Clioquinol - CAS 130-26-7
Catalog number:
130-26-7
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C9H5ClINO
Molecular Weight:
305.50
COA:
Inquire
Targets:
Antifungal
Description:
Clioquinol, a quinoline derivative, is an antifungal and antiprotozoal agent and has also been found to have probable effect against cancer and Alzheimer's disease.
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Purity:
95%
Appearance:
Cream-colored to brownish-yellow powder. Practically odorless.
Synonyms:
5-chloro-7-iodoquinolin-8-ol;clioquinol;5-Chloro-7-iodoquinolin-8-ol;Iodochlorhydroxyquin;130-26-7;Chinoform
Solubility:
10 mM in DMSO
Storage:
2-8ºC
MSDS:
Inquire
Application:
Clioquinol is an antifungal and antiprotozoal agent and has also been found to have probable effect against cancer and Alzheimer's disease.
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Grams-Kilos
Boiling Point:
350.4ºC at 760mmHg
Melting Point:
175-183ºC
Density:
2.047g/cm3
InChIKey:
QCDFBFJGMNKBDO-UHFFFAOYSA-N
InChI:
InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
Canonical SMILES:
C1=CC2=C(C(=C(C=C2Cl)I)O)N=C1
1.Discovery of novel PDE9 inhibitors capable of inhibiting Aβ aggregation as potential candidates for the treatment of Alzheimer's disease.
Su T1, Zhang T1, Xie S1, Yan J1, Wu Y1, Li X1, Huang L1, Luo HB1. Sci Rep. 2016 Feb 25;6:21826. doi: 10.1038/srep21826.
Recently, phosphodiesterase-9 (PDE9) inhibitors and biometal-chelators have received much attention as potential therapeutics for the treatment of Alzheimer's disease (AD). Here, we designed, synthesized, and evaluated a novel series of PDE9 inhibitors with the ability to chelate metal ions. The bioassay results showed that most of these molecules strongly inhibited PDE9 activity. Compound 16 showed an IC50 of 34 nM against PDE9 and more than 55-fold selectivity against other PDEs. In addition, this compound displayed remarkable metal-chelating capacity and a considerable ability to halt copper redox cycling. Notably, in comparison to the reference compound clioquinol, it inhibited metal-induced Aβ1-42 aggregation more effectively and promoted greater disassembly of the highly structured Aβ fibrils generated through Cu(2+)-induced Aβ aggregation. These activities of 16, together with its favorable blood-brain barrier permeability, suggest that 16 may be a promising compound for treatment of AD.
2.Nanoscale Reaction Vessels Designed for Synthesis of Copper-Drug Complexes Suitable for Preclinical Development.
Wehbe M1,2, Anantha M1, Backstrom I1, Leung A1,3, Chen K1, Malhotra A1, Edwards K4, Bally MB1,2,3,5. PLoS One. 2016 Apr 7;11(4):e0153416. doi: 10.1371/journal.pone.0153416. eCollection 2016.
The development of copper-drug complexes (CDCs) is hindered due to their very poor aqueous solubility. Diethyldithiocarbamate (DDC) is the primary metabolite of disulfiram, an approved drug for alcoholism that is being repurposed for cancer. The anticancer activity of DDC is dependent on complexation with copper to form copper bis-diethyldithiocarbamate (Cu(DDC)2), a highly insoluble complex that has not been possible to develop for indications requiring parenteral administration. We have resolved this issue by synthesizing Cu(DDC)2 inside liposomes. DDC crosses the liposomal lipid bilayer, reacting with the entrapped copper; a reaction that can be observed through a colour change as the solution goes from a light blue to dark brown. This method is successfully applied to other CDCs including the anti-parasitic drug clioquinol, the natural product quercetin and the novel targeted agent CX-5461. Our method provides a simple, transformative solution enabling, for the first time, the development of CDCs as viable candidate anticancer drugs; drugs that would represent a brand new class of therapeutics for cancer patients.
3.Effects of Neonatal Iron Feeding and Chronic Clioquinol Administration on the Parkinsonian Human A53T Transgenic Mouse.
Billings JL1, Hare DJ1,2, Nurjono M1, Volitakis I1, Cherny RA1, Bush AI1, Adlard PA1, Finkelstein DI1. ACS Chem Neurosci. 2016 Mar 16;7(3):360-6. doi: 10.1021/acschemneuro.5b00305. Epub 2016 Jan 7.
Increased nigral iron (Fe) is a cardinal feature of Parkinson's disease, as is the accumulation of aggregates comprising α-synuclein. We used wild-type mice and transgenic mice overexpressing the human A53T mutation to α-synuclein to examine the influence of increased Fe (days 10-17 postpartum) on the parkinsonian development phenotype of these animals (including abnormal nigral Fe levels and deficits in both cell numbers and locomotor activity), and to explore the impact of the Fe chelator clioquinol in the model. Both untreated and Fe-loaded A53T mice showed similar levels of nigral cell loss, though 5 months of clioquinol treatment was only able to prevent the loss in the non-Fe-loaded A53T group. Iron levels in the Fe-loaded A53T mice returned to normal at 8 months, though effects of dopamine denervation remained, demonstrated by limited locomotor activity and sustained neuron loss. These data suggest that Fe exposure during a critical developmental window, combined with the overexpression mutant α-synuclein, presents a disease phenotype resistant to intervention using clioquinol later in life.
4.Novel 8-Hydroxyquinoline Derivatives as Multitarget Compounds for the Treatment of Alzheimer's Disease.
Prati F1, Bergamini C1, Fato R1, Soukup O2, Korabecny J2, Andrisano V3, Bartolini M4, Bolognesi ML5. ChemMedChem. 2016 Feb 16. doi: 10.1002/cmdc.201600014. [Epub ahead of print]
We discovered a small series of hit compounds that show multitargeting activities against key targets in Alzheimer's disease (AD). The compounds were designed by combining the structural features of the anti-AD drug donepezil with clioquinol, which is able to chelate redox-active metals, thus decreasing metal-driven oxidative phenomena and β-amyloid (Aβ)-mediated neurotoxicity. The majority of the new hybrid compounds selectively target human butyrylcholinesterase at micromolar concentrations and effectively inhibit Aβ self-aggregation. In addition, compounds 5-chloro-7-((4-(2-methoxybenzyl)piperazin-1-yl)methyl)-8-hydroxyquinoline (1 b), 7-((4-(2-methoxybenzyl)piperazin-1-yl)methyl)-8-hydroxyquinoline (2 b), and 7-(((1-benzylpiperidin-4-yl)amino)methyl)-5-chloro-8-hydroxyquinoline (3 a) are able to chelate copper(II) and zinc(II) and exert antioxidant activity in vitro. Importantly, in the case of 2 b, the multitarget profile is accompanied by high predicted blood-brain barrier permeability, low cytotoxicity in T67 cells, and acceptable toxicity in HUVEC primary cells.
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CAS 130-26-7 Clioquinol

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