Literature DB >> 25367395

Oxidative halogenation of cisplatin and carboplatin: synthesis, spectroscopy, and crystal and molecular structures of Pt(IV) prodrugs.

Timothy C Johnstone1, Sarah M Alexander, Justin J Wilson, Stephen J Lippard.   

Abstract

A series of n class="Chemical">Pt(IV) prodrugs has been obtained by oxidative halogenation of either cisplatin or carboplatin. Iodobenzene dichloride is a general reagent that cleanly provides prodrugs bearing axial chlorides without the need to prepare intervening Pt(IV) intermediates or handle chlorine gas. Elemental bromine and iodine afford Pt(IV) compounds as well, although in the case of the iodine-mediated oxidation of carboplatin, an amido-bridged Pt(IV) side product also formed. A detailed analysis of the changes in spectroscopic and structural parameters induced by varying the axial halide is presented. A number of recurring motifs are observed in the solid state structures of these compounds.

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Year:  2015        PMID: 25367395      PMCID: PMC4252584          DOI: 10.1039/c4dt02627f

Source DB:  PubMed          Journal:  Dalton Trans        ISSN: 1477-9226            Impact factor:   4.390


  28 in total

1.  Cationic intermediates in oxidative addition reactions of Cl2 to [PtCl2(cis-1,4-DACH)].

Authors:  Nicola Margiotta; Rosa Ranaldo; Francesco P Intini; Giovanni Natile
Journal:  Dalton Trans       Date:  2011-11-07       Impact factor: 4.390

Review 2.  195Pt NMR--theory and application.

Authors:  Brett M Still; P G Anil Kumar; Janice R Aldrich-Wright; William S Price
Journal:  Chem Soc Rev       Date:  2006-11-17       Impact factor: 54.564

3.  Carboxylation of Kinetically Inert Platinum(IV) Hydroxy Complexes. An Entr.acte.ee into Orally Active Platinum(IV) Antitumor Agents.

Authors:  C M Giandomenico; M J Abrams; B A Murrer; J F Vollano; M I Rheinheimer; S B Wyer; G E Bossard; J D Higgins
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4.  Kinetics and mechanism for reduction of anticancer-active tetrachloroam(m)ine platinum(IV) compounds by glutathione.

Authors:  K Lemma; J Berglund; N Farrell; L I Elding
Journal:  J Biol Inorg Chem       Date:  2000-06       Impact factor: 3.358

5.  New reduction pathways for ctc-[PtCl2(CH3CO2)2(NH3)(Am)] anticancer prodrugs.

Authors:  Alina Nemirovski; Inbal Vinograd; Khuloud Takrouri; Ana Mijovilovich; Annette Rompel; Dan Gibson
Journal:  Chem Commun (Camb)       Date:  2010-02-12       Impact factor: 6.222

6.  Synthesis and characterization of new platinum(II) and platinum(IV) triphyrin complexes.

Authors:  Zhaoli Xue; Daiki Kuzuhara; Shinya Ikeda; Tetsuo Okujima; Shigeki Mori; Hidemitsu Uno; Hiroko Yamada
Journal:  Inorg Chem       Date:  2013-02-04       Impact factor: 5.165

7.  Modulation of Ligand Fluorescence by the Pt(II)/Pt(IV) Redox Couple.

Authors:  Justin J Wilson; Stephen J Lippard
Journal:  Inorganica Chim Acta       Date:  2012-01-03       Impact factor: 2.545

8.  Systematic differences in electrochemical reduction of the structurally characterized anti-cancer platinum(IV) complexes [Pt{((p-HC6F4)NCH2)2}-(pyridine)2Cl2], [Pt{((p-HC6F4)NCH2)2}(pyridine)2(OH)2], and [Pt{((p-HC6F4)NCH2)2}(pyridine)2(OH)Cl].

Authors:  Si-Xuan Guo; Dayna N Mason; Susan A Turland; Eric T Lawrenz; Lance C Kelly; Gary D Fallon; Bryan M Gatehouse; Alan M Bond; Glen B Deacon; Andrew R Battle; Trevor W Hambley; Silvina Rainone; Lorraine K Webster; Carleen Cullinane
Journal:  J Inorg Biochem       Date:  2012-07-27       Impact factor: 4.155

9.  Multinational, double-blind, phase III study of prednisone and either satraplatin or placebo in patients with castrate-refractory prostate cancer progressing after prior chemotherapy: the SPARC trial.

Authors:  Cora N Sternberg; Daniel P Petrylak; Oliver Sartor; J Alfred Witjes; Tomasz Demkow; Jean-Marc Ferrero; Jean-Christophe Eymard; Silvia Falcon; Fabio Calabrò; Nicholas James; Istvan Bodrogi; Peter Harper; Manfred Wirth; William Berry; Michael E Petrone; Thomas J McKearn; Mojtaba Noursalehi; Martine George; Marcel Rozencweig
Journal:  J Clin Oncol       Date:  2009-10-05       Impact factor: 44.544

10.  Kinetics and mechanism for reduction of the anticancer prodrug trans,trans,trans-[PtCl2(OH)2(c-C6H11NH2)(NH3)] (JM335) by thiols.

Authors:  K Lemma; T Shi; L I Elding
Journal:  Inorg Chem       Date:  2000-04-17       Impact factor: 5.165

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  6 in total

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Authors:  Ashim K Mitra; Vibhuti Agrahari; Abhirup Mandal; Kishore Cholkar; Chandramouli Natarajan; Sujay Shah; Mary Joseph; Hoang M Trinh; Ravi Vaishya; Xiaoyan Yang; Yi Hao; Varun Khurana; Dhananjay Pal
Journal:  J Control Release       Date:  2015-10-09       Impact factor: 9.776

2.  Platinum(II) complexes of imidazophenanthroline-based polypyridine ligands as potential anticancer agents: synthesis, characterization, in vitro cytotoxicity studies and a comparative ab initio, and DFT studies with cisplatin, carboplatin, and oxaliplatin.

Authors:  Carlson Alexander; A Nithyakumar; M Wilson Bosco Paul; N Arockia Samy
Journal:  J Biol Inorg Chem       Date:  2018-06-14       Impact factor: 3.358

3.  N-Heterocyclic Carbene Platinum(IV) as Metallodrug Candidates: Synthesis and 195Pt NMR Chemical Shift Trend.

Authors:  Mathilde Bouché; Bruno Vincent; Thierry Achard; Stéphane Bellemin-Laponnaz
Journal:  Molecules       Date:  2020-07-09       Impact factor: 4.411

4.  Investigations of the Kinetics and Mechanism of Reduction of a Carboplatin Pt(IV) Prodrug by the Major Small-Molecule Reductants in Human Plasma.

Authors:  Yang Liu; Hongwu Tian; Liyao Xu; Li Zhou; Jinhu Wang; Benyan Xu; Chunli Liu; Lars I Elding; Tiesheng Shi
Journal:  Int J Mol Sci       Date:  2019-11-12       Impact factor: 5.923

Review 5.  Clinical developments of antitumor polymer therapeutics.

Authors:  Shazia Parveen; Farukh Arjmand; Sartaj Tabassum
Journal:  RSC Adv       Date:  2019-08-08       Impact factor: 4.036

6.  The Affinity of Carboplatin to B-Vitamins and Nucleobases.

Authors:  Beata Szefler; Przemysław Czeleń; Przemysław Krawczyk
Journal:  Int J Mol Sci       Date:  2021-03-31       Impact factor: 5.923

  6 in total

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