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Merck

P7265

Sigma-Aldrich

Prostaglandin A1

≥98% (HPLC), powder, NF-κB inhibitor

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C20H32O4
Número de CAS:
Peso molecular:
336.47
Beilstein/REAXYS Number:
2003401
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77

product name

Prostaglandin A1, synthetic

biological source

synthetic

Quality Level

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

Health hazardExclamation mark

signalword

Danger

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)


Certificados de análisis (COA)

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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
M G Santoro
Experientia, 50(11-12), 1039-1047 (1994-11-30)
Acute infection of mammalian cells with several types of RNA and DNA viruses often results in induction of heat-shock gene expression. The presence of hsp70 in intact virions, as well as the transient association of HSP with viral proteins and
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
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
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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