Abstract
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/ 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.
Highlights
Gold nanoparticles have been the subject of increasing attention for the past decade, since Brust et al introduced a simple method for the preparation of monodisperse gold nanoparticles stabilized with various thiol-containing ligands [1]
Nuclear magnetic resonance (NMR) resonances of gold nanoparticles are characteristically broadened relative to those of free alkanethiols; factors include broadening of the spin-spin relaxation time (T2, known as transverse relaxation or relaxation in the x-y plane), a distribution in chemical shifts due to differences in GNPs-SR binding sites, and a gradient in
We believe that our findings provide a new pathway for the production of ibuprofen-monolayer protected gold clusters (MPCs) with well-defined size and shape from preformed nanoparticles by a relatively simple heating procedure
Summary
Gold nanoparticles have been the subject of increasing attention for the past decade, since Brust et al introduced a simple method for the preparation of monodisperse gold nanoparticles stabilized with various thiol-containing ligands [1]. As the most stable metallic particles, GNPs are highly attractive because of their distinct surface plasmon resonance (SP) bands which provide easy characterization, incorporating functional ligands to create monolayer protected gold clusters (MPCs) and their biocompatibility [8]. To our knowledge, this is the first attempt in attaching ibuprofen to GNPs to form MPCs. Only a few reports described the loading of ibuprofen into the porous magnetic hollow silica nanosphere (MHSNs) to study their drug loading and control releasing capabilities [9]. We believe that it is an important result in the synthesis of ibuprofen-MPCs as a new category of nano-NSAIDs (Scheme 1)
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