title: Facile preparation of mono-, di- and mixed-carboxylato platinum(IV) complexes for versatile anticancer prodrug design.
abstract: Facile strategies were developed for the versatile functionalization of platinum(IV) axial sites, allowing for easy accessibility to unsymmetric mono- and mixed-carboxylato, as well as symmetric di-substituted platinum(IV) complexes. The first method involves the direct oxidation and carboxylation of the platinum(II) center using an appropriate peroxide and the carboxylate of choice to firstly yield a monocarboxylato monohydroxido platinum(IV) complex. This platinum(IV) intermediate can undergo further carboxylation to give rise to a mixed-carboxylato platinum(IV) complex. The second method involves the activation of the carboxylate of choice by a common carbodiimide coupling reagent, and its reaction with a dihydroxido platinum(IV) precursor to give the monocarboxylato platinum(IV) complex. Uronium salts can be employed to promote efficient dicarboxylation of the dihydroxido platinum(IV) precursor. Lastly, an axial azide pendant group was demonstrated to be suitable for orthogonal "click" conjugation reactions.
authors.affiliation: School of Chemistry, The University of Sydney, Sydney, N.S.W., Australia.
authors.forename: Jenny Z
authors.initials: JZ
authors.lastname: Zhang
authors.forename: Paul
authors.initials: P
authors.lastname: Bonnitcha
authors.forename: Ezequiel
authors.initials: E
authors.lastname: Wexselblatt
authors.forename: Alice V
authors.initials: AV
authors.lastname: Klein
authors.forename: Yousef
authors.initials: Y
authors.lastname: Najajreh
authors.forename: Dan
authors.initials: D
authors.lastname: Gibson
authors.forename: Trevor W
authors.initials: TW
authors.lastname: Hambley
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D015195:Drug Design; D015394:Molecular Structure; D009944:Organoplatinum Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D009944:Organoplatinum Compounds; D011355:Prodrugs