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24880

Sigma-Aldrich

5-Chloro-7-iodo-8-quinolinol

≥95.0% (HPLC)

Synonym(s):

5-Chloro-8-hydroxy-7-iodoquinoline, Clioquinol, Iodochlorhydroxyquin

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About This Item

Empirical Formula (Hill Notation):
C9H5ClINO
CAS Number:
Molecular Weight:
305.50
Beilstein:
153637
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

≥95.0% (HPLC)

form

powder

solubility

dioxane: soluble 0.5 g/10 mL, clear, faintly yellow to yellow

SMILES string

Oc1c(I)cc(Cl)c2cccnc12

InChI

1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

InChI key

QCDFBFJGMNKBDO-UHFFFAOYSA-N

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General description

5-Chloro-7-iodo-8-quinolinol is an antibiotic with metal-binding properties and exhibits anticancer activity in vitro and in vivo. 5-Chloro-7-iodo-8-quinolinol, its glucuronide and sulfate in serum, urine and milk has been quantitated by gas chromatography.

Application

5-Chloro-7-iodo-8-quinolinol has been used in analysis of intracellular free zinc ions with the FluoZin-3 probes using fluorescence microscopy.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

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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Customers Also Viewed

A gas chromatographic determination method of 5-chloro-7-iodo-8-quinolinol and its conjugates in biological fluids.
C Chen et al.
Chemical & pharmaceutical bulletin, 24(1), 97-101 (1976-01-01)
A D Schimmer
Current cancer drug targets, 11(3), 325-331 (2011-01-21)
Clioquinol (5-chloro-7-iodo-quinolin-8-ol) was used in the 1950's-1970's as an oral anti-parasitic agent. More recently, studies have demonstrated that Clioquinol displays preclinical efficacy in the treatment of malignancy. Its anti-cancer activity relates, at least in part, to its ability to inhibit
Amy M Ruschak et al.
Journal of the National Cancer Institute, 103(13), 1007-1017 (2011-05-25)
The proteasome is an intracellular enzyme complex that degrades ubiquitin-tagged proteins and thereby regulates protein levels within the cell. Given this important role in maintaining cellular homeostasis, it is perhaps somewhat surprising that proteasome inhibitors have a therapeutic window. Proteasome
Aaron D Schimmer et al.
Clinical lymphoma, myeloma & leukemia, 12(5), 330-336 (2012-06-12)
Clioquinol is a small-molecule metal ionophore that inhibits the proteasome through a metal-dependent mechanism. Here, we report a phase I study of clioquinol in patients with refractory hematologic malignancies. Neuropathy and abdominal pain were dose-limiting toxicities. Minimal pharmacodynamic effects were
Peter J Crouch et al.
Journal of neurochemistry, 119(1), 220-230 (2011-07-30)
Impaired metal ion homeostasis causes synaptic dysfunction and treatments for Alzheimer's disease (AD) that target metal ions have therefore been developed. The leading compound in this class of therapeutic, PBT2, improved cognition in a clinical trial with AD patients. The

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