Kinetics of acid-induced degradation of tetra- and dihydrobiopterin in relation to their relevance as biomarkers of endothelial function

References

• Berka V, Yeh HC, Gao D, Kiran F, Tsai AL. (2004). Redox function of tetrahydrobiopterin and effect of L-arginine on oxygen binding in endothelial nitric oxide synthase. Biochemistry 43:13137–13148.
   PubMedGoogle Scholar
• Blair JA, Pearson AJ. (1973). A kinetic study of the autoxidation of tetrahydrobiopterin. Tetrahedron Lett 14:203–204.
   Google Scholar
• Cañada-Cañada F, Espinosa-Mansilla A, Muñoz de la Peña A, Mancha de Llanos A. (2009). Determination of marker pteridins and biopterin reduced forms, tetrahydrobiopterin and dihydrobiopterin, in human urine, using a post-column photoinduced fluorescence liquid chromatographic derivatization method. Anal Chim Acta 648:113–122.
   PubMedGoogle Scholar
• Crabtree MJ, Smith CL, Lam G, Goligorsky MS, Gross SS. (2008). Ratio of 5,6,7,8-tetrahydrobiopterin to 7,8-dihydrobiopterin in endothelial cells determines glucose-elicited changes in NO vs. superoxide production by eNOS. Am J Physiol Heart Circ Physiol 294:H1530–H1540.
   PubMedGoogle Scholar
• Dántola ML, Vignoni M, Capparelli AL, Lorente C, Thomas AH. (2008). Stability of 7,8-dihydropterins in air-equilibrated aqueous solutions. Helv Chim Acta 91:411–425.
   Google Scholar
• Davis MD, Kaufman S, Milstien S. (1988). The auto-oxidation of tetrahydrobiopterin. Eur J Biochem 173:345–351.
   PubMedGoogle Scholar
• Espinosa-Mansilla A, Munoz de la Pena A, Canada-Canada F, Mancha de Llanos A. (2008). LC determination of biopterin reduced forms by UV-photogeneration of biopterin and fluorimetric detection. Talanta 77:844–851.
   Google Scholar
• Feillet F, Clarke L, Meli C, Lipson M, Morris AA, Harmatz P, Mould DR, Green B, Dorenbaum A, Giovannini M, Foehr E; Sapropterin Research Group. (2008). Pharmacokinetics of sapropterin in patients with phenylketonuria. Clin Pharmacokinet 47:817–825.
   PubMed Web of Science ®Google Scholar
• Fekkes D, Voskuilen-Kooijman A. (2007). Quantitation of total biopterin and tetrahydrobiopterin in plasma. Clin Biochem 40:411–413.
   PubMedGoogle Scholar
• Fiege B, Ballhausen D, Kierat L, Leimbacher W, Goriounov D, Schircks B, Thöny B, Blau N. (2004). Plasma tetrahydrobiopterin and its pharmacokinetic following oral administration. Mol Genet Metab 81:45–51.
   PubMed Web of Science ®Google Scholar
• Fukushima T, Nixon JC. (1979). Oxidation and conversion of reduced forms of biopterin. In: Kisliuk RLBrown GM (eds). Chemistry and Biology of Pteridines. New York, NY: Elsevier North Holland, Inc., 31–34.
   Google Scholar
• Fukushima T, Nixon JC. (1980). Analysis of reduced forms of biopterin in biological tissues and fluids. Anal Biochem 102:176–188.
   PubMed Web of Science ®Google Scholar
• Heales SJ, Blair JA, Meinschad C, Ziegler I. (1988). Inhibition of monocyte luminol-dependent chemiluminescence by tetrahydrobiopterin, and the free radical oxidation of tetrahydrobiopterin, dihydrobiopterin and dihydroneopterin. Cell Biochem Funct 6:191–195.
   PubMed Web of Science ®Google Scholar
• Heller R, Unbehaun A, Schellenberg B, Mayer B, Werner-Felmayer G, Werner ER. (2001). L-ascorbic acid potentiates endothelial nitric oxide synthesis via a chemical stabilization of tetrahydrobiopterin. J Biol Chem 276:40–47.
   PubMed Web of Science ®Google Scholar
• Howells DW, Hyland K. (1987). Direct analysis of tetrahydrobiopterin in cerebrospinal fluid by high-performance liquid chromatography with redox electrochemistry: prevention of autoxidation during storage and analysis. Clin Chim Acta 167:23–30.
   PubMed Web of Science ®Google Scholar
• Howells DW, Smith I, Hyland K. (1986). Estimation of tetrahydrobiopterin and other pterins in cerebrospinal fluid using reversed-phase high-performance liquid chromatography with electrochemical and fluorescence detection. J Chromatogr 381:285–294.
   PubMed Web of Science ®Google Scholar
• Kar S, Kavdia M. (2011). Modeling of biopterin-dependent pathways of eNOS for nitric oxide and superoxide production. Free Radic Biol Med 51:1411–1427.
   PubMedGoogle Scholar
• Katoh S, Akino M. (1966). In vitro conversion of sepiapterin to isosepiapterin via dihydrobiopterin. Experientia 22:793–794.
   PubMedGoogle Scholar
• Lykkesfeldt J. (2000). Determination of ascorbic acid and dehydroascorbic acid in biological samples by high-performance liquid chromatography using subtraction methods: reliable reduction with tris[2-carboxyethyl]phosphine hydrochloride. Anal Biochem 282:89–93.
   PubMed Web of Science ®Google Scholar
• Lyudnikova T, Dashina O, Telegina T, Kritsky M. (2009). Investigation of the photochemical properties of biopterin and its reduced forms. Appl Biochem Microbiol 45:104–109.
   Google Scholar
• Maharaj G, Selinsky BS, Appleman JR, Perlman M, London RE, Blakley RL. (1990). Dissociation constants for dihydrofolic acid and dihydrobiopterin and implications for mechanistic models for dihydrofolate reductase. Biochemistry 29:4554–4560.
   PubMedGoogle Scholar
• Mochizuki S, Ono J, Yada T, Ogasawara Y, Miyasaka T, Kimoto M, Kashihara N, Kajiya F. (2005). Systemic nitric oxide production rate during hemodialysis and its relationship with nitric oxide-related factors. Blood Purif 23:317–324.
   PubMed Web of Science ®Google Scholar
• Noguchi K, Hamadate N, Matsuzaki T, Sakanashi M, Nakasone J, Uchida T, Arakaki K, Kubota H, Ishiuchi S, Masuzaki H, Sugahara K, Ohya Y, Sakanashi M, Tsutsui M. (2011). Increasing dihydrobiopterin causes dysfunction of endothelial nitric oxide synthase in rats in vivo. Am J Physiol Heart Circ Physiol 301:H721–H729.
   Google Scholar
• Pearson AJ, Blair JA. (1975). Autoxidation of tetrahydropterins. In: Pfleiderer W (eds). Chemistry and Biology of Pteridines. Berlin: Walter de Gruyter, 775–779.
   Google Scholar
• Pearson AJ. (1974). Kinetics and mechanism of the autoxidation of tetrahydropterins. Chemistry and Industry, 233–239.
   Google Scholar
• Pfleiderer W. (1982). Properties of naturally-owccurring pteridines. In: Wachter H, Curtius H-C, Pfleiderer W (eds). Biochemical and Clinical Aspects of Pteridines 1[Cancer, Immunology, Metabolic Diseases]. Berlin: Walter de Gruyter, 3–26.
   Google Scholar
• Powers AG, Young JH, Clayton BE. (1988). Estimation of tetrahydrobiopterin and other pterins in plasma by isocratic liquid chromatography with electrochemical and fluorimetric detection. J Chromatogr 432:321–328.
   PubMedGoogle Scholar
• Presta A, Siddhanta U, Wu C, Sennequier N, Huang L, Abu-Soud HM, Erzurum S, Stuehr DJ. (1998). Comparative functioning of dihydro- and tetrahydropterins in supporting electron transfer, catalysis, and subunit dimerization in inducible nitric oxide synthase. Biochemistry 37:298–310.
   PubMed Web of Science ®Google Scholar
• Schircks B, Bieri JH, Viscontini M. (1978). Über Pterinchemie. 65. Mitteilung [1]. Herstellung von (6R,S)-5,6,7,8-Tetrahydro-L-biopterin, 7,8-Dihydro-L-biopterin, L-Sepiapterin, Deoxysepiapterin, (6R,S)-5,6-Dihydrodeoxysepiapterin und 2′-Deoxybiopterin. Helv Chim Acta 61:2731–2738.
   Google Scholar
• Takeda M, Yamashita T, Shinohara M, Sasaki N, Takaya T, Nakajima K, Inoue N, Masano T, Tawa H, Satomi-Kobayashi S, Toh R, Sugiyama D, Nishimura K, Yokoyama M, Hirata K, Kawashima S. (2009). Plasma tetrahydrobiopterin/dihydrobiopterin ratio: a possible marker of endothelial dysfunction. Circ J 73:955–962.
   PubMedGoogle Scholar
• Valent S, Tóth M. (2006). Activation energy determinations suggest that thiols reverse autooxidation of tetrahydrobiopterin by a different mechanism than ascorbate. Int J Biochem Cell Biol 38:1786–1793.
   PubMedGoogle Scholar
• Vásquez-Vivar J, Martásek P, Whitsett J, Joseph J, Kalyanaraman B. (2002). The ratio between tetrahydrobiopterin and oxidized tetrahydrobiopterin analogues controls superoxide release from endothelial nitric oxide synthase: an EPR spin trapping study. Biochem J 362:733–739.
   PubMed Web of Science ®Google Scholar
• Werner ER, Blau N, Thöny B. (2011). Tetrahydrobiopterin: biochemistry and pathophysiology. Biochem J 438:397–414.
   PubMed Web of Science ®Google Scholar