Molecules 2008, 13(12), 3040-3056; doi:10.3390/molecules13123040
Article

Copper Complexes of Nicotinic-Aromatic Carboxylic Acids as Superoxide Dismutase Mimetics

1email, 2email, 1email, 1email, 1email and 1,* email
Received: 25 September 2008; in revised form: 19 November 2008 / Accepted: 27 November 2008 / Published: 8 December 2008
Download PDF [578 KB, uploaded 18 June 2014]
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.
Keywords: Nicotinic acid; Copper; Carboxylic acid; Superoxide dismutase; Antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


MDPI and ACS Style

Suksrichavalit, T.; Prachayasittikul, S.; Piacham, T.; Isarankura-Na-Ayudhya, C.; Nantasenamat, C.; Prachayasittikul, V. Copper Complexes of Nicotinic-Aromatic Carboxylic Acids as Superoxide Dismutase Mimetics. Molecules 2008, 13, 3040-3056.

AMA Style

Suksrichavalit T, Prachayasittikul S, Piacham T, Isarankura-Na-Ayudhya C, Nantasenamat C, Prachayasittikul V. Copper Complexes of Nicotinic-Aromatic Carboxylic Acids as Superoxide Dismutase Mimetics. Molecules. 2008; 13(12):3040-3056.

Chicago/Turabian Style

Suksrichavalit, Thummaruk; Prachayasittikul, Supaluk; Piacham, Theeraphon; Isarankura-Na-Ayudhya, Chartchalerm; Nantasenamat, Chanin; Prachayasittikul, Virapong. 2008. "Copper Complexes of Nicotinic-Aromatic Carboxylic Acids as Superoxide Dismutase Mimetics." Molecules 13, no. 12: 3040-3056.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert