Synthesis, crystal structures and characterization of late first row transition metal complexes derived from benzothiazole core: anti-tuberculosis activity and special emphasis on DNA binding and cleavage property.
Air and moisture stable coordination compounds of late first row transition metals, viz. Co(II), Ni(II), Cu(II) and Zn(II), with a newly designed ligand, 2-(2-benzo[d]thiazol-2-yl)hydrazono)propan-1-ol (LH), were prepared and successfully characterized using various spectro-analytical techniques. The molecular structures of the ligand and nickel complex were unambiguously determined by single-crystal X-ray diffraction method. The [Ni(LH)2]Cl2.3H2O complex is stabilized by intermolecular CH⋯π stacking interactions between the methyl hydrogen and the C18 atom of the phenyl ring (C11-H11B⋯C18) forming 1D zig-zag chain structure. Both, the ligand and its copper complex, were electrochemically active in the working potential range, showing quasi-reversible redox system. The interactions of all the compounds with calf thymus DNA have been comprehensively investigated using electronic absorption spectroscopy, viscosity, electrochemistry and thermal denaturation studies. The cleavage reaction on pBR322 DNA has been monitored by agarose gel electrophoresis. The results showed that the ligand can bind to CT-DNA through partial intercalation, whereas the complexes bind electrostatically. Further, [Ni(LH)2]Cl2.3H2O and [CuLCl(H2O)2] complexes in the series have high binding and cleavage affinity towards pBR322 DNA. Additionally, all the compounds were screened for anti-tuberculosis activity. All the complexes revealed an MIC value of 0.8 μg/mL, which is almost 8 times active than standard used (Streptomycin, 6.25 μg/mL).
Department of Chemistry, Karnatak University, Pavate Nagar, Dharwad 580 003, Karnataka, India.
Priya P
PP
Netalkar
Department of Chemistry, Karnatak University, Pavate Nagar, Dharwad 580 003, Karnataka, India.
Sandeep P
SP
Netalkar
The School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
Srinivasa
S
Budagumpi
Department of Chemistry, Karnatak University, Pavate Nagar, Dharwad 580 003, Karnataka, India. Electronic address: vkrevankar@rediffmail.com.
Vidyanand K
VK
Revankar
D000818:Animals; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D052160:Benzothiazoles / Q000737:chemistry*; D001665:Binding Sites; D002417:Cattle; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004247:DNA / Q000737:chemistry*; D053837:DNA Cleavage; D008958:Models, Molecular; D015394:Molecular Structure; D010957:Plasmids; D013329:Structure-Activity Relationship; D028561:Transition Elements / Q000737:chemistry*
D000995:Antitubercular Agents; D052160:Benzothiazoles; D056831:Coordination Complexes; D028561:Transition Elements; D004247:DNA; C005465:benzothiazole
DNA binding; NNO donor ligand; Transition metal complex; X-ray diffraction