Aeroplysinin(Aeroplysinin-1)

Names

[ Name ]:
Aeroplysinin(Aeroplysinin-1)

[Synonym ]:
AEROPLYSININ,APLYSINA AEROPHOBA
aeroplysinin 1
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
AEROPLYSININ
Aeroplysinin I

Biological Activity

[Description]:

Aeroplysinin 1 ((+)-Aeroplysinin-1), a secondary metabolite isolated from marine sponges, shows potent antibiotic effects on Gram-positive bacteria and exerts antiviral activity against HIV-1 (IC50=14.6 μM). Aeroplysinin 1 has anti-inflammatory, anti-angiogenic and anti-tumor activities. Aeroplysinin 1 induces apoptosis in endothelial cells[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

Bacterial

HIV-1:14.6 μM (IC50)

Apoptosis

[In Vitro]

Aeroplysinin 1 shows anti-proliferative effect against tumor cells (HT-1080, HTC-116, HeLa, THP-1, NOMO-1 and HL-60 cells), with IC50s ranging from 2.3 to 17 μM[1]. Aeroplysinin-1 also exhibits an antiviral activity toward HIV-1 caused by inhibition of its reverse transcriptase activity[1]. Aeroplysinin 1 inhibits P. phosphoreum, C. wailesii, P. minimum and HIV with IC50s of 3.5, 5.6, 7.0 and 14.6 μM[1]. Aeroplysinin 1 inhibits human endothelial cells (EVLC-2, HMEC, RF-24, and HUVEC cells), with IC50s ranging from 2.6 to 4.7 μM[2]. (+)-Aeroplysinin-1 (0.25-0.5 μM) blocks the EGF-dependent proliferation of both MCF-7 and ZR-75-1 human breast cancer cells and inhibits the ligand-induced endocytosis of the EGF receptor in vitro[3].

[References]

[1]. García-Vilas JA, et al. Aeroplysinin-1, a Sponge-Derived Multi-Targeted Bioactive Marine Drug. Mar Drugs. 2015;14(1):1. Published 2015 Dec 22.

[2]. Martínez-Poveda B, 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.

[3]. Kreuter MH, 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. 1990;97(1):151‐158.

Chemical & Physical Properties

[ Density]:
2.01g/cm3

[ Boiling Point ]:
479.6ºC at 760 mmHg

[ Molecular Formula ]:
C₉H₉Br₂NO₃

[ Molecular Weight ]:
338.98100

[ Flash Point ]:
243.8ºC

[ Exact Mass ]:
336.89500

[ PSA ]:
73.48000

[ LogP ]:
1.53738

[ Vapour Pressure ]:
3.27E-11mmHg at 25°C

[ Index of Refraction ]:
1.645

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GU4735000

CHEMICAL NAME :: 2,4-Cyclohexadiene-1-acetonitrile, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, (1S-trans)-

CAS REGISTRY NUMBER :: 28656-91-9

LAST UPDATED :: 199204

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C9-H9-Br2-N-O3

MOLECULAR WEIGHT :: 339.01

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 202 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ZNCBDA Zeitschrift fuer Naturforschung, Section C: Biosciences. (Verlag der Zeitschrift fuer Naturforschung, Postfach 2645, D-7400 Tuebingen, Fed. Rep. Ger.) V.29- 1974- Volume(issue)/page/year: 44,680,1989