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P7265

Sigma-Aldrich

Prostaglandin A1

≥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:
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

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H360F

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

Storage Class Code

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

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)

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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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
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
David W Stanley et al.
Insect biochemistry and molecular biology, 38(3), 275-284 (2008-02-07)
Prostaglandins (PGs) and other eicosanoids exert important physiological actions in insects and other invertebrates, including influencing ion transport and mediating cellular immune defense functions. Although these actions are very well documented, we have no information on the mechanisms of PGs
S Takahashi et al.
The Biochemical journal, 335 ( Pt 1), 35-42 (1998-09-22)
Cyclopentenone prostaglandins (PGs) are transported into cells and stimulate the expression of various stress genes, such as that coding for BiP (an ER luminal protein). To reveal the site of action of the PGs for the induction of stress-gene expression
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
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