P0409

Sigma-Aldrich

Prostaglandin E2

synthetic, powder, BioReagent, suitable for cell culture

Synonym(s):
PGE2, (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid, Dinoprostone
Empirical Formula (Hill Notation):
C20H32O5
CAS Number:
Molecular Weight:
352.47
Beilstein/REAXYS Number:
4709356
EC Number:
MDL number:
eCl@ss:
42020658
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

synthetic

product line

BioReagent

assay

≥93% (HPLC)

form

powder

potency

0.25-100 ng/mL

application(s)

cell culture | mammalian: suitable

solubility

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

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

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General description

Prostaglandin E2 is a lipid that is obtained from arachidonic acid. Prostaglandin hormone is synthesized by the activity of cycloxygenase-2. Prostaglandin E2 controls inflammatory responses and vascular smooth muscle activity.

Application

Prostaglandin E2 has been used as a α-MEM medium supplement for the co-culture of bone marrow macrophages and differentiated osteoblast. It has also been used in the characterization of cells and in vitro decidualization.

Packaging

1, 5, 10 mg in glass bottle

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.
Prostaglandin E2 is a signaling molecule produced by activated platelets. The release of PGE2 by activated platelets is part of a mechanism by which activated platelets utilize adjacent erythrocytes to help in clot formation. This product was shown to lower the filterability of human erythrocytes by approximately 30% at a concentration of 10-10sup M and also caused a reduction in mean cell volume by about 10%. The cause of cell shrinkage was the induction of a PGE2- stimulated K+ efflux pathway leading to rapid loss of cellular K+ ions. This loss was shown to be Ca2+dependent. PGE2 has been shown to stimulate the production of interleukin-6 (IL-6) by neonatal mouse parietal bones. After 6 hours in culture, cells stimulated with 10-8sup M PGE2 produced significantly more IL-6 than controls. The pyrogenic activity of PGE2 was not inhibited by dexamethasone, unlike prostaglandin F2α.

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.

Physical form

powder -20 °C; stock-frozen in working aliquots, avoid repeated freeze/thaw

pictograms

Exclamation markHealth hazard

signalword

Danger

hazcat

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 Germany

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Potential use of G protein-coupled receptor-blocking monoclonal antibodies as therapeutic agents for cancers
International Review of Cell and Molecular Biology, 297, 45-81 (2012)
Analyses of bone modeling and remodeling using in vitro reconstitution system with two-photon microscopy
Hikita A, et al.
Bone, 76, 5-17 (2015)
Decidualization of the canine uterus: From early until late gestational in vivo morphological observations, and functional characterization of immortalized canine uterine stromal cell lines
Graubner F R, et al.
Reproduction in domestic animals = Zuchthygiene, 52, 137-147 (2017)
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...

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