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P7265

Prostaglandin A₁

Name: Prostaglandin A<SUB>1</SUB>
Brand: SIGMA

≥98% (HPLC), powder, NF-κB inhibitor

Synonyme(s) :

(13E,15S)-15-Hydroxy-9-oxoprosta-10,13-dien-1-oic acid, PGA₁

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About This Item

Formule empirique (notation de Hill):

C₂₀H₃₂O₄

Numéro CAS:

14152-28-4

Poids moléculaire :

336.47

Numéro Beilstein :

2003401

Numéro MDL:

MFCD00077858

Code UNSPSC :

12352211

ID de substance PubChem :

24898834

Nomenclature NACRES :

NA.77

product name

Prostaglandin A₁, synthetic

Source biologique

synthetic

Niveau de qualité

200

Pureté

≥98%

Forme

powder

Température de stockage

−20°C

Chaîne SMILES

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

InChI

1S/C20H32O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+/m0/s1

Clé InChI

BGKHCLZFGPIKKU-LDDQNKHRSA-N

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Actions biochimiques/physiologiques

Prostaglandin A1 (PGA1) is a cyclopentenone prostaglandin containing chemically reactive α,β-unsaturated carbonyl. This cyclooxygenase 2 (COX-2) metabolic product aids in regulating the development and progression of Alzheimer′s disease (AD). In addition, PGA1 also regulates various biological processes via Michael addition. It exhibits antiviral activity against avian influenza A viruses (IAV) by inducing cytoprotective heat shock response in infected cells and by inhibiting nuclear factor-κB (NF-κB) activity.

Pictogrammes

GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H360F

Conseils de prudence

P201 - P301 + P312 + P330 - P308 + P313

Classification des risques

Acute Tox. 4 Oral - Repr. 1B

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Modification and activation of Ras proteins by electrophilic prostanoids with different structure are site-selective.

Marta Renedo et al.

Biochemistry, 46(22), 6607-6616 (2007-05-11)

Cyclopentenone prostanoids (cyP) arise as important modulators of inflammation and cell proliferation. Although their physiological significance has not been fully elucidated, their potent biological effects have spurred their study as leads for the development of therapeutic agents. A key determinant

Preparation and evaluation of o/w type emulsions containing antitumor prostaglandin.

S Fukushima et al.

Advanced drug delivery reviews, 45(1), 65-75 (2000-12-06)

Antitumor prostaglandins(PGs) such as Delta12-PGJ2 and Delta7-PGA1 possess a cyclopentenone or cross-conjugated dienone structures. Antitumor PGs are actively incorporated through cell membrane and control gene expression. Very recent studies clarified that P53 independent expression of p21 and gadd 45, activation

Identification of aldo-keto reductase AKR1B10 as a selective target for modification and inhibition by prostaglandin A(1): implications for antitumoral activity.

Beatriz Díez-Dacal et al.

Cancer research, 71(12), 4161-4171 (2011-04-22)

Cyclopentenone prostaglandins (cyPG) are reactive eicosanoids that may display anti-inflammatory and antiproliferative actions, possibly offering therapeutic potential. Here we report the identification of members of the aldo-keto reductase (AKR) family as selective targets of the cyPG prostaglandin A(1) (PGA(1)). AKR

Prostaglandin A1 Decreases the Phosphorylation of Tau by Activating Protein Phosphatase 2A via a Michael Addition Mechanism at Cysteine 377.

Guo-Biao Xu et al.

Molecular neurobiology, 58(3), 1114-1127 (2020-10-24)

Prostaglandin (PG) A1 is a metabolic product of cyclooxygenase 2 (COX-2) that is potentially involved in regulating the development and progression of Alzheimer's disease (AD). PGA1 is a cyclopentenone (cy) PG characterized by the presence of a chemically reactive α,β-unsaturated

Prostaglandin A1 inhibits avian influenza virus replication at a postentry level: Effect on virus protein synthesis and NF-κB activity.

Stefania Carta et al.

Prostaglandins, leukotrienes, and essential fatty acids, 91(6), 311-323 (2014-08-26)

Influenza A viruses (IAV) have the potential to cause devastating pandemics. In recent years, the emergence of new avian strains able to infect humans represents a serious threat to global human health. The increase in drug-resistant IAV strains underscores the

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