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

- RUS
- 中文
- ES

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

Form of presentation

Articles in international journals and collections

Year of publication

2019

��

��

Authors, employees of KFU

Bogdanov Andrey Vladimirovich, author

Mironov Vladimir Fedorovich, author

Bibliographic description in the original language

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.

Annotation

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 albi�ans 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.

Keywords

biocompatible amphiphilic isatin derivatives, antimicrobial agents

The name of the journal

J MOL LIQ

URL

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

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=215432&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Bogdanov Andrey Vladimirovich	ru_RU
dc.contributor.author	Mironov Vladimir Fedorovich	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/eng/?p_id=215432&p_lang=2	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 albi�ans 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	Articles in international journals and collections	ru_RU