title: In vitro DNA binding, pBR322 plasmid cleavage and molecular modeling study of chiral benzothiazole Schiff-base-valine Cu(II) and Zn(II) complexes to evaluate their enantiomeric biological disposition for molecular target DNA.
abstract: Bicyclic heterocyclic compounds viz. benzothiazoles are key components of deoxyribonucleic acid (DNA) molecules and participate directly in the encoding of genetic information. Benzothiazoles, therefore, represent a potent and selective class of antitumor compounds. The design and synthesis of chiral antitumor chemotherapeutic agents of Cu(II) and Zn(II), L- and -D benzothiazole Schiff base-valine complexes 1a &b and 2a &b, respectively were carried out and thoroughly characterized by spectroscopic and analytical techniques. Interaction of 1a and b and 2a and b with CT DNA by employing UV-vis, florescence, circular dichroic methods and cleavage studies of 1a with pBR322 plasmid, molecular docking were done in order to demonstrate their enantiomeric disposition toward the molecular drug target DNA. Interestingly, these studies unambiguously demonstrated the greater potency of L-enantiomer in comparison to D-enantiomer.
authors.affiliation: Department of Chemistry, Aligarh Muslim University, Aligarh 202002, India.
authors.forename: Rahman
authors.initials: R
authors.lastname: Alizadeh
authors.affiliation: Department of Chemistry, Aligarh Muslim University, Aligarh 202002, India.
authors.forename: Mohd
authors.initials: M
authors.lastname: Afzal
authors.affiliation: Department of Chemistry, Aligarh Muslim University, Aligarh 202002, India. Electronic address: farukh_arjmand@yahoo.co.in.
authors.forename: Farukh
authors.initials: F
authors.lastname: Arjmand
mesh_terms: D000818:Animals; D052160:Benzothiazoles / Q000737:chemistry / Q000494:pharmacology*; D002417:Cattle; D056831:Coordination Complexes / Q000737:chemistry / Q000494:pharmacology*; D003300:Copper / Q000737:chemistry / Q000494:pharmacology*; D004247:DNA / Q000378:metabolism*; D008958:Models, Molecular; D062105:Molecular Docking Simulation; D010957:Plasmids / Q000378:metabolism*; D012545:Schiff Bases / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D014633:Valine / Q000031:analogs & derivatives / Q000494:pharmacology; D015032:Zinc / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D052160:Benzothiazoles; D056831:Coordination Complexes; D012545:Schiff Bases; D003300:Copper; D004247:DNA; C427203:calf thymus DNA; C005465:benzothiazole; D014633:Valine; D015032:Zinc
keywords: Binding studies; Chiral Cu(II)/Zn(II) benzothiazole-valine complexes; Enantiomeric discrimination with DNA; Molecular docking studies