Design, Synthesis, and Characterization of Novel Thiol-Derivatized Ibuprofen Monolayer Protected Gold Clusters

Abstract EN

A series of new thiol-derivatized ibuprofen monolayer protected gold clusters have been prepared by amidation of ibuprofen with alkyl alcohol or aminophenol affording the carboxamides, N-hydroxyalkyl amide 2, and N-hydroxyphenyl amide 6, which were then tosylated with p-toluenesulfonyl chloride at hydroxyl group to give 3 and 7.

Reactions of 3 and 7 with NaSH afforded the mercapto derivatives 4 and 8.

Conducting Brust’s reaction with a 3 : 1 mole ratio of thiolate ibuprofen/AuCl4- yielded polydisperse thiol-derivatized ibuprofen-MPCs 5 and 9.

All compounds have been identified by NMR, MS, UV, and IR spectroscopies.

Compounds 4 and 8 and the MPCs 5 and 9 have been investigated by using the method of 1H NMR spectroscopy.

The broadening of the signals from 0.8 to 2.0 ppm in 1H NMR spectrum of MPCs 5 and 9 confirmed the success of the conjugation of thiol-containing derivatives with nanogold cluster.