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The Interaction of Antitumor Active Vanadocene Dichloride with Sulphur Containing Amino Acids
Authors: Paláčková Hana | Vinklárek Jaromír | Holubová Jana | Císařová Ivana | Erben Milan
Year: 2007
Type of publication: článek v odborném periodiku
Name of source: Journal of Organometallic Chemistry
Page from-to: 3758-3764
Titles:
Language Name Abstract Keywords
cze Interakce vanadocendichloridu s aminokyselinami obsahující síru Vanadocene dichloride (1) reacts with sulphur-containing amino acids, cysteine and methionine, giving new complexes with five- or six-membered chelate ring, but the structure of isolated compounds is affected by the pH value of the reaction mixture. Methionine reacts with aqueous 1 in the pH range of 3 - 8 affording chelate structure [Cp2V(N,O-met)]Cl (4). Similar reaction with cysteine gives two different products depending on pH. In the acidic solution, the complex [Cp2V(O,S-cys)]Cl (2) is present, but in neutral media the compound [Cp2V(N,S-cys)] (3) could be identified. On inspection of spectroscopic measurements, particularly EPR and vibrational spectroscopy, it is evident that sulphur atom of amino acid is bonded directly to the vanadium atom of [Cp2V]2+ moiety. For the purpose of comparison the complexes [Cp2V(O,S-mpa)] (5) and [Cp2V(N,S-csam)]+ (6a) with related chelating ligands, 3-mercaptopropionic acid (mpa) and cysteamine (csam), respectively, were prepared and spectroscopically characterized. The structure of the complex [Cp2V(N,S-csam)]BPh4 (6b) was also determined by X-ray diffraction analysis. vanadocendichlorid; EPR; X-ray
eng The Interaction of Antitumor Active Vanadocene Dichloride with Sulphur Containing Amino Acids Vanadocene dichloride (1) reacts with sulphur-containing amino acids, cysteine and methionine, giving new complexes with five- or six-membered chelate ring, but the structure of isolated compounds is affected by the pH value of the reaction mixture. Methionine reacts with aqueous 1 in the pH range of 3 - 8 affording chelate structure [Cp2V(N,O-met)]Cl (4). Similar reaction with cysteine gives two different products depending on pH. In the acidic solution, the complex [Cp2V(O,S-cys)]Cl (2) is present, but in neutral media the compound [Cp2V(N,S-cys)] (3) could be identified. On inspection of spectroscopic measurements, particularly EPR and vibrational spectroscopy, it is evident that sulphur atom of amino acid is bonded directly to the vanadium atom of [Cp2V]2+ moiety. For the purpose of comparison the complexes [Cp2V(O,S-mpa)] (5) and [Cp2V(N,S-csam)]+ (6a) with related chelating ligands, 3-mercaptopropionic acid (mpa) and cysteamine (csam), respectively, were prepared and spectroscopically characterized. The structure of the complex [Cp2V(N,S-csam)]BPh4 (6b) was also determined by X-ray diffraction analysis. antitumor drugs; vanadocene dichloride; cysteine; methionine; EPR; X-ray

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