≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
(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
| Sonrisas canónicas | 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 |
|---|---|
| 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 |
| InChIKey | GNHIGSRGYXEQEP-QHCPKHFHSA-N |
| 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 |
| Isómeros 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 |
| Términos de entrada MeSH | (R)-BPO-27 |
| Peso molecular | 548.34 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Clase | 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 |
| Descripción | 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 |
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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| Solubilidad | DMSO : ≥ 14.28 mg/mL (26.04 mM) |
|---|---|
| Peso molecular | 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 |
