Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers
In this work, we have proposed a novel universal stimulus-sensitive nanosized polymer system based on decasubstituted macrocyclic structures-pillar[5]arenes and tetrazole-containing polymers. Decasubstituted pillar[5]arenes containing a large, good leaving tosylate, and phthalimide groups were first...
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| Published in: | Nanomaterials (Basel, Switzerland) Vol. 11; no. 4; p. 947 |
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| Main Authors: | , , , , , , , |
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| Abstract | In this work, we have proposed a novel universal stimulus-sensitive nanosized polymer system based on decasubstituted macrocyclic structures-pillar[5]arenes and tetrazole-containing polymers. Decasubstituted pillar[5]arenes containing a large, good leaving tosylate, and phthalimide groups were first synthesized and characterized. Pillar[5]arenes containing primary and tertiary amino groups, capable of interacting with tetrazole-containing polymers, were obtained with high yield by removing the tosylate and phthalimide protection. According to the fluorescence spectroscopy data, a dramatic fluorescence enhancement in the pillar[5]arene/fluorescein/polymer system was observed with decreasing pH from neutral (pH = 7) to acidic (pH = 5). This indicates the destruction of associates and the release of the dye at a pH close to 5. The presented results open a broad range of opportunities for the development of new universal stimulus-sensitive drug delivery systems containing macrocycles and nontoxic tetrazole-based polymers. |
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| AbstractList | In this work, we have proposed a novel universal stimulus-sensitive nanosized polymer system based on decasubstituted macrocyclic structures-pillar[5]arenes and tetrazole-containing polymers. Decasubstituted pillar[5]arenes containing a large, good leaving tosylate, and phthalimide groups were first synthesized and characterized. Pillar[5]arenes containing primary and tertiary amino groups, capable of interacting with tetrazole-containing polymers, were obtained with high yield by removing the tosylate and phthalimide protection. According to the fluorescence spectroscopy data, a dramatic fluorescence enhancement in the pillar[5]arene/fluorescein/polymer system was observed with decreasing pH from neutral (pH = 7) to acidic (pH = 5). This indicates the destruction of associates and the release of the dye at a pH close to 5. The presented results open a broad range of opportunities for the development of new universal stimulus-sensitive drug delivery systems containing macrocycles and nontoxic tetrazole-based polymers. |
| Author | Usachev, Konstantin S Islamov, Daut R Mostovaya, Olga A Makhmutova, Lyaysan I Stoikov, Ivan I Nazarova, Anastasia A Shurpik, Dmitriy N Kizhnyaev, Valeriy N |
| AuthorAffiliation | 1 A. M. Butlerov Chemical Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia; dnshurpik@mail.ru (D.N.S.); lays_9393@mail.ru (L.I.M.); olga.mostovaya@mail.ru (O.A.M.); anas7tasia@gmail.com (A.A.N.) 4 Department of Theoretical and Applied Organic Chemistry and Polymerization Processes, Irkutsk State University, K. Marksa, 1, 664003 Irkutsk, Russia; kizhnyaev@chem.isu.ru 2 Institute of Fundamental Medicine and Biology, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia; k.usachev@mail.ru 3 FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Institute of Organic and Physical Chemistry, Arbuzov St., 8, 420088 Kazan, Russia; daut1989@mail.ru |
| AuthorAffiliation_xml | – name: 1 A. M. Butlerov Chemical Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia; dnshurpik@mail.ru (D.N.S.); lays_9393@mail.ru (L.I.M.); olga.mostovaya@mail.ru (O.A.M.); anas7tasia@gmail.com (A.A.N.) – name: 4 Department of Theoretical and Applied Organic Chemistry and Polymerization Processes, Irkutsk State University, K. Marksa, 1, 664003 Irkutsk, Russia; kizhnyaev@chem.isu.ru – name: 2 Institute of Fundamental Medicine and Biology, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia; k.usachev@mail.ru – name: 3 FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Institute of Organic and Physical Chemistry, Arbuzov St., 8, 420088 Kazan, Russia; daut1989@mail.ru |
| Author_xml | – sequence: 1 givenname: Dmitriy N orcidid: 0000-0002-7914-6533 surname: Shurpik fullname: Shurpik, Dmitriy N organization: A. M. Butlerov Chemical Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia – sequence: 2 givenname: Lyaysan I surname: Makhmutova fullname: Makhmutova, Lyaysan I organization: A. M. Butlerov Chemical Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia – sequence: 3 givenname: Konstantin S surname: Usachev fullname: Usachev, Konstantin S organization: Institute of Fundamental Medicine and Biology, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia – sequence: 4 givenname: Daut R surname: Islamov fullname: Islamov, Daut R organization: FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Institute of Organic and Physical Chemistry, Arbuzov St., 8, 420088 Kazan, Russia – sequence: 5 givenname: Olga A surname: Mostovaya fullname: Mostovaya, Olga A organization: A. M. Butlerov Chemical Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia – sequence: 6 givenname: Anastasia A surname: Nazarova fullname: Nazarova, Anastasia A organization: A. M. Butlerov Chemical Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia – sequence: 7 givenname: Valeriy N surname: Kizhnyaev fullname: Kizhnyaev, Valeriy N organization: Department of Theoretical and Applied Organic Chemistry and Polymerization Processes, Irkutsk State University, K. Marksa, 1, 664003 Irkutsk, Russia – sequence: 8 givenname: Ivan I orcidid: 0000-0002-3019-7866 surname: Stoikov fullname: Stoikov, Ivan I organization: A. M. Butlerov Chemical Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia |
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| Keywords | fluorescein drug delivery systems tetrazole pillararene |
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| Snippet | In this work, we have proposed a novel universal stimulus-sensitive nanosized polymer system based on decasubstituted macrocyclic structures-pillar[5]arenes... In this work, we have proposed a novel universal stimulus-sensitive nanosized polymer system based on decasubstituted macrocyclic structures—pillar[5]arenes... |
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| SubjectTerms | Amino groups Aromatic compounds Drug delivery Drug delivery systems Drugs Fluorescein Fluorescence Fluorescence spectroscopy pH effects Pharmaceutical industry Phthalimide pillararene Polymers Self-assembly Spectrum analysis tetrazole Tetrazoles |
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| Title | Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers |
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