title: Small molecule glycoconjugates with anticancer activity.
abstract: Glycoconjugates are combinations of sugar moieties with organic compounds. Due to their biological resemblance, such structures often have properties that are desirable for drugs. In this study we designed and synthesised several glycoconjugates from small molecular quinolines and substituted gluco- and galactopyranosyl amines. Although the parent quinoline compounds were inactive in affordable concentrations, the glycoconjugates that were obtained appeared to be cytotoxic against cancer cells at the micromolar level. When combined with copper ions, their activity increased even further. Their mechanism of action is connected to the formation of reactive oxygen species and the intercalation of DNA.
authors.affiliation: Silesian University of Technology, Faculty of Chemistry, Chair of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Krzywoustego 4, 44-100 Gliwice, Poland.
authors.forename: Gabriela
authors.initials: G
authors.lastname: Pastuch-Gawołek
authors.affiliation: Institute of Chemistry, University of Silesia, 9 Szkolna Street, 40-006 Katowice, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Malarz
authors.affiliation: A. Chełkowski Institute of Physics, University of Silesia, Uniwersytecka 4, 40-007 Katowice, Poland; Silesian Center for Education and Interdisciplinary Research, University of Silesia, 75 Pułku Piechoty 1A, 41-500 Chorzów, Poland.
authors.forename: Anna
authors.initials: A
authors.lastname: Mrozek-Wilczkiewicz
authors.affiliation: Silesian University of Technology, Faculty of Chemistry, Chair of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Krzywoustego 4, 44-100 Gliwice, Poland.
authors.forename: Marta
authors.initials: M
authors.lastname: Musioł
authors.affiliation: Institute of Chemistry, University of Silesia, 9 Szkolna Street, 40-006 Katowice, Poland.
authors.forename: Maciej
authors.initials: M
authors.lastname: Serda
authors.affiliation: Institute of Chemistry, University of Silesia, 9 Szkolna Street, 40-006 Katowice, Poland.
authors.forename: Barbara
authors.initials: B
authors.lastname: Czaplinska
authors.affiliation: Institute of Chemistry, University of Silesia, 9 Szkolna Street, 40-006 Katowice, Poland. Electronic address: robert.musiol@us.edu.pl.
authors.forename: Robert
authors.initials: R
authors.lastname: Musiol
mesh_terms: D017209:Apoptosis / Q000187:drug effects; D056831:Coordination Complexes / Q000737:chemistry / Q000494:pharmacology; D003300:Copper / Q000737:chemistry / Q000494:pharmacology; D004247:DNA / Q000378:metabolism; D006001:Glycoconjugates / Q000737:chemistry* / Q000494:pharmacology*; D045325:HCT116 Cells; D006801:Humans; D007364:Intercalating Agents / Q000737:chemistry* / Q000494:pharmacology*; D009369:Neoplasms / Q000188:drug therapy / Q000378:metabolism; D011804:Quinolines / Q000737:chemistry* / Q000494:pharmacology*; D017382:Reactive Oxygen Species / Q000378:metabolism; D015032:Zinc / Q000737:chemistry / Q000494:pharmacology
chemical_list: D056831:Coordination Complexes; D006001:Glycoconjugates; D007364:Intercalating Agents; D011804:Quinolines; D017382:Reactive Oxygen Species; D003300:Copper; D004247:DNA; C037219:quinoline; D015032:Zinc
keywords: Anticancer; Chelators; Glycoconjugates; Quinoline; Reactive oxygen species