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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:
130-26-7
Molecular Weight:
305.50
Beilstein:
153637
EC Number:
204-984-4
MDL number:
MFCD00006787
UNSPSC Code:
12352100
PubChem Substance ID:
57648095
NACRES:
NA.22

Quality Level

200

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
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H317,H319

Hazard Classifications

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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
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
Lin W Hung et al.
Future medicinal chemistry, 4(8), 955-969 (2012-06-02)
In 1906, Alois Alzheimer first characterized the disease that bears his name. Despite intensive research, which has led to a better understanding of the pathology, there is no effective treatment for this disease. Of the drugs approved by the US
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