title: New enantiomeric fluorine-containing derivatives of sulforaphane: synthesis, absolute configurations and biological activity.
abstract: Three pairs of enantiomers of the unknown sulforaphane analogs bearing organofluorine substituents bonded to the sulfinyl sulfur atom and having different number of methylene groups in the central carbon chain were synthesized and fully characterized, including determination of their absolute configurations. All the new compounds were tested in vitro for their cytotoxicity against melanoma cells to show increased activity in comparison with the natural sulforaphane. The influence of the particular structural changes in the molecule on the cytotoxicity is discussed.
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, Sienkiewicza 112, 90-363 Łódź, Poland. Electronic address: piokiel@cbmm.lodz.pl.
authors.forename: Piotr
authors.initials: P
authors.lastname: Kiełbasiński
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, Sienkiewicza 112, 90-363 Łódź, Poland.
authors.forename: Jerzy
authors.initials: J
authors.lastname: Łuczak
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, Sienkiewicza 112, 90-363 Łódź, Poland.
authors.forename: Tomasz
authors.initials: T
authors.lastname: Cierpiał
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, Sienkiewicza 112, 90-363 Łódź, Poland.
authors.forename: Jarosław
authors.initials: J
authors.lastname: Błaszczyk
authors.affiliation: Institute of General and Ecological Chemistry, Technical University of Łódź, Żeromskiego 116, 90-924 Łódź, Poland.
authors.forename: Lesław
authors.initials: L
authors.lastname: Sieroń
authors.affiliation: National Medicines Institute, Cell Biology Department, Chełmska 30/34, 00-725 Warszawa, Poland. Electronic address: k.wiktorska@nil.gov.pl.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Wiktorska
authors.affiliation: National Medicines Institute, Cell Biology Department, Chełmska 30/34, 00-725 Warszawa, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Lubelska
authors.affiliation: National Medicines Institute, Cell Biology Department, Chełmska 30/34, 00-725 Warszawa, Poland.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Milczarek
authors.affiliation: National Medicines Institute, Cell Biology Department, Chełmska 30/34, 00-725 Warszawa, Poland.
authors.forename: Zdzisław
authors.initials: Z
authors.lastname: Chilmończyk
mesh_terms: D005461:Fluorine / Q000737:chemistry*; D017879:Isothiocyanates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013454:Sulfoxides
chemical_list: D017879:Isothiocyanates; D013454:Sulfoxides; D005461:Fluorine; C016766:sulforaphane
keywords: Isothiocyanates; Melanoma; Organofluorine compounds; Sulforaphane; Sulfoxides