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P7265

Sigma-Aldrich

Prostaglandin A1

synthetic

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Synonym(s):
(13E,15S)-15-Hydroxy-9-oxoprosta-10,13-dien-1-oic acid, PGA1
Empirical Formula (Hill Notation):
C20H32O4
CAS Number:
14152-28-4
Molecular Weight:
336.47
Beilstein:
2003401
MDL number:
MFCD00077858
UNSPSC Code:
12352211
PubChem Substance ID:
24898834
NACRES:
NA.77

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

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H360F

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
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
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
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