Aeroplysinin 1 ((+)-Aeroplysinin-1), a secondary metabolite (SM, chemical compound) extracted from marine sponges, displays potent antibiotic effects against Gram-positive (Gram+) bacteria (bacteria) and has anti-viral effect against HIV-1 (IC50=14.6 μM). Aeroplysinin 1 has anti~inflammatory, anti-angiogenic and anti-tumor activities. Aeroplysinin 1 causes apoptosis in endothelial cells.

Physicochemical Properties

Molecular Formula	C9H9NO3BR2
Molecular Weight	338.98066
Exact Mass	336.895
CAS #	28656-91-9
PubChem CID	100308
Appearance	Colorless to off-white ointment
Density	2.01g/cm3
Boiling Point	479.6ºC at 760 mmHg
Flash Point	243.8ºC
Vapour Pressure	3.27E-11mmHg at 25°C
Index of Refraction	1.645
LogP	1.537
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Heavy Atom Count	15
Complexity	382
Defined Atom Stereocenter Count	2
SMILES	N#CC[C@@]1(C=C(Br)C(OC)=C(Br)[C@@H]1O)O
InChi Key	BGYNLOSBKBOJJD-IUCAKERBSA-N
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
Chemical Name	2-[(1S,6R)-3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl]acetonitrile
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Aeroplysinin 1 has an IC50 range from 2.3 to 17 μM that has anti-proliferative effects on tumor cells (HT-1080, HTC-116, HeLa, THP-1, NOMO-1, and HL-60 cells) [1]. By preventing HIV-1's reverse transcriptase activity, aeroplysinin-1 also demonstrates antiviral effectiveness against the virus [1]. Aeroplysinin 1 has an IC50 of 3.5, 5.6, 7.0, and 14.6 μM, respectively, against Pseudomonas phosphatae, Pseudomonas weideni, Pseudomonas parimum, and HIV [1]. Aeroplysinin 1 has an IC50 range from 2.6 to 4.7 μM that inhibits human endothelial cells (EVLC-2, HMEC, RF-24, and HUVEC cells) [2]. In vitro, (+)-Aeroplysinin-1 (0.25-0.5 μM) suppresses ligand-induced EGF receptor endocytosis and prevents MCF-7 and ZR-75-1 human breast cancer cells from proliferating in response to EGF [3].
References	[1]. Aeroplysinin-1, a Sponge-Derived Multi-Targeted Bioactive Marine Drug. Mar Drugs. 2015;14(1):1. Published 2015 Dec 22. [2]. 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]. 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.
Additional Infomation	Aeroplysinin 1 is a tertiary alcohol. Aeroplysinin I has been reported in Aplysina aerophoba, Aplysina cavernicola, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.9500 mL	14.7501 mL	29.5003 mL
	5 mM	0.5900 mL	2.9500 mL	5.9001 mL
	10 mM	0.2950 mL	1.4750 mL	2.9500 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.