Page last updated: 2024-10-15

7,8-dihydrobiopterin

Description

7,8-dihydrobiopterin: RN given refers to (S-(R*,S*))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

7,8-dihydrobiopterin : A dihydropterin that is biopterin dihydrogenated at positions 7 and 8. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

L-erythro-7,8-dihydrobiopterin : A 7,8-dihydrobiopterin in which the 1,2-dihydroxypropyl group has (1R,2S)-configuration; naturally occurring form. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID135398687
CHEBI ID43029
SCHEMBL ID22971947
MeSH IDM0067829

Synonyms (31)

Synonym
BH2 ,
4(1h)-pteridinone, 2-amino-6-[(1r,2s)-1,2-dihydroxypropyl]-7,8-dihydro-
4(1h)-pteridinone, 2-amino-6-(1,2-dihydroxypropyl)-7,8-dihydro-, [s-(r*,s*)]-
quinonoid dihydrobiopterin
7,8-dihydro-l-biopterin
1,2-propanediol, 1-(2-amino-7,8-dihydro-4-hydroxy-6-pteridinyl)-, l-erythro-
C02953
l-erythro-7,8-dihydrobiopterin
dihydrobiopterin
6779-87-9
7,8-dihydrobiopterin
l-erythro-dihydrobiopterin
q-bh2
DB04400
l-erythro-q-dihydrobiopterin
2TOH
2-amino-6-((1r,2s)-1,2-dihydroxypropyl)-7,8-dihydro-4(1h)-pteridinone
4(1h)-pteridinone, 2-amino-6-(1,2-dihydroxypropyl)-7,8-dihydro-, (s-(r*,s*))-
4(1h)-pteridinone, 2-amino-6-((1r,2s)-1,2-dihydroxypropyl)-7,8-dihydro-
2-amino-6-[(1r,2s)-1,2-dihydroxypropyl]-7,8-dihydropteridin-4(3h)-one
CHEBI:43029
l-erythro-1-(2-amino-7,8-dihydro-4-hydroxy-6-pteridinyl)-1,2-propanediol
2-amino-6-(1,2-dihydroxypropyl)-7,8-dihydro-4(1h)-pteridinone
(s-(r*,s*))-2-amino-6-(1,2-dihydroxypropyl)-7,8-dihydro-4(1h)-pteridinone
CS-W009362
HY-W008646
DTXSID00987125
Q27104501
2-amino-6-((1r,2s)-1,2-dihydroxypropyl)-7,8-dihydropteridin-4(1h)-one
SCHEMBL22971947
AKOS040744155

Bioavailability

ExcerptReference
" Vitamin C, folate, and other antioxidants enhance endothelial BH4 bioavailability through chemical stabilization or scavenging of reactive oxygen species, thereby contributing to the maintenance of physiological homeostasis in the endothelium."( Regulation of tetrahydrobiopterin synthesis and bioavailability in endothelial cells.
Hatakeyama, K; Haynes, TE; Meininger, CJ; Shi, W; Wu, G, 2004
)
"Tetrahyrobiopterin (BH4) is a required cofactor for the synthesis of nitric oxide by endothelial nitric-oxide synthase (eNOS), and BH4 bioavailability within the endothelium is a critical factor in regulating the balance between NO and superoxide production by eNOS (eNOS coupling)."( Critical role for tetrahydrobiopterin recycling by dihydrofolate reductase in regulation of endothelial nitric-oxide synthase coupling: relative importance of the de novo biopterin synthesis versus salvage pathways.
Alp, NJ; Channon, KM; Crabtree, MJ; Hale, AB; Tatham, AL, 2009
)
"Tetrahydrobiopterin (BH4) is a required cofactor for the synthesis of NO by endothelial nitric oxide synthase (eNOS), and endothelial BH4 bioavailability is a critical factor in regulating the balance between NO and superoxide production (eNOS coupling)."( Dihydrofolate reductase protects endothelial nitric oxide synthase from uncoupling in tetrahydrobiopterin deficiency.
Channon, KM; Crabtree, MJ; Hale, AB, 2011
)
" It is therefore likely that net BH4 cellular bioavailability reflects the balance between de novo BH4 synthesis, loss of BH4 by oxidation to BH2, and the regeneration of BH4 by DHFR."( Synthesis and recycling of tetrahydrobiopterin in endothelial function and vascular disease.
Channon, KM; Crabtree, MJ, 2011
)
" Levels of nitrite and nitrate (NO(x)), as an index of nitric oxide, bioavailability were significantly decreased in the iNOS(-/-) diabetic mouse heart."( Inhibition of nitric oxide synthase uncoupling by sepiapterin improves left ventricular function in streptozotocin-induced diabetic mice.
Fujita, M; Iwasaka, T; Jo, F; Jo, H; Kosaki, A; Okazaki, T; Otani, H; Shimazu, T; Yoshioka, K, 2011
)
" Elimination of tetrahydrobiopterin (BH(4)) and nitric oxide (NO) bioavailability may contribute to the aggravation of DN."( Advanced glycation end products-mediated hypertrophy is negatively regulated by tetrahydrobiopterin in renal tubular cells.
Chuang, LY; Guh, JY; Huang, JS; Lee, YH; Liao, YC; Shi, MD, 2012
)
" Under conditions of low BH4 bioavailability relative to NOS or BH2, oxygen activation is "uncoupled" from L-arginine oxidation, and NOS produces superoxide (O (2) (-) ) instead of NO."( Recoupling the cardiac nitric oxide synthases: tetrahydrobiopterin synthesis and recycling.
Alkaitis, MS; Crabtree, MJ, 2012
)
" Building our knowledge of this regulation is necessary to understand and modulate the bioavailability of nitric oxide, central to the cardiovascular complications of diabetes and other diseases."( L-arginine, tetrahydrobiopterin, nitric oxide and diabetes.
Hoang, HH; Meininger, CJ; Padgham, SV, 2013
)
"The global arginine bioavailability ratio has been proposed as a biomarker reflective of L-arginine availability, arginase activity, and citrulline cycling, as all of these processes impact eNOS activity."( L-arginine, tetrahydrobiopterin, nitric oxide and diabetes.
Hoang, HH; Meininger, CJ; Padgham, SV, 2013
)
"Ascorbate (Asc) has been shown to increase nitric oxide (NO) bioavailability and thereby improve endothelial function in patients showing signs of endothelial dysfunction."( Does vitamin C enhance nitric oxide bioavailability in a tetrahydrobiopterin-dependent manner? In vitro, in vivo and clinical studies.
Lykkesfeldt, J; Mortensen, A, 2014
)

Dosage Studied

ExcerptReference
" However, recent studies suggest the effective BH4 dosing may be narrower than previously thought, potentially due to its oxidation upon oral consumption."( Bi-modal dose-dependent cardiac response to tetrahydrobiopterin in pressure-overload induced hypertrophy and heart failure.
Alp, NJ; Channon, KM; Kass, DA; Ketner, EA; Moens, AL; O'Neill, CA; Schmidt, TS; Takimoto, E; Wolin, MS, 2011
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
7,8-dihydrobiopterinA dihydropterin that is biopterin dihydrogenated at positions 7 and 8.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
biopterin metabolism013
Biopterin biosynthesis08

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Tyrosine 3-monooxygenaseRattus norvegicus (Norway rat)Ki70.000070.000070.000070.0000AID977610
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB1998Biochemistry, Sep-29, Volume: 37, Issue:39
Crystal structure of tyrosine hydroxylase with bound cofactor analogue and iron at 2.3 A resolution: self-hydroxylation of Phe300 and the pterin-binding site.
AID1811Experimentally measured binding affinity data derived from PDB1998Biochemistry, Sep-29, Volume: 37, Issue:39
Crystal structure of tyrosine hydroxylase with bound cofactor analogue and iron at 2.3 A resolution: self-hydroxylation of Phe300 and the pterin-binding site.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (137)

TimeframeStudies, This Drug (%)All Drugs %
pre-199032 (23.36)18.7374
1990's22 (16.06)18.2507
2000's34 (24.82)29.6817
2010's46 (33.58)24.3611
2020's3 (2.19)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (1.44%)5.53%
Reviews7 (5.04%)6.00%
Case Studies13 (9.35%)4.05%
Observational0 (0.00%)0.25%
Other117 (84.17%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]