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SML2692

Sigma-Aldrich

DCPIB

≥98% (HPLC), powder, VRAC or VSOAC blocker

Synonyme(s) :

4-(2-Butyl-6,7-dichloro-2-cyclopentyl-1-oxo-2,3-dihydro-1H-inden-5-yloxy)butanoic acid, 4-[(2-Butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-oxo-1H-inden-5-yl)oxy]butanoic acid, 4-(2-butyl-6,7-dichloro-2-cyclopentylindan-1-on-5-yl)oxybutyric acid

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About This Item

Formule empirique (notation de Hill):
C22H28Cl2O4
Numéro CAS:
82749-70-0
Poids moléculaire :
427.36
Numéro MDL:
MFCD07783995
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

product name

DCPIB, ≥98% (HPLC)

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

CCCCC1(Cc2cc(OCCCC(O)=O)c(Cl)c(Cl)c2C1=O)C3CCCC3

InChI

1S/C22H28Cl2O4/c1-2-3-10-22(15-7-4-5-8-15)13-14-12-16(28-11-6-9-17(25)26)19(23)20(24)18(14)21(22)27/h12,15H,2-11,13H2,1H3,(H,25,26)

Clé InChI

KHKGTPJPBOQECW-UHFFFAOYSA-N

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Actions biochimiques/physiologiques

DCPIB is a potent inhibitor of the volume-sensitive anion channel (VSAC). IC50 = 4.1μM ) versus ICl,swell in calf pulmonary artery endothelial (CPAE) cells. DCPIB does not inhibit CPAE cell ICl,Ca; hCFTR; nor guinea pig ICl,PKA, IKr, IKs,IKl, INa and ICa. DCPIB inhibition is reversible and voltage independent. ICl,swell is believed to be important in cardiovascular function. Studies have been limited by the lack of specific ligands.
DCPIB is a reversible and highly selective volume-regulated anion channel (VRAC or VSOAC) blocker (by 50/98.7% of hypotonic solution-induced Cl current or ICl,swell at 4.1/10 μM in calf pulmonary artery endothelial (CPAE) cells vs. 4.1% inhibition of Ca2+-activated ICl,Ca or CaCC at 10 μM) with little or no inhibition against hminK (IKs), hCFTR, hCLC-1/2/4/5, rCLC-K1, hKv1.5, hKv4.3, HERG (≤5.9% at 10 μM; transpected xenopus oocytes), nor IKs, IKr, IK1, INa, ICa, or ICl,PKA in isolated guinea pig cardiomyocytes. When applied in rats in vivo (10 mg/kg ip.), DCPIB is shown to protect against myocardial ischaemia/reperfusion injury.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Yuesheng Xia et al.
Oncotarget, 7(26), 39345-39362 (2016-10-26)
Excessive reactive oxygen species (ROS) plays an important role in myocardial ischemia/reperfusion (I/R) injury, which triggers not only myocardial cellular apoptosis but also autophagy-related cell death, in which volume-sensitive outwardly rectifying (VSOR) Cl- channel-activated by ROS contributes to cell apoptotic
N Decher et al.
British journal of pharmacology, 134(7), 1467-1479 (2001-11-29)
1. We identified the ethacrynic-acid derivative DCPIB as a potent inhibitor of I(Cl,swell), which blocks native I(Cl,swell) of calf bovine pulmonary artery endothelial (CPAE) cells with an IC(50) of 4.1 microM. Similarly, 10 microM DCPIB almost completely inhibited the swelling-induced
David M Kern et al.
eLife, 8 (2019-02-19)
Hypoosmotic conditions activate volume-regulated anion channels in vertebrate cells. These channels are formed by leucine-rich repeat-containing protein 8 (LRRC8) family members and contain LRRC8A in homo- or hetero-hexameric assemblies. Here, we present single-particle cryo-electron microscopy structures of Mus musculus LRRC8A
R S Bourke et al.
Journal of neurosurgery, 55(3), 364-370 (1981-09-01)
The intact cerebral cortices of cats were exposed in vivo under normothermic conditions and superfused with isotonic artificial cerebrospinal fluid containing added 0.125 mM adenosine. This resulted in chloridecation-rich cerebrocortical swelling which was shown by electron microscopy to be associated
Huiran Zhang et al.
Journal of pharmacological sciences, 143(3), 176-181 (2020-05-11)
The volume-regulated anion channel (VRAC) plays a central role in maintaining cell volume in response to osmotic stress. Leucine-rich repeat-containing 8A (LRRC8A) was recently identified as an essential component of VRAC although other Cl- channels were also suggested to contribute
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