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Our previous studies showed that butaselen is mainly present in human plasma in the form of M2, a\nfree Se-methylated metabolite.<\/jats:p>\n<\/jats:sec>\n<jats:sec>\n<jats:title>Objective:<\/jats:title>\n<jats:p>This study aimed to investigate the metabolic mechanisms of butaselen.<\/jats:p>\n<\/jats:sec>\n<jats:sec>\n<jats:title>Methods and Results:<\/jats:title>\n<jats:p>Butaselen was incubated with human plasma. Butaselen immediately disappeared, and the\nbutaselen-HSA (human serum albumin) adduct was detected by HPLC-HRMS, showing that butaselen covalently\nbinds to HSA. The butaselen-HSA adduct was precipitated using acetonitrile and then incubated with PBS, Cys, and\nGSH for 1 hour. The product was M1, a reduced form of butaselen. The results indicated that HSA, Cys, and GSH\ncan reduce the butaselen-HSA covalent bond. The binding site for butaselen could be the cysteine-34 residue of HSA\nthrough pronase and trypsin hydrolysis. Incubating butaselen with cysteine, butaselen-Cys, butaselen-2Cys, and M1\nwere generated, indicating the covalent binding and reduction of butaselen by cysteine. We incubated liver microsomes\nand cytosol with butaselen, 6.22 and 246 nM M2 were generated, respectively. The results demonstrated that\ncytosolic enzymes are mainly involved in M2 production. The amount of M2 in the liver cytosol decreased from 246\nnM to 2.21 nM when 10 mM m-anisic acid (a specific TPMT enzyme inhibitor) was added, showing that TPMT is\nresponsible for M2 formation.<\/jats:p>\n<\/jats:sec>\n<jats:sec>\n<jats:title>Conclusion:<\/jats:title>\n<jats:p>Butaselen was covalently bound to HSA, and the binding site was the cysteine-34 residue of HSA. The\nbutaselen-HSA adduct was reduced by free thiol compounds to generate M1. M1 was further metabolized to M2 by\ncytosolic TPMT. This study provides a basis for studying the pharmacokinetics of selenium-containing drugs.<\/jats:p>\n<\/jats:sec>","DOI":"10.2174\/1389200223666220520115014","type":"journal-article","created":{"date-parts":[[2022,5,27]],"date-time":"2022-05-27T05:16:26Z","timestamp":1653628586000},"page":"928-939","update-policy":"https:\/\/doi.org\/10.2174\/bsp_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Investigating the Metabolic Mechanisms of Butaselen, An Ebselen Analog"],"prefix":"10.2174","volume":"23","author":[{"given":"Qianqian","family":"Tian","sequence":"first","affiliation":[{"name":"State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201210,\nChina"},{"name":"University of Chinese Academy of Sciences, Beijing 100049, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinfang","family":"Jiang","sequence":"additional","affiliation":[{"name":"HQ Bioscience Co., Ltd., Suzhou, 215123, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hanwei","family":"Yin","sequence":"additional","affiliation":[{"name":"Shanghai Yuanxi Medicine Corp, Shanghai 201203, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yifan","family":"Zhang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201210,\nChina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yilin","family":"Li","sequence":"additional","affiliation":[{"name":"National Facility for Protein Science in Shanghai, Zhangjiang Lab,\nShanghai Advanced Research Institute, Chinese Academy of Science, Shanghai 201210, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ping","family":"Wu","sequence":"additional","affiliation":[{"name":"National Facility for Protein Science in Shanghai, Zhangjiang Lab,\nShanghai Advanced Research Institute, Chinese Academy of Science, Shanghai 201210, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chao","family":"Peng","sequence":"additional","affiliation":[{"name":"National Facility for Protein Science in Shanghai, Zhangjiang Lab,\nShanghai Advanced Research Institute, Chinese Academy of Science, Shanghai 201210, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhijie","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201210,\nChina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jialan","family":"Zhou","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201210,\nChina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huihui","family":"Zeng","sequence":"additional","affiliation":[{"name":"Shanghai Yuanxi Medicine Corp, Shanghai 201203, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dafang","family":"Zhong","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201210,\nChina"},{"name":"University of Chinese Academy of Sciences, Beijing 100049, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"965","reference":[{"key":"ref=1","author":"Zeng H.H.","year":"2010","unstructured":"Zeng H.H.; Bisbenzisoselenazolonyl derivatives having antineoplastics, anti-inflammatory and antithrombotic activities as well as their use. 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