Antimicrobial photodynamic activity of hydrophilic riboflavin derivatives

Bоrodinа, Tatyana N.; Толордава, Э. Р.; Nikolaeva, Maria E.; Соловьев, А. И.; Romanova, Yu. M.; Khaydukov, E. V.; Panchenko, V. Ya.

doi:10.17116/molgen20213904121

Cited by 1 publication

(1 citation statement)

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“…50 An improved solubility of the hydrophobic components could also be achieved by conjugation with highly hydrophilic molecules. Previously, we demonstrated the conjugation of Rf with polyethylene glycol, which resulted in a 100-fold increased solubility compared to untreated riboflavin 51 and retention of photosensitizing properties with subsequent inactivation of pathogenic microorganisms. However, these approaches are based on chemically modified versions of a pharmacologically active compound, which must undergo in vivo transformation to release the active drug.…”

Section: ■ Discussionmentioning

confidence: 99%

Riboflavin Crystals with Extremely High Water Solubility

Krikunova,

Tolordava,

Arkharova

et al. 2024

ACS Appl. Mater. Interfaces

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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.

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Section: ■ Discussionmentioning

confidence: 99%