Exploring the Chemical Space of Proluciferins as Probe Substrates for Human Cytochrome P450 Enzymes.

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Tytuł:: Exploring the Chemical Space of Proluciferins as Probe Substrates for Human Cytochrome P450 Enzymes.
Autorzy:: Zhao J; School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, China.
Zhang X; School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, China.
Wang Y; School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, China.
Huang H; School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, China.
Sharma S; School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, China.
Sharma SS; School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, China.
Wolf CA; Pharmaceutical and Medicinal Chemistry (Computer-Aided Drug Design), Institute of Pharmacy, Freie Universität Berlin, 14195, Berlin, Germany.
Liu S; Pharmaceutical and Medicinal Chemistry (Computer-Aided Drug Design), Institute of Pharmacy, Freie Universität Berlin, 14195, Berlin, Germany.
Wolber G; Pharmaceutical and Medicinal Chemistry (Computer-Aided Drug Design), Institute of Pharmacy, Freie Universität Berlin, 14195, Berlin, Germany.
Sorensen EJ; School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, China.; Department of Chemistry, Princeton University, Princeton, NJ, 08544, USA.
Bureik M; School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, China. .
Źródło:: Applied biochemistry and biotechnology [Appl Biochem Biotechnol] 2023 Feb; Vol. 195 (2), pp. 1042-1058. Date of Electronic Publication: 2022 Oct 26.
Typ publikacji:: Journal Article
Język:: English
Imprint Name(s):: Original Publication: Clifton, N.J. : Humana Press, c1981-
MeSH Terms:: Cytochrome P-450 Enzyme System*
Humans
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Contributed Indexing:: Keywords: Chemical biology; Cytochrome P450; Probe substrate; Proluciferin
Substance Nomenclature:: 9035-51-2 (Cytochrome P-450 Enzyme System)
Entry Date(s):: Date Created: 20221026 Date Completed: 20230123 Latest Revision: 20230123
Update Code:: 20230123
DOI:: 10.1007/s12010-022-04184-0
PMID:: 36287330
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We report the synthesis of 21 new proluciferin compounds that bear a small aliphatic ether group connected to the 6' hydroxy function of firefly luciferin and either contain an acid or methyl ester function at the dihydrothiazole ring. Each of these compounds was found to be a substrate for some members of the human CYP1 and CYP3 families; a total of 92 new enzyme-substrate pairs were identified. In a screen of the whole human P450 complement (CYPome) with three selected proluciferin acid substrates, another 13 enzyme-substrate pairs were detected, which involve enzymes belonging to the CYP2, CYP4, CYP7, CYP21, and CYP27 families. All in all, we identified new probe substrates for members of seven out of 18 human CYP families.
(© 2022. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)

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