title: Investigation of the biological properties of (hetero)aromatic thiosemicarbazones.
abstract: Two series of thiosemicarbazone-based iron chelators (twenty-seven compounds) were designed and synthesized using a microwave-assisted approach. Quinoline and halogenated phenyl were selected as parent scaffolds on the basis of a similarity search. The lipophilicity of the synthesized compounds was measured using HPLC and then calculated. Primary in vitro screening of the synthesized compounds was performed against eight pathogenic fungal strains. Only a few compounds showed moderate activity against fungi, and (E)-2-(quinolin-2-ylvinyl)-N,N-dimethylhydrazine-carbothioamide appeared to be more effective than fluconazole against most of the fungal strains tested. Antiproliferative activity was measured using a human colon cancer cell line (HCT-116). Several of the tested compounds showed submicromolar antiproliferative activity. Compounds were also tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The structure-activity relationships are discussed for all of the compounds.
authors.affiliation: Department of Organic Chemistry, Institute of Chemistry, University of Silesia, PL-40006 Katowice, Poland.
authors.forename: Maciej
authors.initials: M
authors.lastname: Serda
authors.forename: Anna
authors.initials: A
authors.lastname: Mrozek-Wilczkiewicz
authors.forename: Josef
authors.initials: J
authors.lastname: Jampilek
authors.forename: Matus
authors.initials: M
authors.lastname: Pesko
authors.forename: Katarina
authors.initials: K
authors.lastname: Kralova
authors.forename: Marcela
authors.initials: M
authors.lastname: Vejsova
authors.forename: Robert
authors.initials: R
authors.lastname: Musiol
authors.forename: Alicja
authors.initials: A
authors.lastname: Ratuszna
authors.forename: Jaroslaw
authors.initials: J
authors.lastname: Polanski
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D002736:Chloroplasts / Q000187:drug effects / Q000378:metabolism; D004317:Doxorubicin / Q000494:pharmacology; D004579:Electron Transport / Q000187:drug effects; D015725:Fluconazole / Q000494:pharmacology; D045325:HCT116 Cells; D006540:Herbicides / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D020128:Inhibitory Concentration 50; D007502:Iron Chelating Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D010788:Photosynthesis / Q000187:drug effects; D018724:Spinacia oleracea / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000494:pharmacology*
chemical_list: D000935:Antifungal Agents; D000970:Antineoplastic Agents; D006540:Herbicides; D007502:Iron Chelating Agents; D013882:Thiosemicarbazones; D004317:Doxorubicin; D015725:Fluconazole