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P7265

Prostaglandin A₁

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

≥98% (HPLC), powder, NF-κB inhibitor

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₃₂O₄

CAS Number:

14152-28-4

Molecular Weight:

336.47

Beilstein/REAXYS Number:

2003401

MDL number:

MFCD00077858

UNSPSC Code:

12352211

PubChem Substance ID:

24898834

NACRES:

NA.77

product name

Prostaglandin A₁, synthetic

biological source

synthetic

Quality Level

200

assay

≥98%

form

powder

storage temp.

−20°C

SMILES string

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

InChI key

BGKHCLZFGPIKKU-LDDQNKHRSA-N

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Biochem/physiol Actions

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.

pictograms

GHS08,GHS07

signalword

Danger

hcodes

H302,H360F

pcodes

P201 - P301 + P312 + P330 - P308 + P313

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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