5852-78-8 Usage
Description
5-Carboxy-8-hydroxyquinoline, also known as IOX1, is a compound that inhibits the JMJD family of 2-oxoglutarate-dependent histone demethylases. It possesses cell permeability and exhibits a broad spectrum of inhibition against various histone demethylases, making it a valuable tool for studying hypoxic signaling and other biological processes.
Uses
Used in Epigenetic Regulation:
5-Carboxy-8-hydroxyquinoline is used as an inhibitor of KDM2/7 histone demethylase for regulating gene expression and cellular processes. By targeting specific histone demethylases, it can modulate the epigenetic landscape, potentially impacting various cellular functions and disease pathways.
Used in Plant Growth Regulation:
5-Carboxy-8-hydroxyquinoline is used as a regulator of plant growth, potentially influencing the development and productivity of plants. Its application in this field could lead to advancements in agriculture and plant biology.
Used in Antiviral Therapy:
IOX1 is used to eliminate viral latency in latent viruses, sensitizing the viral infections to antiviral therapy. This application could improve the treatment of persistent viral infections and enhance the effectiveness of antiviral drugs.
Used in Cancer Research:
In histone lysine demethylase 4A (KDM4A) inhibition, 5-Carboxy-8-hydroxyquinoline serves as a unique strategy to decrease hypoxia-inducible factors signaling. This could have implications for cancer research and therapy, as hypoxia is often associated with tumor progression and resistance to treatment.
Used in Cellular Senescence Studies:
IOX1 is used to restore oncogene-induced senescence in wild-type mouse embryo fibroblasts. This application could provide insights into the mechanisms of cellular aging and senescence, with potential implications for aging research and age-related diseases.
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
Check Digit Verification of cas no
The CAS Registry Mumber 5852-78-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,8,5 and 2 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5852-78:
(6*5)+(5*8)+(4*5)+(3*2)+(2*7)+(1*8)=118
118 % 10 = 8
So 5852-78-8 is a valid CAS Registry Number.
5852-78-8Relevant articles and documents
Enzyme-like catalysis by single chain nanoparticles that use transition metal cofactors
Alzona, Ariale J.,Chen, Junfeng,Garcia, Edzna S.,Xiong, Thao M.,Zhu, Lingyang,Zimmerman, Steven C.
supporting information, p. 985 - 988 (2022/01/28)
We report a modular approach in which a noncovalently cross-linked single chain nanoparticle (SCNP) selectively binds catalyst cofactors and substrates to increase both the catalytic activity of a Cu-catalyzed alkyne-azide cycloaddition reaction and the Ru-catalyzed cleavage of allylcarbamate groups compared to the free catalysts. This journal is
A cell-permeable ester derivative of the JmjC histone demethylase inhibitor IOX1
Schiller, Rachel,Scozzafava, Giuseppe,Tumber, Anthony,Wickens, James R.,Bush, Jacob T.,Rai, Ganesha,Lejeune, Clarisse,Choi, Hwanho,Yeh, Tzu-Lan,Chan, Mun Chiang,Mott, Bryan T.,McCullagh, James S. O.,Maloney, David J.,Schofield, Christopher J.,Kawamura, Akane
supporting information, p. 566 - 571 (2014/03/21)
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.
