Synthesis and in vitro Toxicity of D -Glucose and D -Fructose Conjugated Curcumin–Ruthenium Complexes

Pröhl, Michael; Buś, Tanja; Czaplewska, Justyna; Träger, Anja; Deicke, Michael; Weiss, Henning; Weigand, Wolfgang; Schubert, Ulrich S.; Gottschaldt, Michael
A series of carbohydrate-conjugated bis(demeth- oxy)curcumin (BDC) ligands were synthesized by using the Huisgen copper(I)-catalyzed cycloaddition between azido-functionalized D-glucose and D-fructose as well as propargyl-modified BDC. The unprotected sugar ligands were treated with Ru(bpy)2Cl2 to form curcumin-conjugated Ru complexes of general formula Ru(bpy)2(L)Cl. The ligands as well as Ru complexes were analyzed by NMR, IR, UV/Vis, and fluorescence spectro- scopy, mass spectrometry as well as by elemental analysis (EA). ncubation of L929, HepG2 and the breast cancer cell line MDA- MB-231 revealed lower cytotoxicity of all carbohydrate-conju- gated ligands compared with BDC. The Ru complexes exhibited higher cytotoxicity than the parent ligands, in particular against HepG2 cells, whereas the noncancerous L929 cell line remained unaffected. Unexpectedly, the D -fructose-conjugated ligand and its corresponding Ru complex did not show any significant toxicity against MDA-MB-231 cells.
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European Joernal of Inorganic Chemistry
5197 - 520