Cu(II) complexes with a sulfonamide derived from benzoguanamine. Oxidative cleavage of DNA in the presence of H2O2 and ascorbate.
Reaction between benzoguanamine (2,4-diamino-6-phenyl-1,3,5-triazine) and 2-mesitylenesulfonyl chloride leads to formation of a sulfonamide able to form two mononuclear Cu(II) complexes with a CuL(2) stoichiometry. The local environment of the metal cation is a distorted octahedron, with two ligands and two solvent molecules; both complexes crystallize in the monoclinic structure, space group P2(1), with Z=2. In the presence of ascorbate/H(2)O(2,) the two complexes significantly cleavage double-strand pUC18 DNA plasmid. Both complexes exhibit more nuclease efficiency that the copper phenantroline complex. From scavenging reactive oxygen studies we conclude that the hydroxyl radical and a singlet oxygen-like entity, such a peroxide copper complex, are the radical species involved in the DNA damage.
Macías
B
B
Departamento de Química Inorgánica, Facultad de Farmacia, Universidad de Salamanca, Campus Unamuno, 37007 Salamanca, Spain. bmacias@usal.es
Villa
M V
MV
Sanz
F
F
Borrás
J
J
González-Alvarez
M
M
Alzuet
G
G
D001205:Ascorbic Acid / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry*; D006146:Guanidines / Q000138:chemical synthesis / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry*; D014227:Triazines / Q000737:chemistry*
D006146:Guanidines; D009942:Organometallic Compounds; D013449:Sulfonamides; D014227:Triazines; C503152:benzoguanamine (2,4-diamino-6-phenyl-1,3,5-triazine); D003300:Copper; D004247:DNA; D006861:Hydrogen Peroxide; D001205:Ascorbic Acid