Merging structural frameworks of imidazolium, pyridinium, and cholinium ionic liquids with cinnamic acid to tune solution state behavior and properties

Merging structural frameworks of imidazolium, pyridinium, and cholinium ionic liquids with cinnamic acid to tune solution state behavior and properties Научная публикация

Журнал

Journal of Molecular Liquids
ISSN: 0167-7322 , E-ISSN: 1873-3166

Вых. Данные

Год: 2022, Том: 352, Номер статьи : 118673, Страниц : DOI: 10.1016/j.molliq.2022.118673

Авторы

Vavina Anna V. ¹ , Seitkalieva Marina M. ¹ , Posvyatenko Alexandra V. ^2,1 , Gordeev Evgeniy G. ¹ , Strukova Elena N. ³ , Egorova Ksenia S. ¹ , Ananikov Valentine P. ¹

Организации

1	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russia
2	Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Ministry of Health of Russian Federation, Moscow 117198, Russia
3	Gause Institute of New Antibiotics, Russian Academy of Sciences, Moscow 119021, Russia

Solubility in water, interactions with the solvent medium and tuning of molecular conformation in the liquid phase are the key issues to discover new biologically active molecules and to understand the mechanisms of their action. In the present article, we report synthesis, structural and biological activity studies, and computational modeling of new ionic compounds. Structural frameworks of well-known imidazolium, pyridinium and cholinium ionic liquids (ILs) were combined with naturally occurring cinnamic acid (CA), which is known to possess a wide spectrum of biological activity. Different combinations of these two structural elements (IL and Cin (cinnamic moiety)) allowed modulating the solubility, physicochemical properties and biological activity of the resulting molecules. A significant increase in the biological activity was achieved for the three studied hybrid molecules - [C4mim-Cin][Cl], [C4py–Cin][Cl], and [C4mim-Cin][Cin]. Multiparameter cytotoxicity mapping was performed to visualize the biological activity of the 28 studied molecules. Detailed experimental investigation and molecular dynamics simulation were performed to gain insight into the structure–activity relationship. Of note, a folding conformational change in the structure of [Cnmim-Cin][Cl] hybrid molecules in solution resulted in a substantial change in chemical reactivity, with the activation energy of the hydrolysis reaction decreasing from 32.1 to 23.9 kcal/mol.

Vavina A.V. , Seitkalieva M.M. , Posvyatenko A.V. , Gordeev E.G. , Strukova E.N. , Egorova K.S. , Ananikov V.P.
Merging structural frameworks of imidazolium, pyridinium, and cholinium ionic liquids with cinnamic acid to tune solution state behavior and properties
Journal of Molecular Liquids. 2022. V.352. 118673 . DOI: 10.1016/j.molliq.2022.118673 WOS Scopus OpenAlex

Web of science:	WOS:000788156600004
Scopus:	2-s2.0-85125863875
OpenAlex:	W4210801856

БД	Цитирований
OpenAlex	6
Scopus	6
Web of science	4