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Photocaged activity-based probes for improved monitoring of protein S-sulfenylation in living cells

Chinese Chemical Letters 2024年第2期35卷 451-454页

作者： Jiahao Zhang Haiyue Peng Zi'an Chen Guorui Li Jing Huang State Key Laboratory of Chemo/Biosensing and Chemometrics Hunan Provincial Key Laboratory of Animal Models and Molecular MedicineSchool of Biomedical SciencesHunan UniversityChangsha 410082China

Protein S-sulfenylation(protein sulfenic acid),as one of the most significant oxidative post-translational modifications(OxiPTMs),plays a vital role in regulating protein function.A variety of activity-based probes have been developed to profile sulfenic acid in living ***,due to the transient presence and low content of sulfenic acid in living cell,high doses of probes are needed to achieve efficient *** importantly,current probes have no temporal control over sulfenic acid *** overcome these limitations,two caged cysteine sulfenic acid probes DYn-2-ONB and DYn-2-Cou with either an o-nitrobenzyl or coumarin protecting group were developed in this *** probes can be efficiently uncaged via irradiation to produce the active C-nucleophile probe *** assay in living cells demonstrated DYn-2-ONB exhibited better labeling capacity compared with DYn-2,providing it as a powerful tool for improved monitoring of protein S-sulfenylation in living cells.

关键词： Cysteine sulfenic acid Activity-based probe Photocage Light activation Protein S-sulfenylation

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Regulation of Cytochrome P450 Enzymes by Reversible Oxidation of Thiols to sulfenic acids

Regulation of Cytochrome P450 Enzymes by Reversible Oxidatio...

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中国生物化学与分子生物学会第十二届全国会员代表大会暨2...

作者： F.Peter Guengerich Matthew E.Albertolle Department of Biochemistry Vanderbilt University School of Medicine

Cytochrome P450(P450) enzymes are the major catalysts involved in the metabolism of drugs,steroids,chemical carcinogens,and fat-soluble *** they are involved in >95% of oxidation/reduction reactions of *** signature spectroscopic properties and the catalytic activities are related to a conserved cysteine thiolate ligand binding to the proximal side of the heme *** found that the activity of one human P450 enzyme,P450 4 A11,was stimulated by the addition of mild reducing agents,***,and attenuated by H2 *** analyzed the enzyme and did not find disulfides but did find that the cysteine sulfur was oxidized to a sulfenic acid(-SOH),a reversible *** then found numerous drug metabolizing enzymes that contained sulfenic acids,including several mouse and human P450 s with the heme-cysteinyl sulfenic *** sulfenic acid was found in mouse and human liver and kidney samples in situ,suggesting physiological *** dynamics simulations suggest roles for specific amino acids in modulating the oxidation of the *** part of our continuing efforts in characterization of these systems in cells,we have synthesized new heavy isotope-labeled reagents with much faster kinetics than dimedone and iodoacetamide,which can be used to label sulfenic acids and disulfides,using liquid chromatography-mass *** phenomenon represents a potential new means of post-transcriptionally regulating the activities of P450 enzymes,although more in vivo evidence is in order.

关键词： Cytochrome P450 redox control sulfenic acid drug metabolism steroidogenesis heme ligands

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