5-Carboxy-8-hydroxyquinoline

Names

[ Name ]:
5-Carboxy-8-hydroxyquinoline

[Synonym ]:
8XQ
8-Hydroxy-chinolin-5-carbonsaeure
5-Quinolinecarboxylic acid, 8-hydroxy-
8-hydroxy-quinoline-5-carboxylic acid
UNII-JM015YQC1C
5-Carboxy-8-hydroxyquinoline
IOX1
8-Hydroxy-5-quinolinecarboxylic acid

Biological Activity

[Description]:

IOX1 is the most potent broad-spectrum inhibitor of 2OG oxygenases, including the JmjC demethylases; IC50 for KDM4A/KDM3A is 0.6/0.1 uM.IC50 value: 0.6/0.1 uM(KDM4A/KDM3A) [1]Target: JmjC KDMs inhibitorIOX1 is the most potent against a representative panel of 2OG oxygenases, including non-JmjC 2OG oxygenases, with an in vitro IC50 value in the micromolar range. However, its efficacy in cells is about a hundred-fold lower (HeLa cells, KDM4A, IC50 = 86uM), possibly due to low cell permeability resulting from itspolar C-5 carboxyl group.

[Related Catalog]:

Signaling Pathways >> Epigenetics >> Histone Demethylase

Research Areas >> Cancer

[References]

[1]. Schiller R, et al. A cell-permeable ester derivative of the JmjC histone demethylase inhibitor IOX1. ChemMedChem. 2014 Mar;9(3):566-71.

[Related Small Molecules]

GSK-J4 | QC6352 | GSK2879552 | SP-2509 | CPI-455 | trans-2-Phenylcyclopropylamine hemisulfate salt | ML324 | GSK-LSD1 Dihydrochloride | NCGC00244536 | Daminozide | ORY-1001(trans) | JIB-04 | AS 8351 | KDM5-IN-1 | KDM5A-IN-1

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
464.5±30.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₀H₇NO₃

[ Molecular Weight ]:
189.167

[ Flash Point ]:
234.7±24.6 °C

[ Exact Mass ]:
189.042587

[ PSA ]:
70.42000

[ LogP ]:
1.81

[ Appearance of Characters ]:
white to brown

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.730

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: soluble10mg/mL, clear

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2933499090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933499090

[ Summary ]:
2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Kdm3a lysine demethylase is an Hsp90 client required for cytoskeletal rearrangements during spermatogenesis.

Mol. Biol. Cell 25(8) , 1216-33, (2014)

The lysine demethylase Kdm3a (Jhdm2a, Jmjd1a) is required for male fertility, sex determination, and metabolic homeostasis through its nuclear role in chromatin remodeling. Many histone-modifying enzy...

IOX1, a JMJD2A inhibitor, suppresses the proliferation and migration of vascular smooth muscle cells induced by angiotensin II by regulating the expression of cell cycle-related proteins.

Int. J. Mol. Med. 37 , 189-96, (2015)

The epigenetic modification of vascular smooth muscle cell (VSMC) phenotypic switching, proliferation, migration, apoptosis and extracellular matrix synthesis is known to occur in atherosclerosis. The...

A scintillation proximity assay for histone demethylases.

Anal. Biochem. 463 , 54-60, (2014)

Covalent modifications, such as methylation and demethylation of lysine residues in histones, play important roles in chromatin dynamics and the regulation of gene expression. The lysine demethylases ...