Clioquinol A metal chelating ligand that inhibits certain enzymes related to DNA replication

Clioquinol (CAS 130-26-7)

Clioquinol | CAS 130-26-7 is rated 5.0 out of 5 by 1.
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Synonym: 5-Chloro-7-iodo-8-quinolinol
Application: A metal chelating ligand that inhibits certain enzymes related to DNA replication
CAS Number: 130-26-7
Purity: ≥96%
Molecular Weight: 305.50
Molecular Formula: C9H5ClINO
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Clioquinol is a member of the hydroxyquinoline family which inhibits certain enzymes related to DNA replication. Clioquinol is a metal chelating ligand which displays protective effects in various neurodegenerative states as well as being a component in antifungal and antiprotozoal agents. It has been shown to modulate amyloid beta-peptide accumulation via upregulation of metalloprotease activity. When co-administered with vitamin B12 (sc-296695), Clioquinol rescues lead-induced impairments of synaptic plasticity in an animal models. In recent animal studies Clioquinol has shown to reverse the progression of Parkinson's, Alzheimer's, and Huntington's diseases. Clioquinol has been observed to induce apoptosis in human cancer cell lines by generating free zinc in lysosomes.


References

1. Rohde, W., et al. 1976. Antimicrob. Agents Chemother. 10: 234-240. PMID: 185949
2. Nguyen, T., et al. 2005. Proc. Natl. Acad. Sci. U.S.A. 102: 11840-11845. PMID: 16087879
3. White, A.R. 2006. J. Biol. Chem. 281: 17670-17680. PMID: 16648635
4. Caragounis, A., et al. 2007. Biochem. J. 407: 435-450. PMID: 17680773
5. Chen, W.H., et al. 2007. Neuroscience. 147: 853-864. PMID: 17555879
6. Adlard, P.A., et al. 2008. Neuron. 59: 43-55. PMID: 18614028
7. Yu, H., et al. 2009. Biochem. J. 417: 133-139. PMID: 18764784

Physical State :
Solid
Solubility :
Soluble in DMSO (>25 mg/ml), boiling alcohol ((1:43)), methanol, and chloroform ((1:120)).
Storage :
Store at room temperature
Melting Point :
172-181° C
Boiling Point :
~350.4° C at 760 mmHg (Predicted)
Density :
~2.0 g/cm3 (Predicted)
Refractive Index :
n20D 1.77 (Predicted)
IC50 :
Kappa opioid receptor: IC50 = 5.79 µM (human); Delta opioid receptor: IC50 = >32 µM (human); Heat shock protein HSP 90-beta: IC50 = >50 µM (human); HIV-1(LAV): IC50 = 2 µM (PBMC); HIV-1(BaL): IC50 = 2 µM (PBMC)
Ki Data :
Carbonic anhydrase 15: Ki= 2.33 µM (mouse)
pK Values :
pKa: 2.32, pKb: 7.23
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
VC5075000
Transport :
UN 2811, Class 6.1, Packing group III
PubChem CID :
2788
Merck Index :
14,5031
MDL Number :
MFCD00006787
EC Number :
204-984-4
Beilstein Registry :
153637
SMILES :
C1=CC2=C(C(=C(C=C2Cl)I)O)N=C1

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Certificate of Analysis

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Rated 5 out of 5 by from Costello LC; et al Costello LC; et al. (PubMed ID: 26273543) determined that Clioquinol may be a possible zinc ionophore treatment for prostate cancer. -SCBT Publication Review
Date published: 2015-07-14
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