Structural and Solution Chemistry of gold(I) and Silver(I) complexes of bidentate pyridyl phosphines: selective antitumour agents

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Title Structural and Solution Chemistry of gold(I) and Silver(I) complexes of bidentate pyridyl phosphines: selective antitumour agents
Author Berners-Price, Sue; Bowen, Richard; Galettis, P.; Healy, Peter Conrad; McKeage, M.J.
Journal Name Coordination Chemistry Reviews
Year Published 1999
Place of publication Switzerland
Publisher Elsevier Science
Abstract The 1:2 adducts of Ag(I) and Au(I) with 1,2-bis(di-n-pyridylphosphino)ethane (dnpype) for n=2, 3 and 4 have been synthesised and solution properties characterised by multinuclear NMR spectroscopy. The complexes are hydrophilic analogs of the lipophilic Au(I) antitumour complex [Au(dppe)2]+ and the degree of hydrophilicity depends critically on the position of the N atom in the pyridyl ring. The complexes of d3pype and d4pype are simple monomeric [M(d3pype)2]+ and [M(d4pype)2]+ species which have a much higher water solubility than the 2-pyridyl complexes which crystallise in the solid state as dimeric [{M(d2pype)2}2]2+. In solution these 1:2 M:d2pype species exist as equilibrium mixtures of monomeric, dimeric and trimeric (Ag) or tetrameric (Au) clusters. The Au(I) and Ag(I)pyridyl phosphine complexes have been evaluated for antitumour activity against a panel of cultured human ovarian carcinoma cell lines. The results show both potent and selective activity for the compounds with IC50 values ranging from 0.18 to 1500 μM. There is a correlation between the degree of antitumour selectivity and the octanol/water partition coefficients with the greatest selectivity (500-fold range) found for the most hydrophilic complex [Au(d4pype)2]Cl. Clinical development of the parent compound [Au(dppe)2]+ was halted by liver toxicity and the hydrophilic pyridylphosphine analogs are significantly less toxic than [Au(dppe)2]+ when exposed to isolated rat hepatocytes. Convenient synthetic routes to the bidentate pyridyl phosphines d2pype, d3pype and d4pype are also described.
Peer Reviewed Yes
Published Yes
Publisher URI http://www.sciencedirect.com/science/journal/00108545
Alternative URI http://dx.doi.org/10.1016/S0010-8545(99)00039-9
Copyright Statement Copyright 1999 Elsevier. Please refer to the journal's website for access to the definitive, published version.
Volume 185-186
Page from 823
Page to 836
ISSN 0010-8545
Date Accessioned 2000-01-01
Language en_AU
Research Centre Institute for Glycomics
Faculty Faculty of Science
Subject PRE2009-Chemical Sciences
URI http://hdl.handle.net/10072/15550
Publication Type Article in Scholarly Refereed Journal
Publication Type Code c1

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