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P5640

Sigma-Aldrich

Prostaglandin E2

≥93% (HPLC), synthetic

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H32O5
CAS Number:
363-24-6
Molecular Weight:
352.47
Beilstein:
4709356
EC Number:
206-656-6
MDL number:
MFCD00077861
UNSPSC Code:
12352401
eCl@ss:
42020658
PubChem Substance ID:
24898683
NACRES:
NA.77

biological source

synthetic

Assay

≥93% (HPLC)

form

powder

functional group

carboxylic acid
hydroxyl

shipped in

ambient

storage temp.

−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

InChI key

XEYBRNLFEZDVAW-ARSRFYASSA-N

Gene Information

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

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Application


  • 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).

Biochem/physiol Actions

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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H360FD

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
José L Maravillas-Montero et al.
Journal of immunology (Baltimore, Md. : 1950), 194(1), 29-33 (2014-11-21)
Chemokines are chemotactic cytokines that direct the traffic of leukocytes and other cells in the body. Chemokines bind to G protein-coupled receptors expressed on target cells to initiate signaling cascades and induce chemotaxis. Although the cognate receptors of most chemokines
Katrin D Mayer-Barber et al.
Nature, 511(7507), 99-103 (2014-07-06)
Tuberculosis remains second only to HIV/AIDS as the leading cause of mortality worldwide due to a single infectious agent. Despite chemotherapy, the global tuberculosis epidemic has intensified because of HIV co-infection, the lack of an effective vaccine and the emergence
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
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