title: Synthesis, characterization and crystal structure of organotin(IV) N-butyl-N-phenyldithiocarbamate compounds and their cytotoxicity in human leukemia cell lines.
abstract: Organotin complexes are recognized as the biologically active compounds in inducing cancerous cells death at very low doses. To date, organotin compounds currently appear among the most potent candidates in research related to the new anticancer drugs. In this study, new organotin(IV) N-butyl-N-phenyldithiocarbamate compounds have been successfully synthesized between the reaction of N-butylaniline amine with organotin(IV) chloride in 1:2/1:1 molar ratio. All compounds were characterized using the elemental analysis, FT-IR and NMR spectroscopy. The single crystal structure was determined by X-ray single crystal analysis. The elemental analysis showed good agreement with the suggested formula (C4H9)2Sn[S2CN(C4H9)(C6H5)]2 (Compound 1 and 2), (C6H5)2Sn[S2CN(C4H9)(C6H5)]2 (Compound 3) and (C6H5)3Sn[S2CN(C4H9)(C6H5)] (Compound 4). The important infrared absorbance peaks, v (C = N) and v(C = S) were detected in range between 1457-1489 cm(-1) and 951-996 cm(-1), respectively. The chemical shift of carbon in NCS2 group obtained from 13C NMR was found in range 198.86-203.53 ppm. The crystal structure of compound 4 showed that the dithiocarbamate ligand coordinates in a monodentate fashion. It crystallized in monoclinic P2(1)/n space group with the crystal cell parameter: a = 10.0488(1) angstroms, b = 18.0008(2) angstroms, c = 15.2054(2) angstroms, beta = 102.442(1) degrees and R = 0.044. The cytotoxicity (IC50) of these compounds against Jurkat E6.1 and K-562 leukemia cells were in the range between 0.4-0.8 and 1.8-5.3 microM, respectively as assessed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazholium bromide (MTT) assay. In conclusion, our study demonstrate that all compounds showed potent cytotoxicity towards both cell lines tested with the triphenyltin(IV) compound displayed the greatest effect.
authors.affiliation: Biomedical Science Programme, Faculty of Health Sciences, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abdul Aziz, 50300 Kuala Lumpur, Malaysia.
authors.forename: Nurul Farahana
authors.initials: NF
authors.lastname: Kamaludin
authors.forename: Normah
authors.initials: N
authors.lastname: Awang
authors.forename: Ibrahim
authors.initials: I
authors.lastname: Baba
authors.forename: Asmah
authors.initials: A
authors.lastname: Hamid
authors.forename: Chan Kok
authors.initials: CK
authors.lastname: Meng
mesh_terms: D018360:Crystallography, X-Ray; D006801:Humans; D019169:Jurkat Cells; D009682:Magnetic Resonance Spectroscopy; D009947:Organotin Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017550:Spectroscopy, Fourier Transform Infrared; D013859:Thiocarbamates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D009947:Organotin Compounds; D013859:Thiocarbamates