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Mirror-image organometallic osmium arene iminopyridine halido complexes exhibit similar potent anticancer activity
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Fu, Ying, Soni, Rina, Romero, Maria, Pizarro, Ana M., Salassa, Luca, Clarkson, Guy J., Hearn, Jessica M., Habtemariam, Abraha, Wills, Martin and Sadler, P. J. (2013) Mirror-image organometallic osmium arene iminopyridine halido complexes exhibit similar potent anticancer activity. Chemistry - A European Journal, Volume 19 (Number 45). pp. 15199-15209. doi:10.1002/chem.201302183 ISSN 0947-6539.
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Official URL: http://dx.doi.org/10.1002/chem.201302183
Abstract
Four chiral OsII arene anticancer complexes have been isolated by fractional crystallization. The two iodido complexes, (SOs,SC)-[Os(η6-p-cym)(ImpyMe)I]PF6 (complex 2, (S)-ImpyMe: N-(2-pyridylmethylene)-(S)-1-phenylethylamine) and (ROs,RC)-[Os(η6-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, (SOs,SC)-[Os(η6-p-cym)(ImpyMe)Cl]PF6, 1, and (ROs,RC)-[Os(η6-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.
Item Type: | Journal Article | ||||||||||
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Subjects: | R Medicine > RC Internal medicine > RC0254 Neoplasms. Tumors. Oncology (including Cancer) | ||||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry Faculty of Science, Engineering and Medicine > Research Centres > Warwick Systems Biology Centre |
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Library of Congress Subject Headings (LCSH): | Antineoplastic agents, Ligands (Biochemistry), Chirality, Organometallic compounds, Osmium | ||||||||||
Journal or Publication Title: | Chemistry - A European Journal | ||||||||||
Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | ||||||||||
ISSN: | 0947-6539 | ||||||||||
Official Date: | 23 October 2013 | ||||||||||
Dates: |
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Volume: | Volume 19 | ||||||||||
Number: | Number 45 | ||||||||||
Number of Pages: | 11 | ||||||||||
Page Range: | pp. 15199-15209 | ||||||||||
DOI: | 10.1002/chem.201302183 | ||||||||||
Status: | Peer Reviewed | ||||||||||
Publication Status: | Published | ||||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||||
Date of first compliant deposit: | 28 December 2015 | ||||||||||
Date of first compliant Open Access: | 28 December 2015 | ||||||||||
Funder: | European Research Council (ERC), Engineering and Physical Sciences Research Council (EPSRC), Science City Research Alliance, European Regional Development Fund (ERDF), Advantage West Midlands (AWM), Fundación "Pedro Barrié de la Maza, Conde de Fenosa", Spain. Ministerio de Ciencia e Innovación (MICINN) | ||||||||||
Grant number: | 247450 BIOINCMED (ERC), RYC-2011–07787 (MICINN) |
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