Synthesis and in vitro Toxicity of d-Glucose and d-Fructose Conjugated Curcumin-Ruthenium Complexes
Synthesis and in vitro Toxicity of d-Glucose and d-Fructose Conjugated Curcumin-Ruthenium Complexes
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DOI：
10.1002/ejic.201600801
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发表时间：
2016-11-01
影响因子：
2.3
通讯作者：
Gottschaldt, Michael
中科院分区：
文献类型：
--
作者：
Proehl, Michael;Bus, Tanja;Gottschaldt, Michael
利用Huisgen铜催化的叠氮基功能化的d-葡萄糖和d-果糖之间的环加成反应以及炔丙基修饰的双（去甲氧基）姜黄素（BDC），合成了一系列碳水化合物共轭的BDC配体。用Ru（bpy）（2）Cl-2处理未保护的糖配体以形成通式Ru（bpy）（2）（L）Cl的姜黄素缀合的Ru络合物。通过NMR、IR、UV/维斯、荧光光谱、质谱和元素分析对配体和钌配合物进行了分析。L929、HepG 2和乳腺癌细胞系MDA-MB-231的孵育显示，与BDC相比，所有碳水化合物缀合的配体的细胞毒性较低。Ru配合物表现出更高的细胞毒性比亲本配体，特别是对HepG 2细胞，而非癌性L929细胞系保持不受影响。出乎意料的是，d-果糖缀合的配体及其相应的Ru络合物对MDA-MB-231细胞没有显示出任何显著的毒性。
A series of carbohydrate-conjugated bis(demethoxy)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)(2)Cl-2 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, the d-fructose-conjugated ligand and its corresponding Ru complex did not show any significant toxicity against MDA-MB-231 cells.