Synthesis, characterization and crystal structure of organotin(IV) N-Butyl-N-phenyldithiocarbamate compounds and their cytotoxicity in human leukemia cell lines

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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 P21/n space group with the crystal cell parameter: a = 10.0488(1)Å, b = 18.0008(2)Å, c = 15.2054(2)Å, β = 102.442(1)o 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 μM, 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.

Original languageEnglish
Pages (from-to)12-21
Number of pages10
JournalPakistan Journal of Biological Sciences
Volume16
Issue number1
DOIs
Publication statusPublished - 2013

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crystal structure
leukemia
crystals
cytotoxicity
cell lines
organotin compounds
synthesis
new drugs
antineoplastic agents
Fourier transform infrared spectroscopy
bromides
amines
absorbance
inhibitory concentration 50
nuclear magnetic resonance spectroscopy
cell death
chlorides
X-radiation
cells
carbon

Keywords

  • Anticancer
  • Butylphenyldihocarbamate
  • Cytotoxicity
  • Dithiocarbamates
  • Leukemia
  • Organotin(IV)

ASJC Scopus subject areas

  • Agronomy and Crop Science

Cite this

@article{6a22c62e0f23489cbefa542031f41b45,
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 P21/n space group with the crystal cell parameter: a = 10.0488(1){\AA}, b = 18.0008(2){\AA}, c = 15.2054(2){\AA}, β = 102.442(1)o 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 μM, 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.",
keywords = "Anticancer, Butylphenyldihocarbamate, Cytotoxicity, Dithiocarbamates, Leukemia, Organotin(IV)",
author = "{Nurul Farahana}, Kamaludin and Normah Awang and Ibrahim Baba and Asmah Hamid and {Kok Meng}, Chan",
year = "2013",
doi = "10.3923/pjbs.2013.12.21",
language = "English",
volume = "16",
pages = "12--21",
journal = "Pakistan Journal of Biological Sciences",
issn = "1028-8880",
publisher = "Asian Network for Scientific Information",
number = "1",

}

TY - JOUR

T1 - Synthesis, characterization and crystal structure of organotin(IV) N-Butyl-N-phenyldithiocarbamate compounds and their cytotoxicity in human leukemia cell lines

AU - Nurul Farahana, Kamaludin

AU - Awang, Normah

AU - Baba, Ibrahim

AU - Hamid, Asmah

AU - Kok Meng, Chan

PY - 2013

Y1 - 2013

N2 - 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 P21/n space group with the crystal cell parameter: a = 10.0488(1)Å, b = 18.0008(2)Å, c = 15.2054(2)Å, β = 102.442(1)o 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 μM, 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.

AB - 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 P21/n space group with the crystal cell parameter: a = 10.0488(1)Å, b = 18.0008(2)Å, c = 15.2054(2)Å, β = 102.442(1)o 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 μM, 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.

KW - Anticancer

KW - Butylphenyldihocarbamate

KW - Cytotoxicity

KW - Dithiocarbamates

KW - Leukemia

KW - Organotin(IV)

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U2 - 10.3923/pjbs.2013.12.21

DO - 10.3923/pjbs.2013.12.21

M3 - Article

VL - 16

SP - 12

EP - 21

JO - Pakistan Journal of Biological Sciences

JF - Pakistan Journal of Biological Sciences

SN - 1028-8880

IS - 1

ER -