Copper complexes of pyridine derivatives with superoxide scavenging and antimicrobial activities

European Journal of Medicinal Chemistry

Volumn 44, Issue 8, 2009, Pages 3259-3265

  Suksrichavalit, Thummaruk ^a   Prachayasittikul, Supaluk ^b   Nantasenamat, Chanin ^a   Isarankura Na Ayudhya, Chartchalerm ^a   Prachayasittikul, Virapong ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

^b SRINAKHARINWIROT UNIVERSITY   (Thailand)

Author keywords

Antimicrobial activity; Antioxidant activity; Copper; Nicotinic acid; Pyridine; Superoxide dismutase

Indexed keywords

2 AMINOPYRIDINE; AMPICILLIN; COPPER COMPLEX; NICOTINIC ACID; NICOTINIC ACID 2 AMINOPYRIDINE COPPER COMPLEX; NICOTINIC ACID 2 HYDROXYPYRIDINE COPPER COMPLEX; NICOTINIC ACID PICOLINIC ACID COPPER COMPLEX; PICOLINIC ACID; PYRIDINE DERIVATIVE; REACTIVE OXYGEN METABOLITE; SUPEROXIDE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

AEROMONAS HYDROPHILA; ANTIMICROBIAL ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BACILLUS CEREUS; BACILLUS SUBTILIS; CANDIDA ALBICANS; CITROBACTER FREUNDII; DENSITY FUNCTIONAL THEORY; DRUG SYNTHESIS; ENZYME ACTIVITY; IC 50; INFRARED SPECTROSCOPY; LISTERIA MONOCYTOGENES; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR MODEL; MORGANELLA MORGANII; NONHUMAN; PLESIOMONAS SHIGELLOIDES; QUANTUM CHEMISTRY; SALMONELLA ENTERITIDIS; SHIGELLA DYSENTERIAE; STREPTOCOCCUS PYOGENES;

ANTI-INFECTIVE AGENTS; BACTERIA; BIOMIMETICS; COPPER; FREE RADICAL SCAVENGERS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PYRIDINES; QUANTUM THEORY; SPECTROPHOTOMETRY, INFRARED; SUPEROXIDE DISMUTASE; SUPEROXIDES; YEASTS;

EID: 67349216170     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.03.033     Document Type: Article

References (58)

1. Banerjee A., Dasgupta N., and De B. Food Chem. 90 (2005) 727-733
2. Valko M., Leibfritz D., Moncol J., Cronin M.T., Mazur M., and Telser J. Int. J. Biochem. Cell Biol. 39 (2007) 44-84
3. Valko M., Rhodes C.J., Moncol J., Izakovic M., and Mazur M. Chem. Biol. Interact. 160 (2006) 1-40
4. Sakurai T., He G., Matsuzawa A., Yu G.Y., Maeda S., Hardiman G., and Karin M. Cancer Cell 14 (2008) 156-165
5. Cathcart M.K. Arterioscler. Thromb. Vasc. Biol. 24 (2004) 23-28
6. Andreadis A.A., Hazen S.L., Comhair S.A., and Erzurum S.C. Free Radic. Biol. Med. 35 (2003) 213-225
7. Emerit J., Edeas M., and Bricaire F. Biomed. Pharmacother. 58 (2004) 39-46
8. Hearn A.S., Tu C., Nick H.S., and Silverman D.N. J. Biol. Chem. 274 (1999) 24457-24460
9. Wang Y., Yang Z.Y., and Wang B.D. Transition Met. Chem. 30 (2005) 879-883
10. Gauter-Fleckenstein B., Fleckenstein K., Owzar K., Jiang C., Batinic-Haberle I., and Vujaskovic Z. Free Radic. Biol. Med. 44 (2008) 982-989
11. Piacham T., Isarankura-Na-Ayudhya C., Nantasenamat C., Yainoy S., Ye L., Bülow L., and Prachayasittikul V. Biochem. Biophys. Res. Commun. 341 (2006) 925-930
12. Suksrichavalit T., Prachayasittikul S., Piacham T., Isarankura-Na-Ayudhya C., Nantasenamat C., and Prachayasittikul V. Molecules 13 (2008) 3040-3056
13. Bodor E.T., and Offermanns S. Br. J. Pharmacol. 153 (2007) S68-S75
14. Brown B.G., and Zhao X.Q. Am. J. Cardiol. 101 (2008) B58-B62
15. Singh R., and Rao R.S.S. J. Mol. Struct. 71 (1981) 23-30
16. El-Saadani M.A., Nassar A.Y., A. El-Ela S.H., Metwally T.H., and Nafady A.M. Biochem. Pharmacol. 46 (1993) 1011-1018
17. Salama R.H., Nassar A.Y., Nafady A.A., and Mohamed H.H. Liver Int. 27 (2007) 454-464
18. Aggett P.J., Fenwick P.K., and Kirk H. J. Nutr. 119 (1989) 1432-1437
19. Heffernan M.P., Nelson M.M., and Anadkat M.J. Br. J. Dermatol. 156 (2007) 548-552
20. Shrivastava R., Nagar R., Ravishankar G.A., Upreti R.K., and Chaturvedi U.C. Indian J. Med. Res. 126 (2007) 440-446
21. Abe S., Hu W., Ishibashi H., Hasumi K., and Yamaguchi H. J. Infect. Chemother. 10 (2004) 181-184
22. Tomioka H., Shimizu T., and Tatano Y. Int. J. Antimicrob. Agents 29 (2007) 460-464
23. Fernandez-Pol J.A., Klos D.J., and Hamilton P.D. Anticancer Res. 21 (2001) 3773-3776
24. Mucci A., Varesio L., Neglia R., Colombari B., Pastorino S., and Blasi E. Med. Microbiol. Immunol. 192 (2003) 71-78
25. Rawson J.M., and Winpenny R.E.P. Coord. Chem. Rev. 139 (1995) 313-374
26. Cheng H., Huq F., Beale P., and Fisher K. Eur. J. Med. Chem. 40 (2006) 772-781
27. Huq F., Tayyem H., Beale P., and Yu J.Q. J. Inorg. Biochem. 101 (2007) 30-35
28. Zhao G., Lin H., Yu P., Sun H., Zhu S., Su X., and Chen Y. J. Inorg. Biochem. 73 (1999) 145-149
29. J.M. Hyvelin, M. Gautier, M.C. Lemaire, P. Bonnet, V. Eder, Pflügers. Arch. Eur. J. Physiol. 457. (2009) 721-730.
30. Williams J.L.R., Fyfe G.K., Sibley C.P., Baker P.N., and Greenwood S.L. Am. J. Physiol. Regul. Integr. Comp. Physiol. 295 (2008) 1204-1213
31. Molgó J., Lemeignan M., Peradejordi F., and Lechat P. J. Pharmacol. 16 (1985) 109-144
32. Pashkov V.N., and Hemmings Jr. H.C. Anesth. Analg. 95 (2002) 1274-1281
33. Mohan G., Nagar R., Agarwal S.C., Mehta K.A., and Rao C.S. J. Enzyme Inhib. Med. Chem. 20 (2005) 55-60
34. Bo S., Durazzo M., Gambino R., Berutti C., Milanesio N., Caropreso A., Gentile L., Cassader M., Cavallo-Perin P., and Pagano G. J. Nutr. 138 (2008) 305-310
35. Olivares M., and Uauy R. Am. J. Clin. Nutr. 63 (1996) 791S-796S
36. Koca E., Buyukasik Y., Cetiner D., Yilmaz R., Sayinalp N., Yasavul U., and Uner A. Leuk. Res. 32 (2008) 495-499
37. Twomey P.J., Reynolds T.M., Wierzbicki A.S., and Viljoen A. Int. J. Clin. Pract. 62 (2008) 485-487
38. Prachayasittikul S., Buraparuangsang P., Worachartcheewan A., Isarankura-Na-Ayudhya C., Ruchirawat S., and Prachayasittikul V. Molecules 13 (2008) 904-921
39. Prachayasittikul S., Suksrichavalit T., Isarankura-Na-Ayudhya C., Ruchirawat S., and Prachayasittikul V. EXCLI J. 7 (2008) 63-70
40. Dennington II R., Keith T., Millam J., Eppinnett K., Hovell W.L., and Gilliland R. GaussView: Version 3.09 (2003), Semichem, Inc., Shawnee Mission, KS
41. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Inc., Wallingford, CT
42. Shen L., Zhang H.Y., and Ji H.F. J. Mol. Struct. Theochem. 817 (2007) 161-162
43. Franklin T.J., and Snow G.A. Biochemistry of Antimicrobial Action. second ed. (1971), Chapman and Hall, London
44. Thimmaiah K.N., Lloyd W.D., and Chandrappa G.T. Inorg. Chim. Acta 106 (1985) 81-83
45. Jadon S.C.S., Gupta N., and Singh R.V. Indian J. Chem. 34 (1995) 733-736
46. Ahmed S., and Ismail D. J. Surfactants Detergent 11 (2008) 231-235
47. Lagutkin N.A., Mitin N.I., Zubairov M.M., Dorokhov V.A., and Mikhailov B.M. Pharm. Chem. J. 16 (1982) 464-467
48. de Oliveira G., Martin J.M., de Proft F., and Geerlings P. Phys. Rev. A 60 (1999) 1034-1045
49. Ji H.F., and Zhang H.Y. Bioorg. Med. Chem. Lett. 15 (2005) 21-24
50. Ji H.F., and Zhang H.Y. Chem. Res. Toxicol. 17 (2004) 471-475
51. Branco R.J.F., Fernandes P.A., and Ramos M.J. Theor. Chem. Acc. 115 (2006) 27-31
52. Branco R.J.F., Fernandes P.A., and Ramos M.J. J. Mol. Struct. Theochem. 729 (2005) 141-146
53. Sun R., Ge J., Yao J., Li S., Shen H., and Gua R. Spectrochim. Acta Part A 71 (2008) 1535-1539
54. Garbutt J.T., Morehouse A.L., and Hanson A.M. J. Agric. Food Chem. 9 (1961) 285-289
55. Schepetkin I., Potapov A., Khlebnikov A., Korotkova E., Lukina A., Malovichko G., Kirpotina L., and Quinn M.T. J. Biol. Inorg. Chem. 11 (2006) 499-513
56. Cappellani E.P., Drouin S.D., Jia G., Maltby P.A., Morris R.H., and Schweitzer C.T. J. Am. Chem. Soc. 116 (1994) 3375-3388
57. Bóka B., Myari A., Sóvágó I., and Hadjiliadis N. J. Inorg. Biochem. 98 (2004) 113-122
58. Li Q.X., Luo Q.H., Li Y.Z., and Shen M.C. Dalton Trans. 15 (2004) 2329-2335