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 ...