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363-24-6

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363-24-6 Usage

Description

Prostaglandin E2 (363-24-6; PGE2) is an endogenous prostaglandin derived from the action of cyclooxygenase on arachidonic acid. PGE2 has diverse biological actions in the areas of inflammation, cancer, immune modulation, fertility, smooth muscle relaxation and hematopoietic stem cell homeostasis. Prostaglandin E2 acts through four distinct receptors: EP1, EP2, EP3, EP4.

Chemical Properties

White to pale yellowish-cream powder

Originator

Prostin E2,Upjohn,UK,1972

Uses

Different sources of media describe the Uses of 363-24-6 differently. You can refer to the following data:
1. The most common and biologically potent of mammalian prostaglandins. Oxytocic; abortifacient.
2. For use in cell culture applications for the study of prostaglandin regulated cell signaling and gene regulation.
3. The most common and most biologically potent of mammalian prostaglandins. Isolated from sheep prostate. Oxytocic; abortifacient.

Definition

ChEBI: Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostagland ns.

Manufacturing Process

Hexamethyldisilazane (1 ml) and trimethylchlorosilane (0.2 ml) are added with stirring to a solution of PGA2 (250 mg) in 4 ml of tetrahydrofuran at 0°C under nitrogen. This mixture is maintained at 5°C for 15 hours. The mixture is then evaporated under reduced pressure. Toluene is added and evaporated twice. Then the residue is dissolved in 6 ml of methanol, and the solution is cooled to -20°C. Hydrogen peroxide (0.45 ml; 30% aqueous) is added. Then, 1N sodium hydroxide solution (0.9 ml) is added dropwise with stirring at - 20°C. After 2 hours at -20°C, an additional 0.3 ml of the sodium hydroxide solution is added with stirring at -20°C. After another hour in the range -10°C to -20°C, an additional 0.1 ml of the sodium hydroxide solution is added. Then, 1.5 ml of 1 N hydrochloric acid is added, and the mixture is evaporated under reduced pressure. The residue is extracted with ethyl acetate, and the extract is washed successively with 1 N hydrochloric acid and ine, dried with anhydrous sodium sulfate and evaporated. The residue is dissolved in 5 ml of diethyl ether. To this solution is added 0.5 ml of methanol and 0.1 ml of water. Amalgamated aluminum made from 0.5 g of aluminum metal is then added in small portions during 3 hours at 25°C. Then, ethyl acetate and 3 N hydrochloric acid are added, and the ethyl acetate layer is separated and washed successively with 1 N hydrochloric acid and ine, dried with anhydrous sodium sulfate, and evaporated. The residue is chromatographed on 50 g of acid-washed silica gel, eluting first with 400 ml of a gradient of 50- 100% ethyl acetate in Skellysolve B, and then with 100 ml of 5% methanol in ethyl acetate, collecting 25 ml fractions. Fractions 9 and 10 are combined and evaporated to give 18 mg of 11β-PGE2. Fractions 17-25 are combined and evaporated to give 39 mg of PGE2.

Brand name

Cervidil (Controlled Therapeutics); Prepidil (Pharmacia & Upjohn); Prostin E2 (Pharmacia & Upjohn);Minprostin;Prostaglandin;Prostarmon e;Prostin vr pediatric.

Therapeutic Function

Oxytocic, Abortifacient

World Health Organization (WHO)

Dinoprostone, prostaglandin E2, was introduced into medicine in 1971 and is primarily used for cervical ripening during the induction of labour. It is available in various formulations for oral, parenteral and vaginal administration. Tablets, ampoules and vaginal dosage forms (tablets, pessaries, gel) remain registered in many countries.

General Description

PGE2 Dinoprostone (Prostin E2;Cervidil) is a naturally occurring prostaglandin that is administeredin a single dose of 10 mg by controlled-release(0.3 mg/hr) vaginal insert to induce cervical ripening. Use ofthis agent will potentiate the effects of oxytocin.

Biological Activity

Endogenous prostaglandin and primary product of arachidonic acid/cyclooxygenase pathway. Binds with high affinity to EP 1 , EP 2 , EP 3 and EP 4 receptors (K d values range between ~ 1-10 nM). Influences a wide range of processes including inflammation, smooth muscle relaxation, fertility and gastric mucosal integrity. Regulates vertebrate hematopoietic stem cell (HSC) homeostasis.

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.

Safety Profile

Poison by subcutaneous and intravenous routes. Moderately toxic by ingestion and intraperitoneal routes. An experimental teratogen. Human reproductive effects by intravenous, intraplacental, and intravaginal routes: changes in the uterus, cervix and vagina; termination of pregnancy; and changes in ferthty. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

in vitro

pge2 can stimulate the gastric nonparietal secretion [3] and has been shown to regulate the function of many cell types including dendritic cells, macrophages, t and b lymphocytes leading to both pro- and anti-inflammatory effects [2].

in vivo

pge2 regulates many physiological systems including the gastrointestinal and immune systems. in the gastrointestinal tract, pge2 plays a protective role in maintaining the integrity of the gastric mucosa. pge2 has also been shown to play a role in the maintenance of blood pressure, particularly in the setting of salt overload [2].

References

1) Healy (1990) Progesterone receptor antagonist and prostaglandins in human fertility regulation: a clinical review; Reprod. Fertil. Dev. 2 477 2) Greenhough et al. (2009) The COX-2/PGE2 pathway: key roles in the hallmarks of cancer and adaptation to the tumour microenvironment; Carcinogenesis, 30 377 3) Kalinski (2012) Regulation of Immune Responses by Prostaglandin E2; J. Immunol., 188 21 4) North et al. (2007) Prostaglandin E2 regulates vertebrate haematopoietic stem cell homeostasis; Nature, 447 1007 5) Hoggatt et al. (2013) Differential stem- and progenitor-cell trafficking by prostaglandin E2; Nature, 495 365 6) Coleman et al. (1994) Classification of prostanoid receptors: Properties, distribution and structure of the receptors and their subtypes; Pharmacol. Rev. 46 205

Check Digit Verification of cas no

The CAS Registry Mumber 363-24-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,6 and 3 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 363-24:
(5*3)+(4*6)+(3*3)+(2*2)+(1*4)=56
56 % 10 = 6
So 363-24-6 is a valid CAS Registry Number.
InChI:InChI=1/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)/p-1/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1

363-24-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (P1884)  Prostaglandin E2  >98.0%(HPLC)

  • 363-24-6

  • 1mg

  • 480.00CNY

  • Detail
  • TCI America

  • (P1884)  Prostaglandin E2  >98.0%(HPLC)

  • 363-24-6

  • 10mg

  • 2,950.00CNY

  • Detail
  • Sigma-Aldrich

  • (D2250000)  Dinoprostone  European Pharmacopoeia (EP) Reference Standard

  • 363-24-6

  • D2250000

  • 1,880.19CNY

  • Detail
  • USP

  • (1213103)  Dinoprostone  United States Pharmacopeia (USP) Reference Standard

  • 363-24-6

  • 1213103-125MG

  • 67,063.23CNY

  • Detail

363-24-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name prostaglandin E2

1.2 Other means of identification

Product number -
Other names PGE2

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:363-24-6 SDS

363-24-6Relevant articles and documents

A NEW SYNTHETIC ROUTE TO PROSTAGLANDINS

Corey, E. J.,Niimura, Koichi,Konishi, Yoshitaka,Hashimoto, Shinsuke,Hamada, Yasumasa

, p. 2199 - 2202 (1986)

A short synthetic route to prostaglandins is described which depends on oxime-based methodology and which involves the joining of intermediates 9, 11, and 12 in a one-flask operation.

Total synthesis of prostaglandins F2-alpha and E2 as the naturally occurring forms.

Corey,Schaaf,Huber,Koelliker,Weinshenker

, p. 397 - 398 (1970)

-

Schneider

, p. 304 (1969)

Inhibition of cyclooxygenase and prostaglandin E2 synthesis by γ-mangostin, a xanthone derivative in mangosteen, in C6 rat glioma cells

Nakatani, Keigo,Nakahata, Norimichi,Arakawa, Tsutomu,Yasuda, Hideyuki,Ohizumi, Yasushi

, p. 73 - 79 (2002)

The fruit hull of mangosteen, Garcinia mangostana L., has been used for many years as a medicine for treatment of skin infection, wounds, and diarrhea in Southeast Asia. In the present study, we examined the effect of γ-mangostin, a tetraoxygenated diprenylated xanthone contained in mangosteen, on arachidonic acid (AA) cascade in C6 rat glioma cells. γ-Mangostin had a potent inhibitory activity of prostaglandin E2 (PGE2) release induced by A23187, a Ca2+ ionophore. The inhibition was concentration-dependent, with the IC50 value of about 5 μM. γ-Mangostin had no inhibitory effect on A23187-induced phosphorylation of p42/p44 extracellular signal regulated kinase/mitogen-activated protein kinase or on the liberation of [14C]-AA from the cells labeled with [14C]-AA. However, γ-mangostin concentration-dependently inhibited the conversion of AA to PGE2 in microsomal preparations, showing its possible inhibition of cyclooxygenase (COX). In enzyme assay in vitro, γ-mangostin inhibited the activities of both constitutive COX (COX-1) and inducible COX (COX-2) in a concentration-dependent manner, with the IC50 values of about 0.8 and 2 μM, respectively. Lineweaver-Burk plot analysis indicated that γ-mangostin competitively inhibited the activities of both COX-1 and -2. This study is a first demonstration that γ-mangostin, a xanthone derivative, directly inhibits COX activity.

Characterization of aldo-keto reductase 1C subfamily members encoded in two rat genes (akr1c19 and RGD1564865). Relationship to 9-hydroxyprostaglandin dehydrogenase

Satoshi Endo,Matsunaga, Toshiyuki,Hara, Akira

, (2021/02/02)

Rat genes, akr1c19 and RGD1564865, encode members (R1C19 and 20HSDL, respectively) of the aldo-keto reductase (AKR) 1C subfamily, whose functions, however, remain unknown. Here, we show that recombinant R1C19 and 20HSDL exhibit NAD+-dependent dehydrogenase activity for prostaglandins (PGs) with 9α-hydroxy group (PGF2α, its 13,14-dihydro- and 15-keto derivatives, 9α,11β-PGF2 and PGD2). 20HSDL oxidized the PGs with much lower Km (0.3–14 μM) and higher kcat/Km values (0.064–2.6 min?1μM?1) than those of R1C19. They also differed in other properties: R1C19, but not 20HSDL, oxidized some 17β-hydroxysteroids (5β-androstane-3α,17β-diol and 5β-androstan-17β-ol-3-one). 20HSDL was specifically inhibited by zomepirac, but not by R1C19-selective inhibitors (hexestrol, flavonoids, ibuprofen and flufenamic acid), although the two enzymes were sensitive to indomethacin and cis-unsaturated fatty acids. The mRNA for 20HSDL was expressed abundantly in rat kidney and at low levels in the liver, testis, brain, heart and colon, in contrast to ubiquitous expression of R1C19 mRNA. The comparison of enzymic features of R1C19 and 20HSDL with rat PG dehydrogenases and other AKRs suggests not only a close relationship of 20HSDL with 9-hydroxy-PG dehydrogenase in rat kidney, but also roles of R1C19 and rat AKRs (1C16 and 1C24) in the metabolism of PGF2α, PGD2 and 9α,11β-PGF2 in other tissues.

15-Hydroperoxy-PGE2: Intermediate in Mammalian and Algal Prostaglandin Biosynthesis

Jagusch, Hans,Werner, Markus,Werz, Oliver,Pohnert, Georg

supporting information, p. 17641 - 17645 (2019/11/13)

Arachidonic-acid-derived prostaglandins (PGs), specifically PGE2, play a central role in inflammation and numerous immunological reactions. The enzymes of PGE2 biosynthesis are important pharmacological targets for anti-inflammatory drugs. Besides mammals, certain edible marine algae possess a comprehensive repertoire of bioactive arachidonic-acid-derived oxylipins including PGs that may account for food poisoning. Described here is the analysis of PGE2 biosynthesis in the red macroalga Gracilaria vermiculophylla that led to the identification of 15-hydroperoxy-PGE2, a novel precursor of PGE2 and 15-keto-PGE2. Interestingly, this novel precursor is also produced in human macrophages where it represents a key metabolite in an alternative biosynthetic PGE2 pathway in addition to the well-established arachidonic acid-PGG2-PGH2-PGE2 route. This alternative pathway of mammalian PGE2 biosynthesis may open novel opportunities to intervene with inflammation-related diseases.

In Situ Methylene Capping: A General Strategy for Efficient Stereoretentive Catalytic Olefin Metathesis. the Concept, Methodological Implications, and Applications to Synthesis of Biologically Active Compounds

Xu, Chaofan,Shen, Xiao,Hoveyda, Amir H.

supporting information, p. 10919 - 10928 (2017/08/15)

In situ methylene capping is introduced as a practical and broadly applicable strategy that can expand the scope of catalyst-controlled stereoselective olefin metathesis considerably. By incorporation of commercially available Z-butene together with robust and readily accessible Ru-based dithiolate catalysts developed in these laboratories, a large variety of transformations can be made to proceed with terminal alkenes, without the need for a priori synthesis of a stereochemically defined disubstituted olefin. Reactions thus proceed with significantly higher efficiency and Z selectivity as compared to when other Ru-, Mo-, or W-based complexes are utilized. Cross-metathesis with olefins that contain a carboxylic acid, an aldehyde, an allylic alcohol, an aryl olefin, an α substituent, or amino acid residues was carried out to generate the desired products in 47-88% yield and 90:10 to >98:2 Z:E selectivity. Transformations were equally efficient and stereoselective with a ~70:30 Z-:E-butene mixture, which is a byproduct of crude oil cracking. The in situ methylene capping strategy was used with the same Ru catechothiolate complex (no catalyst modification necessary) to perform ring-closing metathesis reactions, generating 14- to 21-membered ring macrocyclic alkenes in 40-70% yield and 96:4-98:2 Z:E selectivity; here too, reactions were more efficient and Z-selective than when the other catalyst classes are employed. The utility of the approach is highlighted by applications to efficient and stereoselective syntheses of several biologically active molecules. This includes a platelet aggregate inhibitor and two members of the prostaglandin family of compounds by catalytic cross-metathesis reactions, and a strained 14-membered ring stapled peptide by means of macrocyclic ring-closing metathesis. The approach presented herein is likely to have a notable effect on broadening the scope of olefin metathesis, as the stability of methylidene complexes is a generally debilitating issue with all types of catalyst systems. Illustrative examples of kinetically controlled E-selective cross-metathesis and macrocyclic ring-closing reactions, where E-butene serves as the methylene capping agent, are provided.

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