title: Structure-cytotoxic activity relationship of 3-arylideneflavanone and chromanone (E,Z isomers) and 3-arylflavones.
abstract: The E,Z-isomers of 3-arylidene substituted flavanone, chromanone and 3-aryl substituted flavone derivatives were tested in vitro for their cytotoxic activity against three cancer cell lines (HL-60, NALM-6, WM-115) and normal cell line (HUVEC). It was observed that substitution at C3 position led to significant enhance in cytotoxicity. Isomeric configuration of 3-arylideneflavanones had an influence on the cytotoxic potential. Multiple regression analysis combined with variable selection by genetic algorithm was used to model relationships between molecular descriptors and the cytotoxic activity. The most accurate QSAR models were based on a combination between energy of LUMO, experimental value of logP and partial charge on carbonyl oxygen (δO2).
authors.affiliation: Department of Inorganic and Analytical Chemistry, Collegium Medicum, Nicolaus Copernicus University, Jurasza 2, 85-089 Bydgoszcz, Poland. kupcewicz@cm.umk.pl
authors.forename: Bogumiła
authors.initials: B
authors.lastname: Kupcewicz
authors.forename: Grażyna
authors.initials: G
authors.lastname: Balcerowska-Czerniak
authors.forename: Magdalena
authors.initials: M
authors.lastname: Małecka
authors.forename: Piotr
authors.initials: P
authors.lastname: Paneth
authors.forename: Urszula
authors.initials: U
authors.lastname: Krajewska
authors.forename: Marek
authors.initials: M
authors.lastname: Rozalski
mesh_terms: D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D002839:Chromans / Q000737:chemistry* / Q000633:toxicity; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D044950:Flavanones / Q000737:chemistry* / Q000633:toxicity; D018922:HL-60 Cells; D061307:Human Umbilical Vein Endothelial Cells; D006801:Humans; D008968:Molecular Conformation; D021281:Quantitative Structure-Activity Relationship; D013237:Stereoisomerism
chemical_list: D002839:Chromans; D044950:Flavanones; C028610:flavanone