Synthesis and characterization of organotin(IV) N-benzyl-N-isopropyldithiocarbamate compounds

Cytotoxic assay on human hepatocarcinoma cells (HepG2)

Normah Awang, Ibrahim Baba, Nor Syaidatul Akmal Mohd Yousof, Kamaludin Nurul Farahana

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Problem statement: Several studies on organotin(IV) dithiocarbamate compounds have been carried out but not on the synthesis and characterization together with cytotoxic assay of organotin(IV) N-benzyl-N-isopropyldithiocarbamate compounds. Approach: Three new organotin(IV) compounds of type N-benzyl-N-isopropyldithiocarbamate have been successfully synthesized by direct reaction between secondary amine with organotin(IV) chloride using in situ method. All the compounds were characterized using elemental analysis, gravimetric analysis, infrared spectroscopy and Nuclear Magnetic Resonance (NMR) spectroscopy. Results: Elemental and gravimetric analyses data of these compounds showed that agreed with the predicted formula, (CH3)2Sn[S2CN(C7H7)(i-C3H7)]2 (1), (C4H9)2Sn[S2CN(C7H7)(i-C3H7)]2 (2) and (C6H5)3Sn[S2CN(C7H7)(i-C3H7)] (3). The infrared spectra of these compounds showed the thioureide bond, v(C=N) which occurred at 1438-1440 cm-1 and the v(C=S) band appeared in the range of 967-973 cm-1. The presence of the v(C=N) and v(C=S) bands in the infrared spectra confirmed the presence of dithiocarbamate ligand in that compounds. The bond between sulphur and tin atom were supported with the presence of peak in the range of 365-445 cm-1 that known to be as stretching mode of v(Sn-S). The most important signal in the 13C NMR spectra was the chemical shift of NCS2 group. The 13C NMR spectra of these compound showed a chemical shift in 195.06-202.65 ppm range, which is attributed to the carbon atom of NCS2 group. The crystal structure of compound 2 (dibutyltin(IV) N-benzyl-N-isopropyldithiocarbamate) has been determined by X-ray single crystal analysis, which shows unsymmetrical nature of the ligand towards coordination to tin. It crystallizes in triclinic P1 space group with the crystal cell parameter: a = 17.7745 (2) (Å), b = 19.5463 (3) (Å), c = 26.2062 (4) (Å), α = 102.5254 (7)°, β = 95.1492 (7)°, γ = 110.2569 (8)°, Z = 10, V (Å3) = 8202.1 (2) and R = 0.028. In addition, these compounds were screened for their cytotoxic activity on Human Hepatocarcinoma Cells (HepG2). Based on the cytotoxic activity, compounds 2 and 3 showed cytotoxic activity but compound 1 is inactive against HepG2 cells. Conclusion: The results of this study showed that the studied compounds might indeed be potential sources of anticancer agents and these would further enable us to evaluate their utility in biomedical field.

Original languageEnglish
Pages (from-to)1047-1052
Number of pages6
JournalAmerican Journal of Applied Sciences
Volume7
Issue number8
Publication statusPublished - 2010

Fingerprint

Tin
Chemical shift
Assays
Nuclear magnetic resonance
Ligands
Infrared radiation
Atoms
Gravimetric analysis
Sulfur
Antineoplastic Agents
Nuclear magnetic resonance spectroscopy
Stretching
Amines
Chlorides
Infrared spectroscopy
Carbon
Crystal structure
Single crystals
X rays
Crystals

Keywords

  • Cytotoxic
  • Dithiocarbamate
  • NMR
  • Organotin
  • X-ray

ASJC Scopus subject areas

  • General

Cite this

@article{e79ed4e823ae4758ae0436f26065d795,
title = "Synthesis and characterization of organotin(IV) N-benzyl-N-isopropyldithiocarbamate compounds: Cytotoxic assay on human hepatocarcinoma cells (HepG2)",
abstract = "Problem statement: Several studies on organotin(IV) dithiocarbamate compounds have been carried out but not on the synthesis and characterization together with cytotoxic assay of organotin(IV) N-benzyl-N-isopropyldithiocarbamate compounds. Approach: Three new organotin(IV) compounds of type N-benzyl-N-isopropyldithiocarbamate have been successfully synthesized by direct reaction between secondary amine with organotin(IV) chloride using in situ method. All the compounds were characterized using elemental analysis, gravimetric analysis, infrared spectroscopy and Nuclear Magnetic Resonance (NMR) spectroscopy. Results: Elemental and gravimetric analyses data of these compounds showed that agreed with the predicted formula, (CH3)2Sn[S2CN(C7H7)(i-C3H7)]2 (1), (C4H9)2Sn[S2CN(C7H7)(i-C3H7)]2 (2) and (C6H5)3Sn[S2CN(C7H7)(i-C3H7)] (3). The infrared spectra of these compounds showed the thioureide bond, v(C=N) which occurred at 1438-1440 cm-1 and the v(C=S) band appeared in the range of 967-973 cm-1. The presence of the v(C=N) and v(C=S) bands in the infrared spectra confirmed the presence of dithiocarbamate ligand in that compounds. The bond between sulphur and tin atom were supported with the presence of peak in the range of 365-445 cm-1 that known to be as stretching mode of v(Sn-S). The most important signal in the 13C NMR spectra was the chemical shift of NCS2 group. The 13C NMR spectra of these compound showed a chemical shift in 195.06-202.65 ppm range, which is attributed to the carbon atom of NCS2 group. The crystal structure of compound 2 (dibutyltin(IV) N-benzyl-N-isopropyldithiocarbamate) has been determined by X-ray single crystal analysis, which shows unsymmetrical nature of the ligand towards coordination to tin. It crystallizes in triclinic P1 space group with the crystal cell parameter: a = 17.7745 (2) ({\AA}), b = 19.5463 (3) ({\AA}), c = 26.2062 (4) ({\AA}), α = 102.5254 (7)°, β = 95.1492 (7)°, γ = 110.2569 (8)°, Z = 10, V ({\AA}3) = 8202.1 (2) and R = 0.028. In addition, these compounds were screened for their cytotoxic activity on Human Hepatocarcinoma Cells (HepG2). Based on the cytotoxic activity, compounds 2 and 3 showed cytotoxic activity but compound 1 is inactive against HepG2 cells. Conclusion: The results of this study showed that the studied compounds might indeed be potential sources of anticancer agents and these would further enable us to evaluate their utility in biomedical field.",
keywords = "Cytotoxic, Dithiocarbamate, NMR, Organotin, X-ray",
author = "Normah Awang and Ibrahim Baba and {Mohd Yousof}, {Nor Syaidatul Akmal} and {Nurul Farahana}, Kamaludin",
year = "2010",
language = "English",
volume = "7",
pages = "1047--1052",
journal = "American Journal of Applied Sciences",
issn = "1546-9239",
publisher = "Science Publications",
number = "8",

}

TY - JOUR

T1 - Synthesis and characterization of organotin(IV) N-benzyl-N-isopropyldithiocarbamate compounds

T2 - Cytotoxic assay on human hepatocarcinoma cells (HepG2)

AU - Awang, Normah

AU - Baba, Ibrahim

AU - Mohd Yousof, Nor Syaidatul Akmal

AU - Nurul Farahana, Kamaludin

PY - 2010

Y1 - 2010

N2 - Problem statement: Several studies on organotin(IV) dithiocarbamate compounds have been carried out but not on the synthesis and characterization together with cytotoxic assay of organotin(IV) N-benzyl-N-isopropyldithiocarbamate compounds. Approach: Three new organotin(IV) compounds of type N-benzyl-N-isopropyldithiocarbamate have been successfully synthesized by direct reaction between secondary amine with organotin(IV) chloride using in situ method. All the compounds were characterized using elemental analysis, gravimetric analysis, infrared spectroscopy and Nuclear Magnetic Resonance (NMR) spectroscopy. Results: Elemental and gravimetric analyses data of these compounds showed that agreed with the predicted formula, (CH3)2Sn[S2CN(C7H7)(i-C3H7)]2 (1), (C4H9)2Sn[S2CN(C7H7)(i-C3H7)]2 (2) and (C6H5)3Sn[S2CN(C7H7)(i-C3H7)] (3). The infrared spectra of these compounds showed the thioureide bond, v(C=N) which occurred at 1438-1440 cm-1 and the v(C=S) band appeared in the range of 967-973 cm-1. The presence of the v(C=N) and v(C=S) bands in the infrared spectra confirmed the presence of dithiocarbamate ligand in that compounds. The bond between sulphur and tin atom were supported with the presence of peak in the range of 365-445 cm-1 that known to be as stretching mode of v(Sn-S). The most important signal in the 13C NMR spectra was the chemical shift of NCS2 group. The 13C NMR spectra of these compound showed a chemical shift in 195.06-202.65 ppm range, which is attributed to the carbon atom of NCS2 group. The crystal structure of compound 2 (dibutyltin(IV) N-benzyl-N-isopropyldithiocarbamate) has been determined by X-ray single crystal analysis, which shows unsymmetrical nature of the ligand towards coordination to tin. It crystallizes in triclinic P1 space group with the crystal cell parameter: a = 17.7745 (2) (Å), b = 19.5463 (3) (Å), c = 26.2062 (4) (Å), α = 102.5254 (7)°, β = 95.1492 (7)°, γ = 110.2569 (8)°, Z = 10, V (Å3) = 8202.1 (2) and R = 0.028. In addition, these compounds were screened for their cytotoxic activity on Human Hepatocarcinoma Cells (HepG2). Based on the cytotoxic activity, compounds 2 and 3 showed cytotoxic activity but compound 1 is inactive against HepG2 cells. Conclusion: The results of this study showed that the studied compounds might indeed be potential sources of anticancer agents and these would further enable us to evaluate their utility in biomedical field.

AB - Problem statement: Several studies on organotin(IV) dithiocarbamate compounds have been carried out but not on the synthesis and characterization together with cytotoxic assay of organotin(IV) N-benzyl-N-isopropyldithiocarbamate compounds. Approach: Three new organotin(IV) compounds of type N-benzyl-N-isopropyldithiocarbamate have been successfully synthesized by direct reaction between secondary amine with organotin(IV) chloride using in situ method. All the compounds were characterized using elemental analysis, gravimetric analysis, infrared spectroscopy and Nuclear Magnetic Resonance (NMR) spectroscopy. Results: Elemental and gravimetric analyses data of these compounds showed that agreed with the predicted formula, (CH3)2Sn[S2CN(C7H7)(i-C3H7)]2 (1), (C4H9)2Sn[S2CN(C7H7)(i-C3H7)]2 (2) and (C6H5)3Sn[S2CN(C7H7)(i-C3H7)] (3). The infrared spectra of these compounds showed the thioureide bond, v(C=N) which occurred at 1438-1440 cm-1 and the v(C=S) band appeared in the range of 967-973 cm-1. The presence of the v(C=N) and v(C=S) bands in the infrared spectra confirmed the presence of dithiocarbamate ligand in that compounds. The bond between sulphur and tin atom were supported with the presence of peak in the range of 365-445 cm-1 that known to be as stretching mode of v(Sn-S). The most important signal in the 13C NMR spectra was the chemical shift of NCS2 group. The 13C NMR spectra of these compound showed a chemical shift in 195.06-202.65 ppm range, which is attributed to the carbon atom of NCS2 group. The crystal structure of compound 2 (dibutyltin(IV) N-benzyl-N-isopropyldithiocarbamate) has been determined by X-ray single crystal analysis, which shows unsymmetrical nature of the ligand towards coordination to tin. It crystallizes in triclinic P1 space group with the crystal cell parameter: a = 17.7745 (2) (Å), b = 19.5463 (3) (Å), c = 26.2062 (4) (Å), α = 102.5254 (7)°, β = 95.1492 (7)°, γ = 110.2569 (8)°, Z = 10, V (Å3) = 8202.1 (2) and R = 0.028. In addition, these compounds were screened for their cytotoxic activity on Human Hepatocarcinoma Cells (HepG2). Based on the cytotoxic activity, compounds 2 and 3 showed cytotoxic activity but compound 1 is inactive against HepG2 cells. Conclusion: The results of this study showed that the studied compounds might indeed be potential sources of anticancer agents and these would further enable us to evaluate their utility in biomedical field.

KW - Cytotoxic

KW - Dithiocarbamate

KW - NMR

KW - Organotin

KW - X-ray

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