Identification of a potent and selective cannabinoid CB 1 receptor antagonist from Auxarthron reticulatum

ACS Medicinal Chemistry Letters

Volumn 2, Issue 11, 2011, Pages 866-869

  Elsebai, Mahmoud Fahmi ^a,b   Rempel, Viktor ^a   Schnakenburg, Gregor ^a   Kehraus, Stefan ^a   Müller, Christa E ^a   König, Gabriele M ^a  

^a UNIVERSITY OF BONN   (Germany)

^b MANSOURA UNIVERSITY   (Egypt)

Author keywords

amauromine; Auxarthron reticulatum; cannabinoid receptors; CB 1; CB 2; natural products

Indexed keywords

4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; ALKALOID DERIVATIVE; AMAUROMINE; CANNABINOID 1 RECEPTOR; CANNABINOID 1 RECEPTOR ANTAGONIST; CANNABINOID 2 RECEPTOR; CYCLIC AMP; METHYL PENICINOLINE; NATURAL PRODUCT; PIPERAZINE DERIVATIVE; QUINOLINE DERIVATIVE; RADIOLIGAND; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; AUXARTHRON RETICULATUM; CHO CELL; DRUG ISOLATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; FUNGUS; GENE EXPRESSION; LIGAND BINDING; NONHUMAN; PRIORITY JOURNAL; RECEPTOR AFFINITY; SPONGE (PORIFERA); STRUCTURE ACTIVITY RELATION;

AUXARTHRON RETICULATUM; CRICETULUS GRISEUS; FUNGI; IRCINIA VARIABILIS;

EID: 80955132747     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200183z     Document Type: Article

References (22)

1. Graham, E. S.; Ashton, J. C.; Glass, M. Cannabinoid receptors: A brief history and "what's hot" Front. Biosci. 2009, 14, 944-957
2. Matsuda, L. A.; Lolait, S. J.; Brownstein, M. J.; Young, A. C.; Bonner, T. I. Structure of a cannabinoid receptor and functional expression of the cloned cDNA Nature 1990, 346, 561-564
3. Pacher, P.; Batkai, S.; Kunos, G. The endocannabinoid system as an emerging target of pharmacotherapy Pharmacol. Rev. 2006, 58, 389-462 (Pubitemid 44394908)
4. Racz, I.; Nadal, X.; Alferink, J.; Banos, J. E.; Rehnelt, J.; Martin, M.; Pintado, B.; Gutierrez-Adan, A.; Sanguino, E.; Manzanares, J.; Zimmer, A.; Maldonado, R. Crucial role of CB(2) cannabinoid receptor in the regulation of central immune responses during neuropathic pain J. Neurosci. 2008, 28, 12125-12135
5. Devane, W. A.; Hanus, L.; Breuer, A.; Pertwee, R. G.; Stevenson, L. A.; Griffin, G.; Gibson, D.; Mandelbaum, A.; Etinger, A.; Mechoulam, R. Isolation and structure of a brain constituent that binds to the cannabinoid receptor Science 1992, 258, 1946-1949 (Pubitemid 23026736)
6. Fusar-Poli, P.; Crippa, J. A.; Bhattacharyya, S.; Borgwardt, S. J.; Allen, P.; Martin-Santos, R.; Seal, M.; Surguladze, S. A.; O'Carrol, C.; Atakan, Z.; Zuardi, A. W.; McGuire, P. K. Distinct effects of {delta}9- tetrahydrocannabinol and cannabidiol on neural activation during emotional processing Arch. Gen. Psychiatry 2009, 66, 95-105
7. Pertwee, R. G. Receptors and channels targeted by synthetic cannabinoid receptor agonists and antagonists Curr. Med. Chem. 2010, 17, 1360-1381
8. Scheen, A. J.; Paquot, N. Use of cannabinoid CB1 receptor antagonists for the treatment of metabolic disorders. Best Pract. Res. Clin. Endocrinol. Metab. 2009, 23, 103-116
9. Takase, S.; Kawai, Y.; Uchida, I.; Tanaka, H.; Aoki, H. Structure of amauromine, a new alkaloid with vasodilating activity produced by Amauroascus sp Tetrahedron Lett. 1984, 25, 4673-4676 (Pubitemid 14007386)
10. Takase, S.; Iwami, M.; Ando, T.; Okamoto, M.; Yoshida, K.; Horiai, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. Amauromine, a new vasodilator. Taxonomy, isolation and characterization J. Antibiot. 1984, 37, 1320-1323
11. Takase, S.; Kawai, Y.; Uchida, I.; Tanaka, H.; Aoki, H. Structure of amauromine, a new hypotensive vasodilator produced by Amauroascus sp Tetrahedron 1985, 41, 3037-3048 (Pubitemid 15236262)
12. Laws, I.; Mantle, P. G. Nigrifortine, a diketopiperazine metabolite of Penicillium nigricans Phytochemistry 1985, 24, 1395-1397
13. Zhu, F.; Lin, Y. Marinamide, a novel alkaloid and its methyl ester produced by the application of mixed fermentation technique to two mangrove endophytic fungi from the South China Sea Chin. Sci. Bull. 2006, 51, 1426-1430 (Pubitemid 44432188)
14. Shao, C.-L.; Wang, C.-Y.; Gu, Y.-C.; Wei, M.-Y.; Pan, J.-H.; Deng, D.-S.; She, Z.-G.; Lin, Y.-C. Penicinoline, a new pyrrolyl 4-quinolinone alkaloid with an unprecedented ring system from an endophytic fungus Penicillium sp Bioorg. Med. Chem. Lett. 2010, 20, 3284-3286
15. Behrenswerth, A.; Volz, N.; Torang, J.; Hinz, S.; Bräse, S.; Müller, C. E. Synthesis and pharmacological evaluation of coumarin derivatives as cannabinoid receptor antagonists and inverse agonists Bioorg. Med. Chem. 2009, 17, 2842-2851
16. Drabczynska, A.; Yuzlenko, O.; Köse, M.; Paskaleva, M.; Schiedel, A. C.; Karolak-Wojciechowska, J.; Handzlik, J.; Karcz, T.; Kuder, K.; Müller, C. E.; Kiec-Kononowicz, K. Synthesis and biological activity of tricyclic cycloalkylimidazo-, pyrimido- and diazepinopurinediones Eur. J. Med. Chem. 2011, 46, 3590-3607
17. Poso, A.; Huffman, J. W. Targeting the cannabinoid CB2 receptor: modelling and structural determinants of CB2 selective ligands Br. J. Pharmacol. 2008, 153, 335-346
18. Huffman, J. W.; Zengin, G.; Wu, M.-J.; Lu, J.; Hynd, G.; Bushell, K.; Thompson, A. L. S.; Bushell, S.; Tartal, C.; Hurst, D. P.; Reggio, P. H.; Selley, D. E.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. Structure-activity relationships for 1-alkyl-3-(l-naphthoyl)indoles at the cannabinoid CB1 and CB2 receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB2 receptor agonists Bioorg. Med. Chem. 2005, 13, 89-112 (Pubitemid 39575695)
19. Kitajima, M.; Iwai, M.; Kikura-Hanajiri, R.; Goda, Y.; Iida, M.; Yabushita, H.; Takayama, H. Discovery of indole alkaloids with cannabinoid CB1 receptor antagonistic activity Bioorg. Med. Chem. Lett. 2011, 21, 1962-1964
20. Sink, K. S.; McLaughlin, P. J.; Wood, J. A.; Brown, C.; Fan, P.; Vemuri, V. K.; Peng, Y.; Olszewska, T.; Thakur, G. A.; Makriyannis, A.; Parker, L. A.; Salamone, J. D. The novel cannabinoid CB1 receptor neutral antagonist AM4113 suppresses food intake and food-reinforced behavior but does not induce signs of nausea in rats Neuropsychopharmacology 2008, 33, 946-955 (Pubitemid 351252707)
21. Wiley, J. L.; Breivogel, C. S.; Mahadevan, A.; Pertwee, R. G.; Cascio, M. G.; Bolognini, D.; Huffman, J. W.; Walentiny, D. M.; Vann, R. E.; Razdan, R. K.; Martin, B. R. Structural and pharmacological analysis of O-2050, a putative neutral cannabinoid CB(1) receptor antagonist Eur. J. Pharmacol. 2010, 651, 96-105
22. Heimann, A. S.; Gomes, I.; Dale, C. S.; Pagano, R. L.; Gupta, A.; de Souza, L. L.; Luchessi, A. D.; Castro, L. M.; Giorgi, R.; Rioli, V.; Ferro, E. S.; Devi, L. A. Hemopressin is an inverse agonist of CB1 cannabinoid receptors Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 20588-20593