Abstract
Nicotinic acid (also known as vitamin B3) is a dietary element essential for physiological and antihyperlipidemic functions. This study reports the synthesis of novel mixed ligand complexes of copper with nicotinic and other select carboxylic acids (phthalic, salicylic and anthranilic acids). The tested copper complexes exhibited superoxide dismutase (SOD) mimetic activity and antimicrobial activity against Bacillus subtilis ATCC 6633, with a minimum inhibition concentration of 256 µg/mL. Copper complex of nicotinic-phthalic acids (CuNA/Ph) was the most potent with a SOD mimetic activity of IC50 34.42 µM. The SOD activities were observed to correlate well with the theoretical parameters as calculated using density functional theory (DFT) at the B3LYP/LANL2DZ level of theory. Interestingly, the SOD activity of the copper complex CuNA/Ph was positively correlated with the electron affinity (EA) value. The two quantum chemical parameters, highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), were shown to be appropriate for understanding the mechanism of the metal complexes as their calculated energies show good correlation with the SOD activity. Moreover, copper complex with the highest SOD activity were shown to possess the lowest HOMO energy. These findings demonstrate a great potential for the development of value-added metallovitamin-based therapeutics.
Highlights
Nicotinic acid (NA) or vitamin B3 is essential for many biological processes namely for the production of energy [1], signal transduction, regulation of gene expression [2] and involvement in the synthetic pathway of lipids [3]
In an attempt to obtain small molecule-based metal complexes, we report the synthesis of novel copper complexes as potent superoxide dismutase (SOD) mimics
The novel copper complexes with nicotinic acid and carboxylic acids were synthesized in excellent yields
Summary
Nicotinic acid (NA) or vitamin B3 is essential for many biological processes namely for the production of energy [1], signal transduction, regulation of gene expression [2] and involvement in the synthetic pathway of lipids [3]. The oxidation of lipoproteins, low density lipoprotein and very low density lipoprotein, by free radical, superoxide radical (O2-), causes vascular inflammation, which is involved in the early stage development of atherosclerosis, a disease affecting arterial blood vessels [4]. Nicotinic acid has been reported to decrease the production of free fatty acids and lipoproteins [6], despite of this free radical continues to appear in the human body. To eliminate such superoxide radicals, transition metal complexes were developed as superoxide dismutase mimics. Some examples include metalloporphyrin [7] and metal-drug complexes [8]
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