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J Inorg Biochem. 2012 Oct;115:220-5. doi: 10.1016/j.jinorgbio.2012.04.010. Epub 2012 Apr 27.

Structural and anticancer properties of hydrogen bonded diphenyl phosphate adducts of Pt(IV) complexes: the importance of pKa matching.

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School of Chemistry, The University of Sydney, NSW, 2006, Australia.


Co-crystallisation of diphenyl phosphate (Hdpp) with anticancer active Pt(IV) complexes of the type cis,trans,cis-[PtCl(2)(OH)(2)(am(m)ine)(2)] has produced a new type of supramolecular adduct with short hydrogen bonds from the Hdpp molecules to the hydroxide ligands in all cases. X-ray crystallographic analysis showed within the adduct cis,trans-[PtCl(2)(en)(OH(2))(2)](dpp)(2) (1) a hydrogen bond length of 2.341(6) Å; the shortest O ··· O distance reported in the literature. Similar, though longer hydrogen bonds were observed in three other complexes: [PtCl(2)(OH)(NH(3))(2)(OH(2))]dpp·3H(2)O (2), trans-[Pt(mal)(OH)(OH(2))(S,S-chxn)]dpp·3H(2)O (3), and trans-[Pt(ox)(OH)(OH(2))(S,S-chxn)]dpp·2H(2)O (4). Co-crystallisation with Hdpp leads to higher aqueous solubility than the parent complexes indicating the potential of the adducts for use as active pharmaceutical ingredients. Anticancer testing of [Pt(mal)(OH)(OH(2))(S,S-chxn)]dpp·3H(2)O (3) showed in vitro cytotoxicity is low, as expected for Pt(IV) prodrugs, yet substantial tumour growth inhibition was observed in an in vivo ADJ/PC6 tumour model, with activity retained at maximum tolerated dose (MTD)/2 and MTD/4.

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