Synthesis and characterization of 5-amino-2-((3-hydroxy-4-((3-hydroxyphenyl) phenyl) diazenyl) phenol and its Cu(II) complex – a strategy toward developing azo complexes for reduction of cytotoxicity

Ganguly, Durba; Sarkar, Ratul; Santra, Ramesh Chandra; Deb, T. K.; Sen, Tuhinadri; Das, Saurabh

doi:10.1080/2164232x.2014.883287

Cited by 5 publications

(3 citation statements)

References 29 publications

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“…9 and 10). 52 The study showed that reductive ssion of the azo bond in the enzyme-catalyzed pathway was only slightly higher for HPAN than Cu (II) (HPAN) 2 . Fig.…”

Section: Assay Of Azo-reductase Activity For Hpan and Cu (Ii) (Hpan)mentioning

confidence: 94%

Enhancement of anti-leukemic potential of 2-hydroxyphenyl-azo-2′-naphthol (HPAN) on MOLT-4 cells through conjugation with Cu(ii)

Deb

Gopal²,

Ganguly

et al. 2014

RSC Adv.

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“…9 and 10). 52 The study showed that reductive ssion of the azo bond in the enzyme-catalyzed pathway was only slightly higher for HPAN than Cu (II) (HPAN) 2 . Fig.…”

Section: Assay Of Azo-reductase Activity For Hpan and Cu (Ii) (Hpan)mentioning

confidence: 94%

Enhancement of anti-leukemic potential of 2-hydroxyphenyl-azo-2′-naphthol (HPAN) on MOLT-4 cells through conjugation with Cu(ii)

Deb

Gopal²,

Ganguly

et al. 2014

RSC Adv.

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“…To have a more clear idea on amine formation, an electrochemical experiment was performed where HPIA was subjected to reduction at a constant potential. Reports indicate, amines undergo oxidation in the potential range 0.6–1.2 V ,. Cyclic voltammograms of solutions obtained after reduction of HPIA at constant potential (‐1.25 V) for 15, 30, 45 and 105 minutes respectively revealed the formation of a new oxidation peak at +1.3 V. This peak is not seen if HPIA is not reduced initially.…”

Section: Resultsmentioning

confidence: 99%

Anticancer Activity of a Complex of Cu^II with 2‐(2‐hydroxyphenylazo)‐indole‐3^/‐acetic Acid on three different Cancer Cell Lines: A Novel Feature for Azo Complexes

et al. 2017

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Toxicity of azo dyes and theirinteraction with biological systems has either been overlooked or not exploited properly. A CuII complex of 2‐(2‐hydroxyphenylazo)‐indole‐3/‐acetic acid (HPIA) was synthesized to see role of metal ions on azo toxicity. It was characterized with UV‐Vis, IR, EPR, mass spectrometry, elemental and thermogravimetric analysis. Evidence suggest formation of a bis‐azo complex with stability constant logβ=12.88. DFT calculations based on spectroscopic evidence suggest 1:2::CuII:HPIA complex. Enzyme assay on reductive cleavage of the azo bond shows complex forms less amines than HPIA. Binding of complex to DNA was similar to HPIA. As the complex restricts reduction of azo bond to toxic amines and has comparable binding with DNA it could be less cytotoxic. Cis and trans HPIA and the complex were treated to normal HEK293T cells; activity was comparable at low concentrations. When compounds were treated to human colon carcinomaHCT116 cells, ALL MOLT‐4 human leukemia cells and MCF‐7 breast cancer cells activity of the complex was better than cisor trans HPIA. The study revealed complex formation of HPIA with CuII targets carcinoma cellsmore than HPIA.

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“…16 Earlier, we demonstrated that an azo compound (AHPD) and its Cu II complex show antibacterial activity on Escherichia coli and Staphylococcus aureus and that complex formation was able to modulate cytotoxicity. 21 Such modulation is important to restrict toxic side effects associated with drug action. 22 The most discussed reason for azo-toxicity is the degradation of the azo bond forming primary amines and the ability of the compounds or of the amines to interact with cellular material.…”

Section: Introductionmentioning

confidence: 99%

Modification of the toxicity of an azo compound through complex formation help target bacterial strains

Deb¹,

Ganguly

Sen

et al. 2018

J Chem Sci

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The antibacterial efficacy of a Cu(II) complex of 2-hydroxyphenyl-azo-2-naphthol (HPAN) was studied on gram-positive Bacillus subtilis and gram-negative Escherichia coli. In vitro antimicrobial activity was determined by an agar-well diffusion assay and minimum inhibitory concentration. Cu II (HPAN) 2 was found to be better than HPAN in antibacterial activity. Although both bacterial strains succumbed to high concentrations of each compound, at low concentrations only Cu II (HPAN) 2 was active on B. subtilis. To explain the observations, reductive cleavage of the azo-bond to aromatic amines was followed by an in vitro enzyme assay using cell extracts of E. coli containing azo-reductase. Interaction of Cu II (HPAN) 2 with calf thymus DNA was compared with HPAN for correlation with antibacterial activity. Enzyme-assay on the reductive degradation of azo bond and DNA interaction do not individually explain trends observed in antibacterial activity. Comparable binding of Cu II (HPAN) 2 and HPAN with calf thymus DNA was attributed to the presence of anionic species of the complex in solution. Significant activity of the complex was probably due to effective cellular uptake of it by bacterial cells as shown by a fluorescence study. The activity of the complex resembled some established antimicrobial agents. Since the complex has a moiety, not common to most antibacterial agents, resistance towards it should be significantly less, hence an advantage.

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Synthesis and characterization of 5-amino-2-((3-hydroxy-4-((3-hydroxyphenyl) phenyl) diazenyl) phenol and its Cu(II) complex – a strategy toward developing azo complexes for reduction of cytotoxicity

Abstract: Synthesis and characterization of 5-amino-2-((3hydroxy-4-((3-hydroxyphenyl) phenyl) diazenyl) phenol and its Cu(II) complex-a strategy toward developing azo complexes for reduction of cytotoxicity

Cited by 5 publications

References 29 publications

Enhancement of anti-leukemic potential of 2-hydroxyphenyl-azo-2′-naphthol (HPAN) on MOLT-4 cells through conjugation with Cu(ii)

Enhancement of anti-leukemic potential of 2-hydroxyphenyl-azo-2′-naphthol (HPAN) on MOLT-4 cells through conjugation with Cu(ii)

Anticancer Activity of a Complex of Cu^II with 2‐(2‐hydroxyphenylazo)‐indole‐3^/‐acetic Acid on three different Cancer Cell Lines: A Novel Feature for Azo Complexes

Modification of the toxicity of an azo compound through complex formation help target bacterial strains

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Synthesis and characterization of 5-amino-2-((3-hydroxy-4-((3-hydroxyphenyl) phenyl) diazenyl) phenol and its Cu(II) complex – a strategy toward developing azo complexes for reduction of cytotoxicity

Abstract: Synthesis and characterization of 5-amino-2-((3hydroxy-4-((3-hydroxyphenyl) phenyl) diazenyl) phenol and its Cu(II) complex-a strategy toward developing azo complexes for reduction of cytotoxicity

Cited by 5 publications

References 29 publications

Enhancement of anti-leukemic potential of 2-hydroxyphenyl-azo-2′-naphthol (HPAN) on MOLT-4 cells through conjugation with Cu(ii)

Enhancement of anti-leukemic potential of 2-hydroxyphenyl-azo-2′-naphthol (HPAN) on MOLT-4 cells through conjugation with Cu(ii)

Anticancer Activity of a Complex of CuII with 2‐(2‐hydroxyphenylazo)‐indole‐3/‐acetic Acid on three different Cancer Cell Lines: A Novel Feature for Azo Complexes

Modification of the toxicity of an azo compound through complex formation help target bacterial strains

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Anticancer Activity of a Complex of Cu^II with 2‐(2‐hydroxyphenylazo)‐indole‐3^/‐acetic Acid on three different Cancer Cell Lines: A Novel Feature for Azo Complexes