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D129

Sigma-Aldrich

R-(+)-DIOA

≥98% (HPLC), 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
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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000279870
0000279868
0000279870
0000279868
0000123647

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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)
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
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
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)
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