NDLI: Structure–activity relationships for organometallic osmium arene phenylazopyridine complexes with potent anticancer activity

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Structure–activity relationships for organometallic osmium arene phenylazopyridine complexes with potent anticancer activity

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Structure–activity relationships for organometallic osmium arene phenylazopyridine complexes with potent anticancer activity

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Fu, Ying Habtemariam, Abraha Clarkson, Guy J. Basri, Aida M. B. H. Sadler, Peter J. Braddick, Darren
Description	Author Affiliation: Fu Y ( Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, UK CV4 7AL.)
Abstract	We report the synthesis and characterisation of 32 half sandwich phenylazopyridine $Os^{II}$ arene complexes [Os(η $^{6}-arene)(phenylazopyridine)X]$ $^{+}$ in which X is chloride or iodide , the arene is p-cymene or biphenyl and the pyridine and phenyl rings contain a variety of substituents (F, Cl , Br , I, CF $_{3}$ , OH or NO $_{2}$ ). Ten X-ray crystal structures have been determined. Cytotoxicity towards A2780 human ovarian cancer cells ranges from high potency at nanomolar concentrations to inactivity. In general the introduction of an electron-withdrawing group (e.g. F, Cl , Br or I) at specific positions on the pyridine ring significantly increases cytotoxic activity and aqueous solubility. Changing the arene from p-cymene to biphenyl and the monodentate ligand X from chloride to iodide also increases the activity significantly. Activation by hydrolysis and DNA binding appears not to be the major mechanism of action since both the highly active complex [Os(η $^{6}-bip)(2-F-azpy)I]PF$ $_{6}$ (9) and the moderately active complex [Os(η $^{6}-bip)(3-Cl-azpy)I]PF$ $_{6}$ (23) are very stable and inert towards aquation. Studies of octanol – water partition coefficients (log P) and subcellular distributions of osmium in A2780 human ovarian cancer cells suggested that cell uptake and targeting to cellular organelles play important roles in determining activity. Although complex 9 induced the production of reactive oxygen species (ROS) in A2780 cells , the ROS level did not appear to play a role in the mechanism of anticancer activity. This class of organometallic osmium complexes has new and unusual features worthy of further exploration for the design of novel anticancer drugs .
ISSN	14779226
Issue Number	40
Volume Number	40
e-ISSN	13645447
Journal	Dalton Trans.
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2011-10-28
Publisher Place	Great Britain (UK)
Access Restriction	Subscribed
Subject Keyword	Antineoplastic Agents Chemistry Coordination Complexes Osmium Pyridines Pharmacology Cell Line, Tumor Cell Proliferation Drug Effects Crystallography, X-Ray Female Humans Hydrolysis Molecular Conformation Organometallic Compounds Ovarian Neoplasms Drug Therapy Reactive Oxygen Species Metabolism Structure-Activity Relationship Journal Article Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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