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pseurotin A

Names

[ CAS No. ]:
58523-30-1

[ Name ]:
pseurotin A

[Synonym ]:
(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxyhex-3-en-1-yl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
(5S,8S,9R)-8-Benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
pseurotin A
PB-1
(5S,8S,9R)-8-Benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexen-1-yl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
pseurotin-A
pseurotin
1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione, 8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexen-1-yl]-9-hydroxy-8-methoxy-3-methyl-, (5S,8S,9R)-
(5S)-8c-benzoyl-9t-hydroxy-2-((1S,2S)-1,2-dihydroxy-hex-3c-enyl)-8t-methoxy-3-methyl-(5rO)-1-oxa-7-aza-spiro[4.4]non-2-ene-4,6-dione

Biological Activity

[Description]:

Pseurotin A, a secondary metabolite of Aspergillus and other fungi, is a competitive inhibitor of chitin synthase and a neuritogenic agent. Pseurotin A inhibits IgE production (IC50=3.6 μM). Antitumor activity[1][2][3].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Others >> Others

[In Vitro]

Pseurotin A inhibits the expression of PCSK9 in HepG2 cells, with an IC50 value of 1.2 μM. Pseurotin A (25-100 μM; 72 hours) significantly suppressed the PCSK9 level in a dose dependent manner in BT-474 and T47D BC cell lines. Pseurotin A (25-100 μM; 72 hours) significantly increases LDLR level in a dose dependent manner[3]. Pseurotin A (40-200 μM; 24-72 hours) shows anti-proliferative activity in the hormone-dependent BC cells[3]. Cell Viability Assay[3] Cell Line: BT-474 cells, T47D cells Concentration: 40-200 μM Incubation Time: 24-72 hours Result: Showed weak but time and dose-dependent inhibition of the growth of BT-474 and T47D BC cells, with gradual decrease of the IC50 values over time (260.83-93.64 μM and 267.84-113.08 μM, respectively).

[In Vivo]

Pseurotin A (10 mg/kg; p.o.; 7X/week, 30 days) shows anti-tumor activity[3]. Animal Model: HFD-fed orthotopic athymic mice (bearing BT-474 tumor cells xenograft mode)[1] Dosage: 10 mg/kg Administration: P.o.; 7X/week, 30 days Result: Significantly suppressed the growth of BT474 tumors.

[References]

[1]. Ishikawa M, et al. Pseurotin A and its analogues as inhibitors of immunoglobulin E [correction of immunoglobuline E] production. Bioorg Med Chem Lett. 2009;19(5):1457-1460.

[2]. Maiya S, Grundmann A, Li X, Li SM, Turner G. Identification of a hybrid PKS/NRPS required for pseurotin A biosynthesis in the human pathogen Aspergillus fumigatus. Chembiochem. 2007;8(14):1736-1743.

[3]. Abdelwahed KS, et al. Pseurotin A as a novel suppressor of hormone dependent breast cancer progression and recurrence by inhibiting PCSK9 secretion and interaction with LDL receptor. Pharmacol Res. 2020;158:104847.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
751.5±60.0 °C at 760 mmHg

[ Melting Point ]:
126.0-126.9℃

[ Molecular Formula ]:
C22H25NO8

[ Molecular Weight ]:
431.436

[ Flash Point ]:
408.3±32.9 °C

[ Exact Mass ]:
431.158020

[ PSA ]:
142.39000

[ LogP ]:
3.23

[ Vapour Pressure ]:
0.0±2.6 mmHg at 25°C

[ Index of Refraction ]:
1.626

Safety Information

[ Hazard Codes ]:
Xi

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds