DOI: 10.1124/jpet.300.3.984. A Structure/Activity Relationship Study on Arvanil, an Endocannabinoid and Vanilloid Hybrid

A Structure/Activity Relationship Study on Arvanil, an Endocannabinoid and Vanilloid Hybrid

10.1124/jpet.300.3.984

Crossref journal-article

Elsevier BV

The Journal of Pharmacology and Experimental Therapeutics (78)

Bibliography

Di Marzo, V., Griffin, G., De Petrocellis, L., Brandi, I., Bisogno, T., Williams, W., Grier, M. C., Kulasegram, S., Mahadevan, A., Razdan, R. K., & Martin, B. R. (2002). A Structure/Activity Relationship Study on Arvanil, an Endocannabinoid and Vanilloid Hybrid. The Journal of Pharmacology and Experimental Therapeutics, 300(3), 984â991.

Authors 11

Vincenzo Di Marzo (first)
Graeme Griffin (additional)
Luciano De Petrocellis (additional)
Ines Brandi (additional)
Tiziana Bisogno (additional)
William Williams (additional)
Mark C. Grier (additional)
Sanjitha Kulasegram (additional)
Anu Mahadevan (additional)
Raj K. Razdan (additional)
Billy R. Martin (additional)

References 39 Referenced 73

10.1021/jo960057x / J Org Chem / Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures. by Abdel-Magid (1996)
10.1016/S0022-3565(24)37342-2 / J Pharmacol Exp Ther / Assessment of anandamide interaction with the cannabinoid brain receptor: SR 141716A antagonism studies in mice and autoradiographic analysis of receptor binding in rat brain. by Adams (1998)
10.1074/jbc.272.6.3315 / J Biol Chem / Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes. by Bisogno (1997)
10.1016/S0960-894X(00)00528-X / Bioorg Med Chem Lett / Fatty acid amide hydrolase substrate specificity. by Boger (2000)
10.1016/S0026-895X(24)23059-5 / Mol Pharmacol / Evidence for a new G protein-coupled cannabinoid receptor in mouse brain. by Breivogel (2001)
10.1038/39807 / Nature (Lond) / The capsaicin receptor: a heat-activated ion channel in the pain pathway. by Caterina (1997)
10.1038/384083a0 / Nature (Lond) / Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. by Cravatt (1996)
10.1016/S0040-4020(00)00877-2 / Tetrahedron / The synthesis of N-vanillyl-arachidonoyl-amide (arvanil) and its analogues: an improved procedure for the synthesis of the key synthon methyl-14-hydroxy-(all-cis)-5,8,11-tetradecatrienoate. by Dasse (2000)
10.1124/mol.59.6.1369 / Mol Pharmacol / Role of fatty acid amide hydrolase in the transport of the endogenous cannabinoid anandamide. by Day (2001)
10.1016/S0014-5793(00)02082-2 / FEBS Lett / Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin-like activity. by De Petrocellis (2000)
10.1074/jbc.M003161200 / J Biol Chem / The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase. by Deutsch (2001)
10.1126/science.1470919 / Science (Wash DC) / Isolation and structure of a brain constituent that binds to the cannabinoid receptor. by Devane (1992)
10.2174/1381612003399365 / Curr Pharm Des / Endocannabinoids new targets for drug development. by Di Marzo (2000)
10.1016/S0165-6147(00)01712-0 / Trends Pharmacol Sci / Anandamide: some like it hot. by Di Marzo (2001)
10.1006/bbrc.2001.4354 / Biochem Biophys Res Commun / Highly selective CB(1) cannabinoid receptor ligands and novel CB(1)/VR(1) vanilloid receptor “hybrid” ligands. by Di Marzo (2001)
10.1016/S0014-5793(98)01175-2 / FEBS Lett / Interactions between synthetic vanilloids and the endogenous cannabinoid system. by Di Marzo (1998)
10.1016/S0014-2999(00)00687-7 / Eur J Pharmacol / Neurobehavioral activity in mice of N-vanillyl-arachidonyl-amide. by Di Marzo (2000)
10.1046/j.1471-4159.2000.0752434.x / J Neurochem / Levels, metabolism, and pharmacological activity of anandamide in CB(1) cannabinoid receptor knockout mice: evidence for non-CB(1), non-CB(2) receptor-mediated actions of anandamide in mouse brain. by Di Marzo (2000)
10.1016/S0014-2999(01)01012-3 / Eur J Pharmacol / Hypolocomotor effects in rats of capsaicin and two long chain capsaicin homologues. by Di Marzo (2001)
10.1016/0024-3205(92)90045-Q / Life Sci / Mechanism of action of capsaicin-like molecules on sensory neurons. by Dray (1992)
10.1016/S0014-5793(97)01603-7 / FEBS Lett / Anandamide amidohydrolase reacting with 2-arachidonoylglycerol, another cannabinoid receptor ligand. by Goparaju (1998)
10.1016/S0304-3959(00)00353-5 / Pain / Cloning and functional expression of a human orthologue of rat vanilloid receptor-1. by Hayes (2000)
10.1016/S0009-3084(00)00191-2 / Chem Phys Lipids / The movement of N-arachidonoylethanolamine (anandamide) across cellular membranes. by Hillard (2000)
10.1046/j.1471-4159.2000.0742597.x / J Neurochem / Structure-activity relationships among N-arachidonylethanolamine (Anandamide) head group analogues for the anandamide transporter. by Jarrahian (2000)
10.1016/S0024-3205(99)00283-0 / Life Sci / Structure-activity relationships of anandamide, an endogenous cannabinoid ligand. by Khanolkar (1999)
10.1021/jm980461j / J Med Chem / Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase. by Lang (1999)
10.1016/0091-3057(91)90349-7 / Pharmacol Biochem Behav / Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs. by Martin (1991)
10.1016/S0024-3205(99)00281-7 / Life Sci / Discovery and characterization of endogenous cannabinoids. by Martin (1999)
10.1006/bbrc.1999.1105 / Biochem Biophys Res Commun / Unsaturated long-chain N-acyl-vanillyl-amides (N-AVAMs): vanilloid receptor ligands that inhibit anandamide-facilitated transport and bind to CB1 cannabinoid receptors. by Melck (1999)
10.1021/jm980711w / J Med Chem / Unique analogues of anandamide: arachidonyl ethers and carbamates and norarachidonyl carbamates and ureas. by Ng (1999)
10.1016/S0163-7258(97)82001-3 / Pharmacol Ther / Pharmacology of cannabinoid CB1 and CB2 receptors. by Pertwee (1997)
10.1038/sj.bjp.0703456 / Br J Pharmacol / Vanilloid receptors on capsaicin-sensitive sensory nerves mediate relaxation to methanandamide in the rat isolated mesenteric arterial bed and small mesenteric arteries. by Ralevic (2000)
10.1021/jm00226a002 / J Med Chem / Drugs derived from cannabinoids. 2. Basic esters of nitrogen and carbocyclic analogues. by Razdan (1976)
10.1038/sj.bjp.0703050 / Br J Pharmacol / The endogenous lipid anandamide is a full agonist at the human vanilloid receptor (hVR1). by Smart (2000)
10.1016/S0031-6997(24)01403-0 / Pharmacol Rev / Vanilloid (Capsaicin) receptors and mechanisms. by Szallasi (1999)
10.1016/S0009-3084(00)00190-0 / Chem Phys Lipids / The fatty acid amide hydrolase (FAAH). by Ueda (2000)
10.1021/jm00068a015 / J Med Chem / Analogues of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 2. The amide bond “B-region”. by Walpole (1993)
10.1021/jm00068a014 / J Med Chem / Analogues of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 1. The aromatic “A-region”. by Walpole (1993)
10.1038/22761 / Nature (Lond) / Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. by Zygmunt (1999)

Dates

Type	When
Created	22 years, 7 months ago (Jan. 10, 2003, 1:32 p.m.)
Deposited	6 months, 1 week ago (Feb. 19, 2025, 6:15 p.m.)
Indexed	2 months, 2 weeks ago (June 14, 2025, 4:24 p.m.)
Issued	23 years, 6 months ago (March 1, 2002)
Published	23 years, 6 months ago (March 1, 2002)
Published Print	23 years, 6 months ago (March 1, 2002)

Funders 0

None

BibTeX

@article{Di_Marzo_2002, title={A Structure/Activity Relationship Study on Arvanil, an Endocannabinoid and Vanilloid Hybrid}, volume={300}, ISSN={0022-3565}, url={http://dx.doi.org/10.1124/jpet.300.3.984}, DOI={10.1124/jpet.300.3.984}, number={3}, journal={The Journal of Pharmacology and Experimental Therapeutics}, publisher={Elsevier BV}, author={Di Marzo, Vincenzo and Griffin, Graeme and De Petrocellis, Luciano and Brandi, Ines and Bisogno, Tiziana and Williams, William and Grier, Mark C. and Kulasegram, Sanjitha and Mahadevan, Anu and Razdan, Raj K. and Martin, Billy R.}, year={2002}, month=mar, pages={984–991} }

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      "volume": "56",
      "author": "Dasse",
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      "author": "De Petrocellis",
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      "author": "Deutsch",
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      "volume": "42",
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      "volume": "40",
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      "author": "Martin",
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      "volume": "262",
      "author": "Melck",
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      "first-page": "1975",
      "DOI": "10.1021/jm980711w",
      "article-title": "Unique analogues of anandamide: arachidonyl ethers and carbamates and norarachidonyl carbamates and ureas.",
      "volume": "42",
      "author": "Ng",
      "year": "1999",
      "journal-title": "J Med Chem"
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      "DOI": "10.1016/S0163-7258(97)82001-3",
      "article-title": "Pharmacology of cannabinoid CB1 and CB2 receptors.",
      "volume": "74",
      "author": "Pertwee",
      "year": "1997",
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      "volume": "130",
      "author": "Ralevic",
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      "first-page": "454",
      "DOI": "10.1021/jm00226a002",
      "article-title": "Drugs derived from cannabinoids. 2. Basic esters of nitrogen and carbocyclic analogues.",
      "volume": "19",
      "author": "Razdan",
      "year": "1976",
      "journal-title": "J Med Chem"
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      "first-page": "227",
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      "volume": "129",
      "author": "Smart",
      "year": "2000",
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      "DOI": "10.1016/S0031-6997(24)01403-0",
      "article-title": "Vanilloid (Capsaicin) receptors and mechanisms.",
      "volume": "51",
      "author": "Szallasi",
      "year": "1999",
      "journal-title": "Pharmacol Rev"
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      "first-page": "107",
      "DOI": "10.1016/S0009-3084(00)00190-0",
      "article-title": "The fatty acid amide hydrolase (FAAH).",
      "volume": "108",
      "author": "Ueda",
      "year": "2000",
      "journal-title": "Chem Phys Lipids"
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      "article-title": "Analogues of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 2. The amide bond \u201cB-region\u201d.",
      "volume": "36",
      "author": "Walpole",
      "year": "1993",
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      "author": "Walpole",
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      "DOI": "10.1038/22761",
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      "author": "Zygmunt",
      "year": "1999",
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