(4-FerrocenylphenylJpropargyl ether derived carbohydrate triazoles: influence of a hydrophobic linker on the electrochemical and cytotoxic properties

摘要

In this article we describe a detailed study of the influence of a hydrophobic linker on the properties of a series of ferrocene-carbohydrate conjugates. The alkyne, (4-ferrocenylphenyl)propargyl ether, was prepared from the reaction of propargyl bromide and 4-ferrocenylphenol. The structure of the alkyne was determined using a single crystal X-ray diffraction study. A benzyl triazole (3a) was synthesised for comparison purposes in the electrochemical and cytotoxic study. Herein, we report the synthesis and characterization of a series of carbohydrate triazole conjugates (3b-h) by using the Huisgen 1,3-dipolar cycloaddition reaction of a series of carbohydrate azides and (4-ferrocenylphenyl)propargyl ether. UV-visible spectroscopy and electrochemical studies were performed on the alkyne and triazole compounds. The data generated from the cyclic voltammetric studies was used to calculate the diffusion coefficients (D_f) of the ferrocene-carbohydrate conjugates in DMSO and DMSO-buffer solutions. Slightly higher diffusion coefficient values were obtained for the carbohydrate triazole conjugates (3b-h) in the buffer solution, perhaps due to the hydrophobic nature of the linker and the absence of a hydrogen-bonding substituent adjacent to the ferrocene core. Furthermore, the triazole conjugate (3f) derived from ribofuranose exhibited significant cytotoxicity against a hormone dependent breast cancer cell line (MCF-7) with an IC_(50) value lower than 10 μM.