title: Cytotoxic activity of substituted chalcones in terms of molecular electronic properties.
abstract: Global chemical reactivity descriptors and lipophilicity (logP) were evaluated via density functional theory in order to clarify the structure-cytotoxic activity relationships of substituted chalcones. Stepwise multiple regression was employed to establish correlation between descriptors and cytotoxic activity against three cancer cell lines (HL-60, NALM-6 and WM-115) for 11 compounds. Regression analysis revealed that electrophilicity index and chemical potential significantly contributed in explaining of chalcones cytotoxic potential. Moreover, the established structure-activity relationships based on electronic structure properties allow indicating the substructures responsible for their cytotoxic activity. The study has also been supported by crystallographic data of 2-chloro-2'-hydroxychalcone.
authors.affiliation: Department of Inorganic and Analytical Chemistry, Collegium Medicum, Nicolaus Copernicus University, Jurasza 2, 85-089 Bydgoszcz, Poland. Electronic address: kupcewicz@cm.umk.pl.
authors.forename: Bogumiła
authors.initials: B
authors.lastname: Kupcewicz
authors.affiliation: Brooklyn College Chemistry Department, The Brooklyn College and the Graduate School of the City University of New York, Brooklyn, NY 11210, United States.
authors.forename: Andrzej A
authors.initials: AA
authors.lastname: Jarzęcki
authors.affiliation: Department of Structural Chemistry and Crystallography, University of Lodz, Pomorska 163/165, 90-236 Lodz, Poland.
authors.forename: Magdalena
authors.initials: M
authors.lastname: Małecka
authors.affiliation: Department of Pharmaceutical Biochemistry, Medical University of Lodz, Muszynskiego1, 90-151 Lodz, Poland.
authors.forename: Urszula
authors.initials: U
authors.lastname: Krajewska
authors.affiliation: Department of Pharmaceutical Biochemistry, Medical University of Lodz, Muszynskiego1, 90-151 Lodz, Poland.
authors.forename: Marek
authors.initials: M
authors.lastname: Rozalski
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D047188:Chalcones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity*; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D004583:Electrons; D018922:HL-60 Cells; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory; D012044:Regression Analysis; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D047188:Chalcones
keywords: Chalcone; Cytotoxicity; Density functional theory; Electrophilicity; SAR