Evaluation of Anisole-Substituted Boron Difluoride Formazanate Complexes for Fluorescence Cell Imaging.

Evaluation of three subclasses of boron difluoride formazanate complexes bearing o-, m-, and p-anisole N-aryl substituents (Ar) as readily accessible alternatives to boron dipyrromethene (BODIPY) dyes for cell imaging applications is described. While the wavelengths of maximum absorption (λmax ) and emission (λem ) observed for each subclass of complexes, which differed by their carbon-bound substituents (R), were similar, the emission quantum yields for 7 a-c (R=cyano) were enhanced relative to 8 a-c (R=nitro) and 9 a-c (R=phenyl). Complexes 7 a-c and 8 a-c were also significantly easier to reduce electrochemically to their radical anion and dianion forms compared to 9 a-c.

Potent mutagenicity in the Ames test of 2-cyano-4-nitroaniline and 2,6-dicyano-4-nitroaniline, components of disperse dyes.

Genotoxicity data on commercial azo dyes and their components remain sparse, despite their widespread use. We have tested the mutagenicity of 2-cyano-4-nitroaniline (CNNA) and 2,6-dicyano-4-nitroaniline (CNCNNA), components of azo dyes such as Disperse Blue 165 and Disperse Red 73, in Ames test strains. Both compounds are extraordinarily potent frameshift mutagens, with much greater activity than structurally similar dihalonitroanilines and halodinitroanilines.

Inhibition of human glutathione transferases by dinitronaphthalene derivatives.

Glutathione transferase (GST) enzymes catalyze the conjugation of glutathione with reactive functional groups of endogenous compounds and xenobiotics, including halonitroaromatics. 1-Chloro-2,4-dinitrobenzene (CDNB) is one of the most commonly used substrates for GST activity assays. We have studied the interactions of dinitronaphthalene analogues of CDNB with recombinant human GST enzymes (Alpha, Mu, and Pi classes) expressed in Escherichia coli.