L-Sepiapterin

Names

[ Name ]:
L-Sepiapterin

[Synonym ]:
2-amino-6-(2-hydroxy-propionyl)-7,8-dihydro-3H-pteridin-4-one
MFCD00210214
1-(2-amino-7,8-dihydro-4-hydroxy-6-pteridinyl)-2-hydroxy-1-Propanone
4(3H)-Pteridinone, 2-amino-7,8-dihydro-6-[(2S)-2-hydroxy-1-oxopropyl]-
2-amino-7,8-dihydro-6-[(2S)-2-hydroxy-1-oxopropyl]-4(1H)-Pteridinone
2-amino-7,8-dihydro-6-[(2S)-2-hydroxy-1-oxopropyl]-4(1H)Pteridinone
(S)-2-amino-7,8-dihydro-6-(2-hydroxy-1-oxopropyl)-4(1H)-Pteridinone
Sepiapterine
L-Sepiapterin
Sepiapterin,S-()-2-Amino-7,8-dihydro-6-(2-hydroxy-1-oxopropyl)-4(1H)-pteridinone,L-Sepiapterin
2-Amino-6-[(2S)-2-hydroxypropanoyl]-7,8-dihydro-4(1H)-pteridinone
Sepiapterin
2-Amino-6-L-lactoyl-7,8-dihydro-3H-pteridin-4-on
2-amino-6-(2-hydroxypropanoyl)-7,8-dihydro-1H-pty oeridin-4-one
2-AMINO-7,8-DIHYDRO-6-(2S-HYDROXY-1-OXOPROPYL)-4(1H)-PTERIDINONE
2-amino-6-[(2S)-2-hydroxypropanoyl]-7,8-dihydro-1H-pteridin-4-one
2-Amino-6-[(2S)-2-hydroxypropanoyl]-7,8-dihydropteridin-4(3H)-one
S-(−)-2-Amino-7,8-dihydro-6-(2-hydroxy-1-oxopropyl)-4(1H)-pteridinone
S(-)-2-AMINO-7,8-DIHYDRO-6-(2-HYDROXY-1-OXOPROPYL)-4(1H)-PTERIDINONE
2-amino-6-L-lactoyl-7,8-dihydro-3H-pteridin-4-one

Biological Activity

[Description]:

L-Sepiapterin (Sepiapterin) is a precursor of the endothelial nitric oxide synthase (eNOS) cofactor tetrahydrobiopterin (BH4). L-Sepiapterin improves endothelial dysfunction in small mesenteric arteries from db/db mice, and induces angiogenesis. L-Sepiapterin inhibits cell proliferation and migration of ovarian cancer cells via down-regulation of p70S6K-dependent VEGFR-2 expression[1][2].

[Related Catalog]:

Research Areas >> Cancer

[Target]

Human Endogenous Metabolite

[In Vitro]

L-Sepiapterin (Sepiapterin) (0.1-10 μM; 24 hpurs) Iinduces cell proliferation in a dose-dependent manner[1]. L-Sepiapterin (1-50 μM; 20 minutes) significantly inhibits the phosphorylation of VEGF-A-induced (50 ng/ml) p70S6K[1]. L-Sepiapterin inhibits VEGF-A-induced cell proliferation and migration through NO-independent mechanism[1]. Cell Proliferation Assay[1] Cell Line: SKOV-3 cells Concentration: 0.1, 1, 10 μM Incubation Time: 24 hours Result: Induced cell proliferation in a dose-dependent manner.

[In Vivo]

Sepiapterin (10 mg/kg; p.o. (powder chow); daily for or 8 weeks) significantly improves the relaxation to Ach in small mesenteric arteries (SMA) from db/db mice[2]. Animal Model: Male C57BL/KsJ diabetic mice (db/db)[2] Dosage: 10 mg/kg Administration: P.o. (powder chow); daily for or 8 weeks Result: Significantly improved the relaxation to Ach in SMA from db/db mice.

[References]

[1]. Pannirselvam M, et al. Chronic oral supplementation with sepiapterin prevents endothelial dysfunction and oxidative stress in small mesenteric arteries from diabetic (db/db) mice. Br J Pharmacol. 2003;140(4):701‐706.

[2]. Cho YR, et al. Sepiapterin inhibits cell proliferation and migration of ovarian cancer cells via down-regulation of p70S6K-dependent VEGFR-2 expression. Oncol Rep. 2011;26(4):861‐867.

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
448.1ºC at 760 mmHg

[ Melting Point ]:
> 275 °C (lit.)

[ Molecular Formula ]:
C₉H₁₁N₅O₃

[ Molecular Weight ]:
237.215

[ Flash Point ]:
224.8ºC

[ Exact Mass ]:
237.086182

[ PSA ]:
133.46000

[ LogP ]:
-3.93

[ Vapour Pressure ]:
6.54E-10mmHg at 25°C

[ Index of Refraction ]:
1.822

[ Storage condition ]:
20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2933990090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Bone Morphogenic Protein 4 Mediates NOX1-Dependent eNOS Uncoupling, Endothelial Dysfunction, and COX2 Induction in Type 2 Diabetes Mellitus.

Mol. Endocrinol. 29 , 1123-33, (2015)

We have recently shown that angiotensin II-mediated uncoupling of endothelial nitric oxide synthase (eNOS) contributes to endothelial dysfunction in streptozotocin-induced type 1 diabetes mellitus. Ho...

Sulfa drugs inhibit sepiapterin reduction and chemical redox cycling by sepiapterin reductase.

J. Pharmacol. Exp. Ther. 352(3) , 529-40, (2015)

Sepiapterin reductase (SPR) catalyzes the reduction of sepiapterin to dihydrobiopterin (BH2), the precursor for tetrahydrobiopterin (BH4), a cofactor critical for nitric oxide biosynthesis and alkylgl...

Stromal cell-derived factor 2 is critical for Hsp90-dependent eNOS activation.

Sci. Signal. 8 , ra81, (2015)

Endothelial nitric oxide synthase (eNOS) catalyzes the conversion of l-arginine and molecular oxygen into l-citrulline and nitric oxide (NO), a gaseous second messenger that influences cardiovascular ...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.