Design and synthesis of novel xyloketal derivatives and their vasorelaxing activities in rat thoracic aorta and angiogenic activities in zebrafish angiogenesis screen

Journal of Medicinal Chemistry

Volumn 53, Issue 12, 2010, Pages 4642-4653

  Xu, Zhongliang ^a   Li, Yiying ^a   Xiang, Qi ^b   Pei, Zhong ^a   Liu, Xilin ^a   Lu, Bingtai ^a   Chen, Ling ^a   Wang, Guanlei ^c   Pang, Jiyan ^a   Lin, Yongcheng ^a  

^a SUN YAT SEN UNIVERSITY   (China)

^b JINAN UNIVERSITY   (China)

^c SUN YAT SEN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARDIOVASCULAR AGENT; N(G) NITROARGININE METHYL ESTER; NITRIC OXIDE; UNCLASSIFIED DRUG; XYLOKETAL A; XYLOKETAL B; XYLOKETAL C; XYLOKETAL D; XYLOKETAL H;

ANGIOGENESIS; ANIMAL TISSUE; ARTICLE; CELL DAMAGE; CELL VIABILITY; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; EMBRYO; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; THORACIC AORTA; VASODILATATION; ZEBRA FISH;

ANGIOGENESIS INDUCING AGENTS; ANIMALS; AORTA, THORACIC; CELL SURVIVAL; DRUG DESIGN; EMBRYO, NONMAMMALIAN; ENDOTHELIAL CELLS; ENDOTHELIUM, VASCULAR; LIPOPROTEINS, LDL; MUSCLE, SMOOTH, VASCULAR; NEOVASCULARIZATION, PHYSIOLOGIC; NITRIC OXIDE; PYRANS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; VASODILATOR AGENTS; ZEBRAFISH;

EID: 77953777757     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1001502     Document Type: Article

References (43)

1. Schwartz, C. J.; Valente, A. J.; Sprague, E. A.; Kelley, J. L.; Nerem, R. M. The pathogenesis of atherosclerosis: an overview Clin. Cardiol. 1991, 14, 1-16
2. Arnal, J. F.; Michel, J. B.; Harrison, D. G. Nitric oxide in the pathogenesis of hypertension Curr. Opin. Nephrol. Hypertens. 1995, 4, 182-188
3. Bund, S. J.; Lee, R. M. K. W. Arterial structural changes in hypertension: a consideration of methodology, terminology and functional consequence J. Vasc. Res. 2003, 40, 547-557
4. Bruch, J. E. J.; Faxon, D. P.; Salmon, S.; Jacobs, A. K.; Ryan, T. J. Abnormal endothelium dependent coronary vasomotion in hypertensive patients J. Am. Coll. Cardiol. 1992, 19, 809-815
5. Ross, R. Atherosclerosis is an inflammatory disease Am. Heart J. 1999, 138, 419-420
6. Radomski, M. W.; Palmer, R. M.; Moncada, S. Comparative pharmacology of endothelium-derived relaxing factor, nitric oxide and prostacyclin in platelets Br. J. Pharmacol. 1987, 92, 181-187 (Pubitemid 17134934)
7. Sawamura, T.; Kume, N.; Aoyama, T.; Moriwaki, H.; Hoshikawa, H.; Aiba, Y. An endothelial receptor for oxidized low-density lipoprotein Nature 1997, 386, 73-77
8. Cominacini, L.; Pasini, A. F.; Garbin, U.; Davoli, A.; Tosetti, M. L.; Campagnola, M. Oxidized low density lipoprotein (ox-LDL) binding to ox-LDL receptor-1 in endothelial cells induces the activation of NF-kappaB through an increased production of intracellular reactive oxygen species J. Biol. Chem. 2000, 275, 12633-12638
9. Poli, G.; Leonarduzzi, G.; Biasi, F. Oxidative stress and cell signalling Curr. Med. Chem. 2004, 11, 1163-1182
10. Owens, G. K. Regulation of differentiation of vascular smooth muscle cells Physiol. Rev. 1995, 75, 487-517
11. Troost, R.; Schwedhelm, E.; Rojczyk, S.; Tsikas, D.; Frohlich, J. C. Nebivolol decreases systemic oxidative stress in healthy volunteers Br. J. Clin. Pharmacol. 2000, 50, 377-379
12. Gao, Y. S.; Nagao, T.; Bond, R. A. Nebivolol induces endothelium dependent relaxations of canine coromary arteries J. Cardiovasc. Pharmacol. 1991, 17, 964-969
13. Robert, A. H.; Marie, C. P. Hot off the press Nat. Prod. Rep. 2001, 18, 3-5
14. Robert, A. H.; Marie, C. P. Hot off the press Nat. Prod. Rep. 2003, 20, 29-31
15. Lin, Y.; Wu, X.; Feng, S.; Jiang, G.; Luo, J.; Zhou, S.; Vrijmoed, L. L. P.; Jones, E. B. G.; Krohn, K.; Steingrover, K.; Zsila, F. Five unique compounds: xyloketals from mangrove fungus Xylaria sp from the South China Sea coast J. Org. Chem. 2001, 66, 6252-6256
16. Wu, X.; Liu, X.; Lin, Y.; Luo, J.; She, Z.; Li, H.; Chan, W.; Antus, S.; Kurtan, T.; Elsasser, B.; Krohn, K. Xyloketal F: a strong L-calcium channel blocker from the mangrove fungus Xylaria sp (# 2508) from the South China Sea coast Eur. J. Org. Chem. 2005, 19, 4061-4064
17. Wu, X.; Liu, X.; Jiang, G.; Lin, Y.; Chan, W.; Vrijmoed, L. L. P. Xyloketal G: a novel metabolite from the mangrove fungus Xylaria sp. 2508 Chem. Nat. Compd. 2005, 41, 27-29
18. Liu, X.; Xu, F.; Zhang, Y.; Liu, L.; Huang, H.; Cai, X.; Lin, Y.; Chan, W. Xyloketal H from the mangrove endophytic fungus Xylaria sp. 2508 Russ. Chem. Bull. 2006, 55, 1091-1092 (Pubitemid 44705921)
19. Xu, F.; Zhang, Y.; Wang, J.; Pang, J.; Huang, C.; Wu, X.; She, Z.; Vrijmoed, L. L. P.; Jones, E. B. G.; Lin, Y. Benzofuran derivatives from the mangrove endophytic fungus Xylaria sp. (#2508) J. Nat. Prod. 2008, 71, 1251-1253
20. Chen, W.; Qian, Y.; Meng, W.; Pang, J.; Lin, Y.; Guan, Y.; Chen, S.; Liu, J.; Pei, Z.; Wang, G. A novel marine compound xyloketal B protects against oxidized LDL-induced cell injury in vitro Biochem. Pharmacol. 2009, 78, 941-950
21. Zhao, J.; Li, L.; Chen, L.; Li, J.; Pang, J.; Lin, Y.; Liu, J.; Huang, R.; Wang, G.; Pei, Z.; Zeng, J. Marine compound xyloketal B protects PC12 cells against OGD-induced cell damage Brain Res. 2009, 1302, 240-247
22. Pettigrew, J. D.; Bexrud, J. A.; Freeman, R. P.; Wilson, P. D. Total synthesis of (±)-xyloketal D and model studies towards the total synthesis of (-)-xyloketal A Heterocycles 2004, 62, 445-452
23. Pettigrew, J. D.; Freeman, R. P.; Wilson, P. D. Total synthesis of (-)-xyloketal D and its enantiomer-confirmation of absolute stereochemistry Can. J. Chem. 2004, 82, 1640-1648
24. Pettigrew, J. D.; Jay, A. C.; Simon, S. S. S.; Wilson, P. D. Phenylboronic acid mediated triple condensation reactions of phloroglucinol and unsaturated carbonyl compounds Org. Lett. 2005, 7, 467-470
25. Pettigrew, J. D.; Wilson, P. D. Synthesis of xyloketal A, B, C, D, and G analogues J. Org. Chem. 2006, 71, 1620-1625
26. Pettigrew, J. D.; Wilson, P. D. Total synthesis of (-)-xyloketal A Org. Lett. 2006, 8, 1427-1429
27. Krohn, K.; Riaz, M. Total synthesis of (+)-xyloketal D, a secondary metabolite from the mangrove fungus xylaria sp Tetrahedron Lett. 2004, 45, 293-294
28. Krohn, K.; Riaz, M.; Flörke, U. Synthesis of xyloketals, natural products from the mangrove fungus Xylaria sp Eur. J. Org. Chem. 2004, 1261-1270
29. Graham, S. R.; Murphy, J. A.; Kennedy, A. R. Hypophosphite mediated carbon-carbon bond formation: total synthesis of epialboatrin and structural revision of alboatrin J. Chem. Soc., Perkin Trans. 1 1999, 3071-3073
30. Chan, E. C.; Pannangpetch, P.; Woodman, O. L. Relaxation to flavones and flavonols in rat isolated thoracic aorta: mechanism of action and structure-activity relationships J. Cardiovasc. Pharmacol. 2000, 35, 326-333
31. Woodman, O. L.; Meeker, W. F.; Boujaoude, M. Vasorelaxant and antioxidant activity of flavonols and flavones: structure-activity relationships J. Cardiovasc. Pharmacol. 2005, 46, 302-309
32. Fitzpatrick, D. F.; Hirschfield, S. L.; Coffey, R. G. Endothelium-dependent vasorelaxing activity of wine and other grape products Am. J. Physiol. 1993, 265, 774-778
33. Alzawahra, W.; Liu, X.; Li, H.; Samouilov, A.; Zweier, J. L. Abstract 1439: Nitrite functions as a vascular relaxing factor forming NO and activating guanylate cyclase (sGC): role of sGC in nitrite-mediated NO formation Circulation 2007, 116, 296-296
34. Li, D.; Mehta, J. L. Antisense to LOX-1 inhibits oxidized LDL-mediated upregulation of monocyte chemoattractant protein-1 and monocyte adhesion to human coronary artery endothelial cells Circulation 2000, 101, 2889-2895
35. Keaney, J. F.; Vita, J. A. Atherosclerosis, oxidative stress, and antioxidant protection in endothelium-derived relaxing factor action Prog. Cardiovasc. Dis. 1995, 38, 129-154
36. Pratico, D. Antioxidants and endothelium protection Atherosclerosis 2005, 181, 215-224
37. Kimmel, C. B.; Ballard, W. W.; Kimmel, S. R.; Ullmann, B.; Schilling, T. F. Stages of embryonic development of the zebrafish Dev. Dyn. 1995, 203, 253-310
38. Fishman, M. C. Zebrafish-the canonical vertebrate Science 2001, 294, 1290-1291
39. Thisse, C.; Zon, L. I. Organogenesis-heart and blood formation from the zebrafish point of view Science 2002, 295, 457-462
40. Gates, M. A.; Kim, L.; Egan, E. S.; Cardozo, T.; Sirotkin, H. I.; Dougan, S. T.; Lashkari, D.; Abagyan, R.; Schier, A. F.; Talbot, W. S. A genetic linkage map for zebrafish: comparative analysis and localization of genes and expressed sequences Genome Res. 1999, 9, 334-347
41. Ara, T.; Nakamura, Y.; Egawa, T.; Sugiyama, T.; Abe, K.; Kishimoto, T.; Matsui, Y.; Nagasawa, T. Impaired colonization of the gonads by primordial germ cells in mice lacking a chemokine, stromal cell-derived factor-1 (SDF-1) Proc. Nat. Acad. Sci. U.S.A. 2003, 100, 5319-5323
42. Annelii, N.; Monica, A.; Peter, C. Zebrafish and Xenopus tadpoles: small animal models to study angiogenesis and lymphangiogenesis Exp. Cell Res. 2006, 312, 684-693
43. Cheng, X.; Chen, X.; Richard, A.; Hughes, S. J.; Williams, O. L. Understanding the cardioprotective effects of flavonols: discovery of relaxant flavonols without antioxidant activity J. Med. Chem. 2008, 51, 1874-1884