Abnormalni kanabidiol

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Abnormalni kanabidiol
(IUPAC) ime
4-[(1S,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
Klinički podaci
Identifikatori
CAS broj 78216-32-7
ATC kod nije dodeljen
PubChem[1][2] 3060519
ChemSpider[3] 2321442
Hemijski podaci
Formula C21H30O2 
Mol. masa 314,46
SMILES eMolekuli & PubHem
Farmakoinformacioni podaci
Trudnoća ?
Pravni status

Abnormalni kanabidiol (abn-cbd) je sintetički regioizomer kanabidiola, koji za razliku od većine drugih kanabinoida proizvodi vazodilatorne efekte, snižava krvni pritisak, i podstiče ćelijsku migracija, ćelijsku proliferaciju i aktivira mitogenom-aktivirane proteinske kinaze kod mikroglija, ali ne proizvodi psihoaktivne efekte.[4][5]

Bilo je pokazano da akcije abnormalnog kanabidiola nisu posredovane kroz CB1 i CB2 receptore.[5][6] Abnormalni kanabidiol i O-1602 deluju na receptor čiji endogeni ligandi su: anandamid (AEA), N-arahidonoil glicin (NAGly) i N-arahidonoil L-serin.[7][8][9][10] Višestruke linije dokaza idu u podršku predlogu da je GPR18 receptor za te ligande.[5] Jedan drugi, kontroverzniji biološki cilj abnormalnog kanabidiola je GPR55, koji je zadobio mnogo pažnje jer se smatralo da je kanabinoidni receptor.[11][12] Međutim, sve je više dokaza da je lizofosfatidilinozitol (LPI) endogeni ligand za GPR55.[13][14] Dalja istraživanja su dovela do zaključka da postoji još nekoliko kanabinoidnih receptora.[15][16][17][18]

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Literatura[uredi - уреди | uredi izvor]

  1. Li Q, Cheng T, Wang Y, Bryant SH (2010). "PubChem as a public resource for drug discovery.". Drug Discov Today 15 (23-24): 1052–7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003.  edit
  2. Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). "Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities". Annual Reports in Computational Chemistry 4: 217–241. doi:10.1016/S1574-1400(08)00012-1. 
  3. Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). "Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining". J Cheminform 2 (1): 3. PMID 20331846. doi:10.1186/1758-2946-2-3.  edit
  4. Adams, MD; Earnhardt, JT; Martin, BR; Harris, LS; Dewey, WL; Razdan, RK (1977). "A cannabinoid with cardiovascular activity but no overt behavioral effects". Experientia 33 (9): 1204–5. PMID 891878. 
  5. 5,0 5,1 5,2 McHugh D, Hu SS, Rimmerman N, Juknat A, Vogil Z, Walker JM, Bradshaw HB (March 2010). "N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, the putative abnormal cannabidiol receptor". BMC Neuroscience 11 (1): 44. PMC 2865488. PMID 20346144. doi:10.1186/1471-2202-11-44. 
  6. Járai, Z; Wagner, JA; Varga, K; Lake, KD; Compton, DR; Martin, BR; Zimmer, AM; Bonner, TI; Buckley, NE (1999). "Cannabinoid-induced mesenteric vasodilation through an endothelial site distinct from CB1 or CB2 receptors.". Proceedings of the National Academy of Sciences of the United States of America 96 (24): 14136–41. PMC 24203. PMID 10570211. doi:10.1073/pnas.96.24.14136. 
  7. McHugh D, Hu SS, Rimmerman N, Juknat A, Vogil Z, Walker JM, Bradshaw HB (March 2010). "N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through [[GPR18]], the putative abnormal cannabidiol receptor". BMC Neuroscience 11 (1): 44. PMC 2865488. PMID 20346144. doi:10.1186/1471-2202-11-44.  Wikilink embedded in URL title (help)
  8. Walter, L; Franklin, A; Witting, A; Wade, C; Xie, Y; Kunos, G; MacKie, K; Stella, N (2003). "Nonpsychotropic cannabinoid receptors regulate microglial cell migration.". The Journal of neuroscience : the official journal of the Society for Neuroscience 23 (4): 1398–405. PMID 12598628. 
  9. Offertáler, L; Mo, FM; Bátkai, S; Liu, J; Begg, M; Razdan, RK; Martin, BR; Bukoski, RD; Kunos, G (2003). "Selective ligands and cellular effectors of a G protein-coupled endothelial cannabinoid receptor.". Molecular pharmacology 63 (3): 699–705. PMID 12606780. 
  10. Milman, G; Maor, Y; Abu-Lafi, S; Horowitz, M; Gallily, R; Batkai, S; Mo, FM; Offertaler, L; Pacher, P (2006). "N-arachidonoyl L-serine, an endocannabinoid-like brain constituent with vasodilatory properties.". Proceedings of the National Academy of Sciences of the United States of America 103 (7): 2428–33. PMC 1413724. PMID 16467152. doi:10.1073/pnas.0510676103. 
  11. McCollum, L; Howlett, AC; Mukhopadhyay, S (2007). "Anandamide-mediated CB1/CB2 cannabinoid receptor--independent nitric oxide production in rabbit aortic endothelial cells.". The Journal of pharmacology and experimental therapeutics 321 (3): 930–7. PMID 17379772. doi:10.1124/jpet.106.117549. 
  12. Ryberg, E; Larsson, N; Sjögren, S; Hjorth, S; Hermansson, NO; Leonova, J; Elebring, T; Nilsson, K; Drmota, T (2007). "The orphan receptor GPR55 is a novel cannabinoid receptor.". British journal of pharmacology 152 (7): 1092–101. PMC 2095107. PMID 17876302. doi:10.1038/sj.bjp.0707460. 
  13. Kapur, A; Zhao, P; Sharir, H; Bai, Y; Caron, MG; Barak, LS; Abood, ME (2009). "Atypical responsiveness of the orphan receptor GPR55 to cannabinoid ligands.". The Journal of biological chemistry 284 (43): 29817–27. PMC 2785612. PMID 19723626. doi:10.1074/jbc.M109.050187. 
  14. Henstridge, CM; Balenga, NA; Ford, LA; Ross, RA; Waldhoer, M; Irving, AJ (2009). "The GPR55 ligand L-alpha-lysophosphatidylinositol promotes RhoA-dependent Ca2+ signaling and NFAT activation.". The FASEB journal : official publication of the Federation of American Societies for Experimental Biology 23 (1): 183–93. PMID 18757503. doi:10.1096/fj.08-108670. 
  15. Brown AJ (November 2007). "Novel cannabinoid receptors". British Journal of Pharmacology 152 (5): 567–75. PMC 2190013. PMID 17906678. doi:10.1038/sj.bjp.0707481. 
  16. Johns, DG; Behm, DJ; Walker, DJ; Ao, Z; Shapland, EM; Daniels, DA; Riddick, M; Dowell, S; Staton, PC (2007). "The novel endocannabinoid receptor GPR55 is activated by atypical cannabinoids but does not mediate their vasodilator effects.". British journal of pharmacology 152 (5): 825–31. PMC 2190033. PMID 17704827. doi:10.1038/sj.bjp.0707419. 
  17. McHugh, D; Tanner, C; Mechoulam, R; Pertwee, RG; Ross, RA (2008). "Inhibition of human neutrophil chemotaxis by endogenous cannabinoids and phytocannabinoids: evidence for a site distinct from CB1 and CB2.". Molecular pharmacology 73 (2): 441–50. PMID 17965195. doi:10.1124/mol.107.041863. 
  18. Kreutz, S; Koch, M; Böttger, C; Ghadban, C; Korf, HW; Dehghani, F (2009). "2-Arachidonoylglycerol elicits neuroprotective effects on excitotoxically lesioned dentate gyrus granule cells via abnormal-cannabidiol-sensitive receptors on microglial cells.". Glia 57 (3): 286–94. PMID 18837048. doi:10.1002/glia.20756.