Preparative Biocatalytic Synthesis of α-Ketomethylselenobutyrate—A Putative Agent for Cancer Therapy

Biomedical studies of the role of organic selenium compounds indicate that the amino acid derivative of L-selenomethionine, α-ketomethylselenobutyrate (KMSB), can be considered a potential anticancer therapeutic agent. It was noted that, in addition to a direct effect on redox signaling molecules, α...

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Bibliographic Details
Published in:	Molecules (Basel, Switzerland) Vol. 28; no. 17; p. 6178
Main Authors:	Nikulin, Maksim V, Drobot, Viktor V, Shurubor, Yevgeniya I, Švedas, Vytas K, Krasnikov, Boris F
Format:	Journal Article
Language:	English
Published:	Basel MDPI AG 22-08-2023 MDPI
Subjects:	Amino acids Androgens Antimitotic agents Antineoplastic agents Antioxidants Apoptosis Cancer Cancer therapies cancer therapy Care and treatment Cell cycle Drug dosages Drug therapy Enzymes Health aspects histone deacetylase inhibition L-amino acid oxidase Lung cancer Metabolites Metastasis Nanoparticles Oncology, Experimental organoselenium compounds Oxidases Oxidation preparative biocatalytic synthesis Prostate Selenium Toxicity α-ketomethylselenobutyrate Russia
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Summary:	Biomedical studies of the role of organic selenium compounds indicate that the amino acid derivative of L-selenomethionine, α-ketomethylselenobutyrate (KMSB), can be considered a potential anticancer therapeutic agent. It was noted that, in addition to a direct effect on redox signaling molecules, α-ketoacid metabolites of organoselenium compounds are able to change the status of histone acetylation and suppress the activity of histone deacetylases in cancer cells. However, the wide use of KMSB in biomedical research is hindered not only by its commercial unavailability, but also by the fact that there is no detailed information in the literature on possible methods for the synthesis of this compound. This paper describes in detail the procedure for obtaining a high-purity KMSB preparation (purity ≥ 99.3%) with a yield of the target product of more than 67%. L-amino acid oxidase obtained from C. adamanteus was used as a catalyst for the conversion of L-selenomethionine to KMSB. If necessary, this method can be used as a basis both for scaling up the synthesis of KMSB and for developing cost-effective biocatalytic technologies for obtaining other highly purified drugs.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules28176178