A novel 2,3-diphenyl-4H-pyrido[1,2-a]pyrimidin-4-one derivative inhibits endothelial cell dysfunction and smooth muscle cell proliferation/activation

European Journal of Medicinal Chemistry

Volumn 72, Issue , 2014, Pages 102-109

  Del Turco, Serena ^a   Sartini, Stefania ^b   Sentieri, Cassandra ^a   Saponaro, Chiara ^a   Navarra, Teresa ^a   Dario, Bianca ^b   Da Settimo, Federico ^b   La Motta, Concettina ^b   Basta, Giuseppina ^a  

^a INSTITUTE OF CLINICAL PHYSIOLOGY   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

2,3 Diphenyl 4H pyrido 1,2 a pyrimidin 4 ones; 2 (3,4 Dimethoxyphenyl) 3 phenyl 4H pyrido 1,2 a pyrimidin 4 one; Cell dysfunction; Cell proliferation; Human aortic smooth muscle cells; Human umbilical vein endothelial cells

Indexed keywords

2,3 DIPHENYL 4H PYRIDO[1,2 ALPHA]PYRIMIDIN 4 ONE DERIVATIVE; APIGENIN; CYCLOOXYGENASE 2; GELATINASE B; PROSTAGLANDIN E2; PYRIMIDINE DERIVATIVE; QUERCETIN; UNCLASSIFIED DRUG; VASCULAR CELL ADHESION MOLECULE 1; 2-(3,4-DIMETHOXYPHENYL)-3-PHENYL-4H-PYRIDO(1,2-A)PYRIMIDIN-4-ONE; ENZYME INHIBITOR; PYRIDINE DERIVATIVE; PYRIMIDINONE DERIVATIVE;

AORTA; ARTICLE; CELL ACTIVATION; CELL PROLIFERATION; CONTROLLED STUDY; DRUG EFFECT; DRUG INHIBITION; ENDOTHELIAL DYSFUNCTION; ENZYME ACTIVITY; ENZYME INDUCTION; HEART MUSCLE CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; INCUBATION TIME; PROTEIN EXPRESSION; SMOOTH MUSCLE FIBER; UMBILICAL VEIN ENDOTHELIAL CELL; BIOSYNTHESIS; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; ENDOTHELIUM CELL; GENETICS; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CELL PROLIFERATION; CELLS, CULTURED; DOSE-RESPONSE RELATIONSHIP, DRUG; ENDOTHELIAL CELLS; ENZYME INHIBITORS; HUMANS; MATRIX METALLOPROTEINASE 9; MOLECULAR STRUCTURE; MYOCYTES, SMOOTH MUSCLE; PYRIDINES; PYRIMIDINONES; STRUCTURE-ACTIVITY RELATIONSHIP; VASCULAR CELL ADHESION MOLECULE-1;

EID: 84890819738     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.11.021     Document Type: Article

References (36)

1. M.A. Hlatky, and D.M. Bravata Stents or surgery? New data on the comparative outcomes of percutaneous coronary intervention and coronary artery bypass graft surgery Circulation 118 2008 325 327
2. T.F. Luscher, J. Steffel, F.R. Eberli, M. Joner, G. Nakazawa, F.C. Tanner, and R. Virmani Drug-eluting stent and coronary thrombosis: biological mechanisms and clinical implications Circulation 115 2007 1051 1058 (Pubitemid 46328299)
3. E. Arehart, S. Gleim, Z. Kasza, K.M. Fetalvero, K.A. Martin, and J. Hwa Prostacyclin, atherothrombosis, and cardiovascular disease Curr. Med. Chem. 14 2007 2161 2169 (Pubitemid 47578155)
4. D.I. Simon Inflammation and vascular injury: basic discovery to drug development Circ. J. 76 2012 1811 1818
5. J.W. Jukema, J.J. Verschuren, T.A. Ahmed, and P.H. Quax Restenosis after PCI. Part 1: pathophysiology and risk factors Nat. Rev. Cardiol. 9 2011 53 62
6. Y. Zheng, S.E. Gardner, and M.C. Clarke Cell death, damage-associated molecular patterns, and sterile inflammation in cardiovascular disease Arterioscler. Thromb. Vasc. Biol. 31 2011 2781 2786
7. A. Giordano, and A. Romano Inhibition of human in-stent restenosis: a molecular view Curr. Opin. Pharmacol. 11 2011 372 377
8. N. Fukai, R.D. Kenagy, L. Chen, L. Gao, G. Daum, and A.W. Clowes Syndecan-1: an inhibitor of arterial smooth muscle cell growth and intimal hyperplasia Arterioscler. Thromb. Vasc. Biol. 29 2009 1356 1362
9. Z.X. Qin, P. Yu, D.H. Qian, M.B. Song, H. Tan, Y. Yu, W. Li, H. Wang, J. Liu, Q. Wang, X.J. Sun, H. Jiang, J.K. Zhu, W. Lu, and L. Huang Hydrogen-rich saline prevents neointima formation after carotid balloon injury by suppressing ROS and the TNF-alpha/NF-kappaB pathway Atherosclerosis 220 2012 343 350
10. S.J. Park, S.J. Kang, R. Virmani, M. Nakano, and Y. Ueda In-stent neoatherosclerosis: a final common pathway of late stent failure J. Am. Coll. Cardiol. 59 2012 2051 2057
11. S. Windecker, and B. Meier Late coronary stent thrombosis Circulation 116 2007 1952 1965 (Pubitemid 350287091)
12. M. Serafini, I. Peluso, and A. Raguzzini Flavonoids as anti-inflammatory agents Proc. Nutr. Soc. 69 2010 273 278
13. P. Fasinu, Y.E. Choonara, R.A. Khan, L.C. Du Toit, P. Kumar, V.M. Ndesendo, and V. Pillay Flavonoids and polymer derivatives as CYP3A4 inhibitors for improved oral drug bioavailability J. Pharm. Sci. 102 2013 541 555
14. S.H. Thilakarathna, and H.P. Rupasinghe Flavonoid bioavailability and attempts for bioavailability enhancement Nutrients 5 2013 3367 3387
15. M. Asensi, A. Ortega, S. Mena, F. Feddi, and J.M. Estrela Natural polyphenols in cancer therapy Crit. Rev. Clin. Lab. Sci. 48 2011 197 216
16. L. Mira, M.T. Fernandez, M. Santos, R. Rocha, M.H. Florencio, and K.R. Jennings Interactions of flavonoids with iron and copper ions: a mechanism for their antioxidant activity Free Radic. Res. 36 2002 1199 1208 (Pubitemid 35230240)
17. R.P. Singh, and R. Agarwal A cancer chemopreventive agent silibinin, targets mitogenic and survival signaling in prostate cancer Mutat. Res. 555 2004 21 32 (Pubitemid 39345395)
18. S.K. Shukla, S. Gupta, S.K. Ojha, and S.B. Sharma Cardiovascular friendly natural products: a promising approach in the management of CVD Nat. Prod. Res. 24 2010 873 898
19. C. La Motta, S. Sartini, L. Mugnaini, F. Simorini, S. Taliani, S. Salerno, A.M. Marini, F. Da Settimo, A. Lavecchia, E. Novellino, M. Cantore, P. Failli, and M. Ciuffi Pyrido[1,2-a]pyrimidin-4-one derivatives as a novel class of selective aldose reductase inhibitors exhibiting antioxidant activity J. Med. Chem. 50 2007 4917 4927 (Pubitemid 47525475)
20. C. La Motta, F. Da Settimo, B. Dario, S. Sartini, G. Basta, S. Del Turco, C. Saponaro, Therapeutic agent for treatment of blood vessels (2013) PCT Int. Appl. WO2013144860.
21. T. Navarra, S. Del Turco, A. Papa, D. Battaglia, G. Lazzerini, and G. Basta Lack of effect of alpha-tocopherol on in vitro angiogenesis Microvasc. Res. 72 2006 12 19 (Pubitemid 44118387)
22. G. Yang, X. Sun, and R. Wang Hydrogen sulfide-induced apoptosis of human aorta smooth muscle cells via the activation of mitogen-activated protein kinases and caspase-3 FASEB J. 18 2004 1782 1784 (Pubitemid 39561683)
23. G. Lazzerini, S. Del Turco, G. Basta, A. O'Loghlen, A. Zampolli, and R. De Caterina Prominent role of NF-kappaB in the induction of endothelial activation by endogenous nitric oxide inhibition Nitric Oxide 21 2009 184 191
24. Y.W. Lee, S.Y. Eum, A. Nath, and M. Toborek Estrogen-mediated protection against HIV tat protein-induced inflammatory pathways in human vascular endothelial cells Cardiovasc. Res. 63 2004 139 148 (Pubitemid 38759818)
25. J. Kawagoe, M. Ohmichi, S. Tsutsumi, T. Ohta, K. Takahashi, and H. Kurachi Mechanism of the divergent effects of estrogen on the cell proliferation of human umbilical endothelial versus aortic smooth muscle cells Endocrinology 148 2007 6092 6099 (Pubitemid 350146183)
26. A. Curcio, D. Torella, and C. Indolfi Mechanisms of smooth muscle cell proliferation and endothelial regeneration after vascular injury and stenting: approach to therapy Circ. J. 75 2011 1287 1296
27. G. Baldassarre, M.S. Nicoloso, M. Schiappacassi, E. Chimienti, and B. Belletti Linking inflammation to cell cycle progression Curr. Pharm. Des. 10 2004 1653 1666 (Pubitemid 38750133)
28. M. Sahin, E. Sahin, and S. Gumuslu Cyclooxygenase-2 in cancer and angiogenesis Angiology 60 2009 242 253
29. S. Kanaoka, T. Takai, and K. Yoshida Cyclooxygenase-2 and tumor biology Adv. Clin. Chem. 43 2007 59 78 (Pubitemid 44960960)
30. T.L. Zern, and M.L. Fernandez Cardioprotective effects of dietary polyphenols J. Nutr. 135 2005 2291 2294 (Pubitemid 41429579)
31. D.F. Romagnolo, and O.I. Selmin Flavonoids and cancer prevention: a review of the evidence J. Nutr. Gerontol. Geriatr. 31 2012 206 238
32. Z.S. Galis, C. Johnson, D. Godin, R. Magid, J.M. Shipley, R.M. Senior, and E. Ivan Targeted disruption of the matrix metalloproteinase-9 gene impairs smooth muscle cell migration and geometrical arterial remodeling Circ. Res. 91 2002 852 859 (Pubitemid 35285084)
33. K.M. Southgate, M. Fisher, A.P. Banning, V.J. Thurston, A.H. Baker, R.P. Fabunmi, P.H. Groves, M. Davies, and A.C. Newby Upregulation of basement membrane-degrading metalloproteinase secretion after balloon injury of pig carotid arteries Circ. Res. 79 1996 1177 1187 (Pubitemid 26404150)
34. J.A. Mitchell, F. Ali, L. Bailey, L. Moreno, and L.S. Harrington Role of nitric oxide and prostacyclin as vasoactive hormones released by the endothelium Exp. Physiol. 93 2008 141 147 (Pubitemid 350293980)
35. M. Romano, and J. Claria Cyclooxygenase-2 and 5-lipoxygenase converging functions on cell proliferation and tumor angiogenesis: implications for cancer therapy FASEB J. 17 2003 1986 1995 (Pubitemid 37392443)
36. W. Chang, S. Lim, H. Song, B.W. Song, H.J. Kim, M.J. Cha, J.M. Sung, T.W. Kim, K.C. Hwang, Cordycepin inhibits vascular smooth muscle cell proliferation, Eur. J. Pharmacol. 597 (2008) 64e69.