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Title: Vanadium(IV) complexes with methyl-substituted 8-hydroxyquinolines : catalytic potential in the oxidation of hydrocarbons and alcohols with peroxides and biological activity
Authors: Palion-Gazda, Joanna
Luz, André
Raposo, Luis R.
Choroba, Katarzyna
Nycz, Jacek E.
Bieńko, Alina
Lewińska, Agnieszka
Erfurt, Karol
Babtista, Pedro V.
Machura, Barbara
Fernandes, Alexandra R.
Shul’pina, Lidia
Ikonniko, Nikolai S.
Shul’pin, Georgiy B.
Keywords: vanadium(IV) complexes; biological activity; catalytic properties; 8-hydroxyquinoline; cytotoxicity studies
Issue Date: 2021
Citation: "Molecules" (2021), iss. 21, art. no. 6364, s. 1-23
Abstract: Methyl-substituted 8-hydroxyquinolines (Hquin) were successfully used to synthetize five-coordinated oxovanadium(IV) complexes: [VO(2,6-(Me)2-quin)2] (1), [VO(2,5-(Me)2-quin)2] (2) and [VO(2-Me-quin)2] (3). Complexes 1–3 demonstrated high catalytic activity in the oxidation of hydrocarbons with H2O2 in acetonitrile at 50 C, in the presence of 2-pyrazinecarboxylic acid (PCA) as a cocatalyst. The maximum yield of cyclohexane oxidation products attained was 48%, which is high in the case of the oxidation of saturated hydrocarbons. The reaction leads to the formation of a mixture of cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone. When triphenylphosphine is added, cyclohexyl hydroperoxide is completely converted to cyclohexanol. Consideration of the regioand bond-selectivity in the oxidation of n-heptane and methylcyclohexane, respectively, indicates that the oxidation proceeds with the participation of free hydroxyl radicals. The complexes show moderate activity in the oxidation of alcohols. Complexes 1 and 2 reduce the viability of colorectal (HCT116) and ovarian (A2780) carcinoma cell lines and of normal dermal fibroblasts without showing a specific selectivity for cancer cell lines. Complex 3 on the other hand, shows a higher cytotoxicity in a colorectal carcinoma cell line (HCT116), a lower cytotoxicity towards normal dermal fibroblasts and no effect in an ovarian carcinoma cell line (order of magnitude HCT116 > fibroblasts > A2780).
DOI: 10.3390/molecules26216364
ISSN: 1420-3049
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