КФУ. Карточка публикации. Tunable amphiphilic π-systems based on isatin derivatives containing a quaternary ammonium moiety: The role of alkyl chain length in biological activity.

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TUNABLE AMPHIPHILIC π-SYSTEMS BASED ON ISATIN DERIVATIVES CONTAINING A QUATERNARY AMMONIUM MOIETY: THE ROLE OF ALKYL CHAIN LENGTH IN BIOLOGICAL ACTIVITY.

Форма представления

Статьи в зарубежных журналах и сборниках

Год публикации

2019

Язык

английский

Авторы, сотрудники КФУ

Богданов Андрей Владимирович, автор

Миронов Владимир Федорович, автор

Библиографическое описание на языке оригинала

T.N.Pashirova, A.V.Bogdanov, I.F.Zaripova, E.A.Burilova, A.E.Vandyukov, A.S. Sapunova, I.I.Vandyukova, A.D.Voloshina, V.F.Mironov, L.Ya.Zakharova. Tunable amphiphilic π-systems based on isatin derivatives containing a quaternary ammonium moiety: The role of alkyl chain length in biological activity. // J. Mol. Liquids. 2019. Vol. 290. 111220. 9 p. Doi 10.1016/j.molliq.2019.111220.

Аннотация

This work deals with polyfunctional biocompatible amphiphilic isatin derivatives. Isatin-3-acylhydrazones con-taining a quaternary ammonium moiety (Is-Q-n) with varying hydrophobicity (R = CnH2n+1, wheren= 10,12, 14, 16, 18, 20) were synthesized. Tunable self-assembly behavior, morphology of nanostructures, and theirbiological activity were modulated by hydrophilic-lipophilic balance of π-amphiphiles and solvent polarity. Self-assembly of Is-Q-n was investigated by tensiometry, conductometry, IR and UV–Vis spectroscopy, fluorimetry and dynamic light scattering. The unexpected values of the physicochemical parameters at long alkyl chain length have been interpreted. The CAC of Is-Q-16 is lower than CMC of classical surfactant CTAB. Solvent-induced self-assembly for Is-Q-16 was observed. The hydrophobic dye Orange OT was solubilized in Is-Q-10 solutions twice better than in CTAB solutions. Is -Q-n self-assembled structures with size 50 nm and 100 nm in a concentration range from 0.01 mM (belowCAC) to 10 mM were found. Is-Q-10 forms small associates with size 3 nm. Selective antimicrobial activity oflow toxic ammonium salts against Gram-positive bacteria (S. aureus 209pandB. cereus 8035) and fungus Candida albiсans 855–653 was shown. Newly synthesized 1-dodecylisatin derivatives containing a quaternary ammonium moiety may be recommended as antimicrobial agents and for drug solubilization, in particular for drugs capable for π-π-stacking interactions.

Ключевые слова

biocompatible amphiphilic isatin derivatives, antimicrobial agents

Название журнала

J MOL LIQ

URL

https://www.sciencedirect.com/science/article/pii/S0167732219326698

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https://repository.kpfu.ru/?p_id=215432

Полная запись метаданных

Поле DC	Значение	Язык
dc.contributor.author	Богданов Андрей Владимирович	ru_RU
dc.contributor.author	Миронов Владимир Федорович	ru_RU
dc.date.accessioned	2019-01-01T00:00:00Z	ru_RU
dc.date.available	2019-01-01T00:00:00Z	ru_RU
dc.date.issued	2019	ru_RU
dc.identifier.citation	T.N.Pashirova, A.V.Bogdanov, I.F.Zaripova, E.A.Burilova, A.E.Vandyukov, A.S. Sapunova, I.I.Vandyukova, A.D.Voloshina, V.F.Mironov, L.Ya.Zakharova. Tunable amphiphilic π-systems based on isatin derivatives containing a quaternary ammonium moiety: The role of alkyl chain length in biological activity. // J. Mol. Liquids. 2019. Vol. 290. 111220. 9 p. Doi 10.1016/j.molliq.2019.111220.	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/?p_id=215432	ru_RU
dc.description.abstract	J MOL LIQ	ru_RU
dc.description.abstract	This work deals with polyfunctional biocompatible amphiphilic isatin derivatives. Isatin-3-acylhydrazones con-taining a quaternary ammonium moiety (Is-Q-n) with varying hydrophobicity (R = CnH2n+1, wheren= 10,12, 14, 16, 18, 20) were synthesized. Tunable self-assembly behavior, morphology of nanostructures, and theirbiological activity were modulated by hydrophilic-lipophilic balance of π-amphiphiles and solvent polarity. Self-assembly of Is-Q-n was investigated by tensiometry, conductometry, IR and UV–Vis spectroscopy, fluorimetry and dynamic light scattering. The unexpected values of the physicochemical parameters at long alkyl chain length have been interpreted. The CAC of Is-Q-16 is lower than CMC of classical surfactant CTAB. Solvent-induced self-assembly for Is-Q-16 was observed. The hydrophobic dye Orange OT was solubilized in Is-Q-10 solutions twice better than in CTAB solutions. Is -Q-n self-assembled structures with size 50 nm and 100 nm in a concentration range from 0.01 mM (belowCAC) to 10 mM were found. Is-Q-10 forms small associates with size 3 nm. Selective antimicrobial activity oflow toxic ammonium salts against Gram-positive bacteria (S. aureus 209pandB. cereus 8035) and fungus Candida albiсans 855–653 was shown. Newly synthesized 1-dodecylisatin derivatives containing a quaternary ammonium moiety may be recommended as antimicrobial agents and for drug solubilization, in particular for drugs capable for π-π-stacking interactions.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	biocompatible amphiphilic isatin derivatives	ru_RU
dc.subject	antimicrobial agents	ru_RU
dc.title	Tunable amphiphilic π-systems based on isatin derivatives containing a quaternary ammonium moiety: The role of alkyl chain length in biological activity.	ru_RU
dc.type	Статьи в зарубежных журналах и сборниках	ru_RU