N-Arahidonoil dopamin

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N-Arahidonoil-dopamin
N-Arachidonoyl dopamine.svg
Općenito
Hemijski spojN-Arahidonoil-dopamin
Druga imenaNADA
IUPAC ime: (5Z,8Z,11Z,14Z)-N-[2-(3,4-dihidroksifenil)-etil]ikosa-5,8,11,14-tetraenamid
Molekularna formulaC28H41NO3
CAS registarski broj199875-69-9
InChI1/C28H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-28(32)29-23-22-25-20-21-26(30)27(31)24-25/h6-7,9-10,12-13,15-16,20-21,24,30-31H,2-5,8,11,14,17-19,22-23H2,1H3,(H,29,32)/b7-6-,10-9-,13-12-,16-15-
Osobine1
Molarna masa439,63 g/mol
1 Gdje god je moguće korištene su SI jedinice. Ako nije drugačije naznačeno, dati podaci vrijede pri standardnim uslovima.

N-Arahidonoil-dopamin (NADA) je endokanabinoid koji djeluje kao agonist receptora CB1 i prijenosnik receptorskog potencijiala V1 (TRPV1) ionskog kanala. NADA je prvi puta opisana 2000., kao sumnjivi endokanabinoid (agonist receptora CB1), [1]a naknadno je, 2002. identificiran kao endovaniloid (agonist TRPV1-a).[2] NADA je lipid na bazi endogene arahidonske kiseline, koji se nalazi u mozgu pacova, s posebno visokim koncentracijama u hipokampusu, malom mozgu i strijatumu.[2] Aktivira TRPV1 kanal sa EC50, od približno 50 nM, što ga čini pretpostavljenim endogenim TRPV1 agonistom.[2]

Pokazano da kod miševa NADA inducira tetradne fiziološke paradigme, povezane sa kanabinoidima: hipotermiju, hipolokomociju, katalepsiju i analgeziju.[1][3][4] Otkriveno je da NADA ima regulatornu ulogu i u perifernom i centralnom nervnom sistemu i ispoljava svojstva antioksidanata i neuroprotektanta.[2][5][5][6][7] NADA je također uključena u kontrakciju glatkih mišića i vazorelaksaciju u krvnim sudovima.[8][9][10][11] Pored toga, opaženo je da NADA suzbija upalnu aktivaciju ljudskih Jurkat T-ćelija i inhibira oslobađanje prostaglandina E2 (PGE2) iz astrocita aktiviranih lipopolisaharidom (LPS), mikroglije i mišjeg mozga (MEC-mozak).[12][13][14] NADA also promotes the inflammatory resolution of human endothelial cells activated by both endogenous (i.e. TNF) and exogenous (i.e. bacterial derived LPS (TLR4 agonist) and FSL-1 (TLR2/6 agonist)) inflammatory mediators.[15] Može povećati oslobađanje TRPV1 tvari supstance P i peptida vezanog za kalcitoninski gen (CGRP) u krstima dorzalne leđne moždine pacova.[16] Konačno, NADA može spriječiti degranulaciju i oslobađanje TNF-a iz mastocita RBL-2H3 tretiranih IgE-antigenim kompleksom.[17] Zajedno, ove studije pokazuju da su fiziološke funkcije koje se pripisuju NADA-i višestruke i uključuju sposobnost modulacije imunoskog odgovora.

Biosintetski put N-arahindonoildopamina nije dobro razumljiv. Predloženo je da se konjugira iz arachidonoil-CoA ili arahidinoil fosfolipida i dopamina, ali in vitro eksperimenti ne podržavaju ovu teoriju.[18] Međutim, moguća je indirektna biosinteza fosfolipidnih estera s dopaminom, jer dopamin može inducirati aminolizu veza glicerol-masne kiseline u fosfolipidnim lancima (arahidonoil, palmitoil, linoleil itd.).[19]

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Reference[uredi | uredi izvor]

  1. ^ a b Bisogno, T.; Melck, D.; Bobrov MYu, null; Gretskaya, N. M.; Bezuglov, V. V.; De Petrocellis, L.; Di Marzo, V. (2000-11-01). "N-acyl-dopamines: novel synthetic CB(1) cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo". The Biochemical Journal. 351 (3): 817–824. doi:10.1042/bj3510817. ISSN 0264-6021. PMC 1221424. PMID 11042139.
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