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Complexation of NADH analogs with divalent metal ions: Dependence on the 3-substituent of 1-benzyl-1,4-dihydropyridines

Title
Complexation of NADH analogs with divalent metal ions: Dependence on the 3-substituent of 1-benzyl-1,4-dihydropyridines
Authors
Park K.K.Lee J.H.Park J.W.
Ewha Authors
박준우
SCOPUS Author ID
박준우scopusscopus
Issue Date
1991
Journal Title
Bioorganic Chemistry
ISSN
0045-2068JCR Link
Citation
vol. 19, no. 4, pp. 433 - 444
Indexed
SCI; SCIE; SCOPUS scopus
Abstract
In light of the critical role of divalent metal ions in the chemistry of coenzyme NADH analogs, complexation of 1-benzyl-3-substituted(X)-1,4-dihydropyridines (1, X=CONH2; 2, X=CSNH2; 3, X=COOCH3; 4, X=COCH3) with divalent metal ions (Mg2+, Zn2+, and Co2+) in dry acetonitrile was studied spectroscopically and kinetically. Presence of the metal ions causes red-shift of absorption band of NADH analogs and the rate retardation for the reaction between NADH analogs and N-methylacridinium ion. Analysis of the spectroscopic and kinetic data indicates that the NADH analogs form 1 : 1 complexes with the metal ions. The decreasing order of the magnitude of the association constants, K, is 1 ≅ 2 ≫ 4 ≫ 3 for a given metal ion, and Mg2+ ≫ Zn2+ > Co2+ for a given NADH analog. The results strongly suggest that the primary binding site for the metal ions is the carbonyl oxygen (or thiocarbonyl sulfur) of the 3-substituent and that the amide nitrogen atom of the 3-substituent of 1 and 2 also ligates the metal ions, forming a bidentate structure and providing extra stability to the complexes of 1 and 2. Inhibition of reaction between NADH analogs and N-methylacridinium ion by the metal ions is attributed to inaccessibility of N-methylacridinium ion to the NADH analogs complexed with metal ions due to electrostatic repulsion.
DOI
10.1016/0045-2068(91)90024-J
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자연과학대학 > 화학·나노과학전공 > Journal papers
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