Introduction：Basic information about CAS 17528-72-2|Tetrahydrobiopterin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| 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 | / |
|---|
| MSDS | / | Flash Point | 260.2ºC |
|---|
Names
| Name | 5,6,7,8-tetrahydrobiopterin |
|---|
| Synonym | More Synonyms |
|---|
Tetrahydrobiopterin BiologicalActivity
| 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 SynthaseNatural Products >>Saccharides and GlycosidesResearch 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. |
|---|
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 DATAACUTE 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
|
Synonyms
| 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 |
