Letters in Drug Design & Discovery, 2011, 8, ???-??? 1
1570-1808/11 $58.00+.00 © 2011 Bentham Science Publishers Ltd.
In Silico Studies of (2E,5E)-2,5-bis(3-methoxy-4-hydroxy-benzylidene)
Cyclopentanone on Proteins AChE and BChE Involved in Alzheimer's
disease and Ameliorative Effects on Paraquat Induced Oxidative Stress
Markers in Drosophila melanogaster
Balladka Kunhanna Sarojini*
,a
, Chenna Govindaraju Darshan Raj
a
, Modalkoppalu Kyathegowda
Ramakrishna
b
, Saraf R Ramesh
b
, Basavapattana Rudresh Bharath
c
and Hanumanthappa
Manjunatha
c
a
Department of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore - 574153, Karnataka, India
b
DST Unit on Evolution and Genetics & Drosophila Stock Centre, Department of Studies in Zoology, University of
Mysore, Manasagangotri, Mysore-570006 Karnataka, India
c
Department of P.G. Studies and Research in Biotechnology and Bioinformatics, Jnanasahyadri, Kuvempu University,
Shankaraghatta-577451, Karnataka, India
Received June 28, 2010: Revised October 14, 2010: Accepted December 07, 2010
Abstract: In the present study, the ameliorative effect of a bischalcone (2E,5E)-2,5-bis(3-methoxy-4-hydroxy-
benzylidene) cyclopentanone (CA), a curcumin analog was studied on Drosophila melanogaster (oregon K strain) in vivo
by inducing oxidative stress using paraquat. Curcumin (CU) was taken as standard for studies. In negative geotaxis assay
it was found that CA was able to rescue the flies significantly from deteriorating locomotor dysfunctions. A docking study
for antialzeimer’s activity of CA was carried out by targeting the proteins Acetylcholinesterase (AChE) and Butyrylcho-
linesterase (BChE). It binds effectively to the target proteins.
Keywords: Antioxidant, Alzheimer disease, Bischalcone, Paraquat, Molecular docking, Oxidative stress.
INTRODUCTION
Neurodegenerative disorders remain an important source
of morbidity and suffering for the mankind. The role of free-
radical-mediated oxidative injury in acute insults to the
nervous system including stroke or trauma, as well as in
chronic neurodegenerative disorders, is well recognized. It is
known that, oxygen is an essential molecule for survival of
majority of living organisms. Oxidative stress is a harmful
condition that occurs when there is an excess of free radicals
and/or a decrease in antioxidant levels. The evidence to date
for oxidative stress in Parkinson’s disease (PD), Schizophre-
nia (SCZ), Alzheimer's disease (AD) and other neurodegen-
erative diseases is strongly persuasive. Clinical studies
showed that a number of events associated with Alzheimer’s
are capable of stimulating production of free radicals and
depletion of antioxidant levels. As pointed out, whether oxi-
dative stress is eventually proven to be primary or secondary
in etiologic progression, the therapeutic rewards of antioxi-
dants are likely to be substantial. Clearly, strategies aimed at
limiting free radical induced oxidative stress and damage
may slow the progression of neurodegenerative diseases [1].
Paraquat (1,1-dimethyl-4,4-bipyridynium dichloride) is a
quaternary nitrogen herbicide and highly toxic substance for
humans and animals; many cases of acute poisoning and
death have been reported [2]. The toxicity of paraquat is due
*Address correspondence to this author at the Department of Chemistry, P.
A. College of Engineering, Nadupadavu, Mangalore - 574153, Karnataka,
India; Tel: + 91 824 2284701/2/3; Fax: + 91 824 2284705; E-mails:
bksaroj@yahoo.com, bksaroj35@gmail.com, darshanraj22@gmail.com
to the generation of the superoxide anion which can lead to
the synthesis of more toxic reactive oxygen species (ROS)
such as hydroxyl radicals and hydrogen peroxide [3]. On the
other hand, the oxidation of reduced Nicotinamide Adenine
Dinucleotide Phosphate (NADPH) as a consequence of
paraquat administration results in the disruption of bio-
chemical processes requiring NADPH [4].
The oxidative stress caused by free radicals contributes to
the development of Alzheimer's disease. AD is the most
common form of dementia in adults, which is characterized
by senile plaques and cholinergic deficit as the disease pro-
gresses. Improvement of cholinergic neurotransmission is
the basis of some drugs currently used in the treatment
of AD. It is achieved by AChE inhibition, the enzyme re-
sponsible for acetylcholine hydrolysis. Molecular modeling
techniques are of utmost importance to design a new phar-
maceutical agent against Alzheimer's disease, with potential
inhibitory activity over AChE. Some of the drugs currently
used in the treatment of AD are capable of increasing the
cholinergic transmission through the AChE inhibition and
also the inhibition of human plasma BChE [5].
Curcumin, commonly called diferuloyl methane, is a hy-
drophobic polyphenol derived from the rhizome (turmeric)
of the herb Curcuma longa. It exhibits antioxidant, anti-
inflammatory, antimicrobial, and anticarcinogenic activities.
In spite of its efficacy and safety, curcumin has not yet been
approved as a therapeutic agent. The poor aqueous solubility,
relatively low bioavailability and intense staining color of
curcumin were highlighted as major problems; and conse-
quently search for a ‘‘super curcumin’’ without these prob-