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D129

Sigma-Aldrich

R-(+)-DIOA

≥98% (HPLC), solid

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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
Empirical Formula (Hill Notation):
C20H24Cl2O4
CAS Number:
81166-47-4
Molecular Weight:
399.31
MDL number:
MFCD00069261
UNSPSC Code:
12352200
PubChem Substance ID:
24277830
NACRES:
NA.77

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

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Tatsuya Asai et al.
The European journal of neuroscience, 15(11), 1737-1746 (2002-06-26)
With repetitive electrical stimulation of the dorsal root (20 Hz for 1 s at C-fibre strength), intrinsic optical signals (IOSs), measured as changes in light transmittance, were recorded in the superficial dorsal horn of rat spinal cord slices using a
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
The inhibition of Na(+)-Pi cotransport and Pi self-exchange mechanisms in lactating rat mammary tissue.
J M Shillingford et al.
Biochemical Society transactions, 23(4), 559S-559S (1995-11-01)
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
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