메뉴 건너뛰기




Volumn 65, Issue 9, 2003, Pages 1473-1481

Novel selective and metabolically stable inhibitors of anandamide cellular uptake

Author keywords

Cannabinoid; Endocannabinoid; FAAH; Receptor; Transport; VR1

Indexed keywords

2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; ANANDAMIDE; ARACHIDONOYL N' (4 HYDROXY 3 METHOXYBENZYL)HYDRAZINE; AROMATIC COMPOUND; CANNABINOID RECEPTOR; FATTY ACID AMIDASE; HYDRAZINE DERIVATIVE; N OLEOYLETHANOLAMINE; OLEOYL N' (4 HYDROXY 3 METHOXYBENZYL)HYDRAZINE; RECEPTOR SUBTYPE; RIMONABANT; UNCLASSIFIED DRUG; VANILLOID RECEPTOR;

EID: 0037542450     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(03)00109-6     Document Type: Article
Times cited : (149)

References (44)
  • 1
    • 0030611978 scopus 로고    scopus 로고
    • Pharmacology of cannabinoid CB1 and CB2 receptors
    • Pertwee R.G. Pharmacology of cannabinoid CB1 and CB2 receptors. Pharmacol. Ther. 74:1997;129-180.
    • (1997) Pharmacol. Ther. , vol.74 , pp. 129-180
    • Pertwee, R.G.1
  • 2
    • 0031834745 scopus 로고    scopus 로고
    • 'Endocannabinoids' and other fatty acid derivatives with cannabimimetic properties: Biochemistry and possible physiopathological relevance
    • Di Marzo V. 'Endocannabinoids' and other fatty acid derivatives with cannabimimetic properties: biochemistry and possible physiopathological relevance. Biochim. Biophys. Acta. 1392:1998;53-75.
    • (1998) Biochim. Biophys. Acta , vol.1392 , pp. 53-75
    • Di Marzo, V.1
  • 8
    • 0036019386 scopus 로고    scopus 로고
    • Biosynthesis and degradation of anandamide and 2-arachidonoylglycerol and their possible physiological significance
    • Sugiura T., Kobayashi Y., Oka S., Waku K. Biosynthesis and degradation of anandamide and 2-arachidonoylglycerol and their possible physiological significance. Prostaglandins Leukot. Essent. Fatty Acids. 66:2002;173-192.
    • (2002) Prostaglandins Leukot. Essent. Fatty Acids , vol.66 , pp. 173-192
    • Sugiura, T.1    Kobayashi, Y.2    Oka, S.3    Waku, K.4
  • 9
    • 0036019387 scopus 로고    scopus 로고
    • Cellular transport of anandamide, 2-arachidonoylglycerol and palmitoylethanolamide - Targets for drug development?
    • Fowler C.J., Jacobsson S.O. Cellular transport of anandamide, 2-arachidonoylglycerol and palmitoylethanolamide - targets for drug development? Prostaglandins Leukot. Essent. Fatty Acids. 66:2002;193-200.
    • (2002) Prostaglandins Leukot. Essent. Fatty Acids , vol.66 , pp. 193-200
    • Fowler, C.J.1    Jacobsson, S.O.2
  • 10
    • 0028787812 scopus 로고
    • Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide
    • Ueda N., Kurahashi Y., Yamamoto S., Tokunaga T. Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide. J. Biol. Chem. 270:1995;23823-23827.
    • (1995) J. Biol. Chem. , vol.270 , pp. 23823-23827
    • Ueda, N.1    Kurahashi, Y.2    Yamamoto, S.3    Tokunaga, T.4
  • 11
    • 0029904838 scopus 로고    scopus 로고
    • Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides
    • Cravatt B.F., Giang D.K., Mayfield S.P., Boger D.L., Lerner R.A., Gilula N.B. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature. 384:1996;83-87.
    • (1996) Nature , vol.384 , pp. 83-87
    • Cravatt, B.F.1    Giang, D.K.2    Mayfield, S.P.3    Boger, D.L.4    Lerner, R.A.5    Gilula, N.B.6
  • 12
    • 0032559369 scopus 로고    scopus 로고
    • Anandamide amidohydrolase reacting with 2-arachidonoylglycerol, another cannabinoid receptor ligand
    • Goparaju S.K., Ueda N., Yamaguchi H., Yamamoto S. Anandamide amidohydrolase reacting with 2-arachidonoylglycerol, another cannabinoid receptor ligand. FEBS Lett. 422:1998;69-73.
    • (1998) FEBS Lett. , vol.422 , pp. 69-73
    • Goparaju, S.K.1    Ueda, N.2    Yamaguchi, H.3    Yamamoto, S.4
  • 13
    • 0033567190 scopus 로고    scopus 로고
    • Biosynthesis and inactivation of the endocannabinoid 2-arachidonoylglycerol in circulating and tumoral macrophages
    • Di Marzo V., Bisogno T., De Petrocellis L., Melck D., Orlando P., Wagner J.A., Kunos G. Biosynthesis and inactivation of the endocannabinoid 2-arachidonoylglycerol in circulating and tumoral macrophages. Eur. J. Biochem. 264:1999;258-267.
    • (1999) Eur. J. Biochem. , vol.264 , pp. 258-267
    • Di Marzo, V.1    Bisogno, T.2    De Petrocellis, L.3    Melck, D.4    Orlando, P.5    Wagner, J.A.6    Kunos, G.7
  • 14
    • 0037181180 scopus 로고    scopus 로고
    • Noladin ether, a putative novel endocannabinoid: Inactivation mechanisms and a sensitive method for its quantification in rat tissues
    • Fezza F., Bisogno T., Minassi A., Appendino G., Mechoulam R., Di Marzo V. Noladin ether, a putative novel endocannabinoid: inactivation mechanisms and a sensitive method for its quantification in rat tissues. FEBS Lett. 513:2002;294-298.
    • (2002) FEBS Lett. , vol.513 , pp. 294-298
    • Fezza, F.1    Bisogno, T.2    Minassi, A.3    Appendino, G.4    Mechoulam, R.5    Di Marzo, V.6
  • 15
    • 0032055496 scopus 로고    scopus 로고
    • The novel endogenous cannabinoid 2-arachidonoylglycerol is inactivated by neuronal- and basophil-like cells: Connections with anandamide
    • Di Marzo V., Bisogno T., Sugiura T., Melck D., De Petrocellis L. The novel endogenous cannabinoid 2-arachidonoylglycerol is inactivated by neuronal- and basophil-like cells: connections with anandamide. Biochem. J. 331:1998;15-19.
    • (1998) Biochem. J. , vol.331 , pp. 15-19
    • Di Marzo, V.1    Bisogno, T.2    Sugiura, T.3    Melck, D.4    De Petrocellis, L.5
  • 17
    • 0034070409 scopus 로고    scopus 로고
    • Structure-activity relationships among N-arachidonylethanolamine (Anandamide) head group analogues for the anandamide transporter
    • Jarrahian A., Manna S., Edgemond W.S., Campbell W.B., Hillard C.J. Structure-activity relationships among N-arachidonylethanolamine (Anandamide) head group analogues for the anandamide transporter. J. Neurochem. 74:2000;2597-2606.
    • (2000) J. Neurochem. , vol.74 , pp. 2597-2606
    • Jarrahian, A.1    Manna, S.2    Edgemond, W.S.3    Campbell, W.B.4    Hillard, C.J.5
  • 20
    • 0033584439 scopus 로고    scopus 로고
    • Unsaturated long-chain N-acyl-vanillyl-amides (N-AVAMs): Vanilloid receptor ligands that inhibit anandamide-facilitated transport and bind to CB1 cannabinoid receptors
    • Melck D., Bisogno T., De Petrocellis L., Chuang H., Julius D., Bifulco M., Di Marzo V. Unsaturated long-chain N-acyl-vanillyl-amides (N-AVAMs): vanilloid receptor ligands that inhibit anandamide-facilitated transport and bind to CB1 cannabinoid receptors. Biochem. Biophys. Res. Commun. 262:1999;275-284.
    • (1999) Biochem. Biophys. Res. Commun. , vol.262 , pp. 275-284
    • Melck, D.1    Bisogno, T.2    De Petrocellis, L.3    Chuang, H.4    Julius, D.5    Bifulco, M.6    Di Marzo, V.7
  • 23
    • 0032970173 scopus 로고    scopus 로고
    • Vanilloid (Capsaicin) receptors and mechanisms
    • Szallasi A., Blumberg P.M. Vanilloid (Capsaicin) receptors and mechanisms. Pharmacol. Rev. 51:1999;159-212.
    • (1999) Pharmacol. Rev. , vol.51 , pp. 159-212
    • Szallasi, A.1    Blumberg, P.M.2
  • 26
    • 0034644842 scopus 로고    scopus 로고
    • Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: Inhibitors of anandamide uptake with negligible capsaicin-like activity
    • De Petrocellis L., Bisogno T., Davis J.B., Pertwee R.G., Di Marzo V. Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin-like activity. FEBS Lett. 483:2000;52-56.
    • (2000) FEBS Lett. , vol.483 , pp. 52-56
    • De Petrocellis, L.1    Bisogno, T.2    Davis, J.B.3    Pertwee, R.G.4    Di Marzo, V.5
  • 29
    • 0030865871 scopus 로고    scopus 로고
    • Functional role of high-affinity anandamide transport, as revealed by selective inhibition
    • 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.
    • (1997) Science , vol.277 , pp. 1094-1097
    • Beltramo, M.1    Stella, N.2    Calignano, A.3    Lin, S.Y.4    Makriyannis, A.5    Piomelli, D.6
  • 31
    • 0035116496 scopus 로고    scopus 로고
    • Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens
    • Ross R.A., Gibson T.M., Brockie H.C., Leslie M., Pashmi G., Craib S.J., Di Marzo V., Pertwee R.G. Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens. Br. J. Pharmacol. 132:2001;631-640.
    • (2001) Br. J. Pharmacol. , vol.132 , pp. 631-640
    • Ross, R.A.1    Gibson, T.M.2    Brockie, H.C.3    Leslie, M.4    Pashmi, G.5    Craib, S.J.6    Di Marzo, V.7    Pertwee, R.G.8
  • 32
    • 0035924218 scopus 로고    scopus 로고
    • Design, synthesis and biological evaluation of novel arachidonic acid derivatives as highly potent and selective endocannabinoid transporter inhibitors
    • Lopez-Rodriguez M.L., Viso A., Ortega-Gutierrez S., Lastres-Becker I., Gonzalez S., Fernandez-Ruiz J., Ramos J.A. Design, synthesis and biological evaluation of novel arachidonic acid derivatives as highly potent and selective endocannabinoid transporter inhibitors. J. Med. Chem. 44:2001;4505-4508.
    • (2001) J. Med. Chem. , vol.44 , pp. 4505-4508
    • Lopez-Rodriguez, M.L.1    Viso, A.2    Ortega-Gutierrez, S.3    Lastres-Becker, I.4    Gonzalez, S.5    Fernandez-Ruiz, J.6    Ramos, J.A.7
  • 33
    • 0030852614 scopus 로고    scopus 로고
    • Accumulation of N-arachidonoylethanolamine (anandamide) into cerebellar granule cells occurs via facilitated diffusion
    • Hillard C.J., Edgemond W.S., Jarrahian A., Campbell W.B. Accumulation of N-arachidonoylethanolamine (anandamide) into cerebellar granule cells occurs via facilitated diffusion. J. Neurochem. 69:1997;631-638.
    • (1997) J. Neurochem. , vol.69 , pp. 631-638
    • Hillard, C.J.1    Edgemond, W.S.2    Jarrahian, A.3    Campbell, W.B.4
  • 34
    • 0028959398 scopus 로고
    • 1-Acyl-2-alkylhydrazines by the reduction of acylhydrazones
    • Wu P-L, Peng S-Y, Magrath J. 1-Acyl-2-alkylhydrazines by the reduction of acylhydrazones. Synthesis 1995;435-8.
    • (1995) Synthesis , pp. 435-438
    • Wu, P.-L.1    Peng, S.-Y.2    Magrath, J.3
  • 35
    • 4243960063 scopus 로고
    • The reaction of hydrazones and related compounds with strong base. Part II. Nitriles from phenylhydrazones
    • Grundon MF, Scott MD. The reaction of hydrazones and related compounds with strong base. Part II. Nitriles from phenylhydrazones. J Chem Soc 1964;5674-9.
    • (1964) J Chem Soc , pp. 5674-5679
    • Grundon, M.F.1    Scott, M.D.2
  • 36
    • 0031031557 scopus 로고    scopus 로고
    • Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes
    • Bisogno T., Maurelli S., Melck D., De Petrocellis L., Di Marzo V. Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes. J. Biol. Chem. 272:1997;3315-3323.
    • (1997) J. Biol. Chem. , vol.272 , pp. 3315-3323
    • Bisogno, T.1    Maurelli, S.2    Melck, D.3    De Petrocellis, L.4    Di Marzo, V.5
  • 37
    • 0029619298 scopus 로고
    • Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma 'anandamide amidohydrolase'
    • Maurelli S., Bisogno T., De Petrocellis L., Di Luccia A., Marino G., Di Marzo V. Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma 'anandamide amidohydrolase'. FEBS Lett. 377:1995;82-86.
    • (1995) FEBS Lett. , vol.377 , pp. 82-86
    • Maurelli, S.1    Bisogno, T.2    De Petrocellis, L.3    Di Luccia, A.4    Marino, G.5    Di Marzo, V.6
  • 40
    • 0033850995 scopus 로고    scopus 로고
    • Natural and synthetic endocannabinoids and their structure-activity relationships
    • Palmer S.L., Khanolkar A.D., Makriyannis A. Natural and synthetic endocannabinoids and their structure-activity relationships. Curr. Pharm. Des. 6:2000;1381-1397.
    • (2000) Curr. Pharm. Des. , vol.6 , pp. 1381-1397
    • Palmer, S.L.1    Khanolkar, A.D.2    Makriyannis, A.3
  • 41
    • 0034332637 scopus 로고    scopus 로고
    • N-Acyl-dopamines: Novel synthetic CB(1) cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo
    • Bisogno T., Melck D., Bobrov M.Yu., Gretskaya N.M., Bezuglov V.V., De Petrocellis L., Di Marzo V. N-Acyl-dopamines: novel synthetic CB(1) cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo. Biochem. J. 351:2000;817-824.
    • (2000) Biochem. J. , vol.351 , pp. 817-824
    • Bisogno, T.1    Melck, D.2    Bobrov, M.Yu.3    Gretskaya, N.M.4    Bezuglov, V.V.5    De Petrocellis, L.6    Di Marzo, V.7
  • 43
    • 0037192605 scopus 로고    scopus 로고
    • Arvanil-induced inhibition of spasticity and persistent pain: Evidence for therapeutic sites of action different from the vanilloid VR1 receptor and cannabinoid CB(1)/CB(2) receptors
    • Brooks J.W., Pryce G., Bisogno T., Jaggar S.I., Hankey D.J., Brown P., Bridges D., Ledent C., Bifulco M., Rice A.S., Di Marzo V., Baker D. Arvanil-induced inhibition of spasticity and persistent pain: evidence for therapeutic sites of action different from the vanilloid VR1 receptor and cannabinoid CB(1)/CB(2) receptors. Eur. J. Pharmacol. 439:2002;83-92.
    • (2002) Eur. J. Pharmacol. , vol.439 , pp. 83-92
    • Brooks, J.W.1    Pryce, G.2    Bisogno, T.3    Jaggar, S.I.4    Hankey, D.J.5    Brown, P.6    Bridges, D.7    Ledent, C.8    Bifulco, M.9    Rice, A.S.10    Di Marzo, V.11    Baker, D.12


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.