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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

Deficiency of electroneutral K+-Cl- cotransporter 3 causes a disruption in impulse propagation along peripheral nerves.

Yuan-Ting Sun et al.

Glia, 58(13), 1544-1552 (2010-06-16)

Nerve conduction requires the fine tuning of ionic currents through delicate interactions between axons and Schwann cells. The K(+)-Cl(-) cotransporter (KCC) family includes four isoforms (KCC1-4) that play an important role in the maintenance of cellular osmotic homeostasis via the

Inhibition of P-type ATPases by [(dihydroindenyl)oxy]acetic acid (DIOA), a K+ -Cl- cotransporter inhibitor.

Takuto Fujii et al.

European journal of pharmacology, 560(2-3), 123-126 (2007-02-17)

[(Dihydroindenyl)oxy]acetic acid (DIOA) has been used as a potent inhibitor of K+ -Cl- cotransporter (IC(50)=10 microM). Here we found that DIOA inhibited activities of P-type ATPases such as dog kidney Na+,K+-ATPase (IC(50)=53 microM), hog gastric H+,K+-ATPase (IC(50)=97 microM) and rabbit

K+-Cl- Cotransporter-3a Up-regulates Na+,K+-ATPase in Lipid Rafts of Gastric Luminal Parietal Cells.

Takuto Fujii et al.

The Journal of biological chemistry, 283(11), 6869-6877 (2008-01-08)

Gastric parietal cells migrate from the luminal to the basal region of the gland, and they gradually lose acid secretory activity. So far, distribution and function of K+-Cl(-) cotransporters (KCCs) in gastric parietal cells have not been reported. We found

Mechanisms of chloride influx during KCl-induced swelling in the chicken retina.

L D Ochoa-de la Paz et al.

Pflugers Archiv : European journal of physiology, 449(6), 526-536 (2005-01-05)

An increase in extracellular KCl ([KCl]o) occurs under various pathological conditions in the retina, leading to retinal swelling and possible neuronal damage. The mechanisms of this KCl o-induced retinal swelling were investigated in the present study, with emphasis on the

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Global Trade Item Number

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

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