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82475

Sigma-Aldrich

Prostaglandin E2

≥99.0% (TLC)

Synonyme(s) :

(5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid, Dinoprostone, PGE2

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About This Item

Formule empirique (notation de Hill):
C20H32O5
Numéro CAS:
363-24-6
Poids moléculaire :
352.47
Numéro Beilstein :
4709356
Numéro CE :
206-656-6
Numéro MDL:
MFCD00077861
Code UNSPSC :
12352200

Pureté

≥99.0% (TLC)

Solubilité

acetone: 10 mg/mL, clear, colorless to faintly yellow

Température de stockage

−20°C

Chaîne SMILES 

O[C@@H]1CC([C@H](C/C=C\CCCC(O)=O)[C@H]1/C=C/[C@@H](O)CCCCC)=O

InChI

1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1

Clé InChI

XEYBRNLFEZDVAW-ARSRFYASSA-N

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Actions biochimiques/physiologiques

Most biologically active prostaglandin. PGE2 induces cervical ripening and parturition; mediates bradykinin-induced vasodilation; regulates adenylyl cyclase. Tumor cells that over-express cyclooxygenase 2 display increased invasiveness, angiogenesis, and resistance to apoptosis that may be due to the PGE2-induced expression of angiogenic factors and stabilization of the anti-apoptotic protein, survivin.The effect of PGE2 on the immune system is mixed. It inhibits T cell activation in vitro, suggesting it is an immunosuppressant. However, in vivo, it appears to effect expansion of the Th17 subset and differentiation of the Th1 subset of T helper cells, marking it as an immunoactivator.

Autres remarques

Differential effect of PGE2 on transforming growth factor-β, and insulin-induced collagen formation in lung fibroblasts

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H360FD

Classification des risques

Acute Tox. 4 Oral - Repr. 1B

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificats d'analyse (COA)

Lot/Batch Number
1352589
305356/1
1306029
1299300
1118193

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Consulter la Bibliothèque de documents

A Fine et al.
The Journal of biological chemistry, 264(29), 16988-16991 (1989-10-15)
We examined the effect of prostaglandin (PG) E2 on transforming growth factor-beta (TGF-beta) and insulin-stimulated collagen formation in lung fibroblast cultures. TGF-beta increased type I collagen production 2-3-fold as determined by the densitometric analysis of autoradiograms from polyacrylamide gels and
Alexandra Medeiros et al.
Mediators of inflammation, 2012, 327568-327568 (2012-10-02)
The local and systemic production of prostaglandin E(2) (PGE(2)) and its actions in phagocytes lead to immunosuppressive conditions. PGE(2) is produced at high levels during inflammation, and its suppressive effects are caused by the ligation of the E prostanoid receptors
Sofia Eberstål et al.
International journal of cancer, 134(11), 2748-2753 (2013-11-19)
Immunotherapy has shown effectiveness against experimental malignant brain tumors, but the clinical results have been less convincing most likely due to immunosuppression. Prostaglandin E2 (PGE2 ) is the key immunosuppressive product of cyclooxygenase-2 (COX-2) and increased levels of PGE2 and
Yumeng Mao et al.
Cancer research, 73(13), 3877-3887 (2013-05-02)
Tumors can suppress the host immune system by employing a variety of cellular immune modulators, such as regulatory T cells, tumor-associated macrophages, and myeloid-derived suppressor cells (MDSC). In the peripheral blood of patients with advanced stage melanoma, there is an
Takayuki Nakagawa
Hearing research, 276(1-2), 27-33 (2011-02-08)
Prostaglandins are one of the major groups of chemical mediators in the mammalian body. Among prostaglandins, prostaglandin E2 (PGE2) is the most abundant prostanoid in humans and involved in regulating many different fundamental biological functions. PGE2 signaling is mediated by
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