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Chemical Compound Review:

biopterin 2-amino-6-(1,2- dihydroxypropyl)-1H...

Synonyms: L-Biopterin, Pterin H B2, SureCN258468, AG-K-90904, SureCN4361085, ...

Schallreuter-Wood, K.U. et al., Niederwieser, A. et al., Wood, J.M. et al., Yoshida, M. et al., Ziegler, I. et al., et al.

Schallreuter, Wood, Robson, Vickers, Blows, Crozier,

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High impact information on biopterin

In all cases, there was a significant increase in TNF alpha release, GTP-CH-1 activity, total 6-biopterin level, and PAH activity, indicative of enhanced L-tyrosine production [1].
In addition to 6-biopterin, 7-biopterin was identified in these cells by HPLC analysis of iodine oxidized extracts and by alkaline permanganate oxidation to the 6- and 7-carboxylic acids [2].
Fluorescence spectrophotometry can reliably detect levels of the pteridine 6-biopterin in the heads of individual Drosophila serrata Malloch 1927 [3].
Dihydropterin and 6-biopterin, the oxidation products of 6-BH4, do not inhibit tyrosinase significantly, indicating that melanin biosynthesis is controlled by a 6-BH4/6-biopterin redox-switch mechanism which can be initiated by photo-oxidation of 6-BH4 [4].
Cytotoxicity of 6-biopterin to human melanocytes [5].

Anatomical context of biopterin

Biochemical analysis of the brains of TIQ-treated monkeys revealed significant decrease in dopamine (DA) and total biopterin (BP) concentrations, and tyrosine hydroxylase (TH) activity in the substantia nigra [6].

Associations of biopterin with other chemical compounds

Full oxidation of 6BH(4) to 6 biopterin via H(2)O(2) can lead to a cytotoxic environment for epidermal melanocytes [7].
PH deficient patients excreted more B and Ne than healthy controls and again, newborns more than older children [8].
In PKU variants with deficiency of tetrahydrobiopterin (BH4), extreme pterin patterns were observed: in DHBS- and DHPR-deficient patients, less than 3.5 and more than 81% B were found, respectively [8].

Gene context of biopterin

Since 6-biopterin is cytotoxic to melanocytes and calcium controls the redox status of the 6-biopterin/(6R)5, 6, 7, 8-tetrahydrobiopterin equilibrium via the thioredoxin reductase/thioredoxin system, these results underline the importance of this electron transfer system for both melanocyte function and survival [9].

Analytical, diagnostic and therapeutic context of biopterin

The fluorescent band showing a Rf value identical with synthetic 6-biopterin was eluted; gas liquid chromatography and mass spectrometry of the isolated compound were carried out [10].

References

Pteridines in the control of pigmentation. Schallreuter, K.U., Schulz-Douglas, V., Bünz, A., Beazley, W., Körner, C. J. Invest. Dermatol. (1997) [Pubmed]
Tetrahydro-6-biopterin is associated with tetrahydro-7-biopterin in primary murine mast cells. Ziegler, I., Hültner, L. FEBS Lett. (1992) [Pubmed]
Age determination in individual wild-caught Drosophila serrata using pteridine concentration. Robson, S.K., Vickers, M., Blows, M.W., Crozier, R.H. J. Exp. Biol. (2006) [Pubmed]
A specific tetrahydrobiopterin binding domain on tyrosinase controls melanogenesis. Wood, J.M., Schallreuter-Wood, K.U., Lindsey, N.J., Callaghan, S., Gardner, M.L. Biochem. Biophys. Res. Commun. (1995) [Pubmed]
Cytotoxicity of 6-biopterin to human melanocytes. Schallreuter, K.U., Büttner, G., Pittelkow, M.R., Wood, J.M., Swanson, N.N., Körner, C. Biochem. Biophys. Res. Commun. (1994) [Pubmed]
Parkinsonism produced by tetrahydroisoquinoline (TIQ) or the analogues. Yoshida, M., Ogawa, M., Suzuki, K., Nagatsu, T. Advances in neurology. (1993) [Pubmed]
Thioredoxin reductase - its role in epidermal redox status. Schallreuter, K.U., Wood, J.M. J. Photochem. Photobiol. B, Biol. (2001) [Pubmed]
Excretion of pterins in phenylketonuria and phenylketonuria variants. Niederwieser, A., Curtius, H.C., Gitzelmann, R., Otten, A., Baerlocher, K., Blehovà, B., Berlow, S., Gröbe, H., Rey, F., Schaub, J., Scheibenreiter, S., Schmidt, H., Viscontini, M. Helvetica paediatrica acta. (1980) [Pubmed]
Defective calcium transport in vitiliginous melanocytes. Schallreuter-Wood, K.U., Pittelkow, M.R., Swanson, N.N. Arch. Dermatol. Res. (1996) [Pubmed]
Separation of pineal extracts by gelfiltration. VI. Isolation and identification from sheep pineals of biopterin; comparison of the isolated compound with some synthetic pteridines and the biological activity in in vitro and in vivo bioassays. van der Have-Kirchberg, M.L., de Morée, A., van Laar, J.F., Gerwig, G.J., Versluis, C., Ebels, I. J. Neural Transm. (1977) [Pubmed]

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