Reduction of a platinum(iv) prodrug model by sulfur containing biological reductants: computational mechanistic elucidation

Antony Chipman; Brian F. Yates; Allan J. Canty; Alireza Ariafard

doi:10.1039/C8CC05682J

Reduction of a platinum(iv) prodrug model by sulfur containing biological reductants: computational mechanistic elucidation

Antony Chipman, Brian F. Yates, Allan J. Canty, Alireza Ariafard^*

^*Corresponding author for this work

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

17 Citations (Scopus)

Abstract

A Pt^IV prodrug needs to be reduced to Pt^II by a biomolecule in order to show efficacy. Among biomolecules, those containing an l-Cys residue have the highest potential to be involved in reduction. Tautomerisation from HSCH₂CH(NH₃⁺)CO₂⁻ to the unusual zwitterion form ⁻SCH₂CH(NH₃⁺)CO₂H is the prerequisite for l-Cys to become a potent reductant at a low pH.

Original language	English
Pages (from-to)	10491-10494
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	74
DOIs	https://doi.org/10.1039/C8CC05682J
Publication status	Published - 2018
Externally published	Yes

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abstract = "A PtIV prodrug needs to be reduced to PtII by a biomolecule in order to show efficacy. Among biomolecules, those containing an l-Cys residue have the highest potential to be involved in reduction. Tautomerisation from HSCH2CH(NH3+)CO2− to the unusual zwitterion form −SCH2CH(NH3+)CO2H is the prerequisite for l-Cys to become a potent reductant at a low pH.",

author = "Antony Chipman and Yates, {Brian F.} and Canty, {Allan J.} and Alireza Ariafard",

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AU - Chipman, Antony

AU - Yates, Brian F.

AU - Canty, Allan J.

AU - Ariafard, Alireza

N1 - Publisher Copyright: © The Royal Society of Chemistry.

PY - 2018

Y1 - 2018

N2 - A PtIV prodrug needs to be reduced to PtII by a biomolecule in order to show efficacy. Among biomolecules, those containing an l-Cys residue have the highest potential to be involved in reduction. Tautomerisation from HSCH2CH(NH3+)CO2− to the unusual zwitterion form −SCH2CH(NH3+)CO2H is the prerequisite for l-Cys to become a potent reductant at a low pH.

AB - A PtIV prodrug needs to be reduced to PtII by a biomolecule in order to show efficacy. Among biomolecules, those containing an l-Cys residue have the highest potential to be involved in reduction. Tautomerisation from HSCH2CH(NH3+)CO2− to the unusual zwitterion form −SCH2CH(NH3+)CO2H is the prerequisite for l-Cys to become a potent reductant at a low pH.

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U2 - 10.1039/C8CC05682J

DO - 10.1039/C8CC05682J

M3 - Article

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JO - Chemical Communications

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ER -

Reduction of a platinum(iv) prodrug model by sulfur containing biological reductants: computational mechanistic elucidation

Abstract

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