Synthesis, structural characterization

and morphological studies of 3-

pentadecyl phenol derivatives for drug
delivery

KVPY Project Report

Swastik Biswas
BS-MS First year
Indian Institute of Science Education and Research,Pune
KVPY Registration No. SB-1712058

Mentor: Dr. Jancy Abhraham

Polymer Science and Engineering Division
CSIR-National Chemical Laboratory
 TABLE OF CONTENTS
a) Abbreviations
b) Abstract
c) Introduction
d) Experimental
(1) Materials
(2) Instrumentation Technique
1. Thin layer chromatography
2. Column chromatography
3. Ion Exchange chromatography
4. Nuclear magnetic resonance (NMR)
5. MALDI-TOF
6. SEM
7. TEM
8. IR Spectroscopy
(3) Synthesis
e) Result and Discussion
(a) Characterization
f) Conclusion
g) References
ABSTRACT
[Keywords:Cardanol, Pentadecyl phenol,Tryptophan,Parkinson’s
Disease,Alpha-synuclein ]

Parkinson’s disease is one of the most prevalent amyloid disease, caused by

alpha-synulcein fibrils, formed from gradual degradation of dopaminergic
neurons. The alpha-synuclein is known to undergo self-assembly.
In this report, 3-pentadecyl phenol, one of the derivatives of cardonol,obtained
from Cashew Nut Shell Liquid (CSNL) is explored as a potential antidote to
alpha-synuclein formation. Synthesis of various derivatives of 3-pentadecyl
phenol were done along with physical and chemical studies of it. Preliminary
toxicity assay of 3-pentadecyl phenol was done against common bacteria.
ABBREVIATIONS

 PDP : Pentadecyl phenol

 Fmoc : 9-Fluorenylmethyl carbinyl
 DIPEA : N, N-Diisopropylethylamine
 DMAP : 4-Dimethylaminopyridine
 mix. : Mixture
 r.t. : Room Temperature
 cat. : Catalyst
 DCM : Dichloromethane
 Boc : tert-Butyloxycarbonyl protecting group
 R.B. : Round Bottomed flask
 Conc. :Concetration
 EDC : 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide
 DCC : N,N'-Dicyclohexylcarbodiimide
 Avg. : Average or mean
 SD : Standard Deviation
INTRODUCTION
 Alphasynuclein
Alpha-synuclein is a protein implicated in Parkinson’s disease and thought to
be one of the main pathological drivers in the disease, although it remains
unclear how this protein elicits its neurotoxic effects. Recent findings indicate
that the assembly of toxic oligomeric species of alpha-synuclein may be one of
the key processes for the pathology and spread of the disease.
 Amyloid Disease
Neurodegenerative disease is age-dependent disorder which commonly cause
memory and cognitive impairment, sometimes defects in movement, speech
or breathing depending upon type of disease. Alzheimer's disease, Parkinson's
disease, Huntington's disease, amyotrophic lateral sclerosis, frontotemporal
dementia and the spinocerebellar ataxias.
It is suggested that proteins with altered physiochemical properties (e.g.
misfolding) accumulate and aggregate in human brain and prove to be
potentially toxic as with amyloid-β in Alzheimer’s Disease;α-synuclein in
Parkinson’s Disease and hungtington protein in Huntington’s disease.
Extracellular Peptide Fibrils found in pathological deposits of human tissue,
which exhibits green birefringence in presence of Congo Red dye, are called
amyloid fibrils. Almost all protein can form amyloid fibril upon denaturation
and these fibrils can undergo self-assembly.
 Parkinson’s Disease
Parkinson's disease is a progressive nervous system disorder that affects
movement with gradual symptoms like slight tremor. It commonly causes
stiffness or slowing of movement due to decreased dopamine level as a result
of dopaminergic neurons damage.
 Indole based complexes
Indole is an electron-rich aromatic compound widely found in natural
products and in proteins as the important constituent of essential
amino acid tryptophan. It is known to form a hydrophobic
environment in proteins and to be involved in enzymatic reactions. In
addition to the redox activities and various weak interactions, it
shows versatile metal binding abilities through the nitrogen and
 carbon atoms. Indole based complexes are being exploited as potent
medication of cancers and in drug delivery.
Molecular self-assembly:
Molecular self-assembly is the assembly of molecules without guidance from
an outside source. Molecular self-assembly is, by definition, the spontaneous
organization of molecules under near-thermodynamic equilibrium conditions
into structurally well-defined and stable arrangements through non-covalent
interactions. This is mainly governed by weak non-covalent bonds like
electrostatic interactions (ionic bonds), hydrogen bonds, hydrophobic and
hydrophilic interactions, water-mediated hydrogen bonds, and van der Waals
interactions. Although these forces are weak, their collective interactions can
produce structurally and chemically stable structures. Frequently, molecular
self-assembly relies on chemical complementarity and structural compatibility
[3]
. Self- assembly process is centrally important to life and a single cell itself
contains a wide of self-assembled structures such as lipid membranes, folded
proteins, structured nucleic acids, protein aggregates and others.

Cashew Nut Shell Liquid (CSNL)

 Cardonol
Cardanol, a biomonomer obtained from Cashew Nut Shell Liquid (CNSL) is an
industrial byproduct obtained from the cashew plant Anacardium occidentale
L. The mono/di/tri unsaturated components of cardonol possess functional
flexibility due to three main structural and chemical features. First is the
reactive phenolic –OH group offering synthetic flexibility, and second is the
meta alkyl chain with non-isoprenoic cis double bonds attributing amphiphilic
and lipidic character. Lastly, the aromatic ring allows for p–p stacking and
functionalization. These features make cardanol a tenable precursor for
chemical modifications to generate a library of amphiphiles and functional
monomers. A variety of functional groups can be attached to the reactive
phenoxy group of cardanol for further derivatization
EXPERIMENTAL

MATERIALS
a)Tryptophan-PDP-Tryptophan

BOC deprotection:
Some flakes of boc-W-PDP-W-boc is taken in a round bottomed flask
For half an hour, The crystals were dissolved in 20ml DCM using magnetic
stirrer placed in ice bath and the whole setup was in a fume hood. After
dissolution,20ml of TFA(trifluoroacetic acid) was added to deprotect. After 4
hours, the solution is left to evaporate in rotary evaporator at 60◦C.After
complete evaporation, again DCM was added to evaporate so that TFA would
also evaporate with it also. This process was repeated 4-5 times then kept in a
round-bottomed flask with a rubber stopper wrapped by polythene wrap

b)Tryptophan-hex-Tryptophan
BOC deprotection:
Some flakes of boc-W-hexyl-W-boc is taken in a round bottomed flask
For half an hour, The crystals were dissolved in 20ml DCM using magnetic
stirrer placed in ice bath and the whole setup was in a fume hood. After
dissolution,20ml of TFA(trifluoroacetic acid) was added to deprotect. After 4
hours, the solution is left to evaporate in rotary evaporator at 60◦C.After
complete evaporation, again DCM was added to evaporate so that TFA would
also evaporate with it also. This process was repeated 4-5 times then kept in a
round-bottomed flask with a rubber stopper wrapped by polythene wrap

INSTRUMENTATION TECHNIQUES
1.THIN LAYER CHROMATOGRAPHY
Thin layer chromatography (TLC) is a chromatography technique used to
separate mixtures.Thin layer chromatography is performed on a sheet of glass,
plastic, or aluminum foil, which is coated with a thin layer of adsorbent
material, usually silica gel, aluminum oxide, or cellulose (blotter paper). This
layer of adsorbent is known as the stationary phase. After the sample has been
applied on the plate, a solvent or solvent mixture (known as the mobile phase)
is drawn up the plate via capillary action. Because different analytes ascend
the TLC plate at different rates, separation is achieved. Thin layer
chromatography can be used to: Monitor the progress of a reaction, identify
compounds present in a given substance, determine the purity of a substance.
The behavior of an individual compound in TLC is characterized by a quantity
Known as Rƒ and is expressed as a decimal fraction. The Rƒ is calculated by
dividing the distance the compound traveled from the original position by the
distance the solvent travelled from the original position (the solvent front).[1]
2.COLUMN CHROMATOGRAPHY
Column chromatography in chemistry is a method used to purify individual
chemical compounds from mixtures of compounds. It is often used for
preparative applications on scales from micrograms up to kilograms. The
classical preparative chromatography column, is a glass tube with a diameter
from 5 mm to 50 mm and a height of 5 cm to 1 m with a tap and some kind of
a filter (a glass frit or glass wool plug – to prevent the loss of the stationary
phase) at the bottom. Two methods are generally used to prepare a column:
the dry method, and the wet method. The technique typically requires mesh
70 – 230 (63 –200 μm) silica gel. The mobile phase moves through the
stationary phase(column) picking up the compounds to be tested. As the
mobile phase continues to travel through the stationary phase it takes the
compounds with it.[3]
One method to speed up the process is to use Flash Chromatography. This
method uses a pressure of about 10 psi of air or nitrogen to force the mobile
phase through the column. Because the rate of the mobile phase is increased,
in general, this method gives a poorer separation. However, by using a finer
grade of alumina or silica, flash chromatography can be used to increase the
speed without lowering the quality of the separation.

3. ION EXCHANGE CHROMATOGRAPHY

Ion-exchange chromatography (IEC) is part of ion chromatography which is an
important analytical technique for the separation and determination of ionic
compounds, together with ion-partition/interaction and ion-exclusion
chromatography. In ion exchange chromatography, the stationary phase
consists of a polymeric resin matrix on the surface of which ionic functional
groups, e.g., carboxylic acids or quaternary amines, have been bonded
chemically. As the mobile phase passes over this surface, ionic solutes are
retained by forming electrostatic chemical bonds with the functional groups.
The mobile phase used in this type is always liquid. The principle of separation
is by reversible exchange of ions between the ions present in the solution and
those present in the ion exchange resin. Ion exchange separations are mainly
carried out in columns packed with an ion-exchanger.[3] There are two types of
ion exchanger, namely
1. Cationic exchangers
2. Anionic exchangers

Cationic exchangers:
It possesses negatively charged groups and these will attract positively charged
groups. These exchangers are also called acidic ion exchange materials since
their negative charges result from the proteolysis of acidic groups.
Anionic exchangers:
It has positively charged groups, which will attract negatively charged
molecules. This exchanger is termed as basic ion exchange materials since their
positive charges generally result from the association of protons with basic
groups.
Based upon the affinity of ions towards the matrix the ions like cation and
anion are separated. The ions that have less affinity towards matrices will elute
first and the ions that have more affinity towards matrices it will elute later.[4]

4. NUCLEAR MAGNETIC RESONANCE (NMR)

NMR is a property of the nucleus of an atom, concerned with what is known as
nuclear spin (I). This is equivalent to the nucleus acting like a tiny bar magnet.
Isotopes can have a variety of values for I (including zero). In this NMR
spectroscopy only nucleus containing odd mass number (A) or odd atomic
number (Z) are most useful which includes hydrogen 1 (1H), carbon 13 (13C),
fluorine 19 (19F) and phosphorus 31 (31P). Whereas nucleus containing even
mass number (A) or even atomic number (Z) are not used, This includes 10B, 14N
etc. Resonance frequency of a particle, substance is the key feature of NMR
and is directly proportional to the strength of the applied magnetic field. The
effectiveness of NMR can also be improved by using following techniques

 Hyperpolarization

 Two-dimensional

 Three-dimensional
  Higher-dimensional multi frequency techniques

Although large amounts of sample are needed when compared with mass
spectroscopy, NMR is non-destructive and with modern instruments good data
may be obtained from samples weighing less than a milligram.The 1H nucleus is
most commonly studied by using NMR spectroscopy because of its high natural
abundance (99.98%) and the fact that it is invariably present in the majority of
organic compounds. PMR provides information about the number of different
types of protons and also regarding the nature of the immediate environment
of each of them.

5. MALDI-TOF
Mass spectrometry is an analytical technique in which chemical compounds
are ionized into charged molecules and ratio of their mass to charge (m/z) is
measured. The sample for analysis by MALDI MS is prepared by mixing or
coating with solution of an energy-absorbent, organic compound called matrix.
When the matrix crystallizes on drying, the sample entrapped within the
matrix also co-crystallizes. The sample within the matrix is ionized in an
automated mode with a laser beam. Desorption and ionization with the laser
beam generates singly protonated ions from analytes in the sample. The
protonated ions are then accelerated at a fixed potential, where these
separate from each other on the basis of their mass-to-charge ratio (m/z). The
charged analytes are then detected and measured using different types of
mass analyzers like quadrupole mass analyzers, ion trap analyzers, time of
flight (TOF) analyzers etc.

6. SEM
SEM is a versatile advanced instrument which is largely employed to observe
the surface phenomena of the materials. The sample is shot in a SEM
using high-energy electron, and the outcoming electrons/X-rays are analysed.
These outcoming electrons/X-rays give information about topography,
morphology, composition, orientation of grains, crystallographic information,
etc. of a material. The SEM instrument is based on the principle that the
primary electrons released from the source provide energy to the atomic
electrons of the specimen which can then release as the secondary
electrons (SEs) and an image can be formed by collecting these secondary
electrons from each point of the specimen, the basic requirement for SEM to
operate under a vacuum to avoid interactions of electrons with gas molecules
in order to obtain high resolution. In addition, the primary electrons
produced and emitted from the electron gun are accelerated by heating or
applying high energy in the range of 1−40 keV [2,4]. These emitted electrons
are focused and confined to a monochromatic beam (to a diameter of 100 nm
or less)
The confined primary electrons are scanned across the sample surface by
scanning coils in a raster pattern. Once the primary electron beam hits the
sample surface, it will interact with the near-surface area of the sample to a
certain depth in many different ways. The impringing electrons accelerated
towards the specimens have substantial quantities of kinetic energy, which
lose their energy inside the sample by generating several signals from the
interactions of electrons with specimen. It scattered both elastically and
inelastically in the sample

7. TEM
Transmission electron microscopy (TEM) is a microscopy technique whereby a
beam of electrons is transmitted through an ultra-thin specimen, interacting
with the specimen as it passes through. An image is formed from the
interaction of the electrons transmitted through the specimen; the image is
enlarged and focused onto an imaging device, such as a fluorescent screen, on
a layer of photographic film, or to be detected by a sensor such as a CCD
camera.
The TEM consists of an emission source which is connected to a high voltage
source (typically ~100–300 kV) the gun will, given sufficient current,begin to
emit electrons either by thermionic or field electron emission into the vacuum.
This extraction is usually aided by the use of a Wehnelt cylinder. Once
extracted, the upper lenses of the TEM allow for the formation of the electron
probe to the desired size and location for later interaction with the sample.
Manipulation of the electron beam is performed using magnetic and electric
field.[8]

8. IR SPECTROSCOPY
Molecular bonds vibrate at characteristic frequencies. If a particular molecular
vibration results in a change in the bond's dipole moment, then the molecule
can absorb infrared radiation of that characteristic frequency, exciting that
vibration. Infrared spectroscopy is a sensitive technique to identify specific
functional groups in a molecule.
In IR spectroscopy the sample is irradiated with a broad band of infrared
frequencies, and the intensity of the reflected or transmitted infrared radiation
is measured as a function of frequency. From the knowledge of incident
intensity and reflected/transmitted intensity as a function of infrared
frequency, an infrared absorbance spectrum can be reconstructed. Absorption
at specific frequencies is characteristic of certain bonds. The IR spectrum is a
map of internal vibrational frequencies vs. intensity of interaction with IR
radiation. A vibration will be infrared active if the dipole moment of the
molecule or species changes during the vibration. In contrast, a vibration will
be Raman active if the polarizability changes during the vibration. The
frequency of a given vibration depends on the mass of the atoms involved and
the strength of the bond between them.

SYNTHESIS
1) Synthesis of 4-amino PDP

a)KOH, EtOH
b)Sulphanilic acid + NaNO2
c)Sodium dithionate
d)Acetic acid

 To a 500 ml round-bottomed flask, 5g of PDP added and 4.6g of KOH

pellet. Then to this, 70 ml of ethanol and stir for half-an-hour in ice-cold
condition
 To another 250ml beaker, 3.9g of sulphanilic acid is dissolved in
minimum amount of distilled water (around 10ml H2O).To this solution
Na2CO3 (about 1 spatula-full) was added till the effervescence stops to
neutralize and solubilize the organic acid. The whole set-up is in ice-bath.
 3.4g NaNO2 is added to it and cooled by putting ice inside the beaker
  To the ice-cold solution, conc. HCl is added dropwise till transparent
brown solution observed, then thick, bright yellow solution appears at
pH 6-7. Ice-cold conc. HCl is added with vigorous stirring till precipitate
appears.
 This thick yellow solution was added slowly to the RB containing PDP, a
red azodye forms after complete addition. It is allowed to stir for 2-3
hours in an ice-bath.

2) Synthesis of Fmoc-amino PDP

Dioxane: NaHCO3-H2O mix. (1:1)

+ 0‫ﹾ‬C (15 mins.) then r.t.(24hrs)

 In a 150ml RB,3.234g of Fmoc-Cl is taken and dissolved in about 10ml of

dioxane.
 The reaction is allowed to be stirred for 15 minutes at 0‫ﹾ‬C
 4-amino PDP in dioxane is dissolved slowly in 4g of NaHCO3 in 30ml
water by stirring it in ice-bath 15 minutes
 Fmoc-Cl in dioxane is added slowly to the reaction mixture dropwise
 It was allowed to stir for 2 hours at 0‫ﹾ‬C, followed by stirring in room
temperature for 24 hours

o Workup was done by evaporating dioxane, then distilled water

was added to it
o It was acidified using 6N HCl in ice-bath
o It was then extracted using CHCl3 till the pH 3
3) Synthesis of 2 ethoxy Fmoc -amino-pentadecyl phenoloate
OH
OH O

1. DMF,K2CO3 NH
O NH OH

O
+ 2.KI (cat.),80 C
O
O

Br

 In 100 ml beaker; 500 mg Fmoc-amino-PDP, 100µL of bromoethanol

(measured via T100 micropipette); 382.62mg K2CO3 and 10ml of dry
DMF was added together to obtain a brown solution with pale sediment.
 A small cross-shaped magnetic stirrer added it.Rubber septum attached
to the mouth of RB to cover.
 A pinch of KI is added as a catalyst
 A N2 filled balloon attached with a syringe-needle, is pierced through the
RB septum.
 The setup is kept on paraffin oil bath over magnetic heating plate at
80‫ﹾ‬C. A thermometer kept in oil-bath to monitor temperature.The
reaction is kept for 24 hrs.

o Work-up was done by adding distilled water to reaction mixture taken in

a separating funnel.
o Half-beaker of Ethyl Acetate was added with thorough shaking.
o The coloured upper layer of Ethyl acetate solution was obtained by
letting go of lower aqueous layer.
o To reduce emulsion,saturated NaCl solution was added.
o After obtaining the organic layer, it was again washed with distilled
water following the previous procedure.
4) Synthesis of Fmoc-PDP acrylate

 Fmoc-amino PDP was dissolved in ethyl acetate

 Reflux was done by adding 500µL of acrylic acid,0.524g of DCC and
0.3105g of DMAP to the Fmoc-amino PDP at 65‫ﹾ‬C over a oil bath with
continuous magnetic stirring.
 Workup was done by adding ethyl acetate to the reaction mixture taken
in a separating funnel. It was thoroughly washed with distilled water and
the organic layer was obtained.

5) Synthesis of 4-amino PDP pyrenate

 To a RB 100mg of pyrene-COOH,148.16mg of 4-amino PDP and 49.62mg

of DMAP was added in ice-cold condition for 30 minutes.
 To another beaker containing 93.43mg of EDC-HCl,157.49mg of DIPEA
was added dropwise using a syringe.It was stirred for 2 hours at 0‫ﹾ‬C
 After dissolution, the contents of two containers were thoroughly mixed
at room temperature for 12 hours.
 o The workup was done by adding water and DCM to the reaction
mixture taken in a separating funnel.
o NaCl was added to reduce emulsion formation
o Organic layer was extracted and pale yellow coloured aqueous
layer was discarded. 15 washes were done.
o After washing , it was dried in rotary evaporator at 49◦C.
o It was column purified using 100-200 mesh silica powder. Using
pure pet-ether as eluant, desired product was obtained

PREPARATION OF PRIMARY CELL CULTURE

1. Pups (2 days old mouse) decapitated and the olfactory bulb is removed.
The bulb is placed in HBSS (dissection solution) to maintain cells in non-
CO2 condition.
2. The bulb is mixed using a scalpel and transferred to a falcon containing
HBSS buffer. [ The whole process of dissection must be finished within 1
hour to keep the cells alive]
3. The HBSS is removed from the falcon and 2 ml of 5% P-trypsin is added in
a carbon-dioxide filled oven. The minced tissue is incubated in P-trypsin
(0.25% trypsin) for 10 min. (5 min horizontal + 5 min vertically). Porcine
pancreas trypsin (37‫ﹾ‬C for 15 minutes). Use 0.25% trypsin(α)
4. Add 2 ml DMEM to neutralize the trypsin and centrifuge at 5‫ﹾ‬C for 10
minutes.
5. Remove the supernatant and add 2 ml of buffer solution (HBSS 30ml +
HEPES 1 ml + P/S 300µl) resuspend, centrifuge at 5‫ﹾ‬C for 10 minutes.
6. ÷Remove the supernatant, add 1ml of media and resuspend the cells
7. Count the cells in a haemocytometer chamber, if the cell-count is high,
reduce the cell-count to 1.5 × 106 cells/well (changed 80,000 cells/well).
[Add needed media + cell suspension in another falcon]-calculation-
formula
8. Plate the cells on 12mm coverslips (100-200µl of cell suspension). After
adding cells to coverslip, resuspend the cell suspension over the coverslip-
so that there is uniformity of cells.(addition of more cells to the
coverslip—might lead to overcrowding of the cells)
9. Incubate the plates (4 wells) at 37‫ﹾ‬C, 5% CO2 ÷ (4-6)—helps the cells attach
better.
10. After 4 hours, check if the cells have attached to the coverslip. If they
have attached, add 300µl of the media. (Neurobasal+ B27 + Glutamine +
P/S + FBS)
11. Add 10% FBS+NB+B27+GP/S media for first 2 media change. This helps
the cells to get attached to the cell surface better initiation.
 RESULTS AND DISCUSSION

H1 NMR of 4- amino PDP is done to check the purity of product obtained from column
chromatography. The compound obtained is relatively pure.
1.39
1.34
1.21

dmso boc w pdp w boc.esp

0.25

0.20
0.85
Normalized Intensity

0.15

0.10
7.04
7.20

6.58
7.32
10.85

9.23

2.41
7.67

4.37
9.39
9.16

3.21

0.05
1.68
6.67

0
1.71 0.55 1.09 2.23 4.19 5.16 2.32 1.66 3.53 1.88 17.83 27.13 2.98

11 10 9 8 7 6 5 4 3 2 1 0
Chemical Shift (ppm)
H1 NMR of diBoc-W-PDP-W is done to check the purity of product. The compound obtained is
relatively pure.

ANTIBIOTIC ASSAY
E.coli

10 ug/ml 3 ug/ml 1ug/ml 10 ug/ml 3 ug/ml 1 ug/ml

Avg Avg Avg SD SD SD

AJAS5 11.07169698 19.99398767 19.64126459 2.210705103 2.811563413

1.519151199

AJAS6 99.74147001 100.2946039 21.14835413 0.02267389849 0.03401084773

0.1360433909

Pseudomonas areginosa

10 ug/ml 3 ug/ml 1ug/ml 10 ug/ml 3 ug/ml 1 ug/ml

Avg Avg Avg SD SD SD

AJAS5 -13.00966982 -6.404128463 -0.1513101859 3.775204099 5.203659703

6.926875989

AJAS6 11.80119244 -2.957061977 2.526178666 4.80686648 0.3967932236

2.505465783

Bacillus subtalis

10 ug/ml 3 ug/ml 1ug/ml 10 ug/ml 3 ug/ml 1 ug/ml

Avg Avg Avg SD SD SD

Staphlococcus aureus

10 ug/ml 3 ug/ml 1ug/ml 10 ug/ml 3 ug/ml 1 ug/ml

Avg Avg Avg SD SD SD

AJAS5 79.93060145 36.7580965 16.26900198 0.4860482832 3.065843017

7.963714178
 AJAS6 99.38863186 101.0013219 9.897554527 0.1121649884 0.07477665895
4.935259491

Species IC 50 (µg/ml) MIC(µg/ml)

S aureus 0.156 0.288
Bacillus 0.156 0.288
E. coli 0.224 0.884
Pseudo >10 >10

a b c

a
200
nm
TEM showing spherical aggregates for Trp-PDP-Trp (figure a and c) and Trp-
Hexyl-Trp (figure b)
CONCLUSION
The synthesized compound W-hex-W and W-PDP-W is quite pure as
interpreted from H1 NMR. Antibacterial properties were shown by both of
these compounds proving to be cytotoxic to bacteria. This property could be
used as a potential antibiotic. In the SEM analysis, spherical aggregates of W-
PDP-W and W-hexyl-W were seen suggesting that there might be a gelation
property of these compounds and if fine-tuned could be used in drug-delivery.
Tryptophan being fluorescent molecule, it could act as a potential probe to
study its antimicrobial mechanism inside the bacterial cell and track its path if
it is used a drug-deliverer.
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