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Chemical Compound Review

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

Synonyms: D-Biopterin, Pterin H B2, AG-D-61696, CHEBI:41183, HMDB00633, ...
 
 
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Disease relevance of biopterin

 

Psychiatry related information on biopterin

 

High impact information on biopterin

 

Chemical compound and disease context of biopterin

 

Biological context of biopterin

  • In WT mice, induction of diabetes with streptozotocin (STZ) increased vascular oxidative stress, resulting in oxidative loss of BH4, forming BH2 and biopterin [19].
  • Biopterin accumulation had been demonstrated as the result of normal and, especially, of malignant hemopoietic cell proliferation (Ziegler, I. et al. Blut, 44: 231-240, and 261-270, 1982) [20].
  • Induced fitting structural changes by the biopterin binding expand large conformational changes in GTPCHI peptide segments forming the active site, resulting in inhibition of the activity [21].
  • We have used serial pancreatic biopsy, and measurement of serum biopterin at 30, 60, 90 and 120 days in the BB/S rat to relate histological change to macrophage activation during the course of pre-diabetes [22].
  • These changes were followed by an increase in eNOS activity, demonstrating that high biopterin levels offset inhibition of eNOS phosphorylation and diminished interaction with hsp90 [23].
 

Anatomical context of biopterin

 

Associations of biopterin with other chemical compounds

 

Gene context of biopterin

 

Analytical, diagnostic and therapeutic context of biopterin

References

  1. Hyperphenylalaninemia due to a deficiency of biopterin. A variant form of phenylketonuria. Kaufman, S., Berlow, S., Summer, G.K., Milstien, S., Schulman, J.D., Orloff, S., Spielberg, S., Pueschel, S. N. Engl. J. Med. (1978) [Pubmed]
  2. Effects of tyrosine administration on serum biopterin in normal controls and patients with Parkinson's disease. Yamaguchi, T., Nagatsu, T., Sugimoto, T., Matsuura, S., Kondo, T., Iizuka, R., Narabayashi, H. Science (1983) [Pubmed]
  3. Crystal structure of DCoH, a bifunctional, protein-binding transcriptional coactivator. Endrizzi, J.A., Cronk, J.D., Wang, W., Crabtree, G.R., Alber, T. Science (1995) [Pubmed]
  4. NIH conference. Alzheimer disease: clinical and biological heterogeneity. Friedland, R.P., Koss, E., Haxby, J.V., Grady, C.L., Luxenberg, J., Schapiro, M.B., Kaye, J. Ann. Intern. Med. (1988) [Pubmed]
  5. PTR1: a reductase mediating salvage of oxidized pteridines and methotrexate resistance in the protozoan parasite Leishmania major. Bello, A.R., Nare, B., Freedman, D., Hardy, L., Beverley, S.M. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  6. Biopterin derivatives in senile dementia. Leeming, R.J., Blair, J.A., Melikian, V. Lancet (1979) [Pubmed]
  7. Cerebrospinal fluid biogenic amines and biopterin in Rett syndrome. Zoghbi, H.Y., Milstien, S., Butler, I.J., Smith, E.O., Kaufman, S., Glaze, D.G., Percy, A.K. Ann. Neurol. (1989) [Pubmed]
  8. Cerebrospinal fluid monoamine markers are decreased in dementia of the Alzheimer type with extrapyramidal features. Kaye, J.A., May, C., Daly, E., Atack, J.R., Sweeney, D.J., Luxenberg, J.S., Kay, A.D., Kaufman, S., Milstien, S., Friedland, R.P. Neurology (1988) [Pubmed]
  9. Pterin metabolism in depression: an extension of the amine hypothesis and possible marker of response to ECT. Anderson, D.N., Abou-Saleh, M.T., Collins, J., Hughes, K., Cattell, R.J., Hamon, C.G., Blair, J.A., Dewey, M.E. Psychological medicine. (1992) [Pubmed]
  10. Analysis of Plasma Biopterin Levels in Psychiatric Disorders Suggests a Common BH(4) Deficit in Schizophrenia and Schizoaffective Disorder. Richardson, M.A., Read, L.L., Reilly, M.A., Clelland, J.D., Clelland, C.L. Neurochem. Res. (2007) [Pubmed]
  11. Serum aluminum levels and erythrocyte dihydropteridine reductase activity in patients on hemodialysis. Altmann, P., Al-Salihi, F., Butter, K., Cutler, P., Blair, J., Leeming, R., Cunningham, J., Marsh, F. N. Engl. J. Med. (1987) [Pubmed]
  12. Biopterin cofactor biosynthesis: independent regulation of GTP cyclohydrolase in adrenal medulla and cortex. Viveros, O.H., Lee, C.L., Abou-Donia, M.M., Nixon, J.C., Nichol, C.A. Science (1981) [Pubmed]
  13. Biosynthesis of biopterin: adrenergic cyclic adenosine monophosphate-dependent inhibition in the pineal gland. Kapatos, G., Kaufman, S., Weller, J.L., Klein, D.C. Science (1981) [Pubmed]
  14. Neopterin and biopterin CSF levels in tardive dyskinesia after clozapine treatment. Fleischhacker, W.W., Levine, R.A., Lieberman, J.A., Pollack, S., Johns, C.A., Richardson, M.A. Biol. Psychiatry (1993) [Pubmed]
  15. Paroxysmal tremor and orofacial dyskinesia secondary to a biopterin synthesis defect. Factor, S.A., Coni, R.J., Cowger, M., Rosenblum, E.L. Neurology (1991) [Pubmed]
  16. Tetrahydrobiopterin and total biopterin content of neuroblastoma (N1E-115, N2A) and pheochromocytoma (PC-12) clones and the dependence of catecholamine synthesis on tetrahydrobiopterin concentration in PC-12 cells. Bräutigam, M., Dreesen, R., Herken, H. J. Neurochem. (1984) [Pubmed]
  17. Changes of cerebral biopterin and biogenic amine metabolism in leukemic children receiving 5 g/m2 intravenous methotrexate. Millot, F., Dhondt, J.L., Mazingue, F., Mechinaud, F., Ingrand, P., Guilhot, F. Pediatr. Res. (1995) [Pubmed]
  18. Inhibition of tryptophan hydroxylase by dopamine and the precursor amino acids. Naoi, M., Maruyama, W., Takahashi, T., Ota, M., Parvez, H. Biochem. Pharmacol. (1994) [Pubmed]
  19. Tetrahydrobiopterin-dependent preservation of nitric oxide-mediated endothelial function in diabetes by targeted transgenic GTP-cyclohydrolase I overexpression. Alp, N.J., Mussa, S., Khoo, J., Cai, S., Guzik, T., Jefferson, A., Goh, N., Rockett, K.A., Channon, K.M. J. Clin. Invest. (2003) [Pubmed]
  20. Participation of pterins in the control of lymphocyte stimulation and lymphoblast proliferation. Ziegler, I., Hamm, U., Berndt, J. Cancer Res. (1983) [Pubmed]
  21. Structural basis of biopterin-induced inhibition of GTP cyclohydrolase I by GFRP, its feedback regulatory protein. Maita, N., Hatakeyama, K., Okada, K., Hakoshima, T. J. Biol. Chem. (2004) [Pubmed]
  22. Serum biopterin--a novel marker for immune activation during pre-diabetes in the BB rat. Davies, A.J., Bone, A.J., Wilkin, T.J., Rokos, H., Cole, D.R. Diabetologia (1994) [Pubmed]
  23. Endothelial cell superoxide anion radical generation is not dependent on endothelial nitric oxide synthase-serine 1179 phosphorylation and endothelial nitric oxide synthase dimer/monomer distribution. Whitsett, J., Martásek, P., Zhao, H., Schauer, D.W., Hatakeyama, K., Kalyanaraman, B., Vásquez-Vivar, J. Free Radic. Biol. Med. (2006) [Pubmed]
  24. Human mononuclear phagocyte inducible nitric oxide synthase (iNOS): analysis of iNOS mRNA, iNOS protein, biopterin, and nitric oxide production by blood monocytes and peritoneal macrophages. Weinberg, J.B., Misukonis, M.A., Shami, P.J., Mason, S.N., Sauls, D.L., Dittman, W.A., Wood, E.R., Smith, G.K., McDonald, B., Bachus, K.E. Blood (1995) [Pubmed]
  25. Blood levels of a pteridine-binding alpha 1-acid glycoprotein in cancer patients. Fink, M., Ziegler, I., Maier, K., Wilmanns, W. Cancer Res. (1982) [Pubmed]
  26. Brain biopterin and tyrosine hydroxylase in asymptomatic dopa-responsive dystonia. Furukawa, Y., Kapatos, G., Haycock, J.W., Worsley, J., Wong, H., Kish, S.J., Nygaard, T.G. Ann. Neurol. (2002) [Pubmed]
  27. Full-length cDNA for rabbit tryptophan hydroxylase: functional domains and evolution of aromatic amino acid hydroxylases. Grenett, H.E., Ledley, F.D., Reed, L.L., Woo, S.L. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  28. L-ascorbic acid potentiates endothelial nitric oxide synthesis via a chemical stabilization of tetrahydrobiopterin. Heller, R., Unbehaun, A., Schellenberg, B., Mayer, B., Werner-Felmayer, G., Werner, E.R. J. Biol. Chem. (2001) [Pubmed]
  29. Pteridin-dependent hydroxylases as autoantigens in autoimmune polyendocrine syndrome type I. Ekwall, O., Hedstrand, H., Haavik, J., Perheentupa, J., Betterle, C., Gustafsson, J., Husebye, E., Rorsman, F., Kämpe, O. J. Clin. Endocrinol. Metab. (2000) [Pubmed]
  30. Striatal biopterin and tyrosine hydroxylase protein reduction in dopa-responsive dystonia. Furukawa, Y., Nygaard, T.G., Gütlich, M., Rajput, A.H., Pifl, C., DiStefano, L., Chang, L.J., Price, K., Shimadzu, M., Hornykiewicz, O., Haycock, J.W., Kish, S.J. Neurology (1999) [Pubmed]
  31. Diagnosis of dopa-responsive dystonia and other tetrahydrobiopterin disorders by the study of biopterin metabolism in fibroblasts. Bonafé, L., Thöny, B., Leimbacher, W., Kierat, L., Blau, N. Clin. Chem. (2001) [Pubmed]
  32. Enhanced expression of GTP cyclohydrolase I in V-1-overexpressing PC12D cells. Suzuki, T., Inagaki, H., Yamakuni, T., Nagatsu, T., Ichinose, H. Biochem. Biophys. Res. Commun. (2002) [Pubmed]
  33. Homocysteine induces oxidative stress by uncoupling of NO synthase activity through reduction of tetrahydrobiopterin. Topal, G., Brunet, A., Millanvoye, E., Boucher, J.L., Rendu, F., Devynck, M.A., David-Dufilho, M. Free Radic. Biol. Med. (2004) [Pubmed]
  34. Biopterin and organ transplantation. Dhondt, J.L., Walter, M.P., Bauters, F., Jouet, J.P. Lancet (1988) [Pubmed]
  35. Reduced biopterin as a cofactor in the generation of nitrogen oxides by murine macrophages. Kwon, N.S., Nathan, C.F., Stuehr, D.J. J. Biol. Chem. (1989) [Pubmed]
  36. Changes in tetrahydrobiopterin levels in endothelial cells and adult cardiomyocytes induced by LPS and hydrogen peroxide--a role for GFRP? Kalivendi, S., Hatakeyama, K., Whitsett, J., Konorev, E., Kalyanaraman, B., Vásquez-Vivar, J. Free Radic. Biol. Med. (2005) [Pubmed]
  37. Liquid-chromatographic measurement of biopterin and neopterin in serum and urine. Slazyk, W.E., Spierto, F.W. Clin. Chem. (1990) [Pubmed]
  38. Reduced infectivity of a Leishmania donovani biopterin transporter genetic mutant and its use as an attenuated strain for vaccination. Papadopoulou, B., Roy, G., Breton, M., Kündig, C., Dumas, C., Fillion, I., Singh, A.K., Olivier, M., Ouellette, M. Infect. Immun. (2002) [Pubmed]
 
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