(+)-Aeroplysinin-1

(+)-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(TM) 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.Formal Name: (1S,6R)-3,5-dibromo-1,6-dihydroxy-4-methoxy-2,4-cyclohexadiene-1-acetonitrile. CAS Number: 28656-91-9. Synonyms: NSC 170364. Molecular Formula: C9H9Br2NO3. Formula Weight: 339.0. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: Methanol: Soluble. SMILES: COC1=C(Br)[C@H](O)[C@@](CC#N)(O)C=C1Br. InChi Code: InChI=1S/C9H9Br2NO3/c1-15-7-5(10)4-9(14,2-3-12)8(13)6(7)11/h4,8,13-14H,2H2,1H3/t8-,9-/m0/s1. InChi Key: BGYNLOSBKBOJJD-IUCAKERBSA-N.