Syntheses, spectral characterization, X-ray studies and in vitro cytotoxic activities of triorganotin(IV) derivatives of p-substituted N-methylbenzylaminedithiocarbamates

Naqeebullah Khan, Yang Farina Abdul Aziz, Lo Kong Mun, Nor Fadilah Rajab, Normah Awang

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21 Citations (Scopus)

Abstract

Two new organotin(IV) complexes of the type R3SnL, where (L = p-bromo-N-methylbenzylaminedithiocarbamate and p-fluoro-N-methylbenzylaminedithiocarbamate, and R = phenyl) have been synthesized in 1:1 molar ratio with good yields and isolated as crystalline solids. The newly synthesized compounds gave fairly sharp melting points indicating that the compounds were pure. A systematic investigation of the derivatives were carried out both in solid and in solution and were suitably characterized by elemental analysis, FT-IR, 1H, 13C, 119Sn NMR spectroscopies. The dithiocarbamate ligands chelated to the tin metal monodentately using only one sulfur atom showing a pair of bands due to ν(CS) below 1000 cm-1. This phenomenon was supported by the occurrence of new medium to weak absorptions in the region 411-545, in the spectra of complexes, assigned to ν(SnS) and ν(SnC). The crystal structures of the two triorganotin(IV) complexes have been determined by X-ray crystallography. Both the complexes crystallized in the monoclinic, P2(1)/n space group. The spectral investigations and single crystal X-ray diffraction data illustrate that the two dithiocarbamato ligands in the triphenyltin(IV) derivatives 1 and 2 are monodentate and the geometry at tin is best described as a distorted tetrahedron. The in vitro antiproliferative tests of these two derivatives on three human cell lines, leukemic lymphoblastoma Jurkat cells, lymphoblastoma K-562 cells, hepatoblastoma HepG2 cells and one mouse fibroblast cells L929 show dose-dependent decrease of cell proliferation in all cell lines.

Original languageEnglish
Pages (from-to)403-410
Number of pages8
JournalJournal of Molecular Structure
Volume1076
DOIs
Publication statusPublished - 5 Nov 2014

Fingerprint

Tin
Cells
Derivatives
X rays
Ligands
X ray crystallography
Cell proliferation
Fibroblasts
Sulfur
Nuclear magnetic resonance spectroscopy
Melting point
Crystal structure
Metals
Single crystals
Crystalline materials
X ray diffraction
Atoms
Geometry
Chemical analysis
triphenyltin

Keywords

  • Cytotoxicity
  • NMR
  • Triorganotin(IV) complexes
  • X-ray diffraction

ASJC Scopus subject areas

  • Spectroscopy
  • Analytical Chemistry
  • Inorganic Chemistry
  • Organic Chemistry

Cite this

@article{33a07a4abcf348afbff3101be37e76ee,
title = "Syntheses, spectral characterization, X-ray studies and in vitro cytotoxic activities of triorganotin(IV) derivatives of p-substituted N-methylbenzylaminedithiocarbamates",
abstract = "Two new organotin(IV) complexes of the type R3SnL, where (L = p-bromo-N-methylbenzylaminedithiocarbamate and p-fluoro-N-methylbenzylaminedithiocarbamate, and R = phenyl) have been synthesized in 1:1 molar ratio with good yields and isolated as crystalline solids. The newly synthesized compounds gave fairly sharp melting points indicating that the compounds were pure. A systematic investigation of the derivatives were carried out both in solid and in solution and were suitably characterized by elemental analysis, FT-IR, 1H, 13C, 119Sn NMR spectroscopies. The dithiocarbamate ligands chelated to the tin metal monodentately using only one sulfur atom showing a pair of bands due to ν(CS) below 1000 cm-1. This phenomenon was supported by the occurrence of new medium to weak absorptions in the region 411-545, in the spectra of complexes, assigned to ν(SnS) and ν(SnC). The crystal structures of the two triorganotin(IV) complexes have been determined by X-ray crystallography. Both the complexes crystallized in the monoclinic, P2(1)/n space group. The spectral investigations and single crystal X-ray diffraction data illustrate that the two dithiocarbamato ligands in the triphenyltin(IV) derivatives 1 and 2 are monodentate and the geometry at tin is best described as a distorted tetrahedron. The in vitro antiproliferative tests of these two derivatives on three human cell lines, leukemic lymphoblastoma Jurkat cells, lymphoblastoma K-562 cells, hepatoblastoma HepG2 cells and one mouse fibroblast cells L929 show dose-dependent decrease of cell proliferation in all cell lines.",
keywords = "Cytotoxicity, NMR, Triorganotin(IV) complexes, X-ray diffraction",
author = "Naqeebullah Khan and {Abdul Aziz}, {Yang Farina} and Mun, {Lo Kong} and Rajab, {Nor Fadilah} and Normah Awang",
year = "2014",
month = "11",
day = "5",
doi = "10.1016/j.molstruc.2014.08.015",
language = "English",
volume = "1076",
pages = "403--410",
journal = "Journal of Molecular Structure",
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TY - JOUR

T1 - Syntheses, spectral characterization, X-ray studies and in vitro cytotoxic activities of triorganotin(IV) derivatives of p-substituted N-methylbenzylaminedithiocarbamates

AU - Khan, Naqeebullah

AU - Abdul Aziz, Yang Farina

AU - Mun, Lo Kong

AU - Rajab, Nor Fadilah

AU - Awang, Normah

PY - 2014/11/5

Y1 - 2014/11/5

N2 - Two new organotin(IV) complexes of the type R3SnL, where (L = p-bromo-N-methylbenzylaminedithiocarbamate and p-fluoro-N-methylbenzylaminedithiocarbamate, and R = phenyl) have been synthesized in 1:1 molar ratio with good yields and isolated as crystalline solids. The newly synthesized compounds gave fairly sharp melting points indicating that the compounds were pure. A systematic investigation of the derivatives were carried out both in solid and in solution and were suitably characterized by elemental analysis, FT-IR, 1H, 13C, 119Sn NMR spectroscopies. The dithiocarbamate ligands chelated to the tin metal monodentately using only one sulfur atom showing a pair of bands due to ν(CS) below 1000 cm-1. This phenomenon was supported by the occurrence of new medium to weak absorptions in the region 411-545, in the spectra of complexes, assigned to ν(SnS) and ν(SnC). The crystal structures of the two triorganotin(IV) complexes have been determined by X-ray crystallography. Both the complexes crystallized in the monoclinic, P2(1)/n space group. The spectral investigations and single crystal X-ray diffraction data illustrate that the two dithiocarbamato ligands in the triphenyltin(IV) derivatives 1 and 2 are monodentate and the geometry at tin is best described as a distorted tetrahedron. The in vitro antiproliferative tests of these two derivatives on three human cell lines, leukemic lymphoblastoma Jurkat cells, lymphoblastoma K-562 cells, hepatoblastoma HepG2 cells and one mouse fibroblast cells L929 show dose-dependent decrease of cell proliferation in all cell lines.

AB - Two new organotin(IV) complexes of the type R3SnL, where (L = p-bromo-N-methylbenzylaminedithiocarbamate and p-fluoro-N-methylbenzylaminedithiocarbamate, and R = phenyl) have been synthesized in 1:1 molar ratio with good yields and isolated as crystalline solids. The newly synthesized compounds gave fairly sharp melting points indicating that the compounds were pure. A systematic investigation of the derivatives were carried out both in solid and in solution and were suitably characterized by elemental analysis, FT-IR, 1H, 13C, 119Sn NMR spectroscopies. The dithiocarbamate ligands chelated to the tin metal monodentately using only one sulfur atom showing a pair of bands due to ν(CS) below 1000 cm-1. This phenomenon was supported by the occurrence of new medium to weak absorptions in the region 411-545, in the spectra of complexes, assigned to ν(SnS) and ν(SnC). The crystal structures of the two triorganotin(IV) complexes have been determined by X-ray crystallography. Both the complexes crystallized in the monoclinic, P2(1)/n space group. The spectral investigations and single crystal X-ray diffraction data illustrate that the two dithiocarbamato ligands in the triphenyltin(IV) derivatives 1 and 2 are monodentate and the geometry at tin is best described as a distorted tetrahedron. The in vitro antiproliferative tests of these two derivatives on three human cell lines, leukemic lymphoblastoma Jurkat cells, lymphoblastoma K-562 cells, hepatoblastoma HepG2 cells and one mouse fibroblast cells L929 show dose-dependent decrease of cell proliferation in all cell lines.

KW - Cytotoxicity

KW - NMR

KW - Triorganotin(IV) complexes

KW - X-ray diffraction

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U2 - 10.1016/j.molstruc.2014.08.015

DO - 10.1016/j.molstruc.2014.08.015

M3 - Article

AN - SCOPUS:84906966296

VL - 1076

SP - 403

EP - 410

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

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