New luciferin-based probe substrates for human CYP26A1

Shishir Sharma; Jingyao Liu; Xue Zhang; Sangeeta Shrestha Sharma; Erik J. Sorensen; Matthias Bureik

doi:10.1016/j.bbrep.2020.100861

New luciferin-based probe substrates for human CYP26A1

Shishir Sharma, Jingyao Liu, Xue Zhang, Sangeeta Shrestha Sharma, Erik J. Sorensen, Matthias Bureik

Chemistry

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Activity of human CYP26A1 towards six proluciferin probe substrates and their ester derivatives was monitored. These included three monofluorobenzyl ether isomers and three five-membered heterocycles. Overall, luciferin substrates with a free acid group gave higher activities than the ester compounds. Also, luciferin derivatives with six-ring structures were better metabolized than those with five-rings. The best substrates identified in this study are Luciferin 6′ 3-fluorobenzyl ether (Luciferin-3FBE) and its methyl ester (Luciferin-3FBEME). Taken together, we describe eleven new probe substrates for CYP26A1 and demonstrate for the first time that CYP26A1 does not only accept acid substrates but can also metabolize esters.

Original language	English (US)
Article number	100861
Journal	Biochemistry and Biophysics Reports
Volume	24
DOIs	https://doi.org/10.1016/j.bbrep.2020.100861
State	Published - Dec 2020

All Science Journal Classification (ASJC) codes

Biophysics
Biochemistry

Keywords

CYP enzymes
Esters
Fission yeast
Luminescent probe
Retinoic acid

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10.1016/j.bbrep.2020.100861

Cite this

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title = "New luciferin-based probe substrates for human CYP26A1",

abstract = "Activity of human CYP26A1 towards six proluciferin probe substrates and their ester derivatives was monitored. These included three monofluorobenzyl ether isomers and three five-membered heterocycles. Overall, luciferin substrates with a free acid group gave higher activities than the ester compounds. Also, luciferin derivatives with six-ring structures were better metabolized than those with five-rings. The best substrates identified in this study are Luciferin 6′ 3-fluorobenzyl ether (Luciferin-3FBE) and its methyl ester (Luciferin-3FBEME). Taken together, we describe eleven new probe substrates for CYP26A1 and demonstrate for the first time that CYP26A1 does not only accept acid substrates but can also metabolize esters.",

keywords = "CYP enzymes, Esters, Fission yeast, Luminescent probe, Retinoic acid",

author = "Shishir Sharma and Jingyao Liu and Xue Zhang and Sharma, {Sangeeta Shrestha} and Sorensen, {Erik J.} and Matthias Bureik",

note = "Publisher Copyright: {\textcopyright} 2020",

year = "2020",

month = dec,

doi = "10.1016/j.bbrep.2020.100861",

language = "English (US)",

volume = "24",

journal = "Biochemistry and Biophysics Reports",

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TY - JOUR

T1 - New luciferin-based probe substrates for human CYP26A1

AU - Sharma, Shishir

AU - Liu, Jingyao

AU - Zhang, Xue

AU - Sharma, Sangeeta Shrestha

AU - Sorensen, Erik J.

AU - Bureik, Matthias

PY - 2020/12

Y1 - 2020/12

N2 - Activity of human CYP26A1 towards six proluciferin probe substrates and their ester derivatives was monitored. These included three monofluorobenzyl ether isomers and three five-membered heterocycles. Overall, luciferin substrates with a free acid group gave higher activities than the ester compounds. Also, luciferin derivatives with six-ring structures were better metabolized than those with five-rings. The best substrates identified in this study are Luciferin 6′ 3-fluorobenzyl ether (Luciferin-3FBE) and its methyl ester (Luciferin-3FBEME). Taken together, we describe eleven new probe substrates for CYP26A1 and demonstrate for the first time that CYP26A1 does not only accept acid substrates but can also metabolize esters.

AB - Activity of human CYP26A1 towards six proluciferin probe substrates and their ester derivatives was monitored. These included three monofluorobenzyl ether isomers and three five-membered heterocycles. Overall, luciferin substrates with a free acid group gave higher activities than the ester compounds. Also, luciferin derivatives with six-ring structures were better metabolized than those with five-rings. The best substrates identified in this study are Luciferin 6′ 3-fluorobenzyl ether (Luciferin-3FBE) and its methyl ester (Luciferin-3FBEME). Taken together, we describe eleven new probe substrates for CYP26A1 and demonstrate for the first time that CYP26A1 does not only accept acid substrates but can also metabolize esters.

KW - CYP enzymes

KW - Esters

KW - Fission yeast

KW - Luminescent probe

KW - Retinoic acid

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U2 - 10.1016/j.bbrep.2020.100861

DO - 10.1016/j.bbrep.2020.100861

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SN - 2405-5808

VL - 24

JO - Biochemistry and Biophysics Reports

JF - Biochemistry and Biophysics Reports

M1 - 100861

ER -

New luciferin-based probe substrates for human CYP26A1

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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