Literature DB >> 18597450

Synthesis, structure, spectroscopic properties, and antiproliferative activity in vitro of novel osmium(III) complexes with azole heterocycles.

Iryna N Stepanenko1, Artem A Krokhin, Roland O John, Alexander Roller, Vladimir B Arion, Michael A Jakupec, Bernhard K Keppler.   

Abstract

Reactions of (H 2azole) 2[OsCl 6], where Hazole = pyrazole, Hpz, ( 1), indazole, Hind, ( 2), imidazole, Him, ( 3) and benzimidazole, Hbzim, ( 4) with the corresponding azole heterocycle in 1:4 molar ratio in boiling isoamyl alcohol or hexanol-1 afforded novel water-soluble osmium(III) complexes of the type trans-[OsCl 2(Hazole) 4]Cl, where Hazole = Hpz ( 5a), Hind ( 6a), Him ( 7a), and Hbzim ( 9a) in 50-70% ( 5a, 7a, 9a) and 5% ( 6a) yields. The synthesis of 7a was accompanied by a concurrent reaction which led to minor formation (<4%) of cis-[OsCl 2(Him) 4]Cl ( 8). The complexes were characterized by elemental analysis, IR spectroscopy, UV-vis spectroscopy, ESI mass spectrometry, cyclic voltammetry, and X-ray crystallography. 5a, 7a, and 9a were found to possess remarkable antiproliferative activity in vitro against A549 (non-small cell lung carcinoma), CH1 (ovarian carcinoma), and SW480 (colon carcinoma) cells, which was compared with that of related ruthenium compounds trans-[RuCl 2(Hazole) 4]Cl, where Hazole = Hpz (5b), Hind (6b), Him (7b), and Hbzim (9b).

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Year:  2008        PMID: 18597450     DOI: 10.1021/ic8006958

Source DB:  PubMed          Journal:  Inorg Chem        ISSN: 0020-1669            Impact factor:   5.165


  8 in total

1.  Ruthenium-nitrosyl complexes with glycine, L-alanine, L-valine, L-proline, D-proline, L-serine, L-threonine, and L-tyrosine: synthesis, X-ray diffraction structures, spectroscopic and electrochemical properties, and antiproliferative activity.

Authors:  Anna Rathgeb; Andreas Böhm; Maria S Novak; Anatolie Gavriluta; Orsolya Dömötör; Jean Bernard Tommasino; Eva A Enyedy; Sergiu Shova; Samuel Meier; Michael A Jakupec; Dominique Luneau; Vladimir B Arion
Journal:  Inorg Chem       Date:  2014-02-20       Impact factor: 5.165

2.  Ternary oxovanadium(IV) complexes of ONO-donor Schiff base and polypyridyl derivatives as protein tyrosine phosphatase inhibitors: synthesis, characterization, and biological activities.

Authors:  Caixia Yuan; Liping Lu; Xiaoli Gao; Yanbo Wu; Maolin Guo; Ying Li; Xueqi Fu; Miaoli Zhu
Journal:  J Biol Inorg Chem       Date:  2009-03-17       Impact factor: 3.358

3.  cis-Tetrachlorido-bis(indazole)osmium(iv) and its osmium(iii) analogues: paving the way towards the cis-isomer of the ruthenium anticancer drugs KP1019 and/or NKP1339.

Authors:  Gabriel E Büchel; Susanne Kossatz; Ahmad Sadique; Peter Rapta; Michal Zalibera; Lukas Bucinsky; Stanislav Komorovsky; Joshua Telser; Jörg Eppinger; Thomas Reiner; Vladimir B Arion
Journal:  Dalton Trans       Date:  2017-09-12       Impact factor: 4.390

4.  En route to osmium analogues of KP1019: synthesis, structure, spectroscopic properties and antiproliferative activity of trans-[Os(IV)Cl4(Hazole)2].

Authors:  Gabriel E Büchel; Iryna N Stepanenko; Michaela Hejl; Michael A Jakupec; Bernhard K Keppler; Vladimir B Arion
Journal:  Inorg Chem       Date:  2011-07-08       Impact factor: 5.165

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

Authors:  Gabriel E Büchel; Iryna N Stepanenko; Michaela Hejl; Michael A Jakupec; Bernhard K Keppler; Petra Heffeter; Walter Berger; Vladimir B Arion
Journal:  J Inorg Biochem       Date:  2012-04-10       Impact factor: 4.155

6.  Striking difference in antiproliferative activity of ruthenium- and osmium-nitrosyl complexes with azole heterocycles.

Authors:  Gabriel E Büchel; Anatolie Gavriluta; Maria Novak; Samuel M Meier; Michael A Jakupec; Olesea Cuzan; Constantin Turta; Jean-Bernard Tommasino; Erwann Jeanneau; Ghenadie Novitchi; Dominique Luneau; Vladimir B Arion
Journal:  Inorg Chem       Date:  2013-05-09       Impact factor: 5.165

7.  Mirror-image organometallic osmium arene iminopyridine halido complexes exhibit similar potent anticancer activity.

Authors:  Ying Fu; Rina Soni; María J Romero; Ana M Pizarro; Luca Salassa; Guy J Clarkson; Jessica M Hearn; Abraha Habtemariam; Martin Wills; Peter J Sadler
Journal:  Chemistry       Date:  2013-09-23       Impact factor: 5.236

8.  Heteropentanuclear Oxalato-Bridged nd-4f (n=4, 5) Metal Complexes with NO Ligand: Synthesis, Crystal Structures, Aqueous Stability and Antiproliferative Activity.

Authors:  Paul-Steffen Kuhn; Laura Cremer; Anatolie Gavriluta; Katarina K Jovanović; Lana Filipović; Alfred A Hummer; Gabriel E Büchel; Biljana P Dojčinović; Samuel M Meier; Annette Rompel; Siniša Radulović; Jean Bernard Tommasino; Dominique Luneau; Vladimir B Arion
Journal:  Chemistry       Date:  2015-08-10       Impact factor: 5.236

  8 in total

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