Development of novel copper(II) complexes of benzothiazole- N-sulfonamides as protective agents against superoxide anion. Crystal structures of [Cu( N-2-(4-methylbenzothiazole)benzenesulfonamidate)(2)(py)(2)] and [Cu( N-2-(6-nitrobenzothiazole)naphthalenesulfonamidate)(2)(py)(2)].
Copper(II) ternary complexes based on the novel benzothiazole- N-sulfonamides, HL1 ( N-2-(4-methylbenzothiazole)benzenesulfonamide) and HL2 ( N-2-(6-nitrobenzothiazole)naphthalenesulfonamide) ligands, and pyridine have been synthesized and characterized. Complexes [Cu(L1)(2)(py)(2)] (1). and [Cu(L2)(2)(py)(2)] (2). were chemically characterized and their structures determined by means of single crystal X-ray analysis. In both compounds the Cu(II) ion is coordinated to four N atoms in a nearly square planar arrangement. The Cu-N bond distances are similar to those of Cu(2)Zn(2)SOD. The SOD mimetic activity of the complexes was determined both in vitro and in vivo. For determining the SOD-like activity of the complexes in vivo, we have developed a new method based on the complexes' protective effect on a delta sod1mutant of Saccharomyces cerevisiae against free radicals generated by hydrogen peroxide and menadione as well as free radicals produced in the cellular respiration process. The results have shown that complex 1 presents a protective action against oxidative stress induced by menadione or H(2)O(2) and that both complexes 1 and 2 protect against free radicals generated in cellular respiration.
González-Alvarez
Marta
M
Departamento de Química Inorgánica, Facultad de Farmacia, Universidad de Valencia, Avda. Vicent Andrés Estellés s/n 46100 - Burjassot, Spain.
Alzuet
Gloria
G
Borrás
Joaquín
J
Castillo Agudo
Lucasdel
L
Montejo-Bernardo
Jose Manuel
JM
García-Granda
Santiago
S
D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology; D052160:Benzothiazoles; D019069:Cell Respiration / Q000187:drug effects; D003300:Copper / Q000737:chemistry*; D003460:Crystallization; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D018716:Molecular Mimicry; D009942:Organometallic Compounds / Q000737:chemistry / Q000494:pharmacology; D018384:Oxidative Stress; D012441:Saccharomyces cerevisiae / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D013449:Sulfonamides / Q000737:chemistry* / Q000494:pharmacology; D013482:Superoxide Dismutase / Q000737:chemistry / Q000378:metabolism; D013481:Superoxides / Q000037:antagonists & inhibitors*; D013844:Thiazoles / Q000737:chemistry*; D024483:Vitamin K 3 / Q000494:pharmacology
D000975:Antioxidants; D052160:Benzothiazoles; D009942:Organometallic Compounds; D013449:Sulfonamides; D013844:Thiazoles; D013481:Superoxides; D024483:Vitamin K 3; D003300:Copper; C051353:naphthalenesulfonamide; D013482:Superoxide Dismutase; C005465:benzothiazole