| Identification | Back Directory | [Name]
(+)-AEROPLYSININ-1 | [CAS]
28656-91-9 | [Synonyms]
NSC-170364
AEROPLYSININ
aeroplysinini
(+)-aeroplysinini
(+)-AEROPLYSININ-1
(+)shy-Aeroplysinin-1
Aeroplysinin (Aeroplysinin-1)
AEROPLYSININ, APLYSINA AEROPHOBA
(+)-AEROPLYSININ-1, APLYSINA AEROPHOBA
4-cyclohexadiene-1-acetonitrile,3,5-dibromo-1,6-dihydroxy-4-methoxy-(1s-tr
(1s-trans)-3,5-dibromo-1,6-dihydroxy-4-methoxy-2,4-cyclohexadiene-1-acetonit
(1S)-1,6α-Dihydroxy-3,5-dibromo-4-methoxy-2,4-cyclohexadiene-1α-acetonitrile
(1R)-1,6β-Dihydroxy-3,5-dibromo-4-methoxy-2,4-cyclohexadiene-1β-acetonitrile
(1R)-3,5-Dibromo-1α,6β-dihydroxy-4-methoxy-2,4-cyclohexadiene-1β-acetonitrile
[1S,6R,(+)]-3,5-Dibromo-1,6-dihydroxy-4-methoxy-2,4-cyclohexadiene-1-acetonitrile | [Molecular Formula]
C9H9Br2NO3 | [MDL Number]
MFCD01745659 | [MOL File]
28656-91-9.mol | [Molecular Weight]
338.98 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [Description]
(+)-Aeroplysinin-1 is a metabolite originally isolated from the marine sponge V. aerophoba with diverse biological activities.1 (+)-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.2 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.3 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.4 | [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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Energy Chemical
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