Tetrahydrobiopterin analogues with NO-dependent pulmonary vasodilator properties

European Journal of Pharmacology

Volumn 650, Issue 1, 2011, Pages 371-377

  Kunuthur, Suma P ^a,b   Milliken, Philip H ^a,c   Gibson, Colin L ^a   Suckling, Colin J ^a   Wadsworth, Roger M ^a,b  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Nitric oxide; Nitric oxide synthase; Pulmonary artery; Pulmonary hypertension; Tetrahydrobiopterin

Indexed keywords

6 ACETYL 7,7 DIMETHYL 7,8 DIHYDROPTERIN; 6 HYDROXYMETHYLPTERIN; CALCIMYCIN; CARBACHOL; ENDOTHELIAL NITRIC OXIDE SYNTHASE; N(G) NITROARGININE METHYL ESTER; NITRIC OXIDE; SPERMINE DERIVATIVE; TETRAHYDROBIOPTERIN; UNCLASSIFIED DRUG; VASODILATOR AGENT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTERY DILATATION; ARTICLE; BLOOD PRESSURE MEASUREMENT; CONTROLLED STUDY; DRUG EFFECT; DRUG STABILITY; ENDOTHELIAL DYSFUNCTION; HYPOXIA; LUNG RESISTANCE; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PULMONARY ARTERY OCCLUSION; PULMONARY HYPERTENSION; RAT; VASCULAR ENDOTHELIUM; VASODILATATION;

ANIMALS; ANOXIA; BIOPTERIN; CALCIMYCIN; CALCIUM; ENDOTHELIUM, VASCULAR; GENE EXPRESSION REGULATION, ENZYMOLOGIC; HYPERTENSION, PULMONARY; IONOPHORES; MALE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE TYPE III; PTERINS; PULMONARY ARTERY; RATS; RATS, SPRAGUE-DAWLEY; VASODILATION;

EID: 78649735545     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2010.09.070     Document Type: Article

References (37)

1. S.S. Al Hassan, R.J. Cameron, A.W.C. Curran, W.J.S. Lyall, S.H. Nicholson, D.R. Robinson, A. Stuart, I. Stirling, C.J. Suckling, and H.C.S. Wood Specific inhibitors in vitamin biosynthesis. Part 7 Synthesis of blocked 7, 8-dihydropteridines J. Chem. Soc. Perkin Trans. 1 1985 1645 1659
2. Z. Bagi, and A. Koller Lack of nitric oxide mediation of flow-dependent arteriolar dilation in type I diabetes is restored by sepiapterin J. Vasc. Res. 40 2003 47 57
3. J.A. Blair, and A.J. Pearson Some observations on effects of light and solvent polarity on kinetics of tetrahydribiopterin autoxidation J. Chem. Soc. Perkin Trans. 2 1974 1786 1787
4. H.M. Bömmel, A. Reif, L.G. Fröhlich, A. Frey, H. Hofmann, D.M. Marecak, V. Groehn, P. Kostsonis, M.L. La, S. Koster, M. Meinecke, M. Bernhardt, M. Weeger, S. Ghisla, G.D. Prestwich, W. Pfleiderer, and H.H.W. Schmidt Anti-pterins as tools to characterise the function of tetrahydrobiopterin in NO synthase J. Biol. Chem. 273 1998 33142 33149
5. F. Cosentino, D. Hürlimann, C. Delli Gatti, R. Chenevard, N. Blau, N.J. Alp, K.M. Channon, M. Eto, P. Lerch, F. Enseleit, F. Ruschitzka, M. Volpe, T.F. Lüscher, and G. Noll Chronic treatment with tetrahydrobiopterin reverses 4 endothelial dysfunction and oxidative stress in hypercholesterolaemia Heart 9 2008 487 492
6. M.J. Crabtree, A.L. Tatham, Y. Al-Wakeel, N. Warrick, A.B. Hale, S. Cai, K.M. Channon, and N.J. Alp Quantitative regulation of intracellular endothelial nitric-oxide synthase (eNOS) coupling by both tetrahydrobiopterin-eNOS stoichiometry and biopterin redox status J. Biol. Chem. 284 2009 1136 1144
7. A.T. Demiryürek, M.R. Karamsetty, A.R. McPhaden, R.M. Wadsworth, K.A. Kane, and M.R. MacLean Accumulation of nitrotyrosine correlates with endothelial NO synthase in pulmonary resistance arteries during hypoxia in the rat Pulmon. Pharmacol. Ther. 13 2000 157 165
8. E.A.G. Demoncheaux, T.W. Higenbottam, D.G. Kiely, J.M. Wong, S. Wharton, R. Varcoe, T. Siddons, A.C. Spivey, K. Hall, and A.P. Gize Decreased whole body endogenous nitric oxide production in patients with primary pulmonary hypertension J. Vasc. Res. 42 2005 133 136
9. I. Eskurza, L.A. Myerburgh, Z.D. Kahn, and D.R. Seals Tetrahydrobiopterin augments endothelium-dependent dilatation in sedentary but not in habitually exercising older adults J. Physiol. 568 2005 1057 1065
10. K.N. Farrow, S. Lakshminrusimha, W.J. Reda, S. Wedgwood, L. Czech, S.F. Gugino, J.M. Davis, J.A. Russell, and R.H. Steinhorn Superoxide dismutase restores eNOS expression and function in resistance pulmonary arteries from neonatal lambs with persistent pulmonary hypertension Am. J. Physiol. Lung Cell. Mol. Physiol. 295 2008 L979 L987
11. F. Fitzal, H. Redl, W. Strohmaier, E.R. Werner, and S. Bahrami A 4-amino analogue of tetrahydrobiopterin attenuates endotoxin-induced hemodynamic alterations and organ injury in rats Shock 18 2002 158 162
12. B.N. Francis, M.R. Wilkins, and L. Zhao Tetrahydrobiopterin prevents pulmonary hypertension in monocrotaline rat model Am. J. Respir. Crit. Care Med. 179 2009 A1821
13. L.G. Fröhlich, P. Kotsonis, H. Traub, S. Taghavi-Moghdam, N. Al Masoudi, H. Hofmann, H. Strobel, H. Matter, W. Pfleiderer, and H.H.W. Schmidt Inhibition of neuronal nitric oxide synthase by 4-aminopteridine derivatives: structure-activity relationship of antagonists of (6R)-5, 6, 7, 8-tetrahydrobiopterin cofactor J. Med. Chem. 42 1999 4108 4121
14. H.D. Gibraeil, P. Dittrich, S. Saleh, and B. Mayer Inhibition of endotoxin-induced vascular hyporeactivity by 4-amino-tetrahydrobiopterin Br. J. Pharmacol. 131 2000 757 1765
15. A.C.F. Gorren, A. Schrammel, C. Reithmüller, K. Schmidt, D. Koesling, E.R. Werner, and B. Mayer Nitric oxide-induced autoinhibition of neuronal nitric oxide synthase in the presence of the autoxidation-resistant pteridine 5-mthyltetrahydrobiopterin Biochem. J. 347 2000 475 484
16. S. Grant, E.M. Lutz, A.R. McPhaden, and R.M. Wadsworth Location and function of VPAC1, VPAC2 and NPR-C receptors in VIP-induced vasodilation of porcine basilar arteries J. Cereb. Blood Flow Metab. 26 2006 58 67
17. A.C. Grobe, S.M. Wells, E. Benavidez, P. Oishi, A. Azakie, J.R. Fineman, and S.M. Black Increased oxidative stress in lambs with increased pulmonary blood flow and pulmonary hypertension: role of NADPH oxidase and endothelial NO synthase Am. J. Physiol. Lung Cell. Mol. Physiol. 290 2006 L1069 L1077
18. T. Heitzer, C. Brockhoff, B. Mayer, A. Warnholtz, H. Mollnau, S. Henne, T. Meinertz, and T. Munzel Tetrahydrobiopterin improves endothelium-dependent vasodilation in chronic smokers - evidence for a dysfunctional nitric oxide synthase Circ. Res. 86 2000 E36 E41
19. T. Heitzer, K. Krohn, S. Albers, and T. Meinertz Tetrahydrobiopterin improves endothelium-dependent vasodilation by increasing nitric oxide activity in patients with Type II diabetes mellitus Diabetologia 43 2000 435 1438
20. Y. Higashi, S. Sasaki, K. Nakagawa, M. Kimura, K. Noma, K. Hara, D. Jitsuiki, C. Goto, T. Oshima, K. Chayama, and M. Yoshizumi Tetrahydrobiopterin improves aging-related impairment of endothelium-dependent vasodilation through increase in nitric oxide production Atherosclerosis 186 2006 390 395
21. M.E. Hyndman, S. Verma, R.J. Rosenfeld, T.J. Anderson, and H.G. Parsons Interaction of 5-methyltetrahydrofolate and tetrahydrobiopterin on endothelial function Am. J. Physiol. Heart Circ. Physiol. 282 2002 H2167 H2172
22. J.P. Khoo, L. Zhao, N.J. Alp, J.K. Bendall, T. Nicoli, K. Rockett, M.R. Wilkins, and K.M. Channon Pivotal role for endothelial tetrahydrobiopterin in pulmonary hypertension Circulation 111 2005 2126 2133
23. H. Kinoshita, and Z.S. Katusic Exogenous tetrahydrobiopterin causes endothelium-dependent contractions in isolated canine basilar artery Am. J. Physiol. Heart Circ. Physiol. 271 1996 H738 H743
24. H. Kinoshita, S. Milstien, C. Wambi, and Z.S. Katusic Inhibition of tetrahydrobiopterin biosynthesis impairs endothelium-dependent relaxations in canine basilar artery Am. J. Physiol. Heart Circ. Physiol. 273 1997 H718 H724
25. M. Kirsch, H.G. Korth, V. Stenert, R. Sustmann, and H. de Groot The autoxidation of tetrahydrobiopterin revisited - proof of superoxide formation from reaction of tetrahydrobiopterin with molecular oxygen J. Biol. Chem. 278 2003 24481 24490
26. P. Kotsonis, L.G. Fröhlich, C.S. Raman, H. Li, M. Berg, R. Gerwig, V. Groehn, Y. Kang, N. Al-Masoudi, S. Taghavi-Moghadam, D. Mohr, U. Münch, J. Schnabel, P. Martásek, B.S.S. Masters, H. Strobel, T. Poulos, H. Matter, W. Pfleiderer, and H.H.H.W. Schmidt Structural basis for pterin antagonism in nitric-oxide synthase: development of novel 4-oxo-pteridine antagonists of (5R)-5, 6, 7, 8-tetrahydrobiopterin J. Biol. Chem. 276 2001 49133 49141
27. M. Nandi, J. Leiper, F. Arrigoni, A. Hislop, P. Vallance, and S. Haworth Developmental regulation of GTP-CH1 in the porcine lung and its relationship to pulmonary vascular relaxation Pediatr. Res. 59 2006 767 772
28. M. Nishikimi Generation of superoxide anion in reaction of the tetrahydropteridines with molecular oxygen Arch. Biochem. Biophys. 166 1975 273 279
29. M. Pannirselvam, V. Simon, S. Verma, T. Anderson, and C.R. Triggle Chronic oral supplementation with sepiapterin prevents endothelial dysfunction and oxidative stress in small mesenteric arteries from diabetic (db/db) mice Br. J. Pharmacol. 140 2003 701 706
30. S. Setoguchi, Y. Hirooka, K. Eshima, H. Shimokawa, and A. Takeshita Tetrahydrobiopterin improves impaired endothelium-dependent forearm vasodilation in patients with heart failure J. Cardiovasc. Pharmacol. 39 2002 363 368
31. U. Simonsen, R.M. Wadsworth, N.H. Buus, and M.J. Mulvany In vitro simultaneous measurements of relaxation and nitric oxide concentration in rat superior mesenteric artery J. Physiol. 1999 271 282 516.1
32. C.J. Suckling, C.L. Gibson, J.K. Huggan, R.R. Morthala, B. Clarke, S. Kunuthur, R.M. Wadsworth, S. Daff, and D. Papale 6-Acetyl-7, 7-dimethyl-5, 6, 7, 8-tetrahydropterin is an activator of nitric oxide synthases Bioorg. Med. Chem. Lett. 18 2008 1563 1566
33. C.P. Tiefenbacher, T. Bleeke, C. Vahl, K. Amann, A. Vogt, and W. Kubler Endothelial dysfunction of coronary resistance arteries is improved by tetrahydrobiopterin in atherosclerosis Circulation 102 2000 2172 2179
34. J. Vasquez-Vivar, P. Martasek, J. Whitsett, J. Joseph, and B. Kalyanaraman The ratio between tetrahydrobiopterin and oxidized tetrahydrobiopterin analogues controls superoxide release from endothelial nitric oxide synthase: an EPR spin trapping study Biochem. J. 362 2002 733 739
35. S.X. Wang, J. Xu, P. Song, Y. Wu, J.H. Zhang, H.C. Choi, and M.H. Zou Acute inhibition of guanosine triphosphate cyclohydrolase 1 uncouples endothelial nitric oxide synthase and elevates blood pressure Hypertension 52 2008 484 490
36. R.P. Weerackody, D.J. Welsh, R.M. Wadsworth, and A.J. Peacock Inhibition of p38 MAP kinase reverses hypoxia induced pulmonary artery endothelial dysfunction Am. J. Physiol. Heart Circ. Physiol. 296 2009 H1312 H1320
37. D. Yang, N. Levens, J.N. Zhang, P.M. Vanhoutte, and M. Feletou Specific potentiation of endothelium-dependent contractions in SHR by tetrahydrobiopterin Hypertension 41 2003 136 142 (Pubitemid 36056805)