Abstract
A major drawback of azo compounds is their associated toxicity, often carcinogenic, which is related to the reduction of the azo bond. This study intends to re-investigate this behavior by studying 5-amino-2-((3-hydroxy-4-((3-hydroxyphenyl) phenyl) diazenyl) phenol (AHPD), a compound containing two azo bonds. Interaction of AHPD and its dimeric Cu(II) complex with bacterial strains Escherichia coli and Staphylococcus aureus revealed the complex was less toxic. Reductive cleavage of the azo bond in AHPD and the complex followed using cytochrome c reductase (a model azo-reductase) as well as azo-reductase enzymes obtained from bacterial cell extracts. Degradation of the azo bond was less in the complex allowing us to correlate the observed cytotoxicity. Cyclic voltammetry on AHPD and the complex support observations of enzyme assay experiments. These were particularly useful in realizing the formation of amines as an outcome of the reductive cleavage of azo bonds in AHPD that could not be identified through...
Highlights
The azo bond enjoys a unique position in chemistry
For AHPD, 15 μL of 10−3 M solution in dimethyl sulfoxide (DMSO) was taken in a quartz cuvette to which 495 μL phosphate buffer was added while in case of Cu2(II)(AHPD)2(OAc)2 25 μL was used from a stock of 2 × 10−3 M in DMSO to which 485 μL phosphate buffer was added. 120 μL 0.5 M NaCl and 70 μL NADPH were added
Thermo gravimetric-differential thermal analysis was done on a Mettler Toledo thermo-gravimetric analysis (TGA)/SDTA 851 thermal analyzer. 1H NMR of AHPD was recorded on a Bruker Avance 300 NMR spectrometer
Summary
The azo bond enjoys a unique position in chemistry. If one were to consider a single functional moiety, it would be difficult to find another having such diverse applications [1,2,3,4,5]. Complexes of azo compounds were prepared, few have ventured further to see if complex formation was able to modulate the associated toxicity [23] It would definitely be better if modified forms of azo compounds (for example their complexes) could show similar utility and yet possess reduced toxicity. This could protect the work force involved in preparing such compounds and the end user [13,15,16]. This is important for we cannot do away with a lot of these compounds immediately, as they are extremely useful and a part of our daily routine. A Cu(II) complex was prepared and a comparative study on the reductive cleavage of the azo bond and action on bacterial cells was carried out
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