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Aeroplysinin

Aeroplysinin is a marine sponge alkaloid that exhibits antibiotic, anti-angiogenic, and anticancer activities. Aeroplysinin is used by Aplysia sponges as an antibacterial defense mechanism. In endothelial cells and monocytes, aeroplysinin decreases levels of MCP-1, TSP-1, MMP-1, COX-2, and IL-1α. Additionally, aeroplysinin inhibits capillary tube formation and cell growth and migration in vitro as well as angiogenesis in vivo. This compound also inhibits cell growth and causes cell death in Ehrlich ascites tumor cells.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18836570

Cas No.

28656-91-9

Purity

≥96%

Formula

C9H9Br2NO3

Formula Wt.

338.98

Chemical Name

3,5-dibromo-1,5-dihydroxy-4-methoxy-2,4-cyclo- hexadiene-1-acetonitrile

IUPAC Name

2-[(1S,6R)-3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl]acetonitrile

Synonym

(1S-trans)-3,5-Dibromo-1,6-dihydroxy-4-methoxy-2,4-cyclohexadiene-1-acetonitrile

Solubility

Soluble in DMSO or ethanol.

Appearance

White Crystal Powder

Martínez-Poveda B, García-Vilas JA, Cárdenas C, et al. The brominated compound aeroplysinin-1 inhibits proliferation and the expression of key pro- inflammatory molecules in human endothelial and monocyte cells. PLoS One. 2013;8(1):e55203. PMID: 23383109.

Rodríguez-Nieto S, González-Iriarte M, Carmona R, et al. Antiangiogenic activity of aeroplysinin-1, a brominated compound isolated from a marine sponge. FASEB J. 2002 Feb;16(2):261-3. PMID: 11772945.

Koulman A, Proksch P, Ebel R, et al. Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba. J Nat Prod. 1996 Jun;59(6):591-4. PMID: 8786366.

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