Mater. 2006, 16, 2309– 2316. https://doi.org/10.1002/adfm.200500627
dc.relation.references[87] Anand, P.; Kunnumakkara, A.B.; Newman, R.A. Aggarwal, B.B. Bioavailability of Curcumin: Problems and Promises. Mol. Pharmaceutics 2007, 4, 807–818. https://doi.org/10.1021/mp700113r
dc.relation.references[88] Demchuk, Z.; Savka, M.; Voronov, A.; Budishevska, O.; Donchak, V.; Voronov, S. Amphiphilic Polymers Containing Cholesterol for Drug Delivery Systems. Chem. Chem. Technol. 2016, 10, 561–570. https://doi.org/10.23939/chcht10.04si.561
dc.relation.references[89] Kumar, A.; Ahuja, A.; Ali, J.; Baboota, S. Conundrum and Therapeutic Potential of Curcumin in Drug Delivery. Crit. Rev. Ther. Drug Carrier Syst. 2010, 27, 279–312. https://doi.org/10.1615/CritRevTherDrugCarrierSyst.v27.i4.10
dc.relation.references[90] Khomenko, O.; Budishevska, O.;Voronov, A.; Kudina, O.; Tarnavchyk, I.; Voronov, S. Amphiphilic Oligomers Based on Diesters of Pyromellitic Acid for the Solubilization of Lipophilic Agents. Int. J. Theor. Appl. Nanotechnol. 2013, 1, 17–25. https://doi.org/10.11159/ijtan.2013.002
dc.relation.references[91] Lipophilicity in Drug Action and Toxicology; Plišca, V.; Testa, B.; van de Waterbeemd, H., Eds.; VCH: Weinheim, 1996.
dc.relation.references[92] Popadyuk, N.; Zholobko, O.; Donchak, V.; Harhay, K.; Budishevska, O.; Voronov, A.; Kohut, A.; Voronov, S. Ionically and Covalently Crosslinked Hydrogel Particles Based on Chitosan and Poly(Ethylene Glycol). Chem. Chem. Technol. 2014, 8, 171–176. https://doi.org/10.23939/chcht08.02.171
dc.relation.references[93] Khomenko, O.; Budishevska, O; Varvarenko, S.; Voronov, A.; Kudina, O.; Chekailo, M.; Voronov, S. Micellar structures of amphiphilic diesters of pyromellitic acid for the synthesis of silver nanoparticles. Bulletin of the National University "Lviv Polytechnic" series: "Chemistry, technology of substances and their applications" 2012, 726, 332–340.
dc.relation.references[94] Voronov, A.; Kohut, A.; Vasylyev, S.; Peukert, W. Mechanism of Silver Ion Reduction in Concentrated Solutions of Amphiphilic Invertible Polyesters in Nonpolar Solvent at Room Temperature.Langmuir 2008, 24, 12587–12594. https://doi.org/10.1021/la801769v
dc.relation.referencesen[1] Alkan, B.; Daglar, O.; Luleburgaz, S.; Gungor, B.; Gunay, U.S.; Hizal, G.; Tunca, U.; Durmaz, H. One-Pot Cascade Polycondensation and Passerini Three-Component Reactions for the Synthesis of Functional Polyesters. Polym. Chem. 2022, 13, 258–266. https://doi.org/10.1039/D1PY01528A
dc.relation.referencesen[2] Koziel, K.; Lagiewka, J.; Girek, B.; Folentarska, A.; Girek, T.; Ciesielski, W. Synthesis of New Amino-b-Cyclodextrin Polymer, Cross-Linked with Pyromellitic Dianhydride and Their Use for the Synthesis of Polymeric Cyclodextrin Based Nanoparticles.Polymers 2021, 13, 1332. https://doi.org/10.3390/polym13081332
dc.relation.referencesen[3] Afinjuomo, F.; Barclay, T.; Song, Y.; Parikh, A.; Petrovsky, N.; Garg, S. Synthesis and Characterization of a Novel Inulin Hydrogel Crosslinked with Pyromellitic Dianhydride. React. Funct. Polym. 2019, 134, 104–111. https://doi.org/10.1016/j.reactfunctpolym.2018.10.014
dc.relation.referencesen[4] Arkas, M.; Vardavoulias, M.; Kythreoti, G.; Giannakoudakis, D.A. Dendritic Polymers in Tissue Engineering: Contributions of PAMAM, PPI PEG and PEI to Injury Restoration and Bioactive Scaffold Evolution. Pharmaceutics 2023, 15, 524. https://doi.org/10.3390/pharmaceutics15020524
dc.relation.referencesen[5] Polotti, G. Perspectives from Industry. Adv. Chem. Eng. 2020,56, 259–330. https://doi.org/10.1016/bs.ache.2020.07.003
dc.relation.referencesen[6] Ciesielska, A.; Ciesielski, W.; Girek, B.; Girek, T.; Koziel, K.; Kulawik, D.; Lagiewka, J. Biomedical Application of Cyclodextrin Polymers Cross-Linked via Dianhydrides of Carboxylic Acids. Appl. Sci. 2020, 10, 8463. https://doi.org/10.3390/app10238463
dc.relation.referencesen[7] Peimanfard, S.; Zarrabi, A.; Trotta, F.; Matencio, A.; Cecone, C.; Caldera, F. Developing Novel Hydroxypropyl-b-Cyclodextrin- Based Nanosponges as Carriers for Anticancer Hydrophobic Agents: Overcoming Limitations of Host–Guest Complexes in a Comparative Evaluation Pharmaceutics 2022, 14, 1059. https://doi.org/10.3390/pharmaceutics14051059
dc.relation.referencesen[8] Monfared, Y.K.; Mahmoudian M.; Cecone, C.; Caldera, F.; Zakeri-Milani, P.; Matencio, A.; Trotta, F. Stabilization and Anticancer Enhancing Activity of the Peptide Nisin by Cyclodextrin-Based Nanosponges against Colon and Breast Cancer Cells. Polymers 2022, 14, 594. https://doi.org/10.3390/polym14030594
dc.relation.referencesen[9] Girek, T.; Koziel, K.; Girek, B.; Ciesielski, W. CD Oxyanions as a Tool for Synthesis of Highly Anionic Cyclodextrin Polymers. Polymers 2020, 12, 2845. https://doi.org/10.3390/polym12122845
dc.relation.referencesen[10] Demasi, S.; Caser, M.; Caldera, F.; Dhakar, N.K.; Vidotto, F.; Trotta, F.; Scariot, V. Functionalized Dextrin-Based Nanosponges as Effective Carriers for the Herbicide Ailanthone. Ind. Crops Prod. 2021, 164, 113346. https://doi.org/10.1016/j.indcrop.2021.113346
dc.relation.referencesen[11] Qi, H.; Meng, L.; Lin, X.; Xu, W.; Chen, Y.; Zhang, C.; Qiu, Y. Anti-Wrinkle Finishing of Cotton Fabrics with Pyromellitic Acid Enhanced by Polyol Extenders. J. Donghua Univ. (Engl. Ed.) 2022, 39, 533–541. https://doi.org/10.19884/j.1672-5220.202209006
dc.relation.referencesen[12] Tarnavchyk, I.; Voronov, A.; Donchak, V.; Budishevska, O.; Kudina, O.; Khomenko, O.; Harhay, K.; Samaryk, V.; Voronov, S. Synthesis and Selfassambling of Amphiphilic Oligoesters Based on Pyromellitic Acid. Chem. Chem. Technol. 2016, 10, 159–172. https://doi.org/10.23939/chcht10.02.159
dc.relation.referencesen[13] Müller, R.H. Colloidal Carriers for Controlled Drug delivery and Targeting: Modification, Characterization and in Vivo Distribution; CRC Press, 1991.
dc.relation.referencesen[14] Mishra, P.; Nayak, B.; Dey, R.K. PEGylation in Anti-Cancer Therapy: An Overview. Asian J. Pharm. Sci. 2016, 11, 337–348. https://doi.org/10.1016/j.ajps.2015.08.011
dc.relation.referencesen[15] Kudina, O.; Tarnavchyk, I.; Khomenko, O.; Budishevska, O.; Voronov, S.; Voronov, A. PEG and Cholesterol-Containing Pyromellitates: Synthesis and Self-Assembly. Macromol. Chem. Phys. 2013, 214, 2761–2767. https://doi.org/10.1002/macp.201300488
dc.relation.referencesen[16] Klok, H.-A.; Hwang, J.J.; Iyer, S.N.; Stupp, S.I. Cholesteryl-(L- Lactic Acid)n Building Blocks for Self-Assembling Biomaterials. Macromolecules 2002,35,746–759. https://doi.org/10.1021/ma010907x
dc.relation.referencesen[17] Heino, S.; Lusa, S.; Somerharju, P.; Ehnholm, C.; Olkkonen, V.M.; Ikonen, E. Dissecting the Role of the Golgi Complex and Lipid Rafts in Biosynthetic Transport of Cholesterol to the Cell Surface. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 8375–8380. https://doi.org/10.1073/pnas.140218797
dc.relation.referencesen[18] Klausen, T.K.; Hougaard, C.; Hoffmann, E.K.; Pedersen, S.F. Cholesterol Modulates the Molume-Regulated Anion Current in Ehrlich-Lettre Ascites Cells via Effects on Rho and F-Actin. Am. J. Physiol. Cell Physiol. 2006, 291, P.757–P.771. https://doi.org/10.1152/ajpcell.00029.2006
dc.relation.referencesen[19] Levitan, I.; Christian, A.E.; Tulenko, T.N.; Rothblat, G.H. Membrane Cholesterol Content Modulates Activation of Volume- Regulated Anion Current in Bovine Endothelial Cells. J. Gen.Physiol. 2000, 115, 405–416. https://doi.org/10.1085/jgp.115.4.405
dc.relation.referencesen[20] Maxfield, F.R.; Tabas, I. Role of Cholesterol and Lipid Organization in Disease. Nature 2005, 438, 612–621. https://doi.org/10.1038/nature04399
dc.relation.referencesen[21] Yusa, S. Self-Assembly of Cholesterol-Containing Water- Soluble Polymers. Int. J. Polym. Sci. 2012, 609767. https://doi.org/10.1155/2012/609767
dc.relation.referencesen[22] Ringsdorf, H.; Schlarb, B.; Venzmer, J. Molecular Architecture and Function of Polymeric Oriented Systems: Models for the Study of Organization, Surface Recognition, and Dynamics of Biomembranes. Angew. Chem. Int. Ed. 1988, 27, 113–158. https://doi.org/10.1002/anie.198801131
dc.relation.referencesen[23] Zhou, Y.; Briand, V.A.; Sharma, N.; Ahn, S.; Kasi, R.M. Polymers Comprising Cholesterol: Synthesis, Self-Assembly, and Applications. Materials 2009, 2, 636–660. https://doi.org/10.3390/ma2020636
dc.relation.referencesen[24] Shibaev, V.P.; Platé, N.A.; Freidzon, Ya.S. Thermotropic Liquid Crystalline Polymers. I. Cholesterol-Containing Polymers and Copolymers. J. Polym. Sci. Pol. Chem. 1979, 17, 1655–1670. https://doi.org/10.1002/pol.1979.170170609
dc.relation.referencesen[25] Shibaev, V.P.; Tal’roze, R.V.; Karakhanova, F.I.; Platé, N.A. Thermotropic Liquid Crystalline Polymers. II. Polymers with Amino Acid Fragments in the Side Chains. J. Polym. Sci. Pol.Chem. 1979, 17, 1671–1684. https://doi.org/10.1002/pol.1979.170170610
dc.relation.referencesen[26] Yamaguchi, T.; Asada, T.; Hayashi, H.; Nakamura, N. Dependence of the Packing Structure of Mesogenic Groups on the Flexible Spacer Length of Liquid-Crystalline Side-Chain Polymers. Macromolecules 1989, 22, 1141–1144. https://doi.org/10.1021/ma00193a024
dc.relation.referencesen[27] Knop, K.; Hoogenboom, R.; Fischer, D.; Schubert, U.S. Poly(ethylene glycol) in Drug Delivery: Pros and Cons as Well as Potential Alternatives. Angew. Chem. Int. Ed. 2010, 49, 6288–6308. https://doi.org/10.1002/anie.200902672
dc.relation.referencesen[28] Menger, F.M.; Littau, C.A. Gemini Surfactants: Synthesis and Properties. J. Am. Chem. Soc. 1991, 113, 1451–1452. https://doi.org/10.1021/ja00004a077
dc.relation.referencesen[29] Menger, F.; Littau, C. Gemini Surfactants: A New Class of Self-Assembling Molecules. J. Am. Chem. Soc. 1993, 115, 10083–10090. https://doi.org/10.1021/ja00075a025
dc.relation.referencesen[30] Zana, R.; Xia, J. Gemini Surfactants: Synthesis, Interfacial and Solution-Phase Behavior, and Applications; Marcel Dekker, 2004.
dc.relation.referencesen[31] Sakai, K. Development of Commercially Available Gemini Surfactants. J. Oleo Sci. 2012, 12, 627–633. https://doi.org/10.5650/oleoscience.12.627
dc.relation.referencesen[32] Rosen, M.J. Geminis: A New Generation of Surfactants.Chemtech 1993, 23, 30–33.
dc.relation.referencesen[33] Villa, C.; Baldassari, S.; Martino, D.F.C.; Spinella, A.; Caponetti, E. Green Synthesis, Molecular Characterization and Associative Behavior of Some Gemini Surfactants without a Spacer Group. Materials 2013, 6, 1506–1519. https://doi.org/10.3390/ma6041506
dc.relation.referencesen[34] Zana, R. Gemini (Dimeric) Surfactants. Curr. Opin. Colloid Interface Sci. 1996, 1, 566–571. https://doi.org/10.1016/S1359-0294(96)80093-8
dc.relation.referencesen[35] Brycki, B.E.; Kowalczyk, I.H; Szulc, A.; Kaczerewska, O.; Pakiet, M. Multifunctional Gemini Surfactants: Structure, Synthesis, Properties, and Applications. In Application and Characterization of Surfactants; Intech World's Largest Science, Technology & Medicine Open Access Book Publisher, 2017.
dc.relation.referencesen[36] Song, B.; Hu, Y.; Song, Y.; Zhao, J. Alkyl Chain Length- Dependent Viscoelastic Properties in Aqueous Wormlike Micellar Solutions of Anionic Gemini Surfactants with an Azobenzene Spacer. J. Colloid Interface Sci. 2010, 341, 94–100. https://doi.org/10.1016/j.jcis.2009.09.023
dc.relation.referencesen[37] Ahmady, A. R.; Hosseinzadeh, P.; Solouk, A.; Akbari, S.; Szulc, A.M.; Brycki, B.E. Cationic Gemini Surfactant Properties, Its Potential as a Promising Bioapplication Candidate, and Strategies for Improving Its Biocompatibility: A Review. Adv. Colloid Interface Sci. 2022, 299, 102581. https://doi.org/10.1016/j.cis.2021.102581
dc.relation.referencesen[38] Pei, X.; Zhao, J.; Ye, Y.; You, Y; Wei, X. Wormlike Micelles and Gels Reinforced by Hydrogen Bonding in Aqueous Cationic Gemini Surfactant Systems. Soft Matter 2011, 7, 2953–2960. https://doi.org/10.1039/P.0SM01071E
dc.relation.referencesen[39] Degiorgio, V.; Corti, M. Physics of Amphiphiles: Micelles, Vesicles and Microemulsion; North Holland Physics Publishing, 1985.
dc.relation.referencesen[40] Shrestha, R.G.; Shrestha, L.K.; Matsunaga, T.; Shibayama, M.; Aramaki, K. Lipophilic Tail Architecture and Molecular Structure of Neutralizing Agent for the Controlled Rheology of Viscoelastic Fluid in Amino Acid-Based Anionic Surfactant System. Langmuir 2011, 27, 2229–2236. https://doi.org/10.1021/la1048248
dc.relation.referencesen[41] Shrestha, R.G.; Abezgauz, L.; Danino, D.; Sakai, K.; Sakai, H.; Abe, M. Structure and Dynamics of Poly(oxyethylene) Cholesteryl Ether Wormlike Micelles: Rheometry, SAXS, and Cryo-TEM Studies. Langmuir 2011, 27, 12877–12883. https://doi.org/10.1021/la202879f
dc.relation.referencesen[42] Bhadani, A.; Shrestha, R.G.; Koura, S.; Endo, T.; Sakai, K.; Abe, M.; Sakai, H. Self-Aggregation Properties of New Ester-Based Gemini Surfactants and Their Rheological Behavior in the Presence of Cosurfactant – Monolaurin. Colloids Surf. A: Physicochem. Eng. Asp. 2014, 461, 258–266. https://doi.org/10.1016/j.colsurfa.2014.08.001
dc.relation.referencesen[43] Pei, X.; Xu, Z.; Song, B.; Cui, Z.; Zhao, J. Wormlike Micelles Formed in Catanionic Systems Dominated by Cationic Gemini Surfactant: Synergistic Effect with High Efficiency. Colloids Surf. A: Physicochem. Eng. Asp. 2014, 443, 508–514. https://doi.org/10.1016/j.colsurfa.2013.12.007
dc.relation.referencesen[44] Lin, Z.; Scriven, L.E.; Davis, H.T. Cryogenic Electron Microscopy of Rodlike or Wormlike Micelles in Aqueous Solutions of Nonionic Surfactant Hexaethylene Glycol Monohexadecyl Ether. Langmuir 1992, 8, 2200–2205. https://doi.org/10.1021/la00045a021
dc.relation.referencesen[45] Vinson, P.K.; Talmon, Y. Comments on "Electron Diffraction Observed in the Gigantic Micelle-Producing System of CTAB- Aromatic Additives," by Hirata, Sakaiguchi, and Akai. J. Colloid Interface Sci. 1989, 133, 288–289. https://doi.org/10.1016/0021-9797(89)90305-6
dc.relation.referencesen[46] Jerke, G.; Pedersen, J.S.; Egelhaaf, S.U.; Schurtenberger, P. Flexibility of Charged and Uncharged Polymer-Like Micelles. Langmuir 1998, 14, 6013–6024. https://doi.org/10.1021/la980390r
dc.relation.referencesen[47] Groth, C.; Nydén, M.; Holmberg, K.; Kanicky, J.R.; Shah, D.O. Kinetics of the Self-Assembly of Gemini Surfactants. J. Surfactants Deterg. 2004, 7, 247–255. https://doi.org/10.1007/s11743-004-0308-8
dc.relation.referencesen[48] Rosen, M.J.; Tracy, D.J. Gemini Surfactants. J. Surfactants Deterg. 1998, 1, 547–554. https://doi.org/10.1007/s11743-998-0057-8
dc.relation.referencesen[49] Micich, T.J.; Linfield, W.M. Wetting Properties of Nonionics from Branched Fatty Diamides. J. Am. Oil Chem. Soc. 1988, 65, 820–825. https://doi.org/10.1007/BF02542540
dc.relation.referencesen[50] Quencer, L.B.; Kokke-Hall, S.; Loughney, T. Proceedings of CESIO 4th World Surfactant Congress. 1996, 2, 66.
dc.relation.referencesen[51] Kumar, N.; Tyagi, R. Industrial Applications of Dimeric Surfactants: A Review. J. Dispers. Sci. Technol. 2014, 35, 205–214. https://doi.org/10.1080/01932691.2013.780243
dc.relation.referencesen[52] Rosen, M.J. Gemini Surfactants. Industrial Applications of Surfactants IV 1999, 151–161. https://doi.org/10.1533/9781845698614.151
dc.relation.referencesen[53] Li, J.; Dahanayake, M.; Reierson, R.L.; Tracy, D.J. Amphoteric Surfactants Having Multiple Hydrophobic and Hydrophilic Groups. US patent 5,914,310, June 22, 1999.
dc.relation.referencesen[54] Choi, T.-S.; Shimizu, Y.; Shirai, H.; Hamada, K. Disperse Dyeing of Nylon 6 Fiber Using Gemini Surfactants Containing Ammonium Cations as Auxililiaries. Dyes Pigments 2001, 48, 217–226. https://doi.org/10.1016/S0143-7208(00)00105-4
dc.relation.referencesen[55] Choi, T.-S.; Shimizu, Y.; Shirai, H.; Hamada, K. Disperse Dyeing of Polyester Fiber Using Gemini Surfactants Containing Ammonium Cations as Auxililiaries. Dyes Pigments 2001, 50, 55–65. https://doi.org/10.1016/S0143-7208(01)00033-X
dc.relation.referencesen[56] Choi, T.-S.; Shimizu, Y.; Shirai, H.; Hamada, K. Solubilization of Disperse Dyes in Cationic Gemini Surfactant Micelles. Dyes Pigments 2000, 45, 145–152. https://doi.org/10.1016/S0143-7208(00)00015-2
dc.relation.referencesen[57] Dreja, M.; Tieke, B. Polymerization of Styrene in Ternary Microemulsion Using Cationic Gemini Surfactants Langmuir 1998, 14, 800–807. https://doi.org/10.1021/la9710738
dc.relation.referencesen[58] El-Sadek, B.M. Synthesis of Selected Gemini Surfactants: Surface, Biological Activity and Corrosion Efficiency against Hydrochloric Acid Medium. Der Chemica Sinica 2011, 2, 125–137.
dc.relation.referencesen[59] Mobin, M.; Masroor, S. Cationic Gemini Surfactants as Novel Corrosion Inhibitor for Mild Steel in 1M HCl. Int. J. Electrochem. Sci. 2012, 7, 6920–6940. https://doi.org/10.1016/S1452-3981(23)15758-0
dc.relation.referencesen[60] Chen, X.; Wang, J.; Shen, N.; Luo, Y.; Li, L.; Liu, M.; Thomas, R.K. Gemini Surfactant/DNA Complex Monolayers at the Air−Water Interface: Effect of Surfactant Structure on the Assembly, Stability and Topography of Monolayers. Langmuir 2002, 18, 6222–6228. https://doi.org/10.1021/la025600l
dc.relation.referencesen[61] Yan, X.; Janout, V.; Regen, S.L. Hydrophobic Sponges: Resin- Bound Surfactants as Organic Scavengers. Macromolecules 2002, 35, 8243–8246. https://doi.org/10.1021/ma020568n
dc.relation.referencesen[62] Fielden, M.L.; Perrin, C.; Kremer, A.; Bergsma, M.; Stuart, M.C.; Camilleri, P.; Engberts, J.B.F.N. Sugar-Based Tertiary Amino Gemini Surfactants with a Vesicle-to-Micelle Transition in the Endosomal pH Range Mediate Efficient Transfection in vitro. Eur. J. Biochem. 2001, 268, 1269–1279. https://doi.org/10.1046/j.1432-1327.2001.01995.x
dc.relation.referencesen[63] Buijnsters, P.J.J.A.; Rodriguez, C.L.G.; Willighagen, E.L.; Sommerdijk, N.A.J.M.; Kremer, A.; Camilleri, P.; Feiters, M.C.; Nolte, R.J.M.; Zwanenburg, B. Cationic Gemini Surfactants Based on Tartaric Acid: Synthesis, Aggregation, Monolayer Behaviour, and Interaction with DNA. Eur. J. Org. Chem. 2002, 2002, 1397– 1406. https://doi.org/10.1002/1099-0690(200204)2002:8<1397::AID-EJOC1397>3.0.CO;2-6
dc.relation.referencesen[64] Wilhelm, M.; Zhao, C.L.; Wang, Y.; Xu, R.; Winnik, M.A.; Mura, J.L.; Riess, G.; Croucher, M.D. Poly(Styrene-Ethylene Oxide) Block Copolymer Micelle Formation in Water: A Fluorescence Probe Study. Macromoleules 1991, 24, 1033–1040. https://doi.org/10.1021/ma00005a010
dc.relation.referencesen[65] Schmitz, C.; Mourran, A.; Keul, H.; Möller, M. Synthesis and Association Behaviour of Linear Block Copolymers with Different Microstructures but the Same Composition. Macromol. Chem. Phys. 2008, 209, 1859–1971. https://doi.org/10.1002/macp.200800205
dc.relation.referencesen[66] Matsuoka, H.; Matsutani, M.; Mouri, E.; Matsumoto, K. Polymer Micelle Formation without Gibbs Monolayer Formation: Synthesis and Characteritics of Amphiphilic Diblock Copolymer Having Strong Acid Groups. Macromolecules 2003, 36, 5321–5330. https://doi.org/10.1021/ma0215161
dc.relation.referencesen[67] Khomenko, O.; Budishevska, O.; Voronov, A.; Varvarenko, S.; Kudina, O.; Tarnavchyk, I.; Voronov, S. Amphiphilic Diesters of Pyromellitic Acid with Cholesterol Fragments for Solubilization of Lipophilic Substances. Reports of the National Academy of Sciences of Ukraine 2013, 7, 123–129. http://dspace.nbuv.gov.ua/handle/123456789/85809
dc.relation.referencesen[68] Suckling, K.E.; Benson, G.M.; Bond, B.; Gee, A.; Glen, A.; Haynes, C.; Jackson, B. Cholesterol Lowering and Bile Acid Excretion in the Hamster with Cholestyramine Treatment. Atherosclerosis 1991, 89, 183–190. https://doi.org/10.1016/0021-9150(91)90059-C
dc.relation.referencesen[69] Mol, M.J.T.M.; Erkelens, D.W.; Leuven, J.A.G.; Schouten, J.A.; Stalenhoef, A.F.H. Simvastatin (MK-733): A Potent Cholesterol Synthesis Inhibitor in Heterozygous Familial Hypercholesterolaemia. Atherosclerosis 1988, 69, 131–137. https://doi.org/10.1016/0021-9150(88)90006-8
dc.relation.referencesen[70] Rosenson, R. Patient education: High Cholesterol and Lipids (Beyond the Basics). UpToDate. 2024, Sep 27. UpToDate Inc. www.uptodate.com.
dc.relation.referencesen[71] Molecular probes. Amplex® RedCholesterolAssayKitCatalogno. A12216.
dc.relation.referencesen[72] Okada, H.; Toguchi, H. Biodegradable Microspheres in Drug Delivery. Crit. Rev. Ther. Drug Carrier Syst. 1995, 12, 1–99. https://doi.org/10.1615/CritRevTherDrugCarrierSyst.v12.i1.10
dc.relation.referencesen[73] Scott, G.; Gilead, D. Degradable Polymers, Principles and Applications; Chapman & Hall, 1995.
dc.relation.referencesen[74] Anderson, J.M.; Shive, M.S. Biodegradation and Biocompatibility of PLA and PLGA Microspheres. Adv. Drug Deliv. Rev. 2002, 64, 72–82. https://doi.org/10.1016/j.addr.2012.09.004
dc.relation.referencesen[75] Grizzi, I.; Garreau, H.; Li, S.; Vert, M. Hydrolytic Degradation of Devices Based on Poly(DL-Lactic Acid) Size-Dependence. Biomaterials 1995, 16, 305–311. https://doi.org/10.1016/0142- 9612(95)93258-F
dc.relation.referencesen[76] Vert, M.; Li, S.M.; Garreau, H. Attempts to Map the Structure and Degradation Characteristics of Aliphatic Polyesters Derived from Lactic and Glycolic Acids. J. Biomater. Sci. Polym. Ed. 1995, 6, 639–649. https://doi.org/10.1163/156856294X00581
dc.relation.referencesen[77] Vert, M.; Li, S. M.; Garreau, H. Recent Advances in the Field of Lactic Acid/Glycolic Acid Polymer-Based Therapeutic Systems. Macromol.Symp.1995,98,633–642. https://doi.org/10.1002/masy.19950980154
dc.relation.referencesen[78] Huh, K.M.; Min, H.S.; Lee, S.C.; Lee, H.J.; Kim, S.; Park, K. A New Hydrotropic Block Copolymer Micelle System for Aqueous Solubilization of Paclitaxel. J. Control. Release 2008, 126, 122–129. https://doi.org/10.1016/j.jconrel.2007.11.008
dc.relation.referencesen[79] Konno, T.; Junji, W.; Ishihara, K. Enhanced Solubility of Paclitaxel Using Water-Soluble and Biocompatible 2- Methacryloyloxyethyl Phosphorylcholine Polymers. J. Biomed. Mater. Res, A 2003, 65A, 209–214. https://doi.org/10.1002/jbm.a.10481
dc.relation.referencesen[80] Kim, S.C.; Kim, D.W.; Shim, Y.H.; Bang, J.S.; Oh, H.S.; Kim, S.W.; Seo, M.H. In Vivo Evaluation of Polymeric Micellar Paclitaxel Formulation: Toxicity and Efficacy. J. Control. Release 2001, 72, 191–202. https://doi.org/10.1016/S0168-3659(01)00275-9
dc.relation.referencesen[81] Desai, N.P.; Trieu, V.; Hwang, L.Y.; Wu, R.; Soon-Shiong, P.; Gradishar, W.J. Improved Effectiveness of Nanoparticle Albumin- Bound (NAB) Paclitaxel Versus Polysorbate-Based Docetaxel in Multiple Xenografts as a Function of HER2 and SPARC Status.Anti-Cancer Drugs 2008, 19, 899–909. https://doi.org/10.1097/CAD.0b013e32830f9046
dc.relation.referencesen[82] Wu, J.; Liu, Q.; Lee, R.J. A Folate Receptor-Targeted Liposomal Formulation for Paclitaxel. Int. J. Pharm. 2006, 316, 148–153. https://doi.org/10.1016/j.ijpharm.2006.02.027
dc.relation.referencesen[83] Litzinger, D.C.; Huang, L. Phosphatodylethanolamine Liposomes: Drug Delivery, Gene Transfer and Immunodiagnostic Applications. Biochim. Biophys. Acta, Rev. Biomembr. 1992, 1113, 201–227. https://doi.org/10.1016/0304-4157(92)90039-D
dc.relation.referencesen[84] Sinha, R.; Kim, G.J.; Nie, S.; Shin, D.M. Nanotechnology in Cancer Therapeutics: Bioconjugated Nanoparticles for Drug Delivery. Mol. Cancer Ther. 2006, 5, 1909–1917. https://doi.org/10.1158/1535-7163.MCT-06-0141
dc.relation.referencesen[85] Sakamoto, J.H.; van de Ven, A.L.; Godin, B.; Blanco, E.; Serda, R.E.; Grattoni, A.; Ziemys, A.; Bouamrani, A.; Hu, T.; Ranganathan, S.I. et al. Enabling Individualized Therapy through Nanotechnology. Pharmacol. Res. 2010, 62, 57–89. https://doi.org/10.1016/j.phrs.2009.12.011
dc.relation.referencesen[86] Lo, C.-L.; Lin, K.-M.; Huang, C.-K.; Hsiue, G.-H. Self-Assembly of a Micelle Structure from Graft and Diblock Copolymers: An Example of Overcoming the Limitations of Polyions in Drug Delivery. Adv. Funct. Mater. 2006, 16, 2309– 2316. https://doi.org/10.1002/adfm.200500627
dc.relation.referencesen[87] Anand, P.; Kunnumakkara, A.B.; Newman, R.A. Aggarwal, B.B. Bioavailability of Curcumin: Problems and Promises. Mol. Pharmaceutics 2007, 4, 807–818. https://doi.org/10.1021/mp700113r
dc.relation.referencesen[88] Demchuk, Z.; Savka, M.; Voronov, A.; Budishevska, O.; Donchak, V.; Voronov, S. Amphiphilic Polymers Containing Cholesterol for Drug Delivery Systems. Chem. Chem. Technol. 2016, 10, 561–570. https://doi.org/10.23939/chcht10.04si.561
dc.relation.referencesen[89] Kumar, A.; Ahuja, A.; Ali, J.; Baboota, S. Conundrum and Therapeutic Potential of Curcumin in Drug Delivery. Crit. Rev. Ther. Drug Carrier Syst. 2010, 27, 279–312. https://doi.org/10.1615/CritRevTherDrugCarrierSyst.v27.i4.10
dc.relation.referencesen[90] Khomenko, O.; Budishevska, O.;Voronov, A.; Kudina, O.; Tarnavchyk, I.; Voronov, S. Amphiphilic Oligomers Based on Diesters of Pyromellitic Acid for the Solubilization of Lipophilic Agents. Int. J. Theor. Appl. Nanotechnol. 2013, 1, 17–25. https://doi.org/10.11159/ijtan.2013.002
dc.relation.referencesen[91] Lipophilicity in Drug Action and Toxicology; Plišca, V.; Testa, B.; van de Waterbeemd, H., Eds.; VCH: Weinheim, 1996.
dc.relation.referencesen[92] Popadyuk, N.; Zholobko, O.; Donchak, V.; Harhay, K.; Budishevska, O.; Voronov, A.; Kohut, A.; Voronov, S. Ionically and Covalently Crosslinked Hydrogel Particles Based on Chitosan and Poly(Ethylene Glycol). Chem. Chem. Technol. 2014, 8, 171–176. https://doi.org/10.23939/chcht08.02.171
dc.relation.referencesen[93] Khomenko, O.; Budishevska, O; Varvarenko, S.; Voronov, A.; Kudina, O.; Chekailo, M.; Voronov, S. Micellar structures of amphiphilic diesters of pyromellitic acid for the synthesis of silver nanoparticles. Bulletin of the National University "Lviv Polytechnic" series: "Chemistry, technology of substances and their applications" 2012, 726, 332–340.
dc.relation.referencesen[94] Voronov, A.; Kohut, A.; Vasylyev, S.; Peukert, W. Mechanism of Silver Ion Reduction in Concentrated Solutions of Amphiphilic Invertible Polyesters in Nonpolar Solvent at Room Temperature.Langmuir 2008, 24, 12587–12594. https://doi.org/10.1021/la801769v
dc.relation.urihttps://doi.org/10.1039/D1PY01528A
dc.relation.urihttps://doi.org/10.3390/polym13081332
dc.relation.urihttps://doi.org/10.1016/j.reactfunctpolym.2018.10.014
dc.relation.urihttps://doi.org/10.3390/pharmaceutics15020524
dc.relation.urihttps://doi.org/10.1016/bs.ache.2020.07.003
dc.relation.urihttps://doi.org/10.3390/app10238463
dc.relation.urihttps://doi.org/10.3390/pharmaceutics14051059
dc.relation.urihttps://doi.org/10.3390/polym14030594
dc.relation.urihttps://doi.org/10.3390/polym12122845
dc.relation.urihttps://doi.org/10.1016/j.indcrop.2021.113346
dc.relation.urihttps://doi.org/10.19884/j.1672-5220.202209006
dc.relation.urihttps://doi.org/10.23939/chcht10.02.159
dc.relation.urihttps://doi.org/10.1016/j.ajps.2015.08.011
dc.relation.urihttps://doi.org/10.1002/macp.201300488
dc.relation.urihttps://doi.org/10.1021/ma010907x
dc.relation.urihttps://doi.org/10.1073/pnas.140218797
dc.relation.urihttps://doi.org/10.1152/ajpcell.00029.2006
dc.relation.urihttps://doi.org/10.1085/jgp.115.4.405
dc.relation.urihttps://doi.org/10.1038/nature04399
dc.relation.urihttps://doi.org/10.1155/2012/609767
dc.relation.urihttps://doi.org/10.1002/anie.198801131
dc.relation.urihttps://doi.org/10.3390/ma2020636
dc.relation.urihttps://doi.org/10.1002/pol.1979.170170609
dc.relation.urihttps://doi.org/10.1002/pol.1979.170170610
dc.relation.urihttps://doi.org/10.1021/ma00193a024
dc.relation.urihttps://doi.org/10.1002/anie.200902672
dc.relation.urihttps://doi.org/10.1021/ja00004a077
dc.relation.urihttps://doi.org/10.1021/ja00075a025
dc.relation.urihttps://doi.org/10.5650/oleoscience.12.627
dc.relation.urihttps://doi.org/10.3390/ma6041506
dc.relation.urihttps://doi.org/10.1016/S1359-0294(96)80093-8
dc.relation.urihttps://doi.org/10.1016/j.jcis.2009.09.023
dc.relation.urihttps://doi.org/10.1016/j.cis.2021.102581
dc.relation.urihttps://doi.org/10.1039/C0SM01071E
dc.relation.urihttps://doi.org/10.1021/la1048248
dc.relation.urihttps://doi.org/10.1021/la202879f
dc.relation.urihttps://doi.org/10.1016/j.colsurfa.2014.08.001
dc.relation.urihttps://doi.org/10.1016/j.colsurfa.2013.12.007
dc.relation.urihttps://doi.org/10.1021/la00045a021
dc.relation.urihttps://doi.org/10.1016/0021-9797(89)90305-6
dc.relation.urihttps://doi.org/10.1021/la980390r
dc.relation.urihttps://doi.org/10.1007/s11743-004-0308-8
dc.relation.urihttps://doi.org/10.1007/s11743-998-0057-8
dc.relation.urihttps://doi.org/10.1007/BF02542540
dc.relation.urihttps://doi.org/10.1080/01932691.2013.780243
dc.relation.urihttps://doi.org/10.1533/9781845698614.151
dc.relation.urihttps://doi.org/10.1016/S0143-7208(00)00105-4
dc.relation.urihttps://doi.org/10.1016/S0143-7208(01)00033-X
dc.relation.urihttps://doi.org/10.1016/S0143-7208(00)00015-2
dc.relation.urihttps://doi.org/10.1021/la9710738
dc.relation.urihttps://doi.org/10.1016/S1452-3981(23)15758-0
dc.relation.urihttps://doi.org/10.1021/la025600l
dc.relation.urihttps://doi.org/10.1021/ma020568n
dc.relation.urihttps://doi.org/10.1046/j.1432-1327.2001.01995.x
dc.relation.urihttps://doi.org/10.1002/1099-0690(200204)2002:8<1397::AID-EJOC1397>3.0.CO;2-6
dc.relation.urihttps://doi.org/10.1021/ma00005a010
dc.relation.urihttps://doi.org/10.1002/macp.200800205
dc.relation.urihttps://doi.org/10.1021/ma0215161
dc.relation.urihttp://dspace.nbuv.gov.ua/handle/123456789/85809
dc.relation.urihttps://doi.org/10.1016/0021-9150(91)90059-C
dc.relation.urihttps://doi.org/10.1016/0021-9150(88)90006-8
dc.relation.urihttps://doi.org/10.1615/CritRevTherDrugCarrierSyst.v12.i1.10
dc.relation.urihttps://doi.org/10.1016/j.addr.2012.09.004
dc.relation.urihttps://doi.org/10.1016/0142-
dc.relation.urihttps://doi.org/10.1163/156856294X00581
dc.relation.urihttps://doi.org/10.1002/masy.19950980154
dc.relation.urihttps://doi.org/10.1016/j.jconrel.2007.11.008
dc.relation.urihttps://doi.org/10.1002/jbm.a.10481
dc.relation.urihttps://doi.org/10.1016/S0168-3659(01)00275-9
dc.relation.urihttps://doi.org/10.1097/CAD.0b013e32830f9046
dc.relation.urihttps://doi.org/10.1016/j.ijpharm.2006.02.027
dc.relation.urihttps://doi.org/10.1016/0304-4157(92)90039-D
dc.relation.urihttps://doi.org/10.1158/1535-7163.MCT-06-0141
dc.relation.urihttps://doi.org/10.1016/j.phrs.2009.12.011
dc.relation.urihttps://doi.org/10.1002/adfm.200500627
dc.relation.urihttps://doi.org/10.1021/mp700113r
dc.relation.urihttps://doi.org/10.23939/chcht10.04si.561
dc.relation.urihttps://doi.org/10.1615/CritRevTherDrugCarrierSyst.v27.i4.10
dc.relation.urihttps://doi.org/10.11159/ijtan.2013.002
dc.relation.urihttps://doi.org/10.23939/chcht08.02.171
dc.relation.urihttps://doi.org/10.1021/la801769v
dc.rights.holder© Національний університет “Львівська політехніка”, 2025
dc.rights.holder© Donchak V., Voronov A., Budishevska O., Kohut A., Stetsyshyn Y., 2025
dc.subjectпіромелітова кислота
dc.subjectпіромелітовий діангідрид
dc.subjectполіетиленгліколь
dc.subjectхолестерол
dc.subjectповерхнево-активні “геміні”-речовини
dc.subjectсолюбілізація
dc.subjectкуркумін
dc.subjectpyromellitic acid
dc.subjectpyromellitic dianhydride
dc.subjectpolyethylene glycol
dc.subjectcholesterol
dc.subjectgemini surfactants
dc.subjectsolubilization
dc.subjectcurcumin
dc.titleAmphiphilic Esters of Pyromellitic Acid: Synthesis and Prospects of Applications
dc.title.alternativeАмфіфільні естери піромелітової кислоти: синтез і перспективи застосування
dc.typeArticle

Files

Original bundle

Now showing 1 - 2 of 2
Loading...
Thumbnail Image
Name:
2024v19n1_Donchak_V-Amphiphilic_Esters_of_Pyromellitic_79-90.pdf
Size:
729.85 KB
Format:
Adobe Portable Document Format
Loading...
Thumbnail Image
Name:
2024v19n1_Donchak_V-Amphiphilic_Esters_of_Pyromellitic_79-90__COVER.png
Size:
561.92 KB
Format:
Portable Network Graphics

License bundle

Now showing 1 - 1 of 1
Loading...
Thumbnail Image
Name:
license.txt
Size:
1.81 KB
Format:
Plain Text
Description: