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KHAN et al.
in DMSO) was introduced into the respective wells. frond with two attached daughter fronds and filameꢀ
Other wells were supplemented with DMSO and refꢀ nious root. Sterile Hoagland’s solution (2 ml) plus a
erence antibacterial drugs serving as negative and posꢀ single Lemna minor plant (consisting of mother frond
itive controls, respectively. The plates were incubated together with its daughter frond) are added to each
immediately at 37°C for 20 h. The activity was deterꢀ well of the tissue culture plate. Control wells contained
mined by measuring the diameter of zones showing 2 ml of sterile Hoagland’s solution plus EtOH solution
complete inhibition (mm).
[19].
The antifungal activity of the synthesized comꢀ
pound I was tested against various pathogens, namely,
RESULTS AND DISCUSSION
Trichophyton longiformis ATCC 22397, Candida albicans
ATCC 2192, Aspergillus flavis ATCC 1030, Microsporum
canis ATCC 9865, Fusarium solani ATCC 11712, and
Candida glaberata by using the tube diffusion test [16].
Elemental analysis reveals that the complex is of
good purity and soluble in chloroform and DMSO.
The IR spectra of complex
tinct vibrational bands at 1415 and 1410 cm–1, which
can be assigned to (CN) vibration, and at 976 and
962 cm–1, which can be attributed to
(C=S). No band
due to (SH) vibration is observed in the IR spectrum
I and ligand show disꢀ
The Micoanazole (200
200 g/ml) were used as standards drugs a stock soluꢀ
tion of the pure compound (12 g/ml) was prepared in
μg/ml) and Amphotericin B
ν
(
μ
ν
μ
ν
sterile DMSO. Sabouraud dextrose agar was prepared
by mixing Sabouraud (32.5 g), glucose agar (4%) and
agarꢀagar (4 g) in 500 ml of distilled water followed by
steamed dissolution, 4 ml of media being dispensed
of the complex, indicating the deporotonation of the
ligand. Bands at 228 and 462 cm–1 are assigned to
ν
(Sn–S) and (Sn–O), respectively [20]. IR data are
ν
given in Experimental.
into screw capped tubes and autoclaved at 121
15 min. The test compound (66.6 g/ml) was added
from the stock solution to nonsolidified Sabouraud
agar media (50 ). Tubes were allowed to solidify at
°C for
μ
The reported compound and the ligand exhibit a sinꢀ
gle
The observed
for C–N single bonds (1250–1360 cm–1) and C=N douꢀ
ble bonds (1640–1690 cm–1). This suggests that the C
ν
(C–S) vibration at 1075 and 1003 cm–1, respectively.
°C
ν(C–N) vibrations lie between the range
room temperature and inoculated with 4ꢀmm diameꢀ
ter portion of inoculums derived from a 7 dayꢀold
respective fungal culture. For nonmycelial growth, an
agar surface streak was employed. The tubes were
⎯
N
bonds in the complexes have some partial double bond
character, which would result in some partial double
bond character for the C–S bonds. This type of bonding
for the two C–S bonds can be achieved through the
bonding of the two sulfur atoms with the tin atom. This
interaction can be viewed as the coordination of one norꢀ
mal Sn–S bond and one weak Sn–S bond. The weak
incubated at 27–29 C for 7–10 days and the growth in
°
the compound containing media was determined by
measuring the linear growth (mm) and growth inhibiꢀ
tion with respective control. The amount of growth
inhibition was calculated as
Sn–S bond is possibly through
orbitals of the tin atom and the
π
overlap of the empty
d
A – B
B
Inhibition (%) = ꢀꢀꢀꢀꢀꢀꢀꢀꢀꢀ × 1 0 0 ,
p
orbitals of sulfur. De
Vries and Herber [21] have used the term “anisobidenꢀ
tate” to describe this type of bonding for a series of triphꢀ
enyltin dithiocarbamates. This type of bonding would reꢀ
sult in observing two Sn–S bond distances in the comꢀ
pound. The data shows that the absorption at 555 cm–1
due to Sn–C indicates the formation of the complex.
where
B
A = diameter of fungal colony in control plate,
= diameter of fungal colony in test plate.
Cytotoxicity. The cytotoxicity of the reported orgaꢀ
notin compound against Brine Shrimps was studied by
the Brine Shrimp method [16]. Thirty shrimps were
transferred to each sample vial using a 9 indisposible
pipette (Scientific products, diSPo pipettes), and
artifical sea water was added to make the volume 5 ml.
The nanuplil can be counted macroscopically in the
stem of the pipette against a lighted background. A
drop of dry yeast suspension (Red Star) (3 mg in 5 ml
artifical sea water) was added as food to each vial. The
vials were maintained under illumination. Survivors
The compound I
has been characterized by 1H, and
13C NMR spectroscopy in CDCl3. The 1H, 13C NMR
data are listed in Experimental. In the 1H NMR specꢀ
trum of the reported complex, no resonance is
observed due to SH group, indicating the replacement
of the carbodithioic acid proton of the diorganotin
moiety. The butyl protons of the complex show a mulꢀ
tiplet in the region 1.46–1.60 ppm, while the CH3 proꢀ
tons of the butyl group give triplet at 0.78 with nJ(1H,
1H) 6.6 Hz. The CH3 proton of the Acac group gives a
singlet at 2.25 ppm, while the CH proton gives a sinꢀ
glet at 5.76 ppm.
were counted with a
3 magnifying glass, after 6 and
×
24 h, and the percent deaths at each dose and control
were determined. The 24 h counts were more useful.
In cases, where control deaths accured, the data were
corrected using Abbott’s formula [17]: % deaths =
[(testꢀcontrol)/control] 100. LD50 was determined
from the 24 h counts using the probit analysis method
described by Finney [18].
In 13C NMR the assignment of the 13C signal for the
CSS group is straightforward and is assigned at
198.9 ppm for the organotin(IV) complex indicating
the coordination of sulfur to the tin atom. The C=O
×
Phytotoxicity. Lemna plants are miniature aquatic bond of acetylacetone numbered as
monocot consisting of a central oval frond or mother 196.20 ppm and CH3 numbered as
α
,
α
'
appears at
γ
, γ' gives signal at
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 36
No. 4
2010
Khan
