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

Büchel GE, Stepanenko IN, Hejl M, Jakupec MA, Keppler BK, Heffeter P, Berger W, Arion VB - J. Inorg. Biochem. (2012)

Bottom Line: 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.

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Affiliation: University of Vienna, Institute of Inorganic Chemistry, Währinger Strasse 42, A-1090 Vienna, Austria.

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UV–vis spectra of an aqueous solution of 1 (left) and 2 (right), measured immediately after dissolution and 24 h thereafter.
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f0020: UV–vis spectra of an aqueous solution of 1 (left) and 2 (right), measured immediately after dissolution and 24 h thereafter.

Mentions: The aqueous solubility of 1 is 1.2 mM at 298 K, compared to 1.3 mM for 2. The aqueous solution behavior of 1 and 2 with respect to hydrolysis was studied by optical spectroscopy at 294 K over 24 h (Fig. 3). Both complexes are stable in aqueous solution. Immediate hydrolysis was excluded since the peak at m/z 485 assigned to [OsIVCl5(Hind)]− was observed in the negative ion ESI mass spectrum of the aqueous solution of both 1 and 2 after 24 h. The UV–vis spectra of 1 and 2 are compared in Fig. 4.


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

Büchel GE, Stepanenko IN, Hejl M, Jakupec MA, Keppler BK, Heffeter P, Berger W, Arion VB - J. Inorg. Biochem. (2012)

UV–vis spectra of an aqueous solution of 1 (left) and 2 (right), measured immediately after dissolution and 24 h thereafter.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3400055&req=5

f0020: UV–vis spectra of an aqueous solution of 1 (left) and 2 (right), measured immediately after dissolution and 24 h thereafter.
Mentions: The aqueous solubility of 1 is 1.2 mM at 298 K, compared to 1.3 mM for 2. The aqueous solution behavior of 1 and 2 with respect to hydrolysis was studied by optical spectroscopy at 294 K over 24 h (Fig. 3). Both complexes are stable in aqueous solution. Immediate hydrolysis was excluded since the peak at m/z 485 assigned to [OsIVCl5(Hind)]− was observed in the negative ion ESI mass spectrum of the aqueous solution of both 1 and 2 after 24 h. The UV–vis spectra of 1 and 2 are compared in Fig. 4.

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: University of Vienna, Institute of Inorganic Chemistry, Währinger Strasse 42, A-1090 Vienna, Austria.

Show MeSH
Related in: MedlinePlus