Tetrahydrobiopterin

Modify Date: 2024-01-02 11:01:22

Tetrahydrobiopterin structure	Common Name	Tetrahydrobiopterin
	CAS Number	17528-72-2	Molecular Weight	241.25
	Density	1.89g/cm3	Boiling Point	506.6ºC at 760mmHg
	Molecular Formula	C₉H₁₅N₅O₃	Melting Point	N/A
	MSDS	N/A	Flash Point	260.2ºC

Use of Tetrahydrobiopterin

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.

Name	5,6,7,8-tetrahydrobiopterin
Synonym	More Synonyms

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.

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℃

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

biopterin

CAS#:304-95-0

Tetrahydrobiopterin

CAS#:17528-72-2

Literature: Analytical Chemistry, , vol. 55, p. 1458 - 1462

Precursor 1
CAS#:304-95-0 biopterin
DownStream 3
CAS#:120-80-9 1,2-Benzenediol CAS#:7644-44-2 7,8-dihydrobiopterin CAS#:70110-58-6 2-amino-6-(1,2-...

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

Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: Tetrahydrobiopterin
Price: $Inquiry/100g $Inquiry/1kg $Inquiry/100kg $Inquiry/1000kg
Purity: 98.0%
Stocking Period: Inquiry
Contact: Ms Wang

Henan Tianfu Chemical Co., Ltd.
China
Product Name: 5,6,7,8-tetrahydrobiopterin
Price: $Inquiry/1kg $Inquiry/25kg $Inquiry/1000kg $Inquiry/10ton
Purity: 99.0%
Stocking Period: Inquiry
Contact: Anson

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Tetrahydrobiopterin

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