Prostaglandin E2
SIGMA/P0409 - synthetic, powder, BioReagent, suitable for cell culture
Synonym: (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid; Dinoprostone; PGE2
CAS Number: 363-24-6
Empirical Formula (Hill Notation): C20H32O5
Molecular Weight: 352.47
EC Number: 206-656-6
MDL Number: MFCD00077861
Linear Formula: C20H32O5
Product Type: Chemical
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: P0409-10MG
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: P0409-1MG
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: P0409-5MG
| assay | ≥93% (HPLC) |
| biological source | synthetic |
| form | powder |
| InChI | 1S/C20H32O5/c1-2-3-6-9-15 |
| InChI key | XEYBRNLFEZDVAW-ARSRFYASSA |
| potency | 0.25-100 ng/mL |
| product line | BioReagent |
| Quality Level | 200  |
| shipped in | ambient |
| SMILES string | O[C@@H]1CC([C@H](C/C=CCC |
| solubility | acetone: 10 mg/mL, clear, colorless to faintly yellow |
| storage temp. | −20°C |
| technique(s) | cell culture | mammalian: suitable |
| 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. |
| Biochem/physiol Actions: | Most biologically active prostaglandin. |
| 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. |
| Biochem/physiol Actions: | 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. |
| 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. |
| Packaging: | 1, 5, 10 mg in glass bottle |
| Physical form: | powder -20 °C; stock-frozen in working aliquots, avoid repeated freeze/thaw |
| Symbol |   GHS07,GHS08 |
| Signal word | Danger |
| Hazard statements | H302 - H360FD |
| Precautionary statements | P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313 |
| Hazard Codes | T |
| Risk Statements | 60-61-22 |
| Safety Statements | 53-22-26-36/37/39-45 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Purity | ≥93% (HPLC) |
| Storage Temp. | −20°C |
| UNSPSC | 12352209 |