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Water-Soluble Platinum(II) Complexes Featuring 2-Alkyl-2 H-tetrazol-5-ylacetic Acids: Synthesis, Characterization, and Antiproliferative Activity.
- Source :
-
European Journal of Inorganic Chemistry . Oct2016, Vol. 2016 Issue 28, p4659-4667. 9p. - Publication Year :
- 2016
-
Abstract
- 2-R-2 H-Tetrazol-5-ylacetic acids (abbreviated as 2-R-taa; R = Me, iPr, tBu) react with K2[PtCl4] in 1 m HCl in H2O at r.t. furnishing trans-platinum(II) complexes trans-[PtCl2(2-R-taa)2] ( 1- 3), whereas cis-isomeric species cis-[PtCl2(2-R-taa)2] (R = iPr, 4; tBu, 5) are isolated at lower temperature (4-6 °C). In the presence of EtOH in the reaction mixture, esterification of the tetrazol-5-ylacetoxy group of 2- tBu-taa leads to trans-[PtCl2(ethyl 2- tert-butyl-2 H-tetrazol-5-ylacetate)2] ( 6). Complexes 1- 6 were characterized by elemental analyses (CHN), HRESI+-MS, 1H, 13C{1H}, 195Pt{1H} NMR and IR spectroscopy, differential scanning calorimetry/thermogravimetry (DSC/TG), and X-ray diffraction (for 1·H2O, 2, 3·2H2O, 4, 5·2H2O, and 6). The generation of the tetrazole-based complexes in solution (1 m DCl in D2O, 25 °C) was studied by 1H NMR spectroscopy and HPLC-MS. The obtained data indicate the initial formation of anionic [PtCl3(2-R-taa)]- complexes that are subsequently converted into disubstituted isomeric platinum(II) species cis- and trans-[PtCl2(2-R-taa)2]. By contrast to cis- and trans-[PtCl2(2-R-taa)2] that were inactive in two human cancer models in vitro (IC50 > 100 µ m), complex 6 demonstrated noticeable antiproliferative effects in HT-29 colon and MCF-7 breast carcinoma cell lines with IC50 values of 14.2 ± 1.1 and 5.8 ± 1.2 µ m, respectively. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 14341948
- Volume :
- 2016
- Issue :
- 28
- Database :
- Academic Search Index
- Journal :
- European Journal of Inorganic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 118525732
- Full Text :
- https://doi.org/10.1002/ejic.201600626