Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers

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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Bibliographic Details
Published in:Nanomaterials (Basel, Switzerland) Vol. 11; no. 4; p. 947
Main Authors: Shurpik, Dmitriy N, Makhmutova, Lyaysan I, Usachev, Konstantin S, Islamov, Daut R, Mostovaya, Olga A, Nazarova, Anastasia A, Kizhnyaev, Valeriy N, Stoikov, Ivan I
Format: Journal Article
Language:English
Published: Switzerland MDPI AG 08-04-2021
MDPI
Subjects:
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
United States > US
fluorescein
drug delivery systems
tetrazole
pillararene
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Summary: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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ISSN:2079-4991
2079-4991
DOI:10.3390/nano11040947