New iantherans from the marine sponge Ianthella quadrangulata: Novel agonists of the P2Y11 receptor

Journal of Medicinal Chemistry

Volumn 50, Issue 23, 2007, Pages 5600-5607

  Greve, Hendrik ^a   Meis, Sabine ^b   Kassack, Matthias U ^b   Kehraus, Stefan ^a   Krick, Anja ^a   Wright, Anthony D ^c   König, Gabriele M ^a  

^a UNIVERSITY OF BONN   (Germany)

^b HEINRICH HEINE UNIVERSITY   (Germany)

^c UNIVERSITY OF HAWAII AT HILO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (3,5 DIBROMO 4 METHOXYPHENYL)ACETIC ACID; 3 (3,5 DIBROMO 4 METHOXYPHENYL) 2 (SULFOOXY) 2 PROPENOIC ACID; 8 CARBOXYISOIANTHERAN A; ISOIANTHERAN A; ISOIANTHERAN B; PURINE P2Y11 RECEPTOR; PURINE P2Y11 RECEPTOR AGONIST; PURINERGIC RECEPTOR STIMULATING AGENT; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ISOLATION; DRUG SELECTIVITY; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IANTHELLA QUADRANGULATA; NUCLEOTIDE SEQUENCE; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STRUCTURE ANALYSIS;

ANIMALS; BENZOFURANS; CALCIUM; CELL LINE, TUMOR; HUMANS; LIGANDS; MODELS, MOLECULAR; PORIFERA; RECEPTORS, PURINERGIC P2; STRUCTURE-ACTIVITY RELATIONSHIP; SULFURIC ACID ESTERS; TYROSINE;

EID: 36148961568     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070043r     Document Type: Article

References (42)

1. Burnstock, G. A basis for distinguishing two types of purinergic receptor. In Cell membrane receptors for drugs and hormones: a multi disciplinary approach; Straub, R., Bolis, L., Eds.; Raven Press: New York, 1978; pp 107-118.
2. Burnstock, G. Purinergic signalling. Br. J. Pharmacol. 2006, 147, 172-181.
3. von Kügelgen, I. Pharmacological profiles of cloned mammalian P2Y-receptor subtypes. Pharmacol. Ther. 2006, 110, 415-432.
4. Müller, C. E. P2-Pyrimidinergic Receptors and Their Ligands. Curr. Pharm. Des. 2002, 8, 2353-2369.
5. Qi, A. D.; Kennedy, C.; Harden, T. K.; Nicholas, R. A. Differential coupling of the human P2Y11 receptor to phospholipase C and adenylyl cyclase. Br. J. Pharmacol. 2001, 132, 318-326.
6. Berchtold, S.; Ogilvie, A. L. J.; Bogdan, C.; Muhl-Zurbes, P.; Ogilvie, A.; Schuler, G.; Steinkasserer, A. Human monocyte derived dendritic cells express functional P2X and P2Y receptors as well as ectonucleotidases. FEBS Lett. 1999, 458, 424-428.
7. Marteau, F.; Communi, D.; Boeynaems, J. M.; Suarez-Gonzalez, N. Involvement of multiple P2Y receptors and signaling pathways in the action of adenine nucleotides diphosphates on human monocyte-derived dendritic cells. J. Leukoc. Biol. 2004, 76, 796-803.
8. Wilkin, F.; Duhant, X.; Bruyns, C.; Suarez-Huerta, N.; Boeynaems, J. M.; Robaye, B. The P2Y11 receptor mediates the ATP-induced maturation of human monocyte-derived dendritic cells. J. Immunol. 2001, 166, 7172-7177.
9. Communi, D.; Robaye, B.; Boeynaems, J. M. Pharmacological characterization of the human P2Y11 receptor. Br. J. Pharmacol. 1999, 128, 1199-1206.
10. Burnstock, G. Introduction: P2 Receptors. Curr. Top. Med. Chem. 2004, 4, 793-803.
11. 11 receptor antagonists with nanomolar potency. J. Med. Chem. 2005, 48, 7040-7048.
12. Meis, S.; Hongwiset, D.; Kassack, M. U. Discovery of new potent, non-nucleotide ligands at human P2Y11-receptors results in NF546, the first non-nucleotide P2Y receptor agonist, and NF340, the so far most potent and selective P2Y11 antagonist. Purinergic Signal. 2006, 2, 177.
13. Newman, D. J.; Cragg, G. M. Marine natural products and related compounds in clinical and advanced preclinical trials. J. Nat. Prod. 2004, 67, 1216-1238.
14. Newman, D. J.; Cragg, G. M. Compounds from the Ocean as drugs and drug leads. Suppl. Biocatal. Chim. Oggi/Chem. Today 2006, 24, 42-47.
15. Kazlauskas, R.; Lidgard, R. O.; Murphy, P. T.; Wells, R. J.; Blount, J. F. Brominated tyrosine-derived metabolites from the sponge Ianthella basta. Aust. J. Chem. 1981, 34, 765-786.
16. Aoki, S.; Cho, S.-h.; Ono, M.; Kuwano, T.; Nakao, S.; Kuwano, M.; Nakagawa, S.; Gao, J.-Q.; Mayumi, T.; Shibuya, M.; Kobayashi, M. Bastadin 6, a spongean brominated tyrosine derivative, inhibits tumor angiogenesis by inducing selective apoptosis to endothelial cells. Anticancer Drugs 2006, 17, 269-278.
17. Okamoto, Y.; Ojika, M.; Sakagami, Y. Iantheran A, a dimeric polybrominated benzofuran as a Na,K-ATPase inhibitor from a marine sponge, Ianthella sp. Tetrahedron Lett. 1999, 40, 507-510.
18. Okamoto, Y.; Ojika, M.; Suzuki, S.; Murakami, M.; Sakagami, Y. Iantherans A and B, unique dimeric polybrominated benzofurans as Na,K-ATPase inhibitors from a marine sponge, Ianthella sp. Bioorg. Med. Chem. 2001, 9, 179-183.
19. Pretsch, E.; Bühlmann, P.; Affolter, C. IR Spectroscopy: sulfur-containing functional groups. In Structure determination of organic compounds - tables of spectral data, 3rd ed.; Springer-Verlag: Berlin, Germany, 2000; p 282.
20. Kalinowski, H. O.; Berger, S.; Braun, S. Chapter 3: The chemical shift: Heteroaromatics. In Carbon-13 NMR Spectroscopy; John Wiley & Sons Ltd.: Chichester, England, 1988; p 389.
21. Gulavita, N. K.; Pomponi, S. A.; Wright, A. E. Aplysillin A, A Thrombin receptor antagonist from the marine sponge Aplysina fistularis fulva. J. Nat. Prod. 1995, 58, 954-957.
22. 13C nuclear magnetic resonance spectroscopic investigation. Can. J. Chem. 1978, 56, 2681-2685.
23. Gulavita, N. K.; Wright, A. E.; McCarthy, P. J.; Pomponi, S. A.; Kelly-Borges, M.; Chin, M.; Sills, M. A. Isolation and structure elucidation of 34-Sulfatobastadin 13, an inhibitor of the Endothelin A receptor, from a marine sponge of the genus Ianthella. J. Nat. Prod. 1993, 56, 1613-1617.
24. Franklin, M. A.; Penn, S. G.; Lebrilla, C. B.; Lam, T. H.; Pessah, I. N.; Molinski, T. F. Bastadin 20 and bastadin O-Sulfate esters from Ianthella basta: novel modulators of the Ry1R FKBP12 receptor complex. J. Nat. Prod. 1996, 59, 1121-1127.
25. Berger, S.; Braun, S. The gated 1H-decoupling technique. In 200 and More NMR Experiments, 2nd expanded ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2004; pp 125-127.
26. Vogeli, U.; von Philipsborn, W. Vicinal C, H spin coupling in substituted alkenes. Stereochemical significance and structural effects. Org. Magn. Reson. 1975, 7, 617-627.
27. Coll, J. C.; Mitchell, S. J.; Stokie, G. J. Studies of Australian soft corals. V - A novel furano- sesquiterpene acid from the soft coral Sinularia gonatodes (Kolonko). Tetrahedron Lett. 1977, 18, 1539-1542.
28. Schwarcz, J. A.; Cyr, N.; Perlin, A. S. Orientation effects and the sign of two-bond 13C-1H coupling. Can. J. Chem. 1975, 53, 1872-1875.
29. Parella, T.; Sanchez-Ferrando, F.; Virgili, A. Effect of hydroxyl and carbonyl groups on long-range proton-carbon coupling constants. Magn. Reson. Chem. 1994, 32, 657-664.
30. Weller, D. D.; Stirchak, E. P.; Yokoyama, A. Preparation of oxygenated phenylacetic acids. J. Org. Chem. 1984, 49, 2061-2063.
31. Wassermann, H. H.; Wang, J. Sythese of the marine metabolites verongamine, hemibastadin-2, and aerothionin using the cyano ylide coupling methodology. J. Org. Chem. 1998, 63, 5581-5586.
32. Chantraine, J.-M.; Combaut, G.; Teste, J. Phenols bromes d'une algue rouge, Halopytis incurvus: acides carboxyliques. Phytochemistry 1973, 12, 1793-1796.
33. Kassack, M. U.; Hofgen, B.; Lehmann, J.; Eckstein, N.; Quillan, J. M; Sadee, W. Functional screening of G protein-coupled receptors by measuring intracellular calcium with a fluorescence microplate reader. J Biomol. Screen. 2002, 7, 233-246.
34. Kaulich, M.; Streicher, F.; Mayer, R.; Mueller, I.; Mueller, C. E. Flavonoids - novel lead compounds for the development of P2Y2 receptor antagonists. Drug Dev. Res. 2003, 59, 72-81.
35. Yang, S.-W.; Buivich, A., Chan, T.-M.; Smith, M.; Lachowicz, J.; Pomponi, S. A.; Wright, A. E.; Mierzwa, R.; Patel, M.; Gullo, V.; Chu, M. A new sterol sulfate, Sch 572423, from a marine sponge, Topsentia sp. Bioorg. Med. Chem. Lett. 2003, 13, 1791-1794.
36. Besada, P.; Mamedova, L.; Thomas, C. J.; Costanzi, S.; Jacobson, K. A. Design and synthesis of new bicyclic diketopiperazines as scaffold for receptor probes of structurally diverse functionality. Org. Biomol. Chem. 2005, 3, 2016-2025.
37. Dorsam, R. T.; Kunapuli, S. P. Central role of the P2Y12 receptor in platelet activation. J. Clin. Invest. 2004, 113, 340-345.
38. Nichols, K. K.; Yerxa, B.; Kellerman, D. J. Diquafosol tetrasodium: a novel dry eye therapy. Expert Opin. Investig. Drugs 2004, 13, 47-54.
39. Deterding, R.; Retsch-Bogart, G.; Milgram, L.; Gibson, R.; Daines, C.; Zeitlin, P. L.; Milla, C.; Marshall, B.; Lavange, L.; Engels, J.; Mathews, D.; Gordon, J.; Schaberg, A.; Williams, J.; Ramsey, B.; Cystic, fibrosis foundation therapeutics development network. Safety and tolerability of denufosol tetrasodium inhalation solution, a novel P2Y2 receptor agonist: results of a phase 1/phase 2 multicenter study in mild to moderate cystic fibrosis. Pediatr. Pulmonol. 2005, 39, 339-348.
40. www.inspirepharm.com/pipeline.html.
41. Jacobson, K. A.; Jarvis, M. F.; Williams, M. Purine and pyrimidine (P2) receptors as drug targets. J. Med. Chem. 2002, 45, 4057-4093.
42. Dewick, P. M.; Lignans and Lignin. In Medicinal Natural Products: a biosynthetic approach; John Wiley & Sons Ltd.: Chichester, England 1997; pp 120-125.