Oxidation of cis-Diamminediacetato PtII with Hydrogen Peroxide Can Give Rise to Two Isomeric PtIV Products

D. Khattib; M. Ishan; S. Karmakar; H. Kostrhunova; V. Brabec; D. Gibson

doi:10.1002/chem.202001472

Oxidation of cis-Diamminediacetato Pt^II with Hydrogen Peroxide Can Give Rise to Two Isomeric Pt^IV Products

D. Khattib
, M. Ishan
, S. Karmakar
, H. Kostrhunova
, V. Brabec
, D. Gibson^*

^*Corresponding author for this work

School of Pharmacy

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

6 Scopus citations

Abstract

The oxidation of cis-[Pt(NH₃)₂(OAc)₂] with H₂O₂ yields a mixture of two isomers: ctc-[Pt(NH₃)₂(OH)₂(OAc)₂] and ctc-[Pt(NH₃)₂(OH)(OAc)(OH)(OAc)]. Following modification with 4-phenylbutyric (PhB) anhydride, two isomers were separated and characterized; the symmetric ctc-[Pt(NH₃)₂(PhB)₂(OAc)₂] (1) and the nonsymmetric ctc-[Pt(NH₃)₂(PhB)(OAc)(PhB)(OAc)] (2). They differ in their log P values and despite having similar cellular uptake and similar DNA platination levels, the symmetric ctc-[Pt(NH₃)₂(OH)₂(OAc)₂] is more than 4-fold more potent than the nonsymmetric isomer in a panel of 4 cancer cell lines.

Original language	English
Pages (from-to)	9475-9480
Number of pages	6
Journal	Chemistry - A European Journal
Volume	26
Issue number	43
DOIs	https://doi.org/10.1002/chem.202001472
State	Published - 3 Aug 2020

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Pt anticancer agents
cytotoxicity
diammindiacetatoplatinum(II)
isomerization
oxidation

Access to Document

10.1002/chem.202001472

Cite this

@article{591b0bfe73774f3ea3ecd151968a93e2,

title = "Oxidation of cis-Diamminediacetato PtII with Hydrogen Peroxide Can Give Rise to Two Isomeric PtIV Products",

abstract = "The oxidation of cis-[Pt(NH3)2(OAc)2] with H2O2 yields a mixture of two isomers: ctc-[Pt(NH3)2(OH)2(OAc)2] and ctc-[Pt(NH3)2(OH)(OAc)(OH)(OAc)]. Following modification with 4-phenylbutyric (PhB) anhydride, two isomers were separated and characterized; the symmetric ctc-[Pt(NH3)2(PhB)2(OAc)2] (1) and the nonsymmetric ctc-[Pt(NH3)2(PhB)(OAc)(PhB)(OAc)] (2). They differ in their log P values and despite having similar cellular uptake and similar DNA platination levels, the symmetric ctc-[Pt(NH3)2(OH)2(OAc)2] is more than 4-fold more potent than the nonsymmetric isomer in a panel of 4 cancer cell lines.",

keywords = "Pt anticancer agents, cytotoxicity, diammindiacetatoplatinum(II), isomerization, oxidation",

author = "D. Khattib and M. Ishan and S. Karmakar and H. Kostrhunova and V. Brabec and D. Gibson",

note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2020",

month = aug,

day = "3",

doi = "10.1002/chem.202001472",

language = "אנגלית",

volume = "26",

pages = "9475--9480",

journal = "Chemistry - A European Journal",

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TY - JOUR

T1 - Oxidation of cis-Diamminediacetato PtII with Hydrogen Peroxide Can Give Rise to Two Isomeric PtIV Products

AU - Khattib, D.

AU - Ishan, M.

AU - Karmakar, S.

AU - Kostrhunova, H.

AU - Brabec, V.

AU - Gibson, D.

PY - 2020/8/3

Y1 - 2020/8/3

N2 - The oxidation of cis-[Pt(NH3)2(OAc)2] with H2O2 yields a mixture of two isomers: ctc-[Pt(NH3)2(OH)2(OAc)2] and ctc-[Pt(NH3)2(OH)(OAc)(OH)(OAc)]. Following modification with 4-phenylbutyric (PhB) anhydride, two isomers were separated and characterized; the symmetric ctc-[Pt(NH3)2(PhB)2(OAc)2] (1) and the nonsymmetric ctc-[Pt(NH3)2(PhB)(OAc)(PhB)(OAc)] (2). They differ in their log P values and despite having similar cellular uptake and similar DNA platination levels, the symmetric ctc-[Pt(NH3)2(OH)2(OAc)2] is more than 4-fold more potent than the nonsymmetric isomer in a panel of 4 cancer cell lines.

AB - The oxidation of cis-[Pt(NH3)2(OAc)2] with H2O2 yields a mixture of two isomers: ctc-[Pt(NH3)2(OH)2(OAc)2] and ctc-[Pt(NH3)2(OH)(OAc)(OH)(OAc)]. Following modification with 4-phenylbutyric (PhB) anhydride, two isomers were separated and characterized; the symmetric ctc-[Pt(NH3)2(PhB)2(OAc)2] (1) and the nonsymmetric ctc-[Pt(NH3)2(PhB)(OAc)(PhB)(OAc)] (2). They differ in their log P values and despite having similar cellular uptake and similar DNA platination levels, the symmetric ctc-[Pt(NH3)2(OH)2(OAc)2] is more than 4-fold more potent than the nonsymmetric isomer in a panel of 4 cancer cell lines.

KW - Pt anticancer agents

KW - cytotoxicity

KW - diammindiacetatoplatinum(II)

KW - isomerization

KW - oxidation

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VL - 26

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EP - 9480

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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