Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 45, Pages 15199-15209Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201302183
Keywords
anticancer agents; arene ligands; chirality; organometallic; osmium
Categories
Funding
- ERC [247450 BIOINCMED]
- EPSRC
- Science City/EU ERDF/AWM
- Fundacion Barrie (Spain)
- MICINN of Spain [RYC-2011-07787]
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Four chiral Os-II arene anticancer complexes have been isolated by fractional crystallization. The two iodido complexes, (S-Os,S-C)-[Os((6)-p-cym)(ImpyMe)I]PF6 (complex 2, (S)-ImpyMe: N-(2-pyridylmethylene)-(S)-1-phenylethylamine) and (R-Os,R-C)-[Os((6)-p-cym)(ImpyMe)I]PF6 (complex 4, (R)-ImpyMe: N-(2-pyridylmethylene)-(R)-1-phenylethylamine), showed higher anticancer activity (lower IC50 values) towards A2780 human ovarian cancer cells than cisplatin and were more active than the two chlorido derivatives, (S-Os,S-C)-[Os((6)-p-cym)(ImpyMe)Cl]PF6, 1, and (R-Os,R-C)-[Os((6)-p-cym)(ImpyMe)Cl]PF6, 3. The two iodido complexes were evaluated in the National Cancer Institute 60-cell-line screen, by using the COMPARE algorithm. This showed that the two potent iodido complexes, 2 (NSC: D-758116/1) and 4 (NSC: D-758118/1), share surprisingly similar cancer cell selectivity patterns with the anti-microtubule drug, vinblastine sulfate. However, no direct effect on tubulin polymerization was found for 2 and 4, an observation that appears to indicate a novel mechanism of action. In addition, complexes 2 and 4 demonstrated potential as transfer-hydrogenation catalysts for imine reduction.
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