5-Chloro-8-hydroxyquinoline

CAS: 130-16-5

Ref. 3D-FC40563

Product Information

• Name: 5-Chloro-8-hydroxyquinoline
• Synonyms: 5-Chloro-8-oxyquinoline, 5-Chloro-8-quinolinol, 5-Chloro-quinoline-8-ol, 5-Chlorooxine, 5-Chloroquinolin-8-Ol, 8-Hydroxy-5-chloroquinoline, 8-Quinolinol, 5-chloro-, Cloxiquine, Cloxyquin, Dermofongin, Dermofungin, NSC 35083, NSC 53182, NSC 74943

Description

5-Chloro-8-hydroxyquinoline (5-CQ) is a quinoline derivative that has been used as an anticancer agent. It binds to DNA and inhibits the synthesis of RNA and proteins, leading to cell death. 5-CQ has been shown to be cytotoxic against skin cells in vitro by inhibiting mitochondrial oxidative phosphorylation and decreasing the mitochondrial membrane potential. This compound also has genotoxic effects on cultured choroidal neovascularization cells through the inhibition of DNA synthesis.
5-CQ binds to DNA via hydrogen bonds with nitrogen atoms in the purine ring of nucleobases. The overall geometry is that of a distorted octahedron with two faces, each containing six nitrogens in square planar coordination geometry. The binding constants are low for purines but high for pyrimidines, which is why 5-CQ preferentially targets purine rich regions of the genome.

• Brand: Biosynth

Chemical properties

• Molecular weight: 179.6 g/mol
• Formula: C₉H₆ClNO
• Purity: Min. 95%
• Color/Form: Green To Grey Solid
• InChI: InChI=1S/C9H6ClNO/c10-7-3-4-8(12)9-6(7)2-1-5-11-9/h1-5,12H
• InChI key: InChIKey=CTQMJYWDVABFRZ-UHFFFAOYSA-N
• SMILES: Oc1ccc(Cl)c2cccnc12