New enantiomeric fluorine-containing derivatives of sulforaphane: synthesis, absolute configurations and biological activity

Piotr Kiełbasiński; Jerzy Łuczak; Tomasz Cierpiał; Jarosław Błaszczyk; Lesław Sieroń; Katarzyna Wiktorska; Katarzyna Lubelska; Małgorzata Milczarek; Zdzisław Chilmończyk

doi:10.1016/j.ejmech.2014.02.036

New enantiomeric fluorine-containing derivatives of sulforaphane: synthesis, absolute configurations and biological activity

Eur J Med Chem. 2014 Apr 9:76:332-42. doi: 10.1016/j.ejmech.2014.02.036. Epub 2014 Feb 14.

Authors

Piotr Kiełbasiński¹, Jerzy Łuczak², Tomasz Cierpiał², Jarosław Błaszczyk², Lesław Sieroń³, Katarzyna Wiktorska⁴, Katarzyna Lubelska⁵, Małgorzata Milczarek⁵, Zdzisław Chilmończyk⁵

Affiliations

¹ 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.
² Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, Sienkiewicza 112, 90-363 Łódź, Poland.
³ Institute of General and Ecological Chemistry, Technical University of Łódź, Żeromskiego 116, 90-924 Łódź, Poland.
⁴ National Medicines Institute, Cell Biology Department, Chełmska 30/34, 00-725 Warszawa, Poland. Electronic address: k.wiktorska@nil.gov.pl.
⁵ National Medicines Institute, Cell Biology Department, Chełmska 30/34, 00-725 Warszawa, Poland.

PMID: 24589488
DOI: 10.1016/j.ejmech.2014.02.036

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.

Keywords: Isothiocyanates; Melanoma; Organofluorine compounds; Sulforaphane; Sulfoxides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Fluorine / chemistry*
Isothiocyanates / chemical synthesis
Isothiocyanates / chemistry*
Isothiocyanates / pharmacology
Magnetic Resonance Spectroscopy
Mass Spectrometry
Models, Molecular
Molecular Structure
Stereoisomerism
Sulfoxides

Substances

Isothiocyanates
Sulfoxides
Fluorine
sulforaphane