TY - JOUR
T1 - High anticancer activity in short response time exhibited by a new azobenzene derivative and its copper complex
AU - Dev, Samrat
AU - Mitra, Debarpan
AU - Sinha, Chittaranjan
AU - Das, Gaurav
AU - Murmu, Nabendu
AU - Maity, Amit Ranjan
AU - Pandey, Souvik
N1 - Publisher Copyright:
© 2024 John Wiley & Sons Ltd.
PY - 2024/7/1
Y1 - 2024/7/1
N2 - o-Aminoazotoluene (OAT), capable of photoisomerization, and o-vanillin, a potent comutagen, have been used to synthesize a new ligand, HL, [C6H4(CH3)N=NC6H3(CH3)N=CHC6H3(OH)(OCH3)], which, upon complexation with copper(II), results in a new copper(II) complex-Cu(L)2, [Cu{C6H4(CH3)N=NC6H3(CH3)N=CHC6H3(OCH3)O}2]. Both HL and Cu(L)2 have been characterized by single-crystal X-ray diffraction measurements along with other analytical techniques, for example, IR spectroscopy, NMR spectroscopy, UV–Vis spectroscopy, elemental analysis and mass spectrometry. These compounds were tested with different in vitro anticancer assay as well as with in silico studies. A comparative study has been demonstrated on anticancer activity of HL and Cu(L)2 with the ligand HAZ, {C6H5N=NC6H4N=CHC6H3(OH)(OCH3)} and its Cu-complex, [Cu(AZ)2, Cu{C6H5N=NC6H4N=CHC6H3(OCH3)O}2]. The sensing properties of HAZ, along with the synthesis and structural properties of both HAZ and Cu(AZ)2, have been reported by our group earlier. Cytotoxicity measurements on MCF7 cell lines show that Cu(L)2 and Cu(AZ)2 have higher anticancer activity than their corresponding ligands. The apoptotic effect of Cu-complex was studied through nuclear fragmentation assay and AO/EB dual-staining assay on MCF7 cell line. The IC50 value of Cu(L)2 in 0.01% DMSO/water after 24-h treatment was found 4.2 μM, which is one of the lowest values with this response time compared to the other analogous anticancer compounds. Finally, we have evaluated the expression of hERα protein with respect to Cu-complexes, and it was observed that Cu(L)2 caused more down-regulation of hERα as compared to Cu(AZ)2.
AB - o-Aminoazotoluene (OAT), capable of photoisomerization, and o-vanillin, a potent comutagen, have been used to synthesize a new ligand, HL, [C6H4(CH3)N=NC6H3(CH3)N=CHC6H3(OH)(OCH3)], which, upon complexation with copper(II), results in a new copper(II) complex-Cu(L)2, [Cu{C6H4(CH3)N=NC6H3(CH3)N=CHC6H3(OCH3)O}2]. Both HL and Cu(L)2 have been characterized by single-crystal X-ray diffraction measurements along with other analytical techniques, for example, IR spectroscopy, NMR spectroscopy, UV–Vis spectroscopy, elemental analysis and mass spectrometry. These compounds were tested with different in vitro anticancer assay as well as with in silico studies. A comparative study has been demonstrated on anticancer activity of HL and Cu(L)2 with the ligand HAZ, {C6H5N=NC6H4N=CHC6H3(OH)(OCH3)} and its Cu-complex, [Cu(AZ)2, Cu{C6H5N=NC6H4N=CHC6H3(OCH3)O}2]. The sensing properties of HAZ, along with the synthesis and structural properties of both HAZ and Cu(AZ)2, have been reported by our group earlier. Cytotoxicity measurements on MCF7 cell lines show that Cu(L)2 and Cu(AZ)2 have higher anticancer activity than their corresponding ligands. The apoptotic effect of Cu-complex was studied through nuclear fragmentation assay and AO/EB dual-staining assay on MCF7 cell line. The IC50 value of Cu(L)2 in 0.01% DMSO/water after 24-h treatment was found 4.2 μM, which is one of the lowest values with this response time compared to the other analogous anticancer compounds. Finally, we have evaluated the expression of hERα protein with respect to Cu-complexes, and it was observed that Cu(L)2 caused more down-regulation of hERα as compared to Cu(AZ)2.
KW - anticancer activity
KW - azo derivative ligand
KW - copper complex
KW - copper-azo complex
KW - organometallic chemistry
UR - http://www.scopus.com/inward/record.url?scp=85193538163&partnerID=8YFLogxK
U2 - 10.1002/aoc.7510
DO - 10.1002/aoc.7510
M3 - Article
AN - SCOPUS:85193538163
SN - 0268-2605
VL - 38
JO - Applied Organometallic Chemistry
JF - Applied Organometallic Chemistry
IS - 7
M1 - e7510
ER -
