International Journal of Clinical Pharmacology & Toxicology, 2013 © 66
Ngabireng Marie. Claude, et al., (2013) Drug Design and Analysis In Silico Of Sapelenin G, An Acyclic Triterpenoid as Potential Anti-Inflammatory. Int J Clin Pharmacol Toxicol. 2(4),
66-72.
International Journal of Clinical Pharmacology & Toxicology (IJCPT)
ISSN 2167-910X
Drug Design and Analysis In Silico of Sapelenin G, an Acyclic Triterpenoid as Potential
Anti-Inlammatory
Reserch Article
Ngabireng Marie. Claude
1*
, Menye Cyrille
2
, Kouam F.Simeon
3
, Ntede N .Hyppolite
4
, Tagoudjeu Jacques
1
, Awono Onana
1
1
National Advanced School of Engineering/Department of Mathematics and Physical Science, University of Yaounde I, Yaounde, Cameroon
2
Faculty of sciences/Department of Physics, University of Yaounde I, Yaounde, Cameroon.
3
Higher Teachers’ Training College/Department of Chemistry, University of Yaounde I, Yaounde, Cameroon.
4
National Advanced School of Engineering/Department of Mechanics and materials, University of Yaounde I,Yaounde, Cameroon.
*Corresponding Author:
Ngabireng Marie. Claude
National Advanced School of Engineering/Department of Mathemat-
ics and Physical Science,
University of Yaounde I, Cameroon.
E-mail: cngabire@yahoo.fr
Received: June 06, 2013
Accepted: June 24, 2013
Published: June 27, 2013
Citation: Ngabireng Marie. Claude, et al., (2013) Drug Design and Anal-
ysis In Silico Of Sapelenin G, An Acyclic Triterpenoid as Potential Anti-
Inlammatory. Int J Clin Pharmacol Toxicol. 2(4), 66-72.
Copyright: Ngabireng Marie. Claude
©
2013. This is an open-access
article distributed under the terms of the Creative Commons Attribution
License, which permits unrestricted use, distribution and reproduction in
any medium, provided the original author and source are credited.
Introduction
Sapelenin G, an acyclic triterpenoid, known under its UIPAC
name as (10E, 14E, 18E)-2 ,6,10,15,19,23-hexamethyltetracosa-
10,14,18-triene-2,3,6,7,22,23-hexol (ig.1b) is a molecule extracted
from a sapele tree scientiically known as Entadrophragma cylin-
dricum[1]. It has been reported that triterpenes possess many use-
ful properties among which anti-inlammatory [1,2]. This activity
is manifested by their interaction with a number of targets [3];
including nitric oxide synthase (iNOS), nuclear factor-kB (NF-
kB), heme oxygenase (HO) and cyclooxygenase (COX).
The latest, also known as prostaglandin H Synthase (PGH syn-
thase /PGHS/PHS) is a prominent and well-studied protein
which catalyzes the conversion of arachidonic acid to prostaglan-
din H2 (PGH2), the committed step in prostaglandin (PG) bio-
synthesis. There are two isoforms of this enzyme: cyclooxygenase
1 (COX1) and cyclooxygenase 2 (COX2). COX1 are responsible
for the maintenance and the protection of the gastrointestinal
tract, COX2 is responsible for inlammation and pain [4].
The existing non-steroidal and anti-inlammatory drugs (NSAIDs)
differ in their relative speciicities for COX-1 and COX-2; while
aspirin is equipotent at inhibiting COX-2 and COX-1 enzymes in
vitro [5].
The irst crystal structure of human cyclooxygenase-2, in the
presence of selective inhibitor, is similar to that of cyclooxyge-
nase-1; COX-1 and COX-2 are homodimers. The structure of
NSAID binding site is also well conserved, although there are dif-
ferences in its overall size. COX-1 and COX-2 are both targets of
nonselective nonsteroidal anti-inlammatory drugs including aspi-
rin and ibuprofen, while COX-2 activity is selectively blocked by
COX-2 inhibitors called coxibs (e.g.,celecocib). Aspirin is a unique
inhibitor that causes a time-dependent, covalent inhibition.
In this study, we are reporting probable binding mechanism of sa-
pelenin G with COX by molecular docking. This molecule shows
a good binding to COX than aspirin and has drug-like properties.
Abstract
Diverse non-steriodal anti-inlammatory drugs and COX-2 inhibitors are a class of drugs which selectively inhibit COX-2, provide relief
from pain and inlammation. However, they lack anti-thrombotic activity and hence lead to cardiovascular and renal liabilities apart from
gastrointestinal irritation. To ameliorate this situation, research can be foccuss on the products originating from natural products that could
offer better relief from inlammation than the currently used commercial drugs. Aspirin blocks the cyclooxygenase enzyme (COX 1, 2)
which is involved in the ring closure and the addition of O2 to arachidonic acid, converting it to prostaglandins (which induce inlammation,
pain and fever). The present study is undertaken to analyse the docking eficacy of aspirin with the target molecule (2AW1), to assess the
best ligand for inhibiting COX and to analyze the docking program by Arguslab. Substituting aspirin ligand by sapelenin G, the inding sug-
gests that sapelenin G is a better ligand than aspirin. It satisies Lipinski Rule of 5. The PASS (Prediction of Activity Spectra for Substances)
prediction results show that Sapelenin G has an anti-inlammatory activity. Toxicity estimations of Sapelenin G using Toxtree on humans
and based on the Cramer rules, Verhaar, Structural Alerts for Reactivity in Toxtree (START) biodegradability, eye irritation/corrosion and
skin irritation/corrosion fell into class 3, 5, 1, 2 and 1, respectively. Application of the Benigni-Bossa method showed that this compound
is negative for genotoxic carcinogenicity and negative for non-genotoxic carcinogenicity. The cytochrome P-450 mediated drug metabolism
is negative for Sapelenin G only in SMARTCyp.Rank2.sites of metabolism, and it fell into unreactive group of compounds by Michael ad-
dition. A skin sensitization evaluation reveals that the compound has no skin sensitization alert identiied, moreover, Kroes Threshold of
Toxicological Concern (TTC) decision tree reveals that the Substance would not be expected to be a safety concern.
Keywords: sapelenin G, cyclooxygenase, docking, anti-inlammatory activity.