Biomass-Derived Ionic Liquids Based on a 5-HMF Platform Chemical: Synthesis, Characterization, Biological Activity, and Tunable Interactions at the Molecular Level

Biomass-Derived Ionic Liquids Based on a 5-HMF Platform Chemical: Synthesis, Characterization, Biological Activity, and Tunable Interactions at the Molecular Level Научная публикация

Журнал

ACS Sustainable Chemistry & Engineering
ISSN: 2168-0485

Вых. Данные

Год: 2021, Том: 9, Номер: 9, Страницы: 3552-3570 Страниц : 19 DOI: 10.1021/acssuschemeng.0c08790

Авторы

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

Организации

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russia
2	Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Ministry of Health of Russian Federation, Samory Mashela Street, Moscow 117198, Russia
3	Gause Institute of New Antibiotics, Russian Academy of Sciences, B. Pirogovskaya Street 11/1, Moscow 119021, Russia

A new family of protic ammonium ionic liquids (ILs) with various inorganic anions was synthesized from bio-derived 5-HMF. Starting with cellulose biomass, a complete preservation of the C6 unit was achieved throughout the synthetic sequence (no carbon loss). Evaluation of green metrics showed a significant advantage of the developed bio-derived pathway to access ILs from a natural renewable source, depending on feasible routes to 5-HMF manufacturing. The reduced number of synthetic steps and availability of the starting materials were the key advantages. Experimental physicochemical and biological studies, as well as computational modeling revealed a unique multifunctional intrinsic organization of these bio-derived ILs. The nature of interactions between the cations and anions of the novel ILs was mapped at the molecular level. The substituents in the cationic core and the nature of the original building blocks had a prominent impact on cytotoxicity of the novel ILs. The obtained results suggest possible sustainable applications of the least toxic ILs, while the regulation of biological activity of the ILs via the corresponding structural adjustments can find biological and medicinal applications. The 5-HMF-derived IL with a sulfate anion demonstrated potentially useful properties in dissolution of microcrystalline cellulose.

Seitkalieva M.M. , Vavina A.V. , Posvyatenko A.V. , Egorova K.S. , Kashin A.S. , Gordeev E.G. , Strukova E.N. , Romashov L.V. , Ananikov V.P.
Biomass-Derived Ionic Liquids Based on a 5-HMF Platform Chemical: Synthesis, Characterization, Biological Activity, and Tunable Interactions at the Molecular Level
ACS Sustainable Chemistry & Engineering. 2021. V.9. N9. P.3552-3570. DOI: 10.1021/acssuschemeng.0c08790 WOS Scopus OpenAlex

≡ Web of science:	WOS:000627591900016
≡ Scopus:	2-s2.0-85103383610
≡ OpenAlex:	W3133179360