title: Phenolate based metallomacrocyclic xanthate complexes of Co(II)/Cu(II) and their exclusive deployment in [2 : 2] binuclear N,O-Schiff base macrocycle formation and in vitro anticancer studies.
abstract: Potassium salts of phenolate based polydentate xanthate ligands 4,4'-bis(2-dithiocarbonatobenzylideneamino)diphenyl ether () and 4,4'-bis(2-dithiocarbonatonaphthylmethylideneamino)diphenyl ether () have been synthesized and characterized, prior to use. The reaction of or with M(OAc)2 in Et3N affords access to a rare series of binuclear metallomacrocyclic xanthate complexes of the type [M2-μ(2)-bis-(κ(2)S,S-xan(1)/xan(2))] () which quickly forms [2 : 2] binuclear N,O-bidentate Schiff base macrocyclic complexes of the type [M2-μ(2)-bis-(κ(2)N,O-L(1)/L(2))] ( = 4,4'-bis(2-hydroxybenzylideneamino)diphenyl ether, = 4,4'-bis(2-hydroxynaphthylmethylidene-amino)diphenyl ether) via evolution of CS2 in solution. The compounds were characterized by microanalysis, relevant spectroscopy (FT-IR, UV-visible), mass spectrometry (ESI-MS), and powder and single crystal XRD techniques. In vitro anticancer activity of all the compounds was evaluated against HEP 3B (hepatoma) and IMR 32 (neuroblastoma) by the MTT assay. Remarkably, the binuclear copper(ii) xanthate complexes were found to be extremely active against both the cell lines (IC50: 8.1 ± 0.8 μM (), 8.8 ± 1.7 μM () against HEP 3B and 1.9 ± 0.3 μM () and 7.3 ± 0.6 μM () against IMR 32) and this projects them as good candidates for potent antitumor agents and the IC50 values confirm their better potency than the reference drug cisplatin. The flow-cytometric density plot illustrates the induction of apoptosis in HEP 3B and IMR 32 cells after treatment with , , , and .
authors.affiliation: Department of Chemistry, Faculty of Science, The M. S. University of Baroda, Vadodara-390 002, India. vinay.singh-chem@msu.ac.in.
authors.forename: Vinay K
authors.initials: VK
authors.lastname: Singh
authors.affiliation: Department of Chemistry, Faculty of Science, The M. S. University of Baroda, Vadodara-390 002, India. vinay.singh-chem@msu.ac.in.
authors.forename: Rahul
authors.initials: R
authors.lastname: Kadu
authors.affiliation: Department of Zoology, Faculty of Science, The M. S. University of Baroda, Vadodara-390 002, India.
authors.forename: Hetal
authors.initials: H
authors.lastname: Roy
authors.affiliation: Department of Chemistry, Dr. Harisingh Gour University, Sagar-470003, India.
authors.forename: Pallepogu
authors.initials: P
authors.lastname: Raghavaiah
authors.affiliation: Department of Chemistry, Indian Institute of Technology Indore-452 017, India.
authors.forename: Shaikh M
authors.initials: SM
authors.lastname: Mobin
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D003035:Cobalt / Q000737:chemistry / Q000494:pharmacology*; D003300:Copper / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010636:Phenols / Q000737:chemistry / Q000494:pharmacology*; D012545:Schiff Bases / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D047028:Macrocyclic Compounds; D009942:Organometallic Compounds; D010636:Phenols; D012545:Schiff Bases; D003035:Cobalt; D003300:Copper