Details

Autor(en) / Beteiligte

• Cierpiał, Tomasz
• Łuczak, Jerzy
• Kwiatkowska, Małgorzata
• Kiełbasiński, Piotr
• Mielczarek, Lidia
• Wiktorska, Katarzyna
• Chilmonczyk, Zdzisław
• Milczarek, Małgorzata
• Karwowska, Katarzyna

Titel

Organofluorine Isoselenocyanate Analogues of Sulforaphane: Synthesis and Anticancer Activity

Ist Teil von

• ChemMedChem, 2016-11, Vol.11 (21), p.2398-2409

Ort / Verlag

Germany: Blackwell Publishing Ltd

Erscheinungsjahr

2016

Quelle

Wiley Online Library

Beschreibungen/Notizen

• A series of previously unknown sulforaphane analogues with organofluorine substituents bonded to the sulfinyl sulfur atom, an isoselenocyanate moiety in place of the isothiocyanate group, the central sulfur atom in various oxidation states, and different numbers of methylene groups in the central alkyl chain were synthesized and fully characterized. All new compounds were tested for their biological properties in vitro and demonstrated much higher anticancer activity against two breast cancer cell lines than that shown by native sulforaphane; at the same time, the compounds were less toxic for normal cells. The influence of the particular structural changes in the molecules on the cytotoxicity is discussed. Superior sulforaphanes: Newly synthesized sulforaphane analogues with organofluorine substituents bonded to the sulfinyl sulfur atom, an isoselenocyanate moiety replacing the original isothiocyanate group, and various numbers of methylene groups in the central carbon chain exhibit significantly higher cytotoxicity against some breast cancer cell lines than the original sulforaphane and are also less toxic for model nonmalignant human cells.