Malaysian
Journal of Analytical Sciences Vol 19 No 2 (2015): 349 – 358
SYNTHESIS, CHARACTERISATION AND BIOLOGICAL STUDIES
OF NEW PHENYLTIN(IV) DITHIOCARBAMATE COMPOUNDS
(Sintesis dan Kajian Biologi Sebatian
Fenilstanum(IV) ditiokarbamat)
Amirah Faizah Abdul Muthalib1, Ibrahim
Baba1*, Nazlina Ibrahim2
1School of Chemical Sciences and Food Technology,
2School of Biosciences and Biotechnology,
Faculty of
Science and Technology,
Universiti
Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia
*Corresponding author: aibi2005@gmail.com
Received: 6
November 2014; Accepted: 12 January 2015
Abstract
Nine
chlorophenyltin(IV) dithiocarbamate compounds of general formula PhSnCl[S2CNR’R’’]2
(R’ = CH3, C2H5, C7H7 and
R” = C2H5, C6H11, iC3H7, C7H7)
were prepared in one pot reaction of various secondary amine, carbon disulphide
and phenyltin(1V) trichloride with the ratio of 2:2:1. These compounds have
been characterized by elemental analysis, infrared spectroscopy, ultraviolet
spectroscopy, 1H, 13C NMR spectroscopy as well as single
crystal X-ray crystallography. Data
from X-ray crystallography showed that (C6H5)SnCl[S2CN(C2H5)(iC3H7)]2
is six coordinated bonded with two chelating dithiocarbamate ligands in
bidentate fashion, methyl-C and chloride atom thus form a distorted octahedral
geometry. Five selected compounds, (C6H5)SnCl[S2CN(CH3)(C2H5)]2,
(C6H5)SnCl[S2CN(CH3)(C6H11)]2,
(C6H5)SnCl[S2CN(C2H5)(iC3H7)]2,
(C6H5)SnCl[S2CN(C7H7)(iC3H7)]2
and (C6H5)SnCl[S2CN(C7H7)2]2
were screened for anticancer activity against Chang liver cells. These
compounds were demonstrated no cytotoxic effect for all concentrations under
the condition of the study with no IC50 value. The minimum
inhibitory concentration (MIC) and maximum bactericidal concentration (MBC) determinations for these five compounds used Escherichia coli and Pseudomonas aeruginosa as Gram negative
bacteria together with Staphylococcus
aureus and Staphylococcus epidermis
as Gram positive bacteria. Compound (C6H5)SnCl[S2CN(CH3)(C2H5)]2
was the most active compared to the other compounds by having the lowest MIC
values of 1.25 mg/mL and MBC value of 5.0 mg/mL against E. Coli and S. Aureus
bacteria. Compounds (C6H5)SnCl[S2CN(C7H7)(iC3H7)]2
and (C6H5)SnCl[S2CN(C7H7)2]2
that having a benzyl group showed their MIC and MBC values
slightly higher compared to the other compounds againts certain bacteria
indicating their low antibacterial activities.
Keywords: chlorophenyltin(IV), dithiocarbamate, crystal structure, biological
studies
Abstrak
Sembilan
sebatian fenilklorostanum(IV) ditiokarbamat dengan formula sebatian PhSnCl[S2CNR’R’’]2
(R’ = CH3, C2H5, C7H7 and
R” = C2H5, C6H11, iC3H7, C7H7)
telah disediakan dengan sintesis secara satu pot di antara pelbagai amina
sekunder, karbon disulfida dan fenilstanum(IV) triklorida dengan nisbah 2:2:1.
Kesemua sebatian ini telah dicirikan dengan kaedah analisis unsur, spektroskopi
inframerah, spektroskopi ultralembayung, spektroskopi NMR 1H, 13C
dan kristalografisinar-X. Data daripada kristalografi sinar-X menunjukkan
struktur sebatian (C6H5)SnCl[S2CN(C2H5)(iC3H7)]2 adalah enam koordinatan dan terikat dengan
dua ligan ditiokarbamat yang terkelat secara bidentat, metil-C dan atom klorida
untuk membentuk geometri oktahedron terherot. Lima sebatian pilihan iaitu (C6H5)SnCl[S2CN(CH3)(C2H5)]2,
(C6H5)SnCl[S2CN(CH3)(C6H11)]2,
(C6H5)SnCl[S2CN(C2H5)(iC3H7)]2,
(C6H5)SnCl[S2CN(C7H7)(iC3H7)]2 dan
(C6H5)SnCl[S2CN(C7H7)2]2
telah disaring untuk aktiviti antikanser terhadap sel hati Chang. Sebatian ini
tidak menunjukkan sebarang kesan sitotoksik pada setiap kepekatan dan tidak
mempunyai nilai IC50. Ujian penentuan nilai kepekatan perencatan
minimum (MIC) dan nilai kepekatan minimum bakterisidal (MBC) untuk lima
sebatian ini telah menggunakan Escherichia
coli dan Pseudomonas aeruginosa
sebagai bakteria Gram negatif serta Staphylococcus
aureus dan Staphylococcus epidermis
sebagai bakteria Gram positif. Sebatian (C6H5)SnCl[S2CN(CH3)(C2H5)]2
adalah paling aktif berbanding sebatian lain dengan mempunyai
nilai MIC yang terendah iaitu 1.25 mg/mL dan nilai MBC 5.0 mg/mL terhadap
bakteria Escherichia coli dan Staphylococcus aureus. Sebatian (C6H5)SnCl[S2CN(C7H7)(iC3H7)]2
dan (C6H5)SnCl[S2CN(C7H7)2]2
yang mengandungi kumpulan benzil menunjukkan nilai MIC dan MBC yang lebih
tinggi berbanding sebatian lain terhadap
beberapa jenis bakteria dan menunjukkan aktiviti antibakteria yang lebih
rendah.
Kata kunci:
fenilklorostanum(IV), ditiokarbamat, struktur hablur, kajian biologi
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