TY - JOUR
T1 - Vanadium(IV) complexes with methyl-substituted 8-hydroxyquinolines
T2 - Catalytic potential in the oxidation of hydrocarbons and alcohols with peroxides and biological activity
AU - Palion-Gazda, Joanna
AU - Luz, André
AU - Raposo, Luis R.
AU - Choroba, Katarzyna
AU - Nycz, Jacek E.
AU - Bieńko, Alina
AU - Lewińska, Agnieszka
AU - Erfurt, Karol
AU - Baptista, Pedro V.
AU - Machura, Barbara
AU - Fernandes, Alexandra R.
AU - Shul’pina, Lidia S.
AU - Ikonnikov, Nikolay S.
AU - Shul’pin, Georgiy B.
N1 - info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04378%2F2020/PT#
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04378%2F2020/PT#
Nos. 19-03-00142
RFMEFI61917X0007
State Task 0082-2014-0007
(CITIS): AAAA-A17-117040610283-3
LA/P/0140/2020
PY - 2021/10/21
Y1 - 2021/10/21
N2 - 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 H2 O2 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).
AB - 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 H2 O2 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).
KW - 8-hydroxyquinoline
KW - Biological activity
KW - Catalytic properties
KW - Cytotoxicity studies
KW - Vanadium(IV) complexes
UR - http://www.scopus.com/inward/record.url?scp=85117575015&partnerID=8YFLogxK
U2 - 10.3390/molecules26216364
DO - 10.3390/molecules26216364
M3 - Article
C2 - 34770772
AN - SCOPUS:85117575015
SN - 1420-3049
VL - 26
JO - Molecules
JF - Molecules
IS - 21
M1 - 6364
ER -
