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Tetrahydrobiopterin

Names

[ CAS No. ]:
17528-72-2

[ Name ]:
Tetrahydrobiopterin

[Synonym ]:
6R-BH4
1,2-Propanediol, 1-(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)-, hydrochloride (1:2)
TETRAHYDRO-L-BIOPTERIN,DIHYDROCHLORIDE
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1H)-pteridinone dihydrochloride
THB,2HCL
(6R)-BH4 2HCL
Tetrahydrobiopterin dihydrochloride
(6R)-5,6,7,8-TETRAHYDRO-BIOPTERIN DIHYDROCHLORIDE
(6R)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE
bh4
Tetrahydrobiopterin

Biological Activity

[Description]:

Tetrahydrobiopterin is a cofactor of the aromatic amino acid hydroxylases enzymes and also acts as an essential cofactor for all nitric oxide synthase (NOS) isoforms.

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> NO Synthase
Natural Products >> Saccharides and Glycosides
Research Areas >> Inflammation/Immunology

[Target]

Human Endogenous Metabolite


[In Vitro]

MicMicroglial cell cultures under hyperoxia are supplemented or not with an effective dose of Tetrahydrobiopterin (BH4) (100 μM). Exposure of microglial cells to hyperoxia-induced oxidative stress for 24 h reveals a robust increase in TSP-1 mRNA expression and protein compare to normoxia (21% O2). Tetrahydrobiopterin supplementation significantly prevents hyperoxia-induced microglial activation by diminishing Iba-1 and TSP-1 expression and prevents microvascular injury in choroidal explants[1].

[In Vivo]

To assess the levels of Tetrahydrobiopterin in the retina, three to five pools of retinas are collected from WT and hph-1mice at postnatal age 7, 14, and 22 and evaluated by LC-MS/MS. LC-MS/MS analysis confirm a significant decrease by approximately 90% in the concentration levels of Tetrahydrobiopterin in retinal tissue from hph-1 mice (0.0009±0.0006; p<0.0001, 0.01±0.001; p<0.0001 and 2.45±0.40; p<0.005) compare to the WT group (0.014±0.001, 0.092±0.01, and 23.13±6.44) at P7, P14, and P22, respectively[1].

[Kinase Assay]

Microglia cell line (SIM-A9) is used and cultured. Briefly, microglial cells (800, 000 cells per well) are cultured in 6-well plates with DMEM/F12 (1:1) supplementing with 10% fetal bovine serum (FBS), 5% of horse serum (HS), and 1% penicillin/streptomycin. After 24 h, the cells are starved with DMEM/F12 (1:1) free of FBS and HS for 6 h. Then, microglial cells cultures in presence or absence of 100 μM of Tetrahydrobiopterin are exposed to hyperoxia (75% oxygen and 25% nitrogen) in a modular incubator chamber and maintained in a humidified CO2 incubator at 37 °C for 24 h. Microglial cells in matching controls are incubated at 37 °C in an incubator with 95% air and 5% CO2 and collected at the same time point. Cell lysates are quickly processed for RNA. The conditioning media is stored at -80 and later used in choroidal explant assay[1].

[Animal admin]

Mice pups are exposed with their mothers in a 75% oxygen environment from postnatal day 7 to P9 using oxycycler to induce retinal vaso-obliteration (VO). Animals are anesthetized and injected intravitreally at P7 with 100 μM of Tetrahydrobiopterin or vehicle (sterile PBS 1×) using a syringe equipped with 50-gauge glass capillary. At P9, mice pups are sacrificed and retinas are dissected and stained overnight at 4 °C with fluorescein-labeled Griffonia Simplicifolia Lectin 1 (GSL 1), isolectin B4 (1:100) with 1 mM CaCl2 in PBS. Quantification of VO is assessed using the computer software[1].

[References]

[1]. Rivera JC, et al. Tetrahydrobiopterin (BH4) deficiency is associated with augmented inflammation and microvascular degeneration in the retina. J Neuroinflammation. 2017 Sep 6;14(1):181.


[Related Small Molecules]

3-Methyladenine | Hydrocortisone | Acetylcysteine(N-acetylcysteine) | Retinoic acid | Melatonine | Dinoprostone | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | L-NAME HCl | Dehydroepiandrosterone | Corticosterone | Progesterone | Docosahexaenoic Acid

Chemical & Physical Properties

[ Density]:
1.89g/cm3

[ Boiling Point ]:
506.6ºC at 760mmHg

[ Molecular Formula ]:
C9H15N5O3

[ Molecular Weight ]:
241.25

[ Flash Point ]:
260.2ºC

[ PSA ]:
136.29000

[ LogP ]:
0.76100

[ Storage condition ]:
2-8℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UO3516000
CHEMICAL NAME :
4(1H)-Pteridinone, 5,6,7,8-tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-
CAS REGISTRY NUMBER :
17528-72-2
BEILSTEIN REFERENCE NO. :
0544742
LAST UPDATED :
199612
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C9-H15-N5-O3
MOLECULAR WEIGHT :
241.29

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
258 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 42,183,1986

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds