Synthesis and in vitro Toxicity of d‐Glucose and d‐Fructose Conjugated Curcumin–Ruthenium Complexes. Issue 33 (19th October 2016)

• Record Type: Journal Article
• Authors: Pröhl, Michael; Bus, Tanja; Czaplewska, Justyna A.; Traeger, Anja; Deicke, Michael; Weiss, Henning; Weigand, Wolfgang; Schubert, Ulrich S.; Gottschaldt, Michael
• Is Part Of: European journal of inorganic chemistry. Issue 33(2016)
• Page Start: 5197
• Page End: 5204
• Publication Date: 2016-10-19
• Subjects: Carbohydrates -- Metal complexes -- Curcumin -- Ruthenium -- Click chemistry; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejic.201600801
• Languages: English
• ISSNs: 1434-1948

Abstract

Abstract : A series of carbohydrate‐conjugated bis(demethoxy)curcumin (BDC) ligands were synthesized by using the Huisgen copper(I)‐catalyzed cycloaddition between azido‐functionalizedd ‐glucose andd ‐fructose as well as propargyl‐modified BDC. The unprotected sugar ligands were treated with Ru(bpy)2 Cl2 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 spectroscopy, mass spectrometry as well as by elemental analysis (EA). Incubation of L929, HepG2 and the breast cancer cell line MDA‐MB‐231 revealed lower cytotoxicity of all carbohydrate‐conjugated 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, thed ‐fructose‐conjugated ligand and its corresponding Ru complex did not show any significant toxicity against MDA‐MB‐231 cells. Abstract : Bis(demethoxy)curcumin (BDC) ligands conjugated with sugar moieties (d ‐fructose, d ‐glucose) by a triazol group reacted with Ru(bpy)2 Cl2 to form the corresponding complexes. Cytotoxicity assays confirmed that sugar‐decorated compounds showed reduction in cell viability for liver‐cancerous cells HepG2, whereas the sugar‐free complex showed increased toxicity for breast cancer cells MDA‐MB‐231.