Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens

Ross, Ruth A; Gibson, T Michael; Brockie, Heather C; Leslie, Mark; Pashmi, Ghazaleh; Craib, Susan J; Di Marzo, Vincenzo; Pertwee, Roger G

doi:10.1038/sj.bjp.0703850

Cited by 237Ion Channels and ReceptorsCannabis and Cannabinoid ResearchPain Mechanisms and Treatments

Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens

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Ross, Ruth A, Gibson, T Michael, Brockie, Heather C, Leslie, Mark, Pashmi, Ghazaleh, Craib, Susan J, Di Marzo, Vincenzo, Pertwee, Roger G·2001·British Journal of Pharmacology

DOI 10.1038/sj.bjp.0703850PMC PMC1572597

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Abstract

1. This study was directed at exploring the structure-activity relationship for anandamide and certain of its analogues at the rat VR1 receptor in transfected cells and at investigating the relative extent to which anandamide interacts with CB(1) and vanilloid receptors in the mouse vas deferens. 2. pK(i) values for displacement of [(3)H]-resiniferatoxin from membranes of rVR1 transfected CHO cells were significantly less for anandamide (5.78) than for its structural analogues N-(4-hydroxyphenyl)-arachidonylamide (AM404; 6.18) and N-(3-methoxy-4-hydroxy)benzyl-arachidonylamide (arvanil; 6.77). 3. pEC(50) values for stimulating (45)Ca(2+) uptake into rVR1 transfected CHO cells were significantly less for anandamide (5.80) than for AM404 (6.32) or arvanil (9.29). Arvanil was also significantly more potent than capsaicin (pEC(50)=7.37), a compound with the same substituted benzyl polar head group as arvanil. 4. In the mouse vas deferens, resiniferatoxin was 218 times more potent than capsaicin as an inhibitor of electrically-evoked contractions. Both drugs were antagonized to a similar extent by capsazepine (pK(B)=6.93 and 7.18 respectively) but were not antagonized by SR141716A (1 microM). Anandamide was less susceptible than capsaicin to antagonism by capsazepine (pK(B)=6.02) and less susceptible to antagonism by SR141716A (pK(B)=8.66) than methanandamide (pK(B)=9.56). WIN55212 was antagonized by SR141716A (pK(B)=9.02) but not by capsazepine (10 microM). 5. In conclusion, anandamide and certain of its analogues have affinity and efficacy at the rat VR1 receptor. In the mouse vas deferens, which seems to express vanilloid and CB(1) receptors, both receptor types appear to contribute to anandamide-induced inhibition of evoked contractions.

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Anandamide acts as an endovanilloid at TRPV1 and shows affinity for TRPV1 that is 5-20 fold lower than its affinity for CB1.
“Anandamide also acts as an endovanalloid at the transient receptor potential cation channel (TRPV1) receptor.31 AEA shows affinity for TRPV1 that is 5-20 fold lower than its affinity for CB1.”
From Cannabinoids as Pharmacotherapies for Neuropathic Pain: From the Bench to the Bedside (2009) · cites this paper as [31]

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Authors: Ross, R. A., Gibson, T. M., Brockie, H. C., Leslie, M., Pashmi, G., Craib, S. J., Di Marzo, V., & Pertwee, R. G.
Affiliations: University of Aberdeen (GB)
Corresponding author: Ross, Ruth A
ORCID: Ross, Ruth A
Pertwee, Roger G
Venue: British Journal of Pharmacology
Publisher: Wiley
Published: 2001-02
Volume: 132
Issue: 3
Pages: 631-640
ISSN: 0007-1188 (ISSN-L)
1476-5381
DOI: 10.1038/sj.bjp.0703850
PMC: PMC1572597
OpenAlex: W2021876302
Cited by: 237
References: 28
Citations by year: 2026: 3 · 2025: 1 · 2024: 6 · 2023: 2 · 2022: 1 · 2021: 1 · 2020: 4 · 2019: 2 · 2018: 6 · 2017: 8 · 2016: 4 · 2015: 12 · 2014: 6 · 2013: 12 · 2012: 6
FWCI: 9.89
Type: journal article
Language: en
Open access: bronze
doi.org
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor, 2919 d)
Locations: British Journal of Pharmacology (publishedVersion)
PubMed Central (publishedVersion)
PubMed (publishedVersion)
Funders: Wellcome Trust
National Institute on Drug Abuse (P01DA009789, DA 09789)
Topics: Life Sciences › Neuroscience › Sensory Systems › Ion Channels and Receptors
Health Sciences › Medicine › Pharmacology › Cannabis and Cannabinoid Research
Health Sciences › Medicine › Physiology › Pain Mechanisms and Treatments
Keywords: anandamide, structure-activity relationship, vanilloid receptor 1, CB1 receptor, cannabinoid analogues, AM404, resiniferatoxin, capsaicin, vas deferens contraction, SR141716A, capsazepine, methanandamide, receptor binding affinity
MeSH terms: Rimonabant, Animals, Arachidonic Acids, Binding, Competitive, Biological Transport, Calcium, Calcium Channel Blockers, Cannabinoids, Capsaicin, Drug Interactions, Electric Stimulation, Enzyme Inhibitors, Cricetinae, Male, Morpholines, Muscle Contraction, Naphthalenes, Phenylmethylsulfonyl Fluoride, Piperidines, Pyrazoles, Radioligand Assay, Receptors, Drug, Structure-Activity Relationship, Transfection, Vas Deferens, CHO Cells, Receptors, Cannabinoid, Benzoxazines, TRPV Cation Channels, Mice, Polyunsaturated Alkamides, Endocannabinoids

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Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens

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