Gold(I) chloride adducts of 1,3-bis(di-2-pyridylphosphino)propane: synthesis structural studies and antitumour activity

A.S. Humphreys, Aleksandra Filipovska, Susan Berners-Price, George Koutsantonis, Brian Skelton, Allan White

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

Abstract

The novel water soluble bidentate phosphine ligand 1,3-bis( di-2-pyridylphosphino) propane (d2pypp) has been synthesized by a convenient route involving treatment of 2-pyridyllithium with Cl2P(CH2)(3)PCl2 and isolation in crystalline form as the hydrochloride salt. The synthesis of the precursor Cl2P(CH2)(3)PCl2 has been optimized by the use of triphosgene as the chlorinating agent. The 2 : 1 and 1 : 2 AuCl : d2pypp adducts have been synthesized and characterized by NMR spectroscopy and single crystal X-ray studies, and shown to be of the form ( AuCl)(2)(mu-d2pypp-P,P ') and [ Au(d2pypp-P,P ')(2)]Cl(.3.75H(2)O), respectively. The latter is more lipophilic than analogous 1 : 2 adducts of gold( I) chloride with the diphosphine ligands 1,2-bis(di-n-pyridylphosphino)ethane(dnpype) for n = 2, 3 and 4, based on measurement of the n-octanol-water partition coefficient ( log P= -0.46). A single crystal structure determination of the 1 : 2 Au( I) complex of the 3-pyridyl ethane ligand shows it to be of the form [ Au( d3pype-P,P ')(2)]Cl center dot 5H(2)O. The in vitro cytotoxic activity of [ Au( d2pypp)(2)]Cl was assessed in human normal and cancer breast cells and selective toxicity to the cancer cells found. The significance of these results to the antitumour properties of chelated 1 : 2 Au( I) diphosphine complexes is discussed.
Original languageEnglish
Pages (from-to)4943-4950
JournalDalton Transactions
Volume2007
Issue number43
DOIs
Publication statusPublished - 2007

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