The cannabinoid acids: Nonpsychoactive derivatives with therapeutic potential

Pharmacology and Therapeutics

Volumn 82, Issue 1, 1999, Pages 87-96

  Burstein, Sumner H ^a  

^a UNIVERSITY OF MASSACHUSETTS MEDICAL SCHOOL   (United States)

Author keywords

Analgesia; Anandamide; Anti inflammatory activity; Cannabinoid; Metabolites

Indexed keywords

4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; ACETYLSALICYLIC ACID; ANANDAMIDE; ARACHIDONIC ACID; CANNABINOID; DICLOFENAC; DRONABINOL; DRUG METABOLITE; IBUPROFEN; ICOSANOID; INDOMETACIN; KETOPROFEN; KETOROLAC; NONSTEROID ANTIINFLAMMATORY AGENT;

ADJUVANT ARTHRITIS; ANALGESIA; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARACHIDONIC ACID METABOLISM; CONTROLLED STUDY; DRUG METABOLISM; INFLAMMATION; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; PAIN; PRIORITY JOURNAL; RAT; REVIEW; STRUCTURE ACTIVITY RELATION; ULCEROGENESIS;

ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS; ARACHIDONIC ACIDS; CANNABINOIDS; HUMANS; POLYUNSATURATED ALKAMIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032973507     PISSN: 01637258     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0163-7258(98)00069-2     Document Type: Review

References (75)

1. Adams I.B., Ryan W., Singer M., Thomas B.F., Compton D.R., Razdan R.K., Martin B.R. Evaluation of cannabinoid receptor binding and in vivo activities for anandamide analogs. J. Pharmacol. Exp. Ther. 273:1995;1172-1181.
2. Agurell S., Nilsson I.M., Ohlsson A., Sandberg F. On the metabolism of tritium-labelled THC in the rabbit. Biochem. Pharmacol. 19:1970;1333-1339.
3. Agurell S., Halldin M., Lindgren J.-E., Ohlsson A., Widman M., Gillespie H., Hollister L. Pharmacokinetics and metabolism of THC and other cannabinoids with emphasis on man. Pharmacol. Rev. 38:1986;21-40.
4. Audette C.A., Burstein S.H., Doyle S.A., Hunter S.A. G-Protein mediation of cannabinoid-induced phospholipase activation. Pharmacol. Biochem. Behav. 40:1991;559-563.
5. Beltramo M., Stella N., Calignano A., Lin S.Y., Makriyannis A., Piomelli D. Functional role of high affinity anandamide transport as revealed by selective inhibition. Science. 277:1997;1094-1097.
6. Burstein S. Biotransformations of the cannabinoids. Barnett G., Chiang N. Pharmacokinetics and Pharmacodynamics of Psychoactive Drugs. 1985;396-414 Biomedical Publications, Foster City, California.
7. Burstein S. Eicosanoids as mediators of cannabinoid action. Murphy L., Bartke A. Marijuana/Cannabinoids, Ch. 3. 1992;73-92 CRC Press, Boca Raton, Florida.
8. 1-tetrahydrocannabinol and other cannabinoids. Biochem. Pharmacol. 27:1978;1275-1280.
9. Burstein S., Hunter S.A. Prostaglandins and cannabis. VIII. Elevation of phospholipase A2 activity by cannabinoids in whole cells and subcellular preparations. J. Clin. Pharmacol. 21:1981;240S-248S.
10. Burstein S.H., Hunter S.A. Stimulation of anandamide biosynthesis in N-18TG2 neuroblastoma cells by THC. Biochem. Pharmacol. 49:1995;855-858.
11. 1-tetrahydrocannabinol. Prostaglandins. 2:1972;369-374.
12. 1-tetrahydrocannabinol. Science. 176:1972;422-424.
13. Burstein S., Levin E., Varanelli C. Prostaglandins and cannabis. II. The inhibition of biosynthesis by the naturally occurring cannabinoids. Biochem. Pharmacol. 22:1973;2905-2910.
14. 1-THC. Biochem. Pharmacol. 31:1982;2361-2365.
15. Burstein S., Hunter S.A., Ozman K. Prostaglandins and cannabis. XII. The effect of cannabinoid structure on the synthesis of prostaglandins by human lung fibroblasts. Mol. Pharmacol. 23:1983;121-126.
16. Burstein S., Hunter S.A., Ozman K., Renzulli L.A. Prostaglandins and cannabis. XIII. Cannabinoid induced elevation of lipoxygenase products in mouse peritoneal macrophages. Biochem. Pharmacol. 33:1984;2653-2656.
17. Burstein S., Hunter S.A., Renzulli L.A. Prostaglandins and cannabis. XIV. Tolerance to the stimulatory actions of cannabinoids on arachidonate metabolism. J. Pharmacol. Exp. Ther. 235:1985;87-91.
18. 1-THC action by its metabolites. Biochem. Pharmacol. 35:1986;2553-2558. a.
19. Burstein S., Hunter S.A., Mechoulam R., Melchior D.L., Renzulli L. Prostaglandins and cannabis. XV. Comparison of enantiomeric cannabinoids in stimulating prostaglandin synthesis in fibroblasts. Life Sci. 39:1986;1813-1823. b.
20. 1-THC reduces its cataleptic effect in mice. Experientia. 43:1987;402-403.
21. Burstein S.H., Hull K., Hunter S.A., Latham V. Cannabinoids and pain responses. a possible role for prostaglandins FASEB J. 2:1988;3022-3026.
22. Burstein S.H., Audette C.A., Doyle S.A., Hull K., Hunter S.A., Latham V. Antagonism to the actions of PAF by a nonpsychoactive cannabinoid. J. Pharmacol. Exp. Ther. 251:1989;531-535.
23. Burstein S.H., Audette C.A., Breuer A., Devane W.A., Colodner S., Doyle S.A., Mechoulam R. Synthetic non-psychotropic cannabinoids with potent antiinflammatory, analgesic and leukocyte antiadhesion activities. J. Med. Chem. 35:1992;3135-3141.
24. Burstein S., Budrow J., Debatis M., Hunter S.A., Subramanian A. Phospholipase participation in cannabinoid-induced release of free arachidonic acid. Biochem. Pharmacol. 48:1994;1253-1264.
25. Burstein S., Young J.K., Wright G.E. Relationships between eicosanoids and cannabinoids. Are eicosanoids cannabimimetic agents? Biochem. Pharmacol. 50:1995;1735-1742.
26. Burstein, S., Monaghan, A., Pearson, W., Rooney, T., Yagen, B., Zipkin, R. and Zurier, A. (1997) Studies with analogs of anandamide and indomethacin. In: Proceedings of the International Cannabinoid Research Society, Stone Mountain, GA, June 20-22, p. 31, ICRS, Burlington.
27. 8-THC 11-oic acid (CT3) in mice. Life Sci. 63:1998;161-168.
28. Compton D.R., Prescott W.R. Jr., Martin B.R., Siegel C., Gordon P.M., Razdan R.K. Synthesis and pharmacological evaluation of ether and related analogues of Δ 8-, Δ 9-, and Δ 9,11-tetrahydrocannabinol. J. Med. Chem. 34:1991;3310-3316.
29. Compton D.R., Gold L.H., Ward S.J., Balster R.L., Martin B.R. Aminoalkylindoles analogs. cannabimimetic activity of a class of compounds structurally distinct from Δ9-tetrahydrocannabinol J. Pharmacol. Exp. Ther. 263:1992;1118-1126. a.
30. Compton D.R., Johnson M.R., Melvin L.S., Martin B.R. Pharmacological profile of a series of bicyclic cannabinoid analogs. classification as cannabimimetic agents J. Pharmacol. Exp. Ther. 260:1992;201-209. b.
31. Compton D.R., Rice K.C., DeCosta B.R., Razdan R., Melvin L.S., Johnson M.R., Martin B.R. Cannabinoid structure-activity relationships. correlation of receptor binding and in vivo activities J. Pharmacol. Exp. Ther. 265:1993;218-226.
32. Da Silva A.B.F., Trsic M. Theoretical and conformational studies of a series of cannabinoids. J. Mol. Structure. 356:1995;247-256.
33. Devane W.A. New dawn of cannabinoid pharmacology. Trends Pharmacol. Sci. 15:1994;40-41.
34. 6-THC-7-oic acid. Agents Actions. 31:1990;157-162.
35. Facci L., Dal Toso R., Romanello S., Buriani A., Skaper S.D., Leon A. Mast cells express a peripheral cannabinoid receptor with differential sensitivity to anandamide and palmitoylethanolamide. Proc. Natl. Acad. Sci. USA. 92:1995;3376-3380.
36. Fowler C.J., Tiger G., Stenstrom A. Ibuprofen inhibits rat brain deamidation of anandamide at pharmacologically relevant concentrations. Mode of inhibition and structure-activity relationship. J. Pharmacol. Exp. Ther. 283:1997;729-734.
37. Harvey D., Paton W.D.M. Metabolism of the cannabinoids. Rev. Biochem. Toxicol. 6:1984;221-264.
38. Hillard C.J., Bloom A.S. Possible role of prostaglandins in the effects of cannabinoids on adenylate cyclase activity. Eur. J. Pharmacol. 91:1983;21-27.
39. Howlett A.C. Cannabinoid compounds and signal transduction mechanisms. Pertwee R. Cannabinoid Receptors. 1995;168-204 Academic Press, London. a.
40. Howlett A.C. Pharmacology of cannabinoid receptors. Annu. Rev. Pharmacol. Toxicol. 35:1995;607-634. b.
41. Howlett A.C., Johnson M.R., Melvin L.S., Milne G.M. Nonclassical cannabinoid analgetics inhibit adenylate cyclase. development of a cannabinoid receptor model Mol. Pharmacol. 33:1988;297-302.
42. Hunter S.A., Burstein S.H. Receptor mediation in cannabinoid stimulated arachidonic acid mobilization and anandamide synthesis. Life Sci. 60:1997;1563-1573.
43. Hunter S.A., Burstein S., Sedor C. Stimulation of prostaglandin synthesis in WI-38 human lung fibroblasts following inhibition of acylation. Biochim. Biophys. Acta. 793:1984;202-212.
44. Hunter S.A., Burstein S., Renzulli L. Effects of cannabinoids on the activities of mouse brain lipases. Neurochem. Res. 11:1986;1273-1288.
45. Johnson M.R., Melvin L.S., Milne G.M. Prototype cannabinoid analgetics, prostaglandins and opiates - a search for points of mechanistic interaction. Life Sci. 31:1982;1703-1706.
46. Jouzeau J.-Y., Terlain B., Abid A., Nedelec E., Netter P. Cyclooxygenase isoenzymes. How recent findings affect thinking about nonsteroidal anti-inflammatory drugs. Drugs. 53:1997;563-582.
47. Lichtman A.H., Martin B.R. The selective antagonist SR141716A blocks cannabinoid-induced antinociception in rats. Pharmacol. Biochem. Behav. 57:1997;7-12.
48. Little P.J., Compton D.R., Johnson M.R., Melvin L.S., Martin B.R. Pharmacology and stereoselectivity of structurally novel cannabinoids in mice. J. Pharmacol. Exp. Ther. 247:1988;1046-1051.
49. Loev B., Bender P.E., Dowalo F., Macko E., Fowler P.J. Cannabinoids. structure-activity studies related to 1,2-dimethylheptyl derivatives J. Med. Chem. 16:1973;1200-1206.
50. Makriyannis A., Rapaka R.S. The molecular basis of cannabinoid activity. Life Sci. 47:1990;2173-2184.
51. Martin B.R., Compton D.R., Thomas B.F., Prescott W.R., Little P.J., Razdan R.K., Johnson M.R., Melvin L.S., Mechoulam R., Ward S.J. Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs. Pharmacol. Biochem. Behav. 40:1991;471-478.
52. Martin B.R., Thomas B.F., Razdan R.K. Structural requirements for cannabinoid receptor probes. Pertwee R. Cannabinoid Receptors. 1995;36-79 Academic Press, London.
53. Melvin L.S., Milne G.M., Johnson M.R., Subramanian B., Wilken G.H., Howlett A.C. Structure-activity relationships for cannabinoid receptor binding and analgesic activity. studies of bicyclic cannabinoid analogs Mol. Pharmacol. 44:1993;1008-1015.
54. Melvin L.S., Milne G.M., Johnson M.R., Wilken G.H., Howlett A.C. Structure-activity relationships defining the ACD-tricyclic cannabinoids. cannabinoid receptor binding and analgesic activity Drug Des. Discov. 13:1995;155-166.
55. Perez-Reyes M. Pharmacodynamics of certain drugs of abuse. Barnett G., Chiang N.C. Pharmacokinetics and Pharmacodynamics of Psychoactive Drugs. 1985;287-310 Biomedical Publishers, Foster City, California.
56. Perez-Reyes M., Burstein S.H., White W.R., McDonald S.A., Hicks R.E. Antagonism of marihuana effects by indomethacin. Life Sci. 48:1991;507-515.
57. Pertwee R. Pharmacology of cannabinoid CB1 and CB2 receptors. Pharmacol. Ther. 74:1997;129-180.
58. Pestonjamasp V.K., Burstein S.H. Anandamide synthesis is induced by arachidonate mobilizing agonists in cells of the immune system. Biochim. Biophys. Acta. 1394:1998;249-260.
59. Piomelli D., Voltera A., Dale N., Siegelbaum S.A., Kandel E.R., Schwartz J.H., Belardetti F. Lipoxygenase metabolites of arachidonic acids as second messengers for presynaptic inhibition of Aplysia sensory cells. Nature. 328:1987;38-43.
60. Rapaka, R. S. and Makriyannis, A. (eds.) (1987) Structure-Activity Relationships of Cannabinoids. NIDA Research Monograph 79. U.S. Government Printing Office, Washington, D.C.
61. Razdan R.K. Structure-activity relationships in cannabinoids. Pharmacol. Rev. 38:1986;75-149.
62. Reggio P.H., Greer K.V., Cox S.M. The importance of the orientation of the C9 substituent to cannabinoid activity. J. Med. Chem. 32:1989;1630-1635.
63. Reggio P.H., Panu A.M., Miles S. Characterization of a region of steric interference at the cannabinoid receptor using the active analog approach. J. Med. Chem. 36:1993;1761-1771.
64. Rhee M., Vogel Z., Barg J., Bayewtch M., Levy R., Hanus L., Breuer A., Mechoulam R. Cannabinol derivatives. binding to cannabinoid receptors and inhibition of adenylylcyclase J. Med. Chem. 40:1997;3228-3233.
65. Thomas B.F., Compton D.R., Martin B.R., Semus S.F. Modeling the cannabinoid receptor. a three dimensional quantitative structure-activity analysis Mol. Pharmacol. 40:1991;656-665.
66. Vaughan C.W., Ingram S.L., Conner M.A., Christie M.J. How opioids inhibit GABA-mediated neurotransmission. Nature. 390:1997;611-614.
67. Wall M., Perez-Reyes M. The metabolism of THC and related cannabinoids in man. J. Clin. Pharmacol. 21:1981;178S-189S.
68. Wartmann M., Campbell D., Subramanian A., Burstein S.H., Davis R.J. The MAP kinase signal transduction pathway is activated by the endogenous cannabinoid anandamide. FEBS Lett. 359:1995;133-136.
69. Watanabe K., Yamamoto I., Oguri K., Yoshimura H. Comparison in mice of pharmacological effects of THC and its metabolites. Eur. J. Pharmacol. 63:1980;1-6.
70. Widman M., Halldin M.M., Agurell S. Metabolism of THC in man. Barnett G., Chiang N.C. Pharmacokinetics and Pharmacodynamics of Psychoactive Drugs. 1985;415-426 Biomedical Publishers, Foster City, California.
71. Williams J.T. The painless synergism of aspirin and opium. Nature. 390:1997;557-559.
72. Wilson R.S., May E.L. Analgesic properties of the tetrahydrocannabinols, their metabolites and analogs. J. Med. Chem. 18:1975;700-703.
73. Young J.M., Yee J.P. Ketorolac. Lewis A.J., Furst D.E. NSAIDS. Mechanisms and Clinical Uses. 1994;247-266 Marcel Dekker, New York.
74. 2 ethanolamide from anandamide by COX-2. J. Biol. Chem. 272:1997;21181-21186.
75. Zurier R.B., Rossetti R.G., Lane J.H., Goldberg J.M., Hunter S.A., Burstein S.H. Dimethylheptyl-THC-11-oic acid. a nonpsychoactive antiinflammatory agent with a cannabinoid template structure Arthritis Rheum. 41:1998;163-170.