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D129

R-(+)-DIOA

Name: R-(+)-DIOA
Brand: SIGMA

≥98% (HPLC), potassium/chloride (K+–Cl−) co-transporter inhibitor, solid

Synonym(s):

R(+)-Butylindazone, R-(+)-[(2-n-Butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-oxo-1H-inden-5-yl)oxy]acetic acid

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₂₄Cl₂O₄

CAS Number:

81166-47-4

Molecular Weight:

399.31

UNSPSC Code:

12352200

PubChem Substance ID:

24277830

NACRES:

NA.77

MDL number:

MFCD00069261

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

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Product Name

R-(+)-DIOA, ≥98% (HPLC), solid

Quality Level

100

assay

≥98% (HPLC)

form

solid

optical activity

[α]27/D +18.1°, c = 0.7 in methanol(lit.)

color

white

solubility

H₂O: insoluble <0.11 mg/mL, DMSO: >20 mg/mL, 0.1 M HCl: insoluble, 0.1 M NaOH: soluble, ethanol: soluble

SMILES string

CCCC[C@]1(Cc2cc(OCC(O)=O)c(Cl)c(Cl)c2C1=O)C3CCCC3

InChI

1S/C20H24Cl2O4/c1-2-3-8-20(13-6-4-5-7-13)10-12-9-14(26-11-15(23)24)17(21)18(22)16(12)19(20)25/h9,13H,2-8,10-11H2,1H3,(H,23,24)/t20-/m0/s1

InChI key

YAWWQIFONIPBKT-FQEVSTJZSA-N

Related Categories

Bioactive Small Molecules

Application

R-(+)-DIOA has been used as a potassium/chloride K⁺-Cl^- transport inhibitor to study its effects on:

short circuit current (Isc) in rat semicircular canal duct (SCCD) epithelium
uptake of grepafloxacin by THP-1 monocytes
the uptake of moxifloxacin by THP-1 monocytes

Biochem/physiol Actions

[(dihydroindenyl)oxy]acetic acid (DIOA) acts as a potent inhibitor of potassium/chloride (K⁺–Cl⁻) co-transporter. It does not exert its effects on bumetanimide-sensitive [Na⁺,K⁺,Cl^-]-cotransport system.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000523218

0000515272

0000504658

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The significance of the relative effects of loop diuretics and anti-brain edema agents on the Na+,K+,Cl- cotransport system and the Cl-/NaCO3- anion exchanger.

R P Garay et al.

Naunyn-Schmiedeberg's archives of pharmacology, 334(2), 202-209 (1986-10-01)

3-Amino-5-sulfamoylbenzoic acids and several series of (aryloxy)alkanoic acids were evaluated for their inhibitory effects on two human erythrocyte ion transport systems--the Na+,K+ cotransport system and the DIDS-sensitive anion carrier. Several classic loop diuretics, including the (aryloxy)alkanoic acid-ethacrynic acid and several

Chloride accumulation drives volume dynamics underlying cell proliferation and migration.

Christa W Habela et al.

Journal of neurophysiology, 101(2), 750-757 (2008-11-28)

During brain development, progenitor cells migrate over long distances through narrow and tortuous extracellular spaces posing significant demands on the cell's ability to alter cell volume. This phenotype is recapitulated in primary brain tumors. We demonstrate here that volume changes

A thallium transport FLIPR-based assay for the identification of KCC2-positive modulators.

Di Zhang et al.

Journal of biomolecular screening, 15(2), 177-184 (2010-01-21)

KCC2, potassium chloride cotransporter 2, is expressed exclusively in the CNS (on inhibitory neurons) and plays a major role in maintaining appropriately low intracellular chloride levels that ensure inhibitory actions of GABA(A) and glycine receptors. As such, it plays a

The relationship between volume-sensitive taurine efflux and the anion-exchanger in lactating mammary tissue.

D B Shennan et al.

Biochemical Society transactions, 23(2), 392S-392S (1995-05-01)

K(+)-Cl(-) cotransporter 1 (KCC1) negatively regulates NGF-induced neurite outgrowth in PC12 cells.

Hikaru Nagao et al.

Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 30(3), 538-551 (2012-07-21)

Potassium chloride cotransporters (KCCs) mediate electroneutrally-coupled transport of K(+) and Cl(-), and play crucial roles in various cell functions including regulation of cell volume and homeostasis of cellular Cl(-)content. Four isoforms of KCCs (KCC1, 2, 3, and 4) have been

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Global Trade Item Number

SKU	GTIN
D129-50MG	04061832574288
D129-10MG	04061832574271

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