Riboflavin Crystals with Extremely High Water Solubility

Riboflavin Crystals with Extremely High Water Solubility Full article

Journal

ACS Applied Materials & Interfaces
ISSN: 1944-8244 , E-ISSN: 1944-8252

Output data

Year: 2024, Volume: 16, Number: 5, Pages: 5504-5512 Pages count : 9 DOI: 10.1021/acsami.3c15853

Authors

Krikunova Polina V. ¹ , Tolordava Eteri R. ² , Arkharova Natalya A. ¹ , Karimov Denis N. ¹ , Bukreeva Tatiana V. ¹ , Shirinian Valerii Z. ³ , Khaydukov Evgeny V. ¹ , Pallaeva Tatiana N. ¹

Affiliations

1	FSRC “Crystallography and Photonics” RAS, Moscow 119333, Russia
2	Gamaleya Research Institute of Epidemiology and Microbiology, Moscow 123098, Russia
3	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russia

New insights into the unique biochemical properties of riboflavin (Rf), also known as vitamin B2, are leading to the development of its use not only as a vitamin supplement but also as a potential anti-inflammatory, immunomodulatory, antioxidant, anticancer, and antiviral agent, where it may play a role as an inhibitor of viral proteinases. At the same time, the comparison of the pharmacoactivity of Rf with its known metabolites, namely, flavin mononucleotide (FMN) and flavin adenine dinucleotide (FAD), is very complicated due to its poor water solubility: 0.1–0.3 g/L versus 67 g/L for FMN and 50 g/L for FAD, which is the limiting factor for its administration in clinical practice. In this study, we report the recrystallization procedure of the type A Rf crystals into the slightly hydrophobic type B/C and a new hydrophilic crystal form that has been termed the P type. Our method of Rf crystal modification based on recrystallization from dilute alkaline solution provides an unprecedented extremely high water solubility of Rf, reaching 23.5 g/L. A comprehensive study of the physicochemical properties of type P riboflavin showed increased photodynamic therapeutic activity compared to the known types A and B/C against clinical isolates of Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, and Salmonella typhimurium. Importantly, our work not only demonstrates a simple and inexpensive method for the synthesis of riboflavin with high solubility, which should lead to increased bioactivity, but also opens up opportunities for improving both known and new therapeutic applications of vitamin B2.

Krikunova P.V. , Tolordava E.R. , Arkharova N.A. , Karimov D.N. , Bukreeva T.V. , Shirinian V.Z. , Khaydukov E.V. , Pallaeva T.N.
Riboflavin Crystals with Extremely High Water Solubility
ACS Applied Materials & Interfaces. 2024. V.16. N5. P.5504-5512. DOI: 10.1021/acsami.3c15853 WOS Scopus OpenAlex

Web of science:	WOS:001158703400001
Scopus:	2-s2.0-85184667726
OpenAlex:	W4391269699

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