(+)-AEROPLYSININ-1 Chemical Properties

Boiling point:

479.6±45.0 °C(Predicted)

Density 

2.01±0.1 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

Methanol: Soluble

form 

A solid

pka

10.54±0.70(Predicted)

color 

Colorless to off-white

Safety Information

HS Code 

2941900000

(+)-AEROPLYSININ-1 Usage And Synthesis

Description

(+)-Aeroplysinin-1 is a metabolite originally isolated from the marine sponge V. aerophoba with diverse biological activities. (+)-Aeroplysinin-1 (0.25-0.5 μM) induces cell death in MCF-7 and ZR-75-1 human breast cancer cells in a time- and concentration-dependent manner but has no effect on normal human fibroblasts at concentrations up to 5 μM. It also blocks EGF-induced endocytosis of the EGF receptor (EGFR) and EGF-dependent cell proliferation in MCF-7 cells. (+)-Aeroplysinin-1 inhibits bovine aortic endothelial (BAE) cell proliferation and cord formation in a Matrigel™ assay. It inhibits angiogenesis in a dose-dependent manner in a chick chorioallantoic membrane (CAM) assay when administered from 1.5 to 3 nmol per egg. (+)-Aeroplysinin-1 also has antibacterial activity against Gram-positive bacteria, including S. aureus, S. albus, and B. subtilis, but not Gram-negative bacteria and inhibits HIV-1 replication (IC₅₀ = 14.6 μM) via inhibition of HIV-1 reverse transcriptase.

Uses

(+)shy-Aeroplysinin-1 is a compound that is an inhibitor of EGFR kinase.

Definition

ChEBI: Aeroplysinin 1 is a tertiary alcohol.

IC 50

Bacterial; HIV-1: 14.6 μM (IC₅₀); Apoptosis

References

[1] E FATTORUSSO  G S  L Minale. Aeroplysinin-1, an antibacterial bromo-compound from the sponge Verongia aerophoba.[J]. Journal of the Chemical Society. Perkin transactions 1, 1972, 1: 16-18. DOI: 10.1039/p19720000016
[2] MATTHIAS-H. KREUTER . Inhibition of intrinsic protein tyrosine kinase activity of EGF-receptor kinase complex from human breast cancer cells by the marine sponge metabolite (+)-aeroplysinin-1[J]. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry, 1990, 97 1: Pages 151-158. DOI: 10.1016/0305-0491(90)90194-x
[3] SALVADOR RODRíGUEZ-NIETO. Antiangiogenic activity of aeroplysinin-1, a brominated compound isolated from a marine sponge[J]. FASEB Journal, 2001, 16 2: 1-27. DOI: 10.1096/fj.01-0427fje
[4] JAVIER A. GARCíA-VILAS. Aeroplysinin-1, a Sponge-Derived Multi-Targeted Bioactive Marine Drug[J]. Marine Drugs, 2015, 14 1. DOI: 10.3390/md14010001

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