Intermolecular Interactions, Regioselectivity, and Biological Activity of L-ascorbic Acid, Nicotinic Acid and Their Cocrystal | Sciact - CRIS-system of Boreskov Institute of Catalysis

Intermolecular Interactions, Regioselectivity, and Biological Activity of L-ascorbic Acid, Nicotinic Acid and Their Cocrystal Full article

Journal

CrystEngComm
ISSN: 1466-8033

Output data

Year: 2024, Volume: 26, Pages: 6650-6666 Pages count : 17 DOI: 10.1039/d4ce00770k

Authors

Evtushenko Diana N. ^1,5 , Fateev Alexander V. ^1,4 , Khainovsky Mark A. ⁵ , Polishchuk Julia ¹ , Kokorev Oleg V. ² , Nasibov Temur F. ² , Gorokhova Anna V. ² , Bariev Usman A. ² , Zaitsev Konstantin V. ³ , Khlusov Igor A. ² , Vodyankina Olga V. ¹

Affiliations

1	Faculty of Chemistry, Tomsk State University, 36, Lenin Ave., 634050 Tomsk, Russia
2	Laboratory of Cellular and Microfluidic Technologies, Siberian State Medical University (SibSMU), 2, Moskovsky trakt, 634050 Tomsk, Russia
3	Experimental Laboratory of Biomedical Technologies, Tomsk Scientific Research Institute of Balneology and Physiotherapy, Branch of SibFNC of FMBA of Russia, 1, Luxemburg st., 634009 Tomsk, Russia
4	Faculty of Biology and Chemistry, Tomsk State Pedagogical University, 60, Kievskaya st., 634061 Tomsk, Russia
5	Synchrotron Radiation Facility – Siberian Circular Photon Source “SKlF”, 2, Morskoy Ave., 630090 Novosibirsk, Russia

Funding (2)

1	Ministry of Science and Higher Education of the Russian Federation	FWUR-2024-0040
2	Ministry of Science and Higher Education of the Russian Federation	Приоритет 2030

The systems of intermolecular interactions, including hydrogen bonds, in the crystal structures of the cocrystal of L-ascorbic (L-Asc) and nicotinic (Nic) acids and individual coformers are considered, and the hemolytic and cytotoxic activities of these compounds are studied in vitro. The influence of conformational differences of L-Asc molecules (total effective charge) on the formation of a network of H-bonds in the supramolecular structure of pristine L-Asc is revealed. Calculation of regioselectivity descriptors shows that the conformer of the L-Asc molecule in the L-AscNic cocrystal has higher activity compared to conformer molecules of the pristine L-Asc. No hemolysis caused by the solutions of tested acids and L-AscNic is shown. Selective cytotoxicity (antimetabolic effect according to the MTT test) of solutions of L-AscNic cocrystals against a 72-hour culture of MCF-7 breast cancer cell line versus healthy cells (mesenchymal stem cells and embryonic fibroblasts) is revealed. The possible relationship between the initial conformational state of the L-Asc molecules in the composition/structure of the studied solid compounds and the biological activity of solutions of these compounds requires further studies.

Evtushenko D.N. , Fateev A.V. , Khainovsky M.A. , Polishchuk J. , Kokorev O.V. , Nasibov T.F. , Gorokhova A.V. , Bariev U.A. , Zaitsev K.V. , Khlusov I.A. , Vodyankina O.V.
Intermolecular Interactions, Regioselectivity, and Biological Activity of L-ascorbic Acid, Nicotinic Acid and Their Cocrystal
CrystEngComm. 2024. V.26. P.6650-6666. DOI: 10.1039/d4ce00770k WOS Scopus OpenAlex publication_identifier_short.sciact_skif_identifier_type

Submitted:	Aug 2, 2024
Accepted:	Nov 6, 2024
Published online:	Nov 7, 2024
Published print:	Dec 14, 2024

Web of science:	WOS:001353850100001
Scopus:	2-s2.0-85209544839
OpenAlex:	W4404149071
publication_identifier.sciact_skif_identifier_type:	3599

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