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Key Documents

P5515

Sigma-Aldrich

Prostaglandin E1

≥98% (HPLC), powder, vasodilator 

Synonym(s):

(11α,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid, Alprostadil, PGE1

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€207.00
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€437.00
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€561.00

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1 MG
€207.00
5 MG
€437.00
10 MG
€561.00

About This Item

Empirical Formula (Hill Notation):
C20H34O5
CAS Number:
Molecular Weight:
354.48
Beilstein:
5294062
EC Number:
MDL number:
UNSPSC Code:
12352211
eCl@ss:
42020658
PubChem Substance ID:
NACRES:
NA.77

€207.00


In StockDetails


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Product Name

Prostaglandin E1, ≥98% (HPLC), synthetic

biological source

synthetic

Quality Level

Assay

≥98% (HPLC)

form

(powder to crystals)

solubility

ethanol: 5 mg/mL

storage temp.

−20°C

SMILES string

O=C1[C@H](CCCCCCC(O)=O)[C@@H](/C=C/[C@H](CCCCC)O)[C@H](O)C1

InChI

1S/C20H34O5/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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1

InChI key

GMVPRGQOIOIIMI-DWKJAMRDSA-N

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Application

Prostaglandin E1 has been used:
  • as a platelet inhibitor to analyse its effect on autophagy[1]
  • in platelet adhesion assay[2]
  • to investigate its effect on cAMP production in thyroid glands of normal and growth-retarded mouse in vitro.[3]

Biochem/physiol Actions

Prostaglandin E1 (PGE1) is a hormone synthesized from dihomo-γ-linolenic acid (DGLA) by the action of enzyme prostaglandin synthase.[4] It is a vasodilator and activates adenylate cyclase. It is majorly present in human semen and is a potent platelet aggregation inhibitor. PGE1 infusions is effective in treating limb ischemia and peripheral vascular disease.[5] It is unstable and is hydrolyzed to PGA1 in the lungs. Nanoparticle encapsulation of PGE1 is essential for its delivery at the vascular injury site.[6] It elicits vasodilator effects on the retinal artery and vein in central retinal artery occlusion (CRAO).[7] PGE1 and its synthetic analog misoprostol interact with E-prostanoid receptor 4 (EP4) and elicits protection in chronic myelogenous leukemia (CML). [8]

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Yosuke Okamura et al.
Biophysical journal, 100(8), 1855-1863 (2011-04-21)
Eukaryotic cells respond to signaling molecules with picomolar to nanomolar sensitivities. However, molar concentrations give no suggestion of the sufficient number of molecules per cell and are confusing when referring to physiological situations in which signaling molecules act in an
Synthesis of prostaglandin E 1 phosphate derivatives and their encapsulation in biodegradable nanoparticles
Takeda M, et al.
Pharmaceutical Research, 26(7), 1792-1800 (2009)
Prostaglandins and thromboxanes.
B Samuelsson et al.
Annual review of biochemistry, 47, 997-1029 (1978-01-01)
Prostaglandin E1 and its analog misoprostol inhibit human CML stem cell self-renewal via EP4 receptor activation and repression of AP-1
Li F, et al.
Cell Stem Cell, 21(3), 359-373 (2017)
Intravenous infusion of prostaglandin E1 therapy in extremity ischemia
Ramakrishna P
Indian Journal of Vascular and Endovascular Surgery, 4(2), 38-38 (2017)

Articles

Discover Bioactive Small Molecules for Lipid Signaling Research

Questions

1–2 of 2 Questions  
  1. Is stability in solution information available for the product P5515?

    Is stability in solution information available for the product P5515?

    1 answer
    1. Soluble at 50mg/ml, it can be dissolved in water, but it is recommended to use saline, NaCl, DPBS, Hanks, or culture medium. Please note that a reference in peer- reviewed papers at sial.com isolated glomerular endothelial cells at 0.1% in DMEM. This paper may also be of reference "Differential expression of type IV collagen isoforms in rat glomerular endothelial and mesangial cells (https://www.sciencedirect.com/science/article/pii/S0006291X02006939?via%3Dihub)

      Helpful?

  2. What are the recommended storage temperature conditions for Prostaglandin E1 (P5515) when dissolved in acetone?

    1 answer
    1. The solubility test is designed to ensure the product is free of foreign bodies or other unsoluble substances. Acetone was choosen for the solubility test because appears to have higher solubility in acetone than it does in ethanol. The Quality department will dissolve the product in acetone and discard the solution once the solubility test is complete. So there is no data for what is the preferred storage temperature and length of storage if using acetone as the solvent.

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