5852-78-8

Basic information

• Product Name: 5-Carboxy-8-hydroxyquinoline
• Synonyms: 5-Carboxy-8-hydroxyquinoline;8-Hydroxyquinoline-5-carboxylic Acid;IOX1;8-hydroxy-5-Quinolinecarboxylic acid;IOX 1, >=98%;JMJD2 Inhibitor, 5-carboxy-8HQ
• CAS NO: 5852-78-8
• Molecular Formula: C₁₀H₇NO₃
• Molecular Weight: 189.16748
• Product Categories: Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals;Inhibitors
• Mol File: 5852-78-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 301 °C (decomp)
• Boiling Point: 464.5±30.0 °C(Predicted)
• Appearance: white to brown/
• Density: 1.480±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble10mg/mL, clear
• PKA: 1.82±0.10(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: 5-Carboxy-8-hydroxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Carboxy-8-hydroxyquinoline(5852-78-8)
• EPA Substance Registry System: 5-Carboxy-8-hydroxyquinoline(5852-78-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 5852-78-8(Hazardous Substances Data)

Usage

Description

IOX 1 (5852-78-8) inhibits the JMJD family of 2-oxoglutarate-dependent histone demethylases. IC50 = 0.12, 0.07, 0.2, 0.3, 0.6, and 1 μM for JMJD3, JMJD1A, JMJD2A, JMJD2E, JMJD2C and UTX respectively.1?A broad spectrum 2-oxoglutarate oxygenase inhibitor, IOX 1 may be used to study hypoxic signaling.1?Cell permeable

Uses

Different sources of media describe the Uses of 5852-78-8 differently. You can refer to the following data:
1. 5-Carboxy-8-hydroxyquinoline is an inhibitor of KDM2/7 histone demethylase. 5-Carboxy-8-hydroxyquinoline has also shown potential to be used as a regulator of plant growth.
2. 8-Hydroxyquinoline-5-carboxylic Acid is an inhibitor of KDM2/7 histone demethylase. 8-Hydroxyquinoline-5-carboxylic acid has also shown potential to be used as a regulator of plant growth.
3. IOX1 has been used:To eliminate viral latency in latent viruses in order to sensitize the viral infections to antiviral therapy.In histone lysine demethylase 4A (KDM4A) inhibition, to serve as a unique strategy to decrease hypoxia-inducible factors signalling.to restore oncogene-induced senescence in wild-type mouse embryo fibroblasts.

Biochem/physiol Actions

IOX1 (5-Carboxy-8-hydroxyquinoline) is a broad spectrum inhibitor of 2-oxoglutarate (2OG) oxygenases, including Jumonji C domain (JmjC) demethylases. It is useful for the study of histone demethylation and hypoxic sensing and results in translocation of active site iron on the 2OG oxygenases. For full characterization details, please visit the IOX1 probe summary on the Structural Genomics Consortium (SGC) website.To learn about other SGC chemical probes for epigenetic targets, visit sigma.com/sgc

References

1) King et al. (2010), Quantitative high-throughput screening identifies 8-hydroxyquinolines as cell-active histone demethylase inhibitors; PLoS One, 5 e15535

Upstream product

• 148-24-3 8-quinolinol 
• 5852-79-9 8-hydroxyquinoline-5-carbonitrile 
• 412027-63-5 8-hydroxy-quinoline-5-carboxylic acid anilide 
• 856098-71-0 8-hydroxy-quinoline-5-carboxylic acid ethylamide 
• 536-25-4 methyl 3-amino-4-hydroxybenzoate 
• 56-81-5 glycerol 
• 99970-88-4 8-acetoxy-quinoline-5-carbonitrile 
• 1571-72-8 3-amino-4-hydroxybenzoic acid 
• 107-02-8 acrolein 
• 91569-25-4 1-(8-hydroxy-[5]quinolyl)-propan-1-one 

Downstream Products

• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 104293-76-7 ethyl 8-hydroxyquinoline-5-carboxylate 
• 521-74-4 broxyquinoline 
• 91569-71-0 8-Ethoxy-chinolin-5-carbonsaeure 
• 148887-46-1 quinoline-8-methoxy-5-carboxylic acid 
• 148-24-3 8-quinolinol 

Relevant articles and documents

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A cell-permeable ester derivative of the JmjC histone demethylase inhibitor IOX1

The 2-oxoglutarate (2OG)-dependent Jumonjia C domain (JmjC) family is the largest family of histone lysine demethylases. There is interest in developing small-molecule probes that modulate JmjC activity to investigate their biological roles. 5-Carboxy-8-hydroxyquinoline (IOX1) is the most potent broad-spectrum inhibitor of 2OG oxygenases, including the JmjC demethylases, reported to date; however, it suffers from low cell permeability. Here, we describe structure-activity relationship studies leading to the discovery of an n-octyl ester form of IOX1 with improved cellular potency (EC50 value of 100 to 4a μM). These findings are supported by in vitro inhibition and selectivity studies, docking studies, activity versus toxicity analysis in cell cultures, and intracellular uptake measurements. The n-octyl ester was found to have improved cell permeability; it was found to inhibit some JmjC demethylases in its intact ester form and to be more selective than IOX1. The n-octyl ester of IOX1 should find utility as a starting point for the development of JmjC inhibitors and as a use as a cell-permeable tool compound for studies investigating the roles of 2OG oxygenases in epigenetic regulation.