1286
PARVANEH SHAFIEYOON et al.
1
against gram positive and gram negative bacteria. LUMO analysis, and IR and H NMR spectrum were
Molecular docking calculations were performed to performed by using density functional theory (DFT)
evaluate the medicinal properties of the title com- [24]. The optimization of the title compound was car-
pound as anticancer.
ried out using CAM-B3LYP method Aug.-cc-pVDZ
1
[
25] basis set, and H NMR spectra using B3LYP/6-
11+g(d,p). The RMS error value was calculated for
3
EXPERIMENTAL
Material and Methods
1
H NMR spectrum using the following expression
26]:
[
p-Styrene sulfonic acid sodium salt, PCl , sodium
5
n
1
calc
exp 2
hydroxide, and (S)-(+)-alanine were purchased from
Merck and Sigma–Aldrich companies and were used
without further purification. Fourier transform infra-
red (FT-IR) spectra of prepared compounds were
recorded at 400–4000 cm−1 region using KBr pellets
RMS =
(vi − vi ) .
n −1 i
For calculating the simulated vibrational spectra
B3LYP/6-311g(2d,2p) was used. The potential energy
distribution (PED) of the normal modes among the
respective internal coordinates was calculated for ASS
using the BALGA program [27] and compared with
theoretical and experimental values. PASS (Prediction
of Activity Spectra) technique was applied as an online
tool to predict the activity of compound [28]. The ASS
1
on Shimadzu FT-IR 8400 spectrometer. H NMR
spectrum was recorded on a Brucker Ultrashield
4
00 MHz spectrometer using D O as solvent.
2
Preparation of p-Styrene Sulfonyl Chloride
(
N-alanine p-styrene sulfonamide) as a ligand, was
To prepare the monomer first, p-styrene sulfonyl optimized by using CAM-B3LYP method Aug –cc–
chloride was synthesized as follows: p-styrene sulfonyl pVDZ basis set and prepared for docking. The 3D
chloride was synthesized by the reaction of 5.00 g of crystal structure of employed DNA and BSA were
p-styrene sulfonic acid sodium salt with 7.50 g of PCl , obtained from Protein Data Bank (PDB ID: 423D,
5
as chlorination agent. The product was separated from 4F5S). Molecular docking is an important tool to get
inorganic materials by chloroform and ice water. The an insight into ligand–receptor interaction and to
chloroform was evaporated from the p-styrene sulfonyl screen molecule for the binding affinities against a
chloride. Experimental details are described in [22].
selected receptor. All molecular docking calculations
were performed on AutoDock-Vina software [29]. As
the most popular algorithm, Lamarckian Genetic
Algorithm (LGA), available in Autodock was
employed for docking [30, 31]. The graphical repre-
sentation of ligand-DNA and ligand-BSA interaction
was obtained using ligplot software [32].
Preparation of N-(Alanine)–p-Styrene
Sulfonamide (ASS)
The synthetic method for the preparation of the
ASS with chemical formula (C H NO S) is as fol-
11
13
4
lows: in a 100 mL round-bottomed flask, equipped
with magnetic stirrer, 4.86 g p-styrene sulfonyl chlo-
Antibacterial Assays
ride (24 mmol) in 50 mL CHCl as a solvent and 2.14 g
3
The minimal inhibitory concentration (MIC) of
the ASS as antibacterial agent against Escherichia coli
and Staphylococcus aureus will be reported in the next
section. The ASS was tested for its antimicrobial activ-
ity against Staphylococcus aureus, as the model from
Gram-positive and Escherichia coli as Gram-negative
bacteria by the disk diffusion method [33].
(
2
S)-(+)-alanine (24 mmol) were placed. Then,
.4 mL NaOH 1M was slowly added. The reaction
mixture was stirred for 4 h at room temperature. After
the reaction time, the solvent was evaporated and ASS
as the product was obtained. The obtained product
was washed 3 times with water and analyzed without
further purification (yield 5.20 g, 85.0%; m.p. 123°C).
–1
FT-IR (KBr, cm ): 3620, 3460, 3267, 3096, 2941,
837, 1712, 1651, 1595, 1425, 1344, 1228, 1157, 1091,
Preparation of Nutrient-Agar Medium
2
1
053.
For this work, 3.80 g of Nutrient-Agar (NA)
medium was dissolved in 100 mL of distilled water.
This solution was sterilized at 120°C for 20 min in an
autoclave. Then, 20 mL of this solution was solidified
in Petri plate.
1
H-NMR (D O, ppm): 1.42 (CH ), 3.97 (CH),
2
3
4
.70 (NH) 5.42 (CH in vinyl), 5.92 (CH in vinyl), 6.77
CH in vinyl), 7.59 (CH benzene), 7.75 (CH benzene),
.96 (COOH).
(
9
RESULT AND DISCUSSION
Synthesis and Characterization
ASS was prepared by reactions of p-styrene sulfonyl
geometry optimization(opt-freq), MEP, HOMO– chloride with (S)-alanine in the presence of CHCl as
3
Computational Details
Calculations of the ASS were performed using
Gaussian 09 software [23]. The calculations including
RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A
Vol. 93
No. 7
2019