a
School of Bio-Science and Technology, VIT University, Vellore, Tamil Nadu, India
Email:
Original Article
ANALGESIC, ANTI-INFLAMMATORY AND ANTIPYRETIC EVALUATIONS OF NEW
ISOQUINOLINE DERIVATIVES
MANIKANDAN A.
a
, SIVAKUMAR A.*
a
siva_kumar.a@vit.ac.in
Received: 14 Jan 2016 Revised and Accepted: 01 Mar 2016
ABSTRACT
Objective: To evaluate the isoquinoline (N-substituted (E)-4-arylidene-isoquinoline-1,3-dione) derivatives (5a-h) for their anti-inflammatory,
analgesic and antipyretic activity potentials in animal models using indomethacin and diclofenac sodium as the standard.
Methods: Peripheral and central analgesic activities were determined by induced writhing and tail immersion tests. Carrageenan stimulated rat
paw edema model was used to evaluate the anti-inflammatory activities by examining the increase in paw volume and percentage inhibition of paw
volume was calculated with plethysmometer at different time periods. Brewer’s yeast induced pyresis model was used to assessing the anti-pyretic
activity by measuring the decreased rectal temperature.
Results: Compounds 5g>5d>5h showed anti-inflammatory, analgesic and antipyretic activities and they were significant with p<0.001 and
comparable with the control group. The results coincided with our previous report which suggests that the compounds 5g>5d>5h may take into
further druggability evaluations.
Conclusion: New isoquinoline derivatives produced significant anti-inflammatory, analgesic, and antipyretic activities and this suggests that these
derivatives need further drug development evaluations especially for the compounds 5g>5d>5h.
Keywords: N-substituted (E)-4-arylidene-isoquinoline-1,3-dione, Carrageenan, Anti-inflammatory, Analgesic, Diclofenac sodium, Antipyretic,
Indomethacin
© 2016 The Authors. Published by Innovare Academic Sciences Pvt Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/ )
INTRODUCTION
Inflammation is a common and serious predicament in cases of
hypersensitivity, autoimmune diseases, and negative response of
transplanted organs [1]. Healing alternatives for inflammatory
diseases generate unfavourable effects and being evidence being
deficient in effectiveness. Non-steroidal anti-inflammatory drugs
(NSAIDs) are precious in the healing of severe and persistent
inflammation [2], fever [3], and pain [4] but long-term use of NSAIDs
is related through the gastrointestinal wound, hemorrhage, and
nephrotoxicity [5]. A number of isoquinoline alkaloids were
reported for anti-inflammatory activity [6, 7]. We already have
evaluated the in vitro anti-inflammatory [8], anticancer [9]
properties of the proposed compounds. In this report, the in vivo
anti-inflammatory, analgesic, and antipyretic potentials were
evaluated and reported as mentioned in our previous report [8].
MATERIALS AND METHODS
Chemicals
λ-Carrageenan was procured from Sigma (St Louis, MO), Diclofenac
Sodium was a legacy sample from Blessing Pharmaceuticals India
(Maharashtra, India), Indomethacin and Brewer’s yeast from Sigma-
Aldrich Chemicals, USA and all other chemicals & reagents were
used analytical grade. The test compounds (E)-4-arylidene
isoquinoline-1,3-diones derivatives 5(a–h) were synthesized and
reported previously [8] was taken for animal studies.
Chemical compounds for animal studies
A mixture of homophthalic acid (1) and substituted anilines (2a-c)
(1:1 ratio) in toluene and 5 mol % ZnO were amended to the
suspension and refluxed. The obtained pale yellow solid compounds
N-substituted homopthalimides (3a-c) were purified and
characterized by FT-IR, GC-MS,
1
H NMR and [13]C NMR.
Condensation of aromatic aldehydes (4a-c) with 3a-c in ethanol
using oxalic acid as a catalyst to obtain the (E)-4-arylidene
isoquinoline-1,3-diones derivatives 5(a–h).
Animals
Wistar albino rats of either sex, 50-100g, were procured from the
animal house, Annamalai University, India. They were in a controlled
room with a 12 h dark-light cycle and fed with commercial pellet feed
from Hindustan Lever Ltd. (Mumbai, India); water was freely available.
The animal model study was approved (Vide No.1038, 2013) by the
Institutional Animal ethics committee of Annamalai University, India
and was conducted in accordance with the “Guidelines for care and
Use of Laboratory Animals", Government of India.
Test of peripheral analgesic activity by acetic acid-induced
writhing response
The acetic acid-induced writhing test was carried out in accordance
with Collier et al. [10]. The rats were intraperitoneally injected with
0.6 % acetic acid (10 ml/kg b. wt) to elicit a writhing response.
Immediately after the administration of acetic acid, the animals were
placed in glass cages, and the number of writhes was recorded for the
following 30 min. A considerable reduction in the number of writhes
by drug treatment as compared to control animals was considered as a
positive analgesic response. Test compounds (50 and 100 mg/kg) and
diclofenac sodium (50 mg/kg b. wt) were administered
intraperitoneally 30 min before the acetic acid injection. Mean
writhing and average protection values were calculated.
Test of central analgesic activity of p-CA (p-Coumaric acid) by
tail-immersion test
The tail-immersion test was carried out as described by Janssen et
al. 1963, was immersed in a water bath thermostatically maintained
at 55±1 °C [11]. The time in seconds for the tail withdrawal from the
water was taken as the tail withdrawal latency or reaction time, with
a cut-off time of immersion set at 10 seconds. The reaction time was
measured before drug treatment at 15, 30, 45 and 60 min after the
drugs were administered. Test compounds (50 and 100 mg/kg) and
diclofenac sodium (50 mg/kg b. wt) were administered at a lower 5-
cm portion of the tail. Writhing values and average protection
percentage values were calculated and tabulated.
International Journal of Pharmacy and Pharmaceutical Sciences
ISSN- 0975-1491 Vol 8, Issue 4, 2016