Characterization of the mechanism of reduction of trans-diamminetetrachloroplatinum(IV) by l-cysteine and dl-

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• 作者：Taotao Lu ; Jingran Dong ; Chunxia Nan ; Shuying Huo…
• 刊名：Transition Metal Chemistry
• 出版年：2015
• 出版时间：November 2015
• 年：2015
• 卷：40
• 期：8
• 页码：869-875
• 全文大小：1,021 KB
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• 作者单位：Taotao Lu (1)
  Jingran Dong (1)
  Chunxia Nan (1)
  Shuying Huo (1)
  Shigang Shen (1)
  Sufang Sun (1)
  Tiesheng Shi (1)
  
  1. College of Chemistry and Environmental Science, and the MOE Key Laboratory of Medicinal Chemistry and Molecular Diagnostics, Hebei University, Baoding, 071002, Hebei Province, People’s Republic of China
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Catalysis
  Physical Chemistry
  Inorganic Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1572-901X

文摘

The interactions between Pt(IV) anticancer prodrugs incorporating two ammines/amines in trans positions in their equatorial planes and some important thiols have not been exploited to date. In this work, the reduction of one such Pt(IV) prodrug, namely trans-[Pt(NH₃)₂Cl₄], by two thiol-containing amino acids l-cysteine (Cys) and dl-homocysteine (Hcy) which are prevalent in human plasma has been characterized by stopped-flow spectroscopic and ESI high-resolution mass spectral methods. The reduction process obeys overall second-order kinetics. The dependencies of the observed second-order rate constants k-on pH have been established between pH 4.03 and 11.24. Mass spectral analysis indicates that cystine and homocystine are the dominant products for the Cys and Hcy oxidations, respectively. The suggested reaction mechanism involves all possible protolytic species of Cys/Hcy, which attack one of the two apically coordinated chlorides in parallel (all as rate-determining steps), leading to a Cl+ transfer to the attacking sulfur atom. The rate expression has been derived, and the rate constants for the rate-determining steps have been calculated. Features of the reduction process are discussed based on the obtained rate constants. The overall kinetic and mechanistic picture enables an in-depth understanding of the reduction process of this type of Pt(IV) anticancer prodrug.