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DNA binding and in vitro anticancer activity of 2‐((1 H ‐benzimidazol‐2‐yl)methylamino)acetic acid and its copper(II) mixed‐polypyridyl complexes: Synthesis and crystal structure
Author(s) -
Sabithakala Thatituri,
Chittireddy Venkata Ramana Reddy
Publication year - 2018
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4550
Subject(s) - chemistry , stereochemistry , ligand (biochemistry) , docking (animal) , square pyramidal molecular geometry , crystallography , hydrogen bond , dna , crystal structure , molecule , organic chemistry , receptor , biochemistry , medicine , nursing
New copper(II) ternary complexes formulated as [Cu(N‐N)BIG]ClO 4 , where BIG is deprotonated 2‐((1 H ‐benzimidazol‐2‐yl)methylamino)acetic acid and N‐N represents 2,2′‐bipyridine ( 1 ) or 4,4′‐dimethyl‐2,2′‐bipyridine ( 2 ) or 5,5′‐dimethyl‐2,2′‐bipyridine ( 3 ) or 1,10‐phenanthroline ( 4 ) or 4,5‐diazafluoren‐9‐one ( 5 ) or dipyridylamine ( 6 ), were synthesized and characterized using analytical and spectral methods. Complex 1 was characterized using single‐crystal X‐ray diffraction analysis and found to be monomeric in nature with distorted square pyramidal geometry. The binding interactions of 1 – 6 with calf thymus DNA were studied using UV–visible absorption and emission spectroscopy and viscosity measurements. The DNA cleavage ability of 1 – 6 with pUC19 DNA shows that the complexes can cleave DNA without any external agents. The ligand and complexes were investigated for their in vitro antibacterial activity against Bacillus subtilis and Staphylococcus aureus . The complexes showed enhanced antibacterial activities compared to the free ligand. Molecular docking studies of complexes 1 – 6 were made using Genetic Optimization of Ligand Docking (GOLD) software. The study indicated that LEU23, ASP25, ILE84, ASN144 and ARG87 of COX‐2 were important for strong hydrogen bonding interaction with the complexes. Among the complexes, 2 showed the best docking result with COX‐2. Cytotoxicity assay was performed using MTT reagent against human cervical cancer cells, human breast cancer cells and human lung cancer cells. The complexes were found to show moderate anticancer activity.