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Merck

82475

Sigma-Aldrich

Prostaglandin E2

≥99.0% (TLC)

Synonym(e):

(5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-diensäure, Dinoproston, PGE2

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About This Item

Empirische Formel (Hill-System):
C20H32O5
CAS-Nummer:
Molekulargewicht:
352.47
Beilstein:
4709356
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352200

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Assay

≥99.0% (TLC)

Löslichkeit

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

Lagertemp.

−20°C

SMILES String

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

InChIKey

XEYBRNLFEZDVAW-ARSRFYASSA-N

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Biochem./physiol. Wirkung

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.

Sonstige Hinweise

Differential effect of PGE2 on transforming growth factor-β, and insulin-induced collagen formation in lung fibroblasts[1]

Piktogramme

Health hazardExclamation mark

Signalwort

Danger

H-Sätze

Gefahreneinstufungen

Acute Tox. 4 Oral - Repr. 1B

Lagerklassenschlüssel

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

WGK

WGK 3

Persönliche Schutzausrüstung

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


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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
Sanjiv Dhingra et al.
Circulation, 128(11 Suppl 1), S69-S78 (2013-10-18)
Allogeneic mesenchymal stem cells (MSCs) were immunoprivileged early after cardiac implantation and improved heart function in preclinical and clinical studies. However, long-term preclinical studies demonstrated that allogeneic MSCs lost their immunoprivilege and were rejected in the injured myocardium, resulting in
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
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

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