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Journal of the Brazilian Chemical Society
versión impresa ISSN 0103-5053
DOMINGUES, Vanessa O. et al. In vitro evaluation of triazenes: DNA cleavage, antibacterial activity and cytotoxicity against acute myeloid leukemia cells. J. Braz. Chem. Soc. [online]. 2010, vol.21, n.12, pp.2226-2237. ISSN 0103-5053. http://dx.doi.org/10.1590/S0103-50532010001200009.
The asymmetric diazoamines 1-(2-chlorophenyl)-3-(4-carboxyphenyl)triazene (1), 1-(2-fluorophenyl)-3-(4-carboxyphenyl)triazene (2) and 1-(2-fluorophenyl)-3-(4-amidophenyl)triazene (3) were evaluated for their ability to cleave pUC18 and pBSKII plasmid DNA, antibacterial activity and in vitro cytotoxicity against acute myeloid leukemia cells and normal leukocytes using the bioassay of reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). The triazenes showed ability to cleave the two types of plasmid DNA: triazene 1 at pH 8.0 and 50 ºC; triazene 2 at pH 6.5 and 37 and 50 ºC; triazene 3 at pH 6.5 and 37 ºC. The compounds presented cytotoxic activity against myeloid leukemia cells. Compound 1 showed high activity against B. cereus (MIC = 32 mg mL-1). The observation of intermolecular hydrogen bonding in the solid state of compound 3, based on the structural analysis by X-ray crystallography, as well as the results of IR and UV-Vis spectroscopic analyses of compounds 1, 2 and 3 are discussed in the present work.
Palabras clave : triazenes; DNA cleavage; antibacterial activity; cytotoxicit.