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(+)-Aeroplysinin-1

Item № 21498
CAS № 28656-91-9
Purity ≥95%
product image
                (CAS 28656-91-9)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     100 µg $35.00 0.00

Pricing updated 2019-05-26. Prices are subject to change without notice.

Description
Synonyms
  • NSC 170364

(+)-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

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Technical Information
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
A solid
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

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Fattorusso, E., Minale, L., and Sodano, G. Aeroplysinin-1, an antibacterial bromo-compound from the sponge Verongia aerophoba J. Chem. Soc. Perkin 1 1(0), 16-18 (1972).

2. Kreuter, M.H., Leake, R.E., Müller-Klieser, W., et al. Inhibition of intrinsic protein tyrosine kinase activity of EGF-receptor kinase complex from human breast cancer cells by the marine sponge metabolite (+)-aeroplysinin-1 Comp. Biochem. Physiol. B 97(1), 151-158 (1990).

3. 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. 16(2), 261-263 (2002).

4. García-Vilas, J.A., Martínez-Poveda, B., Quesada, A.R., et al. Aeroplysinin-1, a sponge-derived multi-targeted bioactive marine drug Mar. Drugs 14(1), (2015).

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