29266-96-4

Usage

Uses

Used in Pharmaceutical Applications:
8-Hydroxyquinoline-beta-D-glucopyranoside is used as a therapeutic agent for its potential in treating various diseases and conditions, including cancer, neurodegenerative disorders, and microbial infections. Its antioxidant and antimicrobial properties contribute to its efficacy in these areas.
Used in Cosmetics Industry:
In the cosmetics industry, 8-Hydroxyquinoline-beta-D-glucopyranoside is used as an ingredient for its antioxidant properties, which can help protect the skin from oxidative stress and promote overall skin health.
Used in Food Preservation:
8-Hydroxyquinoline-beta-D-glucopyranoside is used as a preservative in the food industry due to its antimicrobial properties, which help to extend the shelf life of food products by inhibiting the growth of spoilage-causing microorganisms.
Used in Metal Ion Chelation Therapy:
8-Hydroxyquinoline-beta-D-glucopyranoside is used as a chelating agent in metal ion chelation therapy, where it can bind to metal ions and help to remove them from the body, potentially useful in treating heavy metal poisoning.
Used as a Fluorescent Probe for Metal Ions:
In analytical chemistry, 8-Hydroxyquinoline-beta-D-glucopyranoside is used as a fluorescent probe for detecting and quantifying metal ions, providing a sensitive and selective method for metal ion analysis.

InChI:InChI=1/C15H17NO6/c17-7-10-12(18)13(19)14(20)15(22-10)21-9-5-1-3-8-4-2-6-16-11(8)9/h1-6,10,12-15,17-20H,7H2/t10-,12-,13+,14-,15?/m1/s1

Upstream product

• 148-24-3 8-quinolinol 
• 2280-44-6 D-Glucose 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 148-24-3 8-quinolinol 
• 492-61-5 β-D-glucose 

Relevant academic research and scientific papers

Synthesis of 8-hydroxyquinoline glycoconjugates and preliminary assay of their β1,4-GalT inhibitory and anti-cancer properties

8-Hydroxyquinoline scaffold is a privileged structure used in designing a new active agents with therapeutic potential. Its connections with the sugar unit is formed to improve the pharmacokinetic properties. The broad spectrum of activity of quinoline derivatives, especially glycoconjugates, is often associated with the ability to chelate metal ions or with the ability to intercalate into DNA. Simple and effective methods of synthesis glycoconjugates of 8-hydroxyquinoline and 8-hydroxyquinaldine derivatives, containing an O-glycosidic bond or a 1,2,3-triazole linker in their structure, have been developed. The obtained glycoconjugates were tested for their ability to inhibit β-1,4-Galactosyltransferase, as well as inhibit cancer cell proliferation. It was found that used glycoconjugation strategy influenced both improvement of activity and improvement of the bioavailability of 8-HQ derivatives. Their activity depends on type of attached sugar, presence of protecting groups in sugar moiety and presence of a linker between sugar and quinolone aglycone.

Gluconjugates of 8-hydroxyquinolines as potential anti-cancer prodrugs

8-Hydroxyquinolines are systems of great interest in the field of inorganic and bioinorganic chemistry. They are metal-binding compounds and are known to exhibit a variety of biological activities, such as antibacterial and anticancer activities. Among these systems, clioquinol has been the focus of a renewed interest in recent years. In this scenario, we synthesized and characterized the new clioquinol glucoconjugate, 5-chloro-7-iodo-8-quinolinyl-β-d- glucopyranoside in order to compare this system to that of clioquinol. We also synthesized, 8-quinolinyl-β-d-glucopyranoside, an 8-hydroxyquinoline glucoconjugate. The reason for the development of glucoconjugates is the glucose avidity, and the over-expression of glucose transporters in cancer cells. Here we demonstrate that glycoconjugates are cleaved in vitro by β-glucosidase and these systems exhibit antiproliferative activity against different tumor cell lines in the presence of copper(ii) ions.