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P5640

Sigma-Aldrich

Prostaglandin E2

≥93% (HPLC), synthetic

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C20H32O5
Número CAS:
363-24-6
Peso molecular:
352.47
Beilstein:
4709356
Número CE:
206-656-6
Número MDL:
MFCD00077861
Código UNSPSC:
12352401
eCl@ss:
42020658
ID de substância PubChem:
24898683
NACRES:
NA.77

fonte biológica

synthetic

Ensaio

≥93% (HPLC)

forma

powder

grupo funcional

carboxylic acid
hydroxyl

Condições de expedição

ambient

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

XEYBRNLFEZDVAW-ARSRFYASSA-N

Informações sobre genes

human ... PTGER1(5731) , PTGER2(5732) , PTGER3(5733) , PTGER4(5734) , PTGIR(5739)
mouse ... Ptger1(19216) , Ptger2(19217) , Ptger3(19218) , Ptger4(19219)

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Aplicação


  • Post-resolution macrophages shape long-term tissue immunity and integrity in a mouse model of pneumococcal pneumonia.: Investigating the influence of prostaglandin E2 within the resolution phase of inflammation, this study demonstrates its essential role in macrophage-mediated tissue repair and immune memory following bacterial lung infections, providing insights into immune system regulation and recovery processes (Feehan et al., 2024).

Ações bioquímicas/fisiológicas

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.

Pictogramas

Health hazardExclamation mark
GHS08,GHS07

Palavra indicadora

Danger

Frases de perigo

H302,H360FD

Classificações de perigo

Acute Tox. 4 Oral - Repr. 1B

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

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

Certificados de análise (COA)

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International Union of Pharmacology classification of prostanoid receptors: properties, distribution, and structure of the receptors and their subtypes.
R A Coleman et al.
Pharmacological reviews, 46(2), 205-229 (1994-06-01)
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
Jean L Tan et al.
Stem cell research & therapy, 6, 8-8 (2015-01-31)
The immunomodulatory properties of human amnion epithelial cells (hAECs) have been previously described in several disease models. We previously reported on the ability of hAECs to influence macrophage phenotype and chemotaxis. In this study, we aim to elucidate the contribution
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
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