Synthesis, Molecular Docking, DNA Binding and Anticancer Studies of Transition Metal Complex of N'-[Phenylmethylidene]-1,3-Benzothiazole-2-Carbohydrazone

Posted: 4 Feb 2020

See all articles by Sudeepa Kunche

Sudeepa Kunche

Nizam College

Sree Kanth S

Nizam College Osmania University

Narsimha N

Department of Chemistry UCS Osmania University

Ravi MUDAVATH

Department of Chemistry UCS Osmania University

Sarala Devi Ch

Department of Chemistry UCS Osmania University

Date Written: February 1, 2020

Abstract

Deoxyribonucleic acid (DNA) is the molecular target for a number of clinically useful anticancer and antimicrobial drugs. Metallointercalators are the most extensively studied group of molecules as DNA intercalators. Transition metals complexed with aromatic organic compounds that can make a significant Arene-nucleobase stacking interaction can have a considerable antimicrobial and anticancer activity. In the present work we report design, synthesis, molecular docking, cytotoxicity and DNA binding studies of N'-[Phenylmethylidene]-1,3-benzothiazole-2-carbohydrazone (PMBC) and its Cu(II), Ni(II), Co(II) and Zn(II) metal complexes. The quantum chemical calculations of the title compounds were carried out using HyperChem 7.5 to obtain eigen values for molecular orbitals (HOMO and LUMO) of geometry optimized molecular structure of ligand. The computed data is informative to understand possible donor sites in PMBC that can bind with metal ions in the formation of metal complexes. The synthesized complexes were characterized by various spectro-analytical techniques and plausible structure was elucidated. Autodock 4.0 was used to dock the metal complexes into the interacalative site of DNA, and there binding affinity were estimated which were further determined experimentally by Absorption and Fluorescence studies with CT-DNA. The Kb values estimated by both absorption and fluorescence titrations were in good agreement and follow the order Zn(II)-PMBC > Ni(II) PMBC > Cu(II) PMBC > Co(II)-PMBC. Experimental binding affinity values were also corroborating with molecular docking results which provided further evidence of intercalation. Antitumor activity of ligand and its corresponding complexes against Hela Cervical cancer cell line by MTT reduction assay revealed zinc complex exhibits more anti-proliferative activity than PMBC and other complexes.

Keywords: Hydrazone and its complexes, DNA binding, Antitumor activity, Antimicrobial activity, Docking

Suggested Citation

Kunche, Sudeepa and Sivan, Sree Kanth and Nagula, Narsimha and MUDAVATH, RAVI and Ch, Sarala Devi, Synthesis, Molecular Docking, DNA Binding and Anticancer Studies of Transition Metal Complex of N'-[Phenylmethylidene]-1,3-Benzothiazole-2-Carbohydrazone (February 1, 2020). Proceedings of International Conference on Drug Discovery (ICDD) 2020, Available at SSRN: https://ssrn.com/abstract=3529839

Sudeepa Kunche (Contact Author)

Nizam College ( email )

Basheerbagh
Hyderabad, 500001
India

Sree Kanth Sivan

Nizam College Osmania University ( email )

Basheerbagh
Hyderabad
Hyderabad, 500001
India

Narsimha Nagula

Department of Chemistry UCS Osmania University ( email )

Tarnaka
Osmania University
Hyderabad, 500007
India

RAVI MUDAVATH

Department of Chemistry UCS Osmania University ( email )

Tarnaka
Osmania University
Hyderabad, 500007
India

Sarala Devi Ch

Department of Chemistry UCS Osmania University ( email )

Tarnaka
Osmania University
Hyderabad, 500007
India

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