Copper complexes of pyridine derivatives with superoxide scavenging and antimicrobial activities.
Superoxide anions are reactive oxygen species that can attack biomolecules such as DNA, lipids and proteins to cause many serious diseases. This study reports the synthesis of copper complexes of nicotinic acid with related pyridine derivatives. The copper complexes were shown to possess superoxide dismutase (SOD) and antimicrobial activities. The copper complexes exerted SOD activity in range of 49.07-130.23 microM. Particularly, copper complex of nicotinic acid with 2-hydroxypyridine was the most potent SOD mimic with an IC(50) of 49.07 microM. In addition, the complexes exhibited antimicrobial activity against Bacillus subtilis ATCC 6633 and Candida albicans ATCC 90028 with MIC range of 128-256 microg/mL. The SOD activities were well correlated with the theoretical parameters as calculated by density functional theory at the B3LYP/LANL2DZ level of theory. Interestingly, the SOD activity of the copper complexes was demonstrated to be inversely correlated with the electron affinity, but was well correlated with both HOMO and LUMO energies. The vitamin-metal complexes described in this report are great examples of the value-added benefits of vitamins for medicinal applications.
Department of Clinical Microbiology, Faculty of Medical Technology, Mahidol University, Bangkok, Thailand.
Thummaruk
T
Suksrichavalit
Supaluk
S
Prachayasittikul
Chanin
C
Nantasenamat
Chartchalerm
C
Isarankura-Na-Ayudhya
Virapong
V
Prachayasittikul
D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D032701:Biomimetics; D003300:Copper / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D011725:Pyridines / Q000737:chemistry*; D011789:Quantum Theory; D013055:Spectrophotometry, Infrared; D013482:Superoxide Dismutase / Q000737:chemistry / Q000378:metabolism; D013481:Superoxides / Q000378:metabolism*; D015003:Yeasts / Q000187:drug effects
D000890:Anti-Infective Agents; D016166:Free Radical Scavengers; D009942:Organometallic Compounds; D011725:Pyridines; D013481:Superoxides; D003300:Copper; D013482:Superoxide Dismutase; C023666:pyridine