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(R)-BPO-27 - 99%, high purity , CAS No.1415390-47-4

COA COA
    Grade & Purity:
  • ≥99%
In stock
Item Number
B650766
Grouped product items
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Availability
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B650766-1mg
1mg
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Production requires sourcing of materials. We appreciate your patience and understanding.
$180.90
B650766-5mg
5mg
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Production requires sourcing of materials. We appreciate your patience and understanding.
$420.90
B650766-10mg
10mg
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$600.90
B650766-50mg
50mg
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$1,800.90
B650766-100mg
100mg
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$2,520.90
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Basic Description

Specifications & Purity ≥99%
Biochemical and Physiological Mechanisms (R)-BPO-27, the R enantiomer of BPO-27, is a potent, orally active and ATP-competitive CFTR inhibitor with an IC 50 of 4 nM.
Storage Temp Store at -20°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Product Description

(R)-BPO-27, the R enantiomer of BPO-27, is a potent, orally active and ATP-competitive CFTR inhibitor with an IC 50 of 4 nM.

In Vitro

(R)-BPO-27 exhibits a dose-response inhibition and inhibits the CFTR current by 50% at 0.53 nM in HEK-293T cells. (R)-BPO-27 acts from the cytoplasmic side and has low membrane permeability. (R)-BPO-27 reduces the channel open probability (NPo) from 0.29 to 0.08, modestly reduces in mean channel open time, and strongly increases mean channel closed time in HEK-293T cells expressing human wild-type CFT in a single-channel patch-clamp experiment. Meanwhile, (S)-BPO-27 does not affect any of these parameters. (R)-BPO-27 is applied directly to the cytoplasmic membrane surface and stabilizes the CFTR channel closed state with an IC 50 of 600 pM in Single-channel electrophysiology assay. (R)-BPO-27 (10 μM, 10 min pretreatment) inhibits Cl - current with apparent IC 50 values of 5 and 10 nM for CPT-cAMP and 8-Br-cGMP, respectively, in CFTR-expressing FRT cells after CFTR stimulation by cAMP agonist. the IC 50 of 4 nM for inhibition of forskolin-stimulated CFTR Cl - current in FRT cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

(R)-BPO-27 (interperitoneal administration; 10 mg/kg) decays with t 1/2 ≈1.6 h and gives sustained therapeutic concentrations in kidney in a PK study . (R)-BPO-27 (intraperitoneal injection; 5 mg/kg; 30 min before abdominal surgery) prevents fluid accumulation in closed midjejunal loops produced by cholera toxin, giving an intestinal loop weight/length ratio similar to that in PBS-injected loops. This effect is dose-dependently and the IC 50 value is 0.1 mg/kg. (R)-BPO-27 (intraperitoneal injection or oral administration; 5 mg/kg) shows a slow (R)-BPO-27 metabolism and produces sustained serum (R)-BPO-27 levels for at least 4 h. The AUC analysis gave an oral bioavailability of ∼94% for (R)-BPO-27 in mouse pharmacokinetics and toxicity study. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Female CD1 mice (age 8–10 wk)Dosage: 0.05, 0.15, 0.5, 1.5, and 5 mg/kg Administration: Intraperitoneal injection; 5 mg/kg; 30 min before abdominal surgery Result: Exhibited apparent efficacy in mice models of cholera and traveler’s diarrhea.

Form:Solid

IC50& Target:IC50: 4 nM

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Organoheterocyclic compounds
Class Pyrroles
Subclass Substituted pyrroles
Intermediate Tree Nodes Not available
Direct Parent Phenylpyrroles
Alternative Parents Pyrimidones  Alkyl aryl ethers  Aryl bromides  Benzene and substituted derivatives  Vinylogous amides  Furans  Heteroaromatic compounds  Ureas  Lactams  Oxacyclic compounds  Azacyclic compounds  Carboxylic acids  Organobromides  Organonitrogen compounds  Organic oxides  Hydrocarbon derivatives  
Molecular Framework Aromatic heteropolycyclic compounds
Substituents 2-phenylpyrrole - Alkyl aryl ether - Pyrimidone - Aryl bromide - Aryl halide - Monocyclic benzene moiety - Benzenoid - Pyrimidine - Heteroaromatic compound - Furan - Vinylogous amide - Lactam - Urea - Carboxylic acid derivative - Carboxylic acid - Ether - Oxacycle - Azacycle - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organohalogen compound - Organobromide - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
Description This compound belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
External Descriptors Not available

Associated Targets(Human)

Liver microsomes (16955 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Serum (58 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name (9R)-9-(5-bromofuran-2-yl)-12,14-dimethyl-13,15-dioxo-17-phenyl-8-oxa-1,12,14-triazatetracyclo[8.7.0.02,7.011,16]heptadeca-2(7),3,5,10,16-pentaene-4-carboxylic acid
INCHI InChI=1S/C26H18BrN3O6/c1-28-21-19(24(31)29(2)26(28)34)20(13-6-4-3-5-7-13)30-15-12-14(25(32)33)8-9-16(15)36-23(22(21)30)17-10-11-18(27)35-17/h3-12,23H,1-2H3,(H,32,33)/t23-/m0/s1
InChIKey GNHIGSRGYXEQEP-QHCPKHFHSA-N
Smiles CN1C2=C3C(OC4=C(N3C(=C2C(=O)N(C1=O)C)C5=CC=CC=C5)C=C(C=C4)C(=O)O)C6=CC=C(O6)Br
Isomeric SMILES CN1C2=C3[C@@H](OC4=C(N3C(=C2C(=O)N(C1=O)C)C5=CC=CC=C5)C=C(C=C4)C(=O)O)C6=CC=C(O6)Br
PubChem CID 71108905
MeSH Entry Terms (R)-BPO-27
Molecular Weight 548.34

Certificates（CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

Solubility DMSO : ≥ 14.28 mg/mL (26.04 mM)
Molecular Weight 548.300 g/mol
XLogP3 3.800
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 6
Rotatable Bond Count 3
Exact Mass 547.038 Da
Monoisotopic Mass 547.038 Da
Topological Polar Surface Area 105.000 Ų
Heavy Atom Count 36
Formal Charge 0
Complexity 914.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 1
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 0
Covalently-Bonded Unit Count 1

Solution Calculators

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