Chemistry:N-Arachidonoyl dopamine

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Short description: Chemical compound


N-Arachidonoyl dopamine
N-Arachidonoyl dopamine.svg
N-arachidonoyl dopamine 3D BS.png
Names
Preferred IUPAC name
(5Z,8Z,11Z,14Z)-N-[2-(3,4-Dihydroxyphenyl)ethyl]icosa-5,8,11,14-tetraenamide
Other names
NADA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
Properties
C28H41NO3
Molar mass 439.63 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

N-Arachidonoyl dopamine (NADA) is an endocannabinoid that acts as an agonist of the CB1 receptor and the transient receptor potential V1 (TRPV1) ion channel. NADA was first described as a putative endocannabinoid (agonist for the CB1 receptor) in 2000[1] and was subsequently identified as an endovanilloid (agonist for TRPV1) in 2002.[2] NADA is an endogenous arachidonic acid based lipid found in the brain of rats, with especially high concentrations in the hippocampus, cerebellum, and striatum.[2] It activates the TRPV1 channel with an EC50 of approximately of 50 nM which makes it the putative endogenous TRPV1 agonist.[2]

In mice, NADA was shown to induce the tetrad of physiological paradigms associated with cannabinoids: hypothermia, hypo-locomotion, catalepsy, and analgesia.[1][3][4] NADA has been found to play a regulatory role in both the peripheral and central nervous systems, and displays antioxidant and neuroprotectant properties.[2][5][6][7] NADA has also been implicated in smooth muscle contraction and vasorelaxation in blood vessels.[8][9][10][11] Additionally, NADA has been observed to suppress inflammatory activation of human Jurkat T cells and to inhibit the release of prostaglandin E2 (PGE2) from lipopolysaccharide (LPS)-activated astrocytes, microglia and mouse brain ECs (MEC-Brain).[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] It can increase the TRPV1-mediated release of substance P and calcitonin gene-related peptide (CGRP) in rat dorsal spinal cord slices.[2] Furthermore, NADA also displays inhibitory activity in HIV-1 replication assays.[16] Finally, NADA can prevent the degranulation and release of TNF from RBL- 2H3 mast cells treated with an IgE-antigen complex.[17] Together, these studies show that physiological functions attributed to NADA are multifaceted, and include the ability to modulate the immune response.

The biosynthetic pathway of N-arachindonoyldopamine is not well understood. It has been proposed to be conjugated from arachidonoyl-CoA or arachidonoyl phospholipids and dopamine, but in vitro experiments do not support this theory.[18] However, the indirect biosynthesis of phospholipid esters with dopamine may be possible, as dopamine can induce the aminolysis of the glycerol-fatty acid bonds in phospholipid chains (arachidonoyl, palmitoyl, linoleyl, etc.).[19]

See also

  • Endocannabinoid

References

  1. ↑ 1.0 1.1 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. PMID 11042139. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 Huang, Susan M.; Bisogno, Tiziana; Trevisani, Marcello; Al-Hayani, Abdulmonem; Petrocellis, Luciano De; Fezza, Filomena; Tognetto, Michele; Petros, Timothy J. et al. (2002-06-11). "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. doi:10.1073/pnas.122196999. PMID 12060783. Bibcode: 2002PNAS...99.8400H. 
  3. ↑ Bezuglov, V.; Bobrov, M.; Gretskaya, N.; Gonchar, A.; Zinchenko, G.; Melck, D.; Bisogno, T.; Di Marzo, V. et al. (2001-02-26). "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. (1988-12-01). "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. ↑ Price, Theodore J.; Patwardhan, Amol; Akopian, Armen N.; Hargreaves, Kenneth M.; Flores, Christopher M. (2004-04-01). "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. PMID 15006899. 
  6. ↑ Marinelli, Silvia; Di Marzo, Vincenzo; Florenzano, Fulvio; Fezza, Filomena; Viscomi, Maria Teresa; van der Stelt, Mario; Bernardi, Giorgio; Molinari, Marco et al. (2007-02-01). "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 (2004-07-01). "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. (2008-01-24). "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 (2003-08-15). "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. (2004-03-01). "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. PMID 14769783. 
  11. ↑ O'Sullivan, Saoirse E.; Kendall, David A.; Randall, Michael D. (2009-01-01). "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. 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. et al. (2009-04-01). "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 (2010-06-15). "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 (2004-02-15). "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 (2014-05-09). "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. PMID 24644287. 
  16. ↑ Sancho, Rocío; de la Vega, Laureano; Macho, Antonio; Appendino, Giovanni; Di Marzo, Vincenzo; Muñoz, Eduardo (2005-09-15). "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 (2013-04-01). "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 et al. (2009-10-01). "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. PMID 19570666. 
  19. ↑ Pajouhesh, H; Hancock, A J (1984-03-01). "Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine.". Journal of Lipid Research 25 (3): 310–312. doi:10.1016/S0022-2275(20)37828-7. ISSN 0022-2275. PMID 6726084. http://www.jlr.org/content/25/3/310.abstract. Retrieved 2017-12-15. 

External links



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