Clioquinol (Iodochlorhydroxyquin)
(Synonyms: 氯碘羟喹,Iodochlorhydroxyquin) 目录号 : GC32078
A metal-chelating antimicrobial agent
Cas No.:130-26-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Clioquinol is a metal-chelating antimicrobial agent with neuroprotective properties.1,2,3 It inhibits the growth of A. fumigatus with MIC values of 1, >32, 8, and 16 ?g/ml in media containing no metal, iron, zinc, and copper, respectively.1 Clioquinol (37 mg/kg) decreases neuronal loss in the substantia nigra pars compacta (SNc) and increases time spent in the novel arm of a Y-maze in the α-synuclein hA53T transgenic mouse model of Parkinson's disease.2 It reduces brain atrophy and iron content, increases nigral tyrosine hydroxylase phosphorylation, and rescues behavioral impairments in the rotarod and Y-maze tests in tau knockout mice.3
1.Ben Yaakov, D., Shadkchan, Y., Albert, N., et al.The quinoline bromoquinol exhibits broad-spectrum antifungal activity and induces oxidative stress and apoptosis in Aspergillus fumigatusJ. Antimicrob. Chemother.72(8)2263-2272(2017) 2.Finkelstein, D.I., Hare, D.J., Billings, J.L., et al.Clioquinol improves cognitive, motor function, and microanatomy of the α-Synuclein hA53T transgenic miceACS Chem. Neurosci.7(1)119-129(2016) 3.Lei, P., Ayton, S., Appukuttan, A.T., et al.Clioquinol rescues Parkinsonism and dementia phenotypes of the tau knockout mouseNeurobiol. Dis.81168-175(2015)
| Cas No. | 130-26-7 | SDF | |
| 别名 | 氯碘羟喹,Iodochlorhydroxyquin | ||
| Canonical SMILES | ClC1=C(C=CC=N2)C2=C(O)C(I)=C1 | ||
| 分子式 | C9H5ClINO | 分子量 | 305.5 |
| 溶解度 | DMSO : ≥ 53.33 mg/mL (174.57 mM);Water : < 0.1 mg/mL (insoluble) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.2733 mL | 16.3666 mL | 32.7332 mL |
| 5 mM | 0.6547 mL | 3.2733 mL | 6.5466 mL |
| 10 mM | 0.3273 mL | 1.6367 mL | 3.2733 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The toxicology of Clioquinol
Toxicol Lett 2008 Nov 10;182(1-3):1-6.PMID:18812216DOI:10.1016/j.toxlet.2008.08.015.
5-Chloro-7-iodo-quinolin-8-ol (Clioquinol) is a halogenated 8-hydroxyquinoline that was used in 1950-1970s as an oral anti-parasitic agent for the treatment and prevention of intestinal amebiasis. However in the 1970s oral Clioquinol was withdrawn from the market due to reports of neurotoxicity in Japanese patients. Recently, reports have demonstrated that Clioquinol has activities beyond its use as an antimicrobial. For example, Clioquinol inhibits the function of the proteasome and displays preclinical efficacy in the treatment of malignancy. In addition, due to its ability to bind copper and dissolve beta-amyloid plaques in the brain, Clioquinol has been investigated for the treatment of Alzheimer's disease. As such, efforts are underway to repurpose Clioquinol. In light of the reemergence of oral Clioquinol, we review the toxicology of this compound in animals and humans with an emphasis on its neurotoxicity. Such information will aid in the design of clinical trials of oral Clioquinol for new indications such as cancer therapy.
Feasibility of Repurposing Clioquinol for Cancer Therapy
Recent Pat Anticancer Drug Discov 2020;15(1):14-31.PMID:32106803DOI:10.2174/1574892815666200227090259.
Background: Cancer is a prevalent disease in the world and is becoming more widespread as time goes on. Advanced and more effective chemotherapeutics need to be developed for the treatment of cancer to keep up with this prevalence. Repurposing drugs is an alternative to discover new chemotherapeutics. Clioquinol is currently being studied for reposition as an anti-cancer drug. Objective: This study aimed to summarize the anti-cancer effects of Clioquinol and its derivatives through a detailed literature and patent review and to review their potential re-uses in cancer treatment. Methods: Research articles were collected through a PubMed database search using the keywords "Clioquinol" and "Cancer." The keywords "Clioquinol Derivatives" and "Clioquinol Analogues" were also used on a PubMed database search to gather research articles on Clioquinol derivatives. Patents were gathered through a Google Patents database search using the keywords "Clioquinol" and "Cancer." Results: Clioquinol acts as a copper and zinc ionophore, a proteasome inhibitor, an anti-angiogenesis agent, and is an inhibitor of key signal transduction pathways responsible for its growth-inhibitory activity and cytotoxicity in cancer cells preclinically. A clinical trial conducted by Schimmer et al., resulted in poor outcomes that prompted studies on alternative clioquinol-based applications, such as new combinations, new delivery methods, or new clioquinol-derived analogues. In addition, numerous patents claim alternative uses of Clioquinol for cancer therapy. Conclusion: Clioquinol exhibits anti-cancer activities in many cancer types, preclinically. Low therapeutic efficacy in a clinical trial has prompted new studies that aim to discover more effective clioquinol- based cancer therapies.
Clioquinol - a novel copper-dependent and independent proteasome inhibitor
Curr Cancer Drug Targets 2011 Mar;11(3):325-31.PMID:21247386DOI:10.2174/156800911794519770.
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 the proteasome through mechanisms dependent and independent of its ability to bind heavy metals such as copper. By acting as a metal ionophore Clioquinol transports metal ions from the extracellular environment into the cell and mobilizes weakly bound intracellular stores. It then directs the metal to the proteasome resulting in disruption of this enzymatic complex. In addition, Clioquinol is capable of directly inhibiting the proteasome at higher concentrations. Thus, Clioquinol represents a novel therapeutic strategy to inhibit the proteasome. Given the prior toxicology and pharmacology studies, Clioquinol could be rapidly repositioned for a new anti-cancer indication. This review highlights the mechanism of action of Clioquinol as a proteasome inhibitor. In addition, it discusses the human pharmacology and toxicology studies and how this information would guide a phase I clinical trial of this agent for patients with malignancy.
Antimicrobial activity of Clioquinol and nitroxoline: a scoping review
Arch Microbiol 2022 Jul 30;204(8):535.PMID:35907036DOI:10.1007/s00203-022-03122-2.
Clioquinol and nitroxoline, two drugs with numerous pharmacological properties fallen into disuse for many decades. The first was considered dangerous due to contraindications and the second mainly because was taken as ineffective, despite its known antibacterial activity. In the last decades, the advances in pharmaceutical chemistry, molecular biology, toxicology and genetics allowed to better understand the cellular action of these compounds, some toxicological issues and/or activity scopes. Thus, a new opportunity for these drugs to be considered as potential antimicrobial agents has arisen. This review contemplates the trajectory of Clioquinol and nitroxoline from their emergence to the present day, emphasizing the new studies that indicate the possibility of reintroduction for specific cases.
Iodochlorhydroxyquin-hydrocortisone treatment of fungal infections. Double-blind trial
Arch Dermatol 1978 Dec;114(12):1773-5.PMID:153729doi
A double-blind multicenter study compared the antifungal effectiveness of an iodochlorhydroxyquin-hydrocoritsone cream with that of its individual components in 354 patients with cutaneous fungal infections. After seven days of treatment, the combination was considerably better than hydrocortisone or the cream vehicle with respect to erythema, scaling, itching, and patients' and physicians' evaluations. The proportion of patients in the iodochlorhydroxyquin-hydrocortisone and Iodochlorhydroxyquin groups who changed from positive results on potassium hydroxide examination at baseline to negative results on potassium hydroxide examination after treatment was significantly greater than that in the hydrocortisone and placebo groups. The conversion rate associated with the iodochlorhydroxyquin-hydrocortisone and the Iodochlorhydroxyquin treatments was significantly different from that associated with hydrocortisone alone or placebo treatment.