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In vitro TRPV1 activity of piperine derived amides

Andres Correa, Edwin; Högestätt, Edward LU ; Sterner, Olov LU ; Echeverri, Fernando and Zygmunt, Peter LU (2010) In Bioorganic & Medicinal Chemistry 18(9). p.3299-3306
Abstract
A series of natural and synthetic piperine amides were evaluated for activity on the human TRPV1 expressed in HEK293 cells. The agonistic effect of piperine amides was mainly dependent on the length of the carbon chain. Structural changes of double bonds and stereochemistry in the aliphatic chain of these compounds did not change their potency or efficacy, indicating that increased rigidity or planarity of the piperine structure does not affect the activity. The opening of the methylenedioxy ring or changes in the heterocyclic ring of the piperine molecule reduced or abolished activity. Furthermore, inactive compounds did not display functional antagonistic activity. (C) 2010 Elsevier Ltd. All rights reserved.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Fluorometric assays, vanilloid 1, Transient receptor potential, Piperine, Piperine-derived amides, Pain, Analgesic activity
in
Bioorganic & Medicinal Chemistry
volume
18
issue
9
pages
3299 - 3306
publisher
Elsevier
external identifiers
  • wos:000277083400032
  • scopus:77951295220
ISSN
0968-0896
DOI
10.1016/j.bmc.2010.03.013
language
English
LU publication?
yes
id
1646da8c-75df-49cf-ad84-ed71151fd48f (old id 1619532)
date added to LUP
2010-06-18 10:55:05
date last changed
2018-05-29 10:36:16
@article{1646da8c-75df-49cf-ad84-ed71151fd48f,
  abstract     = {A series of natural and synthetic piperine amides were evaluated for activity on the human TRPV1 expressed in HEK293 cells. The agonistic effect of piperine amides was mainly dependent on the length of the carbon chain. Structural changes of double bonds and stereochemistry in the aliphatic chain of these compounds did not change their potency or efficacy, indicating that increased rigidity or planarity of the piperine structure does not affect the activity. The opening of the methylenedioxy ring or changes in the heterocyclic ring of the piperine molecule reduced or abolished activity. Furthermore, inactive compounds did not display functional antagonistic activity. (C) 2010 Elsevier Ltd. All rights reserved.},
  author       = {Andres Correa, Edwin and Högestätt, Edward and Sterner, Olov and Echeverri, Fernando and Zygmunt, Peter},
  issn         = {0968-0896},
  keyword      = {Fluorometric assays,vanilloid 1,Transient receptor potential,Piperine,Piperine-derived amides,Pain,Analgesic activity},
  language     = {eng},
  number       = {9},
  pages        = {3299--3306},
  publisher    = {Elsevier},
  series       = {Bioorganic & Medicinal Chemistry},
  title        = {In vitro TRPV1 activity of piperine derived amides},
  url          = {http://dx.doi.org/10.1016/j.bmc.2010.03.013},
  volume       = {18},
  year         = {2010},
}