N-Arahidonoil dopamin

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N-Arahidonoil-dopamin
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. (1. 11. 2000). "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.
  2. ^ a b c d Huang, Susan M.; Bisogno, Tiziana; Trevisani, Marcello; Al-Hayani, Abdulmonem; Petrocellis, Luciano De; Fezza, Filomena; Tognetto, Michele; Petros, Timothy J.; Krey, Jocelyn F.; Chu, Constance J.; Miller, Jeffrey D.; Davies, Stephen N.; Geppetti, Pierangelo; Walker, J. Michael; Marzo, Vincenzo Di (11. 6. 2002). "An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors". Proceedings of the National Academy of Sciences of the United States of America. 99 (12): 8400–8405. Bibcode:2002PNAS...99.8400H. doi:10.1073/pnas.122196999. PMC 123079. PMID 12060783.
  3. ^ Bezuglov, V.; Bobrov, M.; Gretskaya, N.; Gonchar, A.; Zinchenko, G.; Melck, D.; Bisogno, T.; Di Marzo, V.; Kuklev, D. (26. 2. 2001). "Synthesis and biological evaluation of novel amides of polyunsaturated fatty acids with dopamine". Bioorganic & Medicinal Chemistry Letters. 11 (4): 447–449. doi:10.1016/s0960-894x(00)00689-2. ISSN 0960-894X. PMID 11229744.
  4. ^ Little, P. J.; Compton, D. R.; Johnson, M. R.; Melvin, L. S.; Martin, B. R. (1. 12. 1988). "Pharmacology and stereoselectivity of structurally novel cannabinoids in mice". The Journal of Pharmacology and Experimental Therapeutics. 247 (3): 1046–1051. ISSN 0022-3565. PMID 2849657.
  5. ^ a b Price, Theodore J.; Patwardhan, Amol; Akopian, Armen N.; Hargreaves, Kenneth M.; Flores, Christopher M. (1. 4. 2004). "Modulation of trigeminal sensory neuron activity by the dual cannabinoid-vanilloid agonists anandamide, N-arachidonoyl-dopamine and arachidonyl-2-chloroethylamide". British Journal of Pharmacology. 141 (7): 1118–1130. doi:10.1038/sj.bjp.0705711. ISSN 0007-1188. PMC 1574881. PMID 15006899.
  6. ^ Marinelli, Silvia; Di Marzo, Vincenzo; Florenzano, Fulvio; Fezza, Filomena; Viscomi, Maria Teresa; van der Stelt, Mario; Bernardi, Giorgio; Molinari, Marco; Maccarrone, Mauro (1. 2. 2007). "N-arachidonoyl-dopamine tunes synaptic transmission onto dopaminergic neurons by activating both cannabinoid and vanilloid receptors". Neuropsychopharmacology. 32 (2): 298–308. doi:10.1038/sj.npp.1301118. ISSN 0893-133X. PMID 16760924.
  7. ^ Sagar, Devi R.; Smith, Paul A.; Millns, Paul J.; Smart, Darren; Kendall, David A.; Chapman, Victoria (1. 7. 2004). "TRPV1 and CB(1) receptor-mediated effects of the endovanilloid/endocannabinoid N-arachidonoyl-dopamine on primary afferent fibre and spinal cord neuronal responses in the rat". The European Journal of Neuroscience. 20 (1): 175–184. doi:10.1111/j.1460-9568.2004.03481.x. ISSN 0953-816X. PMID 15245490.
  8. ^ Bobrov, Mikhail Yu; Lizhin, Anatoly A.; Andrianova, Ekaterina L.; Gretskaya, Natalia M.; Frumkina, Lidia E.; Khaspekov, Leonid G.; Bezuglov, Vladimir V. (24. 1. 2008). "Antioxidant and neuroprotective properties of N-arachidonoyldopamine". Neuroscience Letters. 431 (1): 6–11. doi:10.1016/j.neulet.2007.11.010. ISSN 0304-3940. PMID 18069125.
  9. ^ Harrison, Selena; De Petrocellis, Luciano; Trevisani, Marcello; Benvenuti, Francesca; Bifulco, Maurizio; Geppetti, Pierangelo; Di Marzo, Vincenzo (15. 8. 2003). "Capsaicin-like effects of N-arachidonoyl-dopamine in the isolated guinea pig bronchi and urinary bladder". European Journal of Pharmacology. 475 (1–3): 107–114. doi:10.1016/s0014-2999(03)02114-9. ISSN 0014-2999. PMID 12954366.
  10. ^ O'Sullivan, Saoirse E.; Kendall, David A.; Randall, Michael D. (1. 3. 2004). "Characterisation of the vasorelaxant properties of the novel endocannabinoid N-arachidonoyl-dopamine (NADA)". British Journal of Pharmacology. 141 (5): 803–812. doi:10.1038/sj.bjp.0705643. ISSN 0007-1188. PMC 1574254. PMID 14769783.
  11. ^ O'Sullivan, Saoirse E.; Kendall, David A.; Randall, Michael D. (1. 1. 2009). "Time-dependent vascular effects of Endocannabinoids mediated by peroxisome proliferator-activated receptor gamma (PPARγ)". PPAR Research. 2009: 425289. doi:10.1155/2009/425289. ISSN 1687-4757. PMC 2676321. PMID 19421417.
  12. ^ Navarrete, Carmen M.; Fiebich, Bernd L.; de Vinuesa, Amaya García; Hess, Sandra; de Oliveira, Antonio C. P.; Candelario-Jalil, Eduardo; Caballero, Francisco J.; Calzado, Marco A.; Muñoz, Eduardo (1. 4. 2009). "Opposite effects of anandamide and N-arachidonoyl dopamine in the regulation of prostaglandin E and 8-iso-PGF formation in primary glial cells". Journal of Neurochemistry. 109 (2): 452–464. doi:10.1111/j.1471-4159.2009.05966.x. ISSN 1471-4159. PMID 19200337.
  13. ^ Navarrete, Carmen M.; Pérez, Moisés; de Vinuesa, Amaya García; Collado, Juan A.; Fiebich, Bernd L.; Calzado, Marco A.; Muñoz, Eduardo (15. 6. 2010). "Endogenous N-acyl-dopamines induce COX-2 expression in brain endothelial cells by stabilizing mRNA through a p38 dependent pathway". Biochemical Pharmacology. 79 (12): 1805–1814. doi:10.1016/j.bcp.2010.02.014. ISSN 1873-2968. PMID 20206142.
  14. ^ Sancho, Rocío; Macho, Antonio; de La Vega, Laureano; Calzado, Marco A.; Fiebich, Bernd L.; Appendino, Giovanni; Muñoz, Eduardo (15. 2. 2004). "Immunosuppressive activity of endovanilloids: N-arachidonoyl-dopamine inhibits activation of the NF-kappa B, NFAT, and activator protein 1 signaling pathways". Journal of Immunology. 172 (4): 2341–2351. doi:10.4049/jimmunol.172.4.2341. ISSN 0022-1767. PMID 14764703.
  15. ^ Wilhelmsen, Kevin; Khakpour, Samira; Tran, Alphonso; Sheehan, Kayla; Schumacher, Mark; Xu, Fengyun; Hellman, Judith (9. 5. 2014). "The endocannabinoid/endovanilloid N-arachidonoyl dopamine (NADA) and synthetic cannabinoid WIN55,212-2 abate the inflammatory activation of human endothelial cells". The Journal of Biological Chemistry. 289 (19): 13079–13100. doi:10.1074/jbc.M113.536953. ISSN 1083-351X. PMC 4036321. PMID 24644287.
  16. ^ Sancho, Rocío; de la Vega, Laureano; Macho, Antonio; Appendino, Giovanni; Di Marzo, Vincenzo; Muñoz, Eduardo (15. 9. 2005). "Mechanisms of HIV-1 inhibition by the lipid mediator N-arachidonoyldopamine". Journal of Immunology. 175 (6): 3990–3999. doi:10.4049/jimmunol.175.6.3990. ISSN 0022-1767. PMID 16148147.
  17. ^ Yoo, Jae-Myung; Park, Eun Seok; Kim, Mee Ree; Sok, Dai-Eun (1. 4. 2013). "Inhibitory effect of N-Acyl dopamines on IgE-mediated allergic response in RBL-2H3 cells". Lipids. 48 (4): 383–393. doi:10.1007/s11745-013-3758-6. ISSN 1558-9307. PMID 23377981.
  18. ^ Shu-Jung Hu, Sherry; Bradshaw, Heather B.; Benton, Valery M.; Shih-Chieh Chen, Jay; Huang, Susan M.; Minassi, Alberto; Bisogno, Tiziana; Masuda, Kim; Tan, Bo; Roskoski, Robert; Cravatt, Benjamin F.; Di Marzo, Vincenzo; Walker, J. Michael (1. 10. 2009). "The biosynthesis of N-arachidonoyl dopamine (NADA), a putative endocannabinoid and endovanilloid, via conjugation of arachidonic acid with dopamine". Prostaglandins, Leukotrienes and Essential Fatty Acids. 81 (4): 291–301. doi:10.1016/j.plefa.2009.05.026. ISSN 0952-3278. PMC 2757501. PMID 19570666.
  19. ^ Pajouhesh, H; Hancock, A J (1. 3. 1984). "Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine". Journal of Lipid Research. 25 (3): 310–312. ISSN 0022-2275. PMID 6726084. Pristupljeno 15. 12. 2017.

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