PROSTAGLANDIN A1 Chemical Properties

Melting point:

43°C

Boiling point:

392.93°C (rough estimate)

Density 

1.0192 (rough estimate)

refractive index 

1.4434 (estimate)

storage temp. 

-20°C

solubility 

acetone: 10 mg/mL, clear

form 

White solid.

pka

4.77±0.10(Predicted)

color 

Off-white

biological source

synthetic

BRN 

2003401

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

GY5977900

F 

8-10

HS Code 

2937500000

MSDS

• Language:English Provider:SigmaAldrich

PROSTAGLANDIN A1 Usage And Synthesis

Description

Prostaglandin A₁ (PGA₁) was first isolated as a dehydration product of the PGE₁ compounds found in human semen. It has been shown to cause renal vasodilation, increased urine sodium excretion, and lowered arterial pressure in hypertensive patients. It also has growth-inhibitory activity on tumor cells; the IC₅₀ value for the inhibition of human ovarian cancer is 7.5 μM.

Uses

Prostaglandin A1 has been shown to inhibit human immunodeficiency virus type 1 (HIV-1) replication in various cell types. In addition, as a precursor to the anti-inflammatory prostaglandins, it activates pro-inflammatory PGD2 receptor CRTH2 initiating the anti-inflammatory response.

Definition

ChEBI: Prostaglandin A1 is a prostaglandins A. It is a conjugate acid of a prostaglandin A1(1-).

General Description

Prostaglandin A1(PGA1) belongs to the class of cyclopentenone prostaglandin. PGA1 is generated by the dehydration of prostaglandin E1 (PGE1).

Biochem/physiol Actions

Prostaglandin A1 (PGA1) boosts the expression of human liver-specific cytochrome P450 4F3B (CYP4F3B) and stimulates the synthesis of 20-hydroxy-eicosatetraenoic acids (HETEs). It has an ability to stimulate cell differentiation, ferritin synthesis and heat shock response in human cells. PGA1 exhibits antitumor and antiviral activities. In addition, it also elicits anti-inflammatory effects by activating peroxisome proliferator-activated receptor (PPAR). Elevated levels of PGA1 has been observed in hypertension patients.

Enzyme inhibitor

This eicosanoid (FWfree-acid = 336.47 g/mol; CAS 14152-28-4; Symbol: PGA1) induces apoptosis and stimulates the expression of stress genes. The structure and role of the prostaglandin A1 was investigated by Bergstr?m and Samuelsson, who shared the 1982 Nobel Prize in Physiology or Medicine for their pioneering work on the eicosanoids. Target(s): CYP4F2; DNA topoisomerase II; HIV-1 transcription; 3ahydroxysteroid dehydrogenase, NADP+-dependent; IkB kinase; Mayaro virus replication; stress-induced NF-kB activation; and virus protein biosynthesis, or translation.

References

[1] SANDRA J. LEE . Renal effects of prostaglandin A1 in patients with essential hypertension[J]. Kidney international, 1972, 1 4: Pages 254-262. DOI:10.1038/ki.1972.35
[2] MOKHTAR K. TOPPOZADA MD. Treatment of preeclampsia with prostaglandin A1[J]. American journal of obstetrics and gynecology, 1988, 159 1: Pages 160-165. DOI:10.1016/0002-9378(88)90514-5
[3] ANTONIO ROSSI. Anti-inflammatory cyclopentenone prostaglandins are direct inhibitors of IκB kinase[J]. Nature, 2000, 403 6765: 103-108. DOI:10.1038/47520
[4] ASIM K MANDAL. Yin-yang: balancing act of prostaglandins with opposing functions to regulate inflammation.[J]. Journal of immunology, 2005, 175 10: 6271-6273. DOI:10.4049/jimmunol.175.10.6271
[5] STEFANIA CARTA . Prostaglandin A1 inhibits avian influenza virus replication at a postentry level: Effect on virus protein synthesis and NF-κB activity[J]. Prostaglandins, leukotrienes, and essential fatty acids, 2014, 91 6: Pages 311-323. DOI:10.1016/j.plefa.2014.07.009
[6] ATSUKO TSUKIMOTO . A new role for PGA1 in inhibiting hepatitis C virus-IRES-mediated translation by targeting viral translation factors[J]. Antiviral research, 2015, 117: Pages 1-9. DOI:10.1016/j.antiviral.2015.01.013
[7] BEATRIZ DÍEZ-DACAL. Identification of aldo-keto reductase AKR1B10 as a selective target for modification and inhibition by prostaglandin A(1): implications for antitumoral activity.[J]. Cancer research, 2011: 4161-4171. DOI:10.1158/0008-5472.can-10-3816
[8] B ANTA. PGA1-induced apoptosis involves specific activation of H-Ras and N-Ras in cellular endomembranes[J]. Cell Death & Disease, 2016, 7 7: e2311-e2311. DOI:10.1038/cddis.2016.219

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