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Titolo:
Unsaturated long-chain N-acyl-vanillyl-amides (N-AVAMs): Vanilloid receptor ligands that inhibit anandamide-facilitated transport and bind to CB1 cannabinoid receptors
Autore:
Melck, D; Bisogno, T; De Petrocellis, L; Chuang, HH; Julius, D; Bifulco, M; Di Marzo, V;
Indirizzi:
CNR, Ist Chim Mol Interesse Biol, Natl Inst Chem Biol Syst, I-80072 Arco, Napoli, Italy CNR Arco Napoli Italy I-80072 Chem Biol Syst, I-80072 Arco, Napoli, Italy CNR, Ist Cibernet, I-80072 Arco, Napoli, Italy CNR Arco Napoli Italy I-80072 , Ist Cibernet, I-80072 Arco, Napoli, Italy Univ Calif San Francisco, Dept Mol & Cellular Pharmacol, San Francisco, CA94143 USA Univ Calif San Francisco San Francisco CA USA 94143 rancisco, CA94143 USA Univ Naples, CNR, CEOS, I-80131 Naples, Italy Univ Naples Naples Italy I-80131 aples, CNR, CEOS, I-80131 Naples, Italy Univ Naples, Dipartimento Biol & Patol Cellulare & Mol, I-80131 Naples, Italy Univ Naples Naples Italy I-80131 Cellulare & Mol, I-80131 Naples, Italy
Titolo Testata:
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS
fascicolo: 1, volume: 262, anno: 1999,
pagine: 275 - 284
SICI:
0006-291X(19990819)262:1<275:ULN(VR>2.0.ZU;2-W
Fonte:
ISI
Lingua:
ENG
Soggetto:
HUMAN BREAST-CANCER; FATTY-ACID AMIDES; CAPSAICIN RECEPTOR; CELL-PROLIFERATION; SENSORY NEURONS; MAST-CELLS; OLVANIL; ANALOGS; BRAIN; PALMITOYLETHANOLAMIDE;
Keywords:
cannabinoid; endocannabinoid; capsaicin; analgesics; breast cancer cells; carrier;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
38
Recensione:
Indirizzi per estratti:
Indirizzo: Di Marzo, V CNR, Ist Chim Mol Interesse Biol, Natl Inst Chem Biol Syst, Via Toiano 6, I-80072 Arco, Napoli, Italy CNR Via Toiano 6 Arco Napoli Italy I-80072 Arco, Napoli, Italy
Citazione:
D. Melck et al., "Unsaturated long-chain N-acyl-vanillyl-amides (N-AVAMs): Vanilloid receptor ligands that inhibit anandamide-facilitated transport and bind to CB1 cannabinoid receptors", BIOC BIOP R, 262(1), 1999, pp. 275-284

Abstract

We investigated the effect of changing the length and degree of unsaturation of the fatty acyl chain of N-(3-methoxy-4-hydroxy)-benzyl-cis-9-octadecenoamide (olvanil), a ligand of vanilloid receptors, on its capability to: (i) inhibit anandamide-facilitated transport into cells and enzymatic hydrolysis, (ii) bind to CB1 and CB2 cannabinoid receptors, and (iii) activate the VR1 vanilloid receptor. Potent inhibition of [C-14]anandamide accumulation into cells was achieved with C20:4 n-6, C18:3 n-6 and n-3, and C18:2 n-6 N-acyl-vanillyl-amides (N-AVAMs). The saturated analogues and Delta(9)-trans-olvanil were inactive. Activity in CB1 binding assays increased when increasing the number of cis-double bonds in a n-6 fatty acyl chain and, in saturated N-AVAMs, was not greatly sensitive to decreasing the chain length, The C20:4 n-6 analogue (arvanil) was a potent inhibitor of anandamide accumulation (IC50 = 3.6 mu M) and was 4-fold more potent than anandamide on CB1 receptors (Ki = 0.25-0.52 mu M), whereas the C18:3 n-3 N-AVAM was more selective than arvanil for the uptake (IC50 = 8.0 mu M) vs CB1 receptors (Ki = 3.4 mu M). None of the compounds efficiently inhibited [C-14]anandamide hydrolysis or bound to CB2 receptors, All N-AVAMs activated the cation currents coupled to VR1 receptors overexpressed in Xenopus oocytes, In a simple, intact cell model of both vanilloid- and anandamide-like activity, i.e., theinhibition of human breast cancer cell (HBCC) proliferation, arvanil was shown to behave as a "hybrid" activator of cannabinoid and vanilloid receptors. (C) 1999 Academic Press.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/12/20 alle ore 13:17:47