In vitro TRPV1 activity of piperine derived amides.
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.
Correa
Edwin Andrés
EA
Grupo de Química Orgánica de Productos Naturales, Instituto de Química, Universidad de Antioquia, Medellín, Colombia.
Högestätt
Edward D
ED
Sterner
Olov
O
Echeverri
Fernando
F
Zygmunt
Peter M
PM
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D052117:Benzodioxoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002211:Capsaicin / Q000031:analogs & derivatives / Q000494:pharmacology; D002460:Cell Line; D004305:Dose-Response Relationship, Drug; D006801:Humans; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D053284:Polyunsaturated Alkamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013050:Spectrometry, Fluorescence; D050916:TRPV Cation Channels / Q000819:agonists / Q000037:antagonists & inhibitors / Q000378:metabolism*
D000470:Alkaloids; D000577:Amides; D052117:Benzodioxoles; D010880:Piperidines; D053284:Polyunsaturated Alkamides; D050916:TRPV Cation Channels; C494482:TRPV1 protein, human; C071423:capsazepine; D002211:Capsaicin; C008922:piperine