Osmium(IV) complexes with 1H- and 2H-indazoles: tautomer identity versus spectroscopic properties and antiproliferative activity.

Abstract

A one-pot synthesis of osmium(IV) complexes with two different tautomers of indazole, 1H-indazole and 2H-indazole, namely (H(2)ind)[Os(IV)Cl(5)(2H-ind)] (1) and (H(2)ind)[Os(IV)Cl(5)(1H-ind)] (2) is reported. Both compounds have been comprehensively characterized by NMR spectroscopy, ESI (electrospray ionization) mass spectrometry, electronic absorption spectroscopy, IR spectroscopy, cyclic voltammetry and tested for antiproliferative activity in vitro in three human cancer cell lines, CH1 (ovarian carcinoma), A549 (non-small cell lung cancer) and SW480 (colon carcinoma), as well as in vivo in a Hep3B SCID mouse xeno-transplantation model. 2H-Indazole tautomer stabilization in 1 has been confirmed by X-ray diffraction.

• Authors: Gabriel E Büchel, Iryna N Stepanenko, Michaela Hejl, Michael A Jakupec, Bernhard K Keppler, Petra Heffeter, Walter Berger, Vladimir B Arion
• Journal: Journal of inorganic biochemistry (J Inorg Biochem) Vol. 113 Pg. 47-54 (Aug 2012) ISSN: 1873-3344 [Electronic] United States
• PMID: 22687494 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2012 Elsevier Inc. All rights reserved.

Chemical References

• Antineoplastic Agents
• Coordination Complexes
• Indazoles
• Osmium

Topics

• Animals
• Antineoplastic Agents (chemical synthesis, pharmacology)
• Cell Line, Tumor
• Cell Survival (drug effects)
• Coordination Complexes (chemical synthesis, pharmacology)
• Dose-Response Relationship, Drug
• Humans
• Indazoles (chemistry)
• Isomerism
• Magnetic Resonance Spectroscopy
• Mice
• Mice, SCID
• Neoplasms (drug therapy, pathology)
• Osmium (chemistry)
• Spectrometry, Mass, Electrospray Ionization
• Spectrophotometry, Infrared
• Tumor Burden (drug effects)
• X-Ray Diffraction
• Xenograft Model Antitumor Assays