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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
Open accessAbstract
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 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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International Union of Pharmacology. XXVII. Classification of Cannabinoid Receptors
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“AM404 is another anandamide analog that activates vanilloid receptors (Jerman et al., 2000; Zygmunt et al., 2000; Ross et al., 2001), albeit at concentrations no higher than those at which it inhibits anandamide membrane transport (Beltramo et al., 1997; Piomelli et al., 1999).”
BackgroundInfluentialPertwee, R. G., Howlett, A. C., Abood, M. E., Alexander, S. P. H., Marzo, V. D., Elphick, M. R., Greasley, P. J., Hansen, H. S., Kunos, G., Mackie, K., et al. (2010) · Pharmacological Reviews · doi:10.1124/pr.110.003004 · Cited by 1,666
“…including immune cells (Howlett et al., 2002), and 2) that CB 2 receptors are expressed by some neurons, both within the brain and elsewhere (Skaper et al., 1996; Ross et al., 2001a; Van Sickle et al., 2005; Wotherspoon et al., 2005; Beltramo et al., 2006; Gong et al., 2006; Baek et al., 2008).”
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“…was assessed by means of displacement assays carried out with membranes (50 mg tube71) from HEKhVR1 cells, prepared as described previously (Ross et al., 2001), and the high a nity VR1 ligand [3H]-resiniferatoxin (48 Ci mmol71, NEN-Dupont), using the incubation conditions described…”
BackgroundMethodModulation of transmitter release via presynaptic cannabinoid receptors
Schlicker, E., & Kathmann, M. (2001) · Trends in Pharmacological Sciences · doi:10.1016/s0165-6147(00)01805-8 · Cited by 671
Anandamide and vanilloid TRPV1 receptors
Ross, R. A. (2003) · British Journal of Pharmacology · doi:10.1038/sj.bjp.0705467 · Cited by 603
Metadata
- 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
- Venue
- British Journal of Pharmacology
- Publisher
- Wiley
- Published
- 2001-02
- Volume
- 132
- Issue
- 3
- Pages
- 631-640
- ISSN
- 0007-1188 (ISSN-L)
- 1476-5381
- 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
- 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 (medical) › Cannabis and Cannabinoid Research
- Health Sciences › Medicine › Physiology (medical) › 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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