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Journal of Nanomaterials
Volume 2013 (2013), Article ID 931815, 8 pages
http://dx.doi.org/10.1155/2013/931815
Research Article

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

1Department of Pharmacy, Chia Nan University of Pharmacy and Science, Tainan 71710, Taiwan
2Drug Discovery and Development Center, Chia Nan University of Pharmacy and Science, Tainan 71710, Taiwan
3Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan

Received 24 December 2012; Revised 31 January 2013; Accepted 14 February 2013

Academic Editor: Zhenhui Kang

Copyright © 2013 Kuan-Han Lee et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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.