Pentabromopseudilin (PBrP) is a marine antibiotic extracted from the marine bacteria Pseudomonas bromoutilis and Alteromonas luteoviolaceus. PBrP has antibacterial, antitumor, and phytotoxic activities. PBrP is a reversible allosteric inhibitor of myosin Va (MyoVa). PBrP is also a potent inhibitor of transforming growth factor-β (TGF-β) activity. PBrP may be utilized in research on fibrotic diseases and cancer.

Physicochemical Properties

Molecular Formula	C10H4BR5NO
Molecular Weight	553.66486
Exact Mass	548.621
CAS #	10245-81-5
PubChem CID	324093
Appearance	Typically exists as solid at room temperature
Density	2.606g/cm3
Boiling Point	464.2ºC at 760 mmHg
Flash Point	234.5ºC
Vapour Pressure	3.07E-09mmHg at 25°C
Index of Refraction	1.739
LogP	6.199
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Heavy Atom Count	17
Complexity	281
Defined Atom Stereocenter Count	0
SMILES	BrC1C=C(Br)C(O)=C(C2NC(Br)=C(Br)C=2Br)C=1
InChi Key	LXMNWKJHYOZUQL-UHFFFAOYSA-N
InChi Code	InChI=1S/C10H4Br5NO/c11-3-1-4(9(17)5(12)2-3)8-6(13)7(14)10(15)16-8/h1-2,16-17H
Chemical Name	2,4-dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol
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	Pentabromopseudilin (PBrP) (0.01-1 μM, 6 h) inhibits nuclear translocation and Smad protein phosphorylation produced by TGF-β [1]. PBrP (0.5 μM, 6 h) suppresses transcriptional responses induced by TGF-β [1]. In A549 cells, PBrP (0-1 μM, 6 h) suppresses TGF-β-induced EMT[1]. PBrP (0.2 μM, 20 h) prevents cell migration caused by TGF-β [1]. TGF-β signaling is inhibited by PBrP (0.01-1μM, 6 h) by promoting TβRII degradation [1]. Through caveolae, PBrP (0.5μM, 0, 1, 3 h) enhances the degradation of TβRII, hence blocking TGF-β signaling[1].
Cell Assay	Western Blot Analysis[1] Cell Types: Mv1Lu, A549, Clone 9 and HepG2 cells Tested Tested Concentrations: 0.01-1 μM (Mv1Lu, A549, Clone 9 and HepG2 cells); 0.5 μM (Mv1Lu, A549 and HepG2 cells) Incubation Duration: 6 h (Mv1Lu, A549, Clone 9 and HepG2 cells); 0.5, 1, 2, 4, 6 h (Mv1Lu, A549 and HepG2 cells) Experimental Results: Suppressed the TGF-β-stimulated Smad2/3 phosphorylation in a dose-dependent manner in these cell lines. Prevented TGF-β induced the nuclear translocation of Smad2/3 and PBrP alone did not alter the localization of Smad proteins. Immunofluorescence[1] Cell Types: A549 cells Tested Tested Concentrations: 0.2 μM Incubation Duration: 6 h Experimental Results: Abolished TGF-β-induced Smad2/3 nuclear translocation. Cell Migration Assay [1] Cell Types: A549 cells Tested Tested Concentrations: 0.2 μM Incubation Duration: 20 h Experimental Results: Suppressed TGF-β-stimulated cell migration and did not close the wound.
References	[1]. Pentabromopseudilin: a myosin V inhibitor suppresses TGF-β activity by recruiting the type II TGF-β receptor to lysosomal degradation. J Enzyme Inhib Med Chem. 2018;33(1):920-935.
Additional Infomation	Pentabromopseudilin is a member of pyrroles. It has a role as a metabolite. Pentabromopseudilin has been reported in Pseudoalteromonas luteoviolacea 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	1.8062 mL	9.0308 mL	18.0616 mL
	5 mM	0.3612 mL	1.8062 mL	3.6123 mL
	10 mM	0.1806 mL	0.9031 mL	1.8062 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.