BPO-27 | CAS# 1415390-47-4 | CFTR Inhibitor

MedKoo Cat#: 564177 | Name: BPO-27

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

BPO-27 is a potent and metabolically stable CFTR inhibitor.

Chemical Structure

BPO-27

CAS#1415390-47-4

Theoretical Analysis

MedKoo Cat#: 564177

Name: BPO-27

CAS#: 1415390-47-4

Chemical Formula: C26H18BrN3O6

Exact Mass: 547.0379

Molecular Weight: 548.35

Elemental Analysis: C, 56.95; H, 3.31; Br, 14.57; N, 7.66; O, 17.51

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 385.00	2 Weeks

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Synonym

BPO27; BPO 27; BPO-27; (R)-BPO-27; (R)-BPO27; (R)-BPO 27;

IUPAC/Chemical Name

(6R)-6-(5-Bromo-2-furanyl)-7,8,9,10-tetrahydro-7,9-dimethyl-8,10-dioxo-11-phenyl-6H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]benzoxazine-2-carboxylic acid

InChi Key

GNHIGSRGYXEQEP-QHCPKHFHSA-N

InChi Code

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

SMILES Code

O=C(C1=CC=C(O[C@@H](C2=CC=C(Br)O2)C3=C(N(C)C4=O)C(C(N4C)=O)=C(C5=CC=CC=C5)N36)C6=C1)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

(R)-BPO-27, the R enantiomer of BPO-27, is a potent, orally active and ATP-competitive CFTR inhibitor with an IC50 of 4 nM.

In vitro activity:

Figure 1B shows inhibition of Cl− current by (R)-BPO-27 in CFTR-expressing FRT cells after CFTR stimulation by the cell-permeable cAMP agonist CPT-cAMP (left) and the cell-permeable cGMP agonist 8-Br-cGMP (right). Measurements were done in the presence of a transepithelial chloride gradient and after basolateral membrane permeabilization with amphotericin B; therefore, short-circuit current is a linear, quantitative measure of CFTR Cl− conductance. Increasing concentrations of (R)-BPO-27 inhibited Cl− current, with apparent IC50 values of ∼5 and ∼10 nM for CPT-cAMP and 8-Br-cGMP, respectively. Reference: FASEB J. 2017 Feb;31(2):751-760. https://pubmed.ncbi.nlm.nih.gov/27871064/

In vivo activity:

A closed intestinal loop model in mice was used to assess (R)-BPO-27 efficacy in reducing fluid secretion caused by bacterial enterotoxins. (R)-BPO-27 at 5 mg/kg administered intraperitoneally prevented fluid accumulation in closed midjejunal loops produced by cholera toxin, giving an intestinal loop weight/length ratio similar to that in PBS-injected loops (Fig. 2A). A dose-response study showed an IC50 of ∼0.1 mg/kg (Fig. 2B). Intestinal fluid secretion was also prevented by orally administered (R)-BPO-27 at 5 mg/kg given 60 min before creation of loops and administration of cholera toxin (Fig. 2C). Reference: FASEB J. 2017 Feb;31(2):751-760. https://pubmed.ncbi.nlm.nih.gov/27871064/

	Solvent	mg/mL	mM
Solubility
	DMSO	14.3	26.04

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 548.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Cil O, Phuan PW, Gillespie AM, Lee S, Tradtrantip L, Yin J, Tse M, Zachos NC, Lin R, Donowitz M, Verkman AS. Benzopyrimido-pyrrolo-oxazine-dione CFTR inhibitor (R)-BPO-27 for antisecretory therapy of diarrheas caused by bacterial enterotoxins. FASEB J. 2017 Feb;31(2):751-760. doi: 10.1096/fj.201600891R. Epub 2016 Nov 8. PMID: 27871064; PMCID: PMC5240666.

In vitro protocol:

In vivo protocol:

1: Snyder DS, Tradtrantip L, Yao C, Kurth MJ, Verkman AS. Potent, metabolically stable benzopyrimido-pyrrolo-oxazine-dione (BPO) CFTR inhibitors for polycystic kidney disease. J Med Chem. 2011 Aug 11;54(15):5468-77. doi: 10.1021/jm200505e. Epub 2011 Jul 12. PubMed PMID: 21707078; PubMed Central PMCID: PMC3314378. 2: Snyder DS, Tradtrantip L, Battula S, Yao C, Phuan PW, Fettinger JC, Kurth MJ, Verkman AS. ABSOLUTE CONFIGURATION AND BIOLOGICAL PROPERTIES OF ENANTIOMERS OF CFTR INHIBITOR BPO-27. ACS Med Chem Lett. 2013 May 9;4(5):456-459. PubMed PMID: 23814642; PubMed Central PMCID: PMC3694630.