Influence of chirality of V(V) Schiff base complexes on DNA, BSA binding and cleavage activity

• Published in: European journal of medicinal chemistry Vol. 46; no. 10; pp. 5074 - 5085
• Main Authors: Khan, Noor-ul H., Pandya, Nirali, Maity, Nabin Ch, Kumar, Manoj, Patel, Rajesh M., Kureshy, Rukhsana I., Abdi, Sayed H.R., Mishra, Sandhya, Das, Satyabrata, Bajaj, Hari C.
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Masson SAS 01-10-2011; Elsevier
• Subjects: Animals; Antineoplastic agents; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Biological and medical sciences; BSA cleavage; Cattle; Cell Survival - drug effects; Chiral Schiff base complexes; Circular Dichroism; Coordination Complexes - chemistry; Coordination Complexes - pharmacology; Crystal structure; Crystallography, X-Ray; Cytotoxicity assay; DNA - metabolism; DNA binding; DNA cleavage; DNA Cleavage - drug effects; General aspects; Hep G2 Cells; Humans; Medical sciences; Models, Molecular; Neoplasms - drug therapy; Pharmacology. Drug treatments; Protein Binding - drug effects; Schiff Bases - chemistry; Schiff Bases - pharmacology; Serum Albumin, Bovine - metabolism; Stereoisomerism; Vanadium - chemistry; Vanadium - pharmacology; T m; CD; SDS; TLC; Chiral Schiff base complexes; DNA binding; ds DNA; SC; Cytotoxicity assay; BSA; CT-DNA; NC; DNA cleavage; BSA cleavage; EB; Crystal structure; Cytotoxicity; Thermal denaturation; Stability constant; Serum albumin; Transition metal Complexes; Imine; Serum protein; Biological activity; Oxo complex; Schiff base; Biological fixation; Chirality; DNA; Cleavage; Thermodynamic properties; Vanadyl Complexes; Crystalline structure
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2011.08.020

New chiral V(V) Schiff base complexes (
S)-[VO(OMe)
L] and (
R)-[VO(OMe)
L] were synthesized and characterized by microanalysis, infrared (IR), UV–Visible, Circular dichroism (CD) spectroscopy and single crystal X-ray studies. The interaction of these complexes with calf thymus (CT) DNA and bovine serum albumin (BSA) protein showed chiral expression DNA/protein binding strength. The influence of chirality was also observed in cytotoxicity assay of Hep 2 cells. (
R)-[VO(OMe)
L] enantiomer exhibited higher binding constant (5 ± 1 × 10
5 M
−1) as compared to (
S)-[VO(OMe)
L] (8 ± 1 × 10
4 M
−1). The fluorescence quenching, thermal melting and viscosity data suggest DNA surface and/or groove binding nature of the complexes and electrophoresis studies also showed greater activity for (
R)-[VO(OMe)
L] in cleaving DNA and protein as against (
S)-[VO(OMe)
L].
The interaction of chiral Schiff base complexes with DNA and protein was investigated with a goal to examine the effect of chirality in metal complex vis-à-vis DNA/protein binding strength.
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► The novel chiral vanadium (V) Schiff base complexes were synthesized. ► Influence of chirality on DNA interaction and anticancer activity were evaluated. ►
R enantiomer of complex interacted more strongly with DNA. ►
R enantiomer of complex cleave DNA and protein stronger than
S enantiomer. ► Chiral vanadium complexes showed anticancer activity against Hep2 cell line.