MedKoo Cat#: 531013 | Name: Clioquinol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Clioquinol metal ion chelator that crosses the blood brain barrier and acts as a neurotoxic antibiotic. Clioquinol reduced adhesions at significant level via decreasing the inflammation and fibroblastic activity in the adhesion-induced rats. At macroscopic level, carboxymethylcellulose and clioquinol were the most potent agents in reducing adhesions. Clioquinol recently has shown promising results in the treatment of Alzheimer's disease and in cancer therapy, both of which also are thought to be due to clioquinol's ability as a lipophilic copper chelator.

Chemical Structure

Clioquinol
Clioquinol
CAS#130-26-7 (free base)

Theoretical Analysis

MedKoo Cat#: 531013

Name: Clioquinol

CAS#: 130-26-7 (free base)

Chemical Formula: C9H5ClINO

Exact Mass: 304.9104

Molecular Weight: 305.50

Elemental Analysis: C, 35.38; H, 1.65; Cl, 11.60; I, 41.54; N, 4.58; O, 5.24

Price and Availability

Size Price Availability Quantity
25g USD 350.00 2 Weeks
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Synonym
Clioquinol, Iodochlorhydroxyquin, Chinoform, Vioform, EnteroVioform, Entero Septol; Iodochlorohydroxyquin; NSC 3531; NSC3531; NSC-3531; NSC 74938; NSC74938; NSC-74938
IUPAC/Chemical Name
5-chloro-7-iodoquinolin-8-ol
InChi Key
QCDFBFJGMNKBDO-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
SMILES Code
OC1=C2N=CC=CC2=C(Cl)C=C1I
Appearance
Light yellow to brown solid powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 305.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Pushie MJ, Nienaber KH, Summers KL, Cotelesage JJ, Ponomarenko O, Nichol HK, Pickering IJ, George GN. The solution structure of the copper clioquinol complex. J Inorg Biochem. 2014 Apr;133:50-6. doi: 10.1016/j.jinorgbio.2014.01.003. Epub 2014 Jan 16. PubMed PMID: 24503514. 2: Kawamura K, Kuroda Y, Sogo M, Fujimoto M, Inui T, Mitsui T. Superoxide dismutase as a target of clioquinol-induced neurotoxicity. Biochem Biophys Res Commun. 2014 Sep 12;452(1):181-5. doi: 10.1016/j.bbrc.2014.04.067. Epub 2014 Apr 19. PubMed PMID: 24755073. 3: Katsuyama M, Ibi M, Matsumoto M, Iwata K, Ohshima Y, Yabe-Nishimura C. Clioquinol increases the expression of VGF, a neuropeptide precursor, through induction of c-Fos expression. J Pharmacol Sci. 2014;124(4):427-32. Epub 2014 Mar 19. PubMed PMID: 24646654. 4: Yildiz T, Ilce Z, Yildirim M, Akdogan M, Yurumez Y, Varlikli O, Dilek FH. Antienflamatuar and antiadhesive effect of clioquinol. Int J Surg. 2015 Mar;15:17-22. doi: 10.1016/j.ijsu.2015.01.022. Epub 2015 Jan 29. PubMed PMID: 25638731. 5: Wang Z, Wang Y, Li W, Mao F, Sun Y, Huang L, Li X. Design, synthesis, and evaluation of multitarget-directed selenium-containing clioquinol derivatives for the treatment of Alzheimer's disease. ACS Chem Neurosci. 2014 Oct 15;5(10):952-62. doi: 10.1021/cn500119g. Epub 2014 Aug 22. PubMed PMID: 25121395. 6: Rodríguez-Santiago L, Alí-Torres J, Vidossich P, Sodupe M. Coordination properties of a metal chelator clioquinol to Zn(2+) studied by static DFT and ab initio molecular dynamics. Phys Chem Chem Phys. 2015 May 28;17(20):13582-9. doi: 10.1039/c5cp01615k. PubMed PMID: 25939963. 7: Chan-On W, Huyen NT, Songtawee N, Suwanjang W, Prachayasittikul S, Prachayasittikul V. Quinoline-based clioquinol and nitroxoline exhibit anticancer activity inducing FoxM1 inhibition in cholangiocarcinoma cells. Drug Des Devel Ther. 2015 Apr 8;9:2033-47. doi: 10.2147/DDDT.S79313. eCollection 2015. PubMed PMID: 25897210; PubMed Central PMCID: PMC4396583. 8: Bareggi SR, Cornelli U. Clioquinol: review of its mechanisms of action and clinical uses in neurodegenerative disorders. CNS Neurosci Ther. 2012 Jan;18(1):41-6. doi: 10.1111/j.1755-5949.2010.00231.x. Epub 2010 Dec 27. Review. PubMed PMID: 21199452. 9: Oyama TM, Ishida S, Okano Y, Seo H, Oyama Y. Clioquinol-induced increase and decrease in the intracellular Zn2+ level in rat thymocytes. Life Sci. 2012 Dec 10;91(23-24):1216-20. doi: 10.1016/j.lfs.2012.09.014. Epub 2012 Oct 5. PubMed PMID: 23044228. 10: Mao F, Yan J, Li J, Jia X, Miao H, Sun Y, Huang L, Li X. New multi-target-directed small molecules against Alzheimer's disease: a combination of resveratrol and clioquinol. Org Biomol Chem. 2014 Aug 21;12(31):5936-44. doi: 10.1039/c4ob00998c. PubMed PMID: 24986600. 11: Abdel-Aleem EA, Hegazy MA, Sayed NW, Abdelkawy M, Abdelfatah RM. Novel spectrophotometric determination of flumethasone pivalate and clioquinol in their binary mixture and pharmaceutical formulation. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Feb 5;136 Pt B:707-13. doi: 10.1016/j.saa.2014.09.085. Epub 2014 Sep 30. PubMed PMID: 25448970. 12: Geiser J, De Lisle RC, Finkelstein D, Adlard PA, Bush AI, Andrews GK. Clioquinol synergistically augments rescue by zinc supplementation in a mouse model of acrodermatitis enteropathica. PLoS One. 2013 Aug 28;8(8):e72543. doi: 10.1371/journal.pone.0072543. eCollection 2013. PubMed PMID: 24015258; PubMed Central PMCID: PMC3755987. 13: Wang Z, Wang Y, Wang B, Li W, Huang L, Li X. Design, Synthesis, and Evaluation of Orally Available Clioquinol-Moracin M Hybrids as Multitarget-Directed Ligands for Cognitive Improvement in a Rat Model of Neurodegeneration in Alzheimer's Disease. J Med Chem. 2015 Nov 12;58(21):8616-37. doi: 10.1021/acs.jmedchem.5b01222. Epub 2015 Oct 27. PubMed PMID: 26473791. 14: Schimmer AD, Jitkova Y, Gronda M, Wang Z, Brandwein J, Chen C, Gupta V, Schuh A, Yee K, Chen J, Ackloo S, Booth T, Keays S, Minden MD. A phase I study of the metal ionophore clioquinol in patients with advanced hematologic malignancies. Clin Lymphoma Myeloma Leuk. 2012 Oct;12(5):330-6. doi: 10.1016/j.clml.2012.05.005. Epub 2012 Jun 9. PubMed PMID: 22683301. 15: Zheng J, Benbrook DM, Yu H, Ding WQ. Clioquinol suppresses cyclin D1 gene expression through transcriptional and post-transcriptional mechanisms. Anticancer Res. 2011 Sep;31(9):2739-47. PubMed PMID: 21868515. 16: Kharadi GJ. Effect of substituent of terpyridines on the in vitro antioxidant, antitubercular, biocidal and fluorescence studies of copper(II) complexes with clioquinol. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jan 3;117:662-8. doi: 10.1016/j.saa.2013.09.049. Epub 2013 Sep 28. PubMed PMID: 24128919. 17: Ghalkhani M, Fernandes IP, Oliveira SC, Shahrokhian S, Oliveira-Brett AM. Anodic behavior of clioquinol at a glassy carbon electrode. Bioelectrochemistry. 2011 Feb;80(2):175-81. doi: 10.1016/j.bioelechem.2010.10.001. Epub 2010 Oct 16. PubMed PMID: 21111689. 18: Finkelstein DI, Hare DJ, Billings JL, Sedjahtera A, Nurjono M, Arthofer E, George S, Culvenor JG, Bush AI, Adlard PA. Clioquinol Improves Cognitive, Motor Function, and Microanatomy of the Alpha-Synuclein hA53T Transgenic Mice. ACS Chem Neurosci. 2016 Jan 20;7(1):119-29. doi: 10.1021/acschemneuro.5b00253. Epub 2015 Oct 30. PubMed PMID: 26481462. 19: Cater MA, Haupt Y. Clioquinol induces cytoplasmic clearance of the X-linked inhibitor of apoptosis protein (XIAP): therapeutic indication for prostate cancer. Biochem J. 2011 Jun 1;436(2):481-91. doi: 10.1042/BJ20110123. Erratum in: Biochem J. 2011 Aug 1;437(3):575. PubMed PMID: 21426304. 20: Mussani F, Poon D, Skotnicki-Grant S. Systemic contact dermatitis to topical clioquinol/hydrocortisone combination cream. Dermatitis. 2013 Jul-Aug;24(4):196-7. doi: 10.1097/DER.0b013e3182910430. PubMed PMID: 23857012.