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Molecules 2016, 21(11), 1444; doi:10.3390/molecules21111444

Evidence of the Disassembly of α-Cyclodextrin-octylamine Inclusion Compounds Conjugated to Gold Nanoparticles via Thermal and Photothermal Effects

1
Department of Chemistry, Universidad of Chile, Las Palmeras 3425, Santiago 7800003, Chile
2
Department of Chemistry of Materials, Universidad de Santiago de Chile, Av. Libertador Bernardo O’Higgins 3363, Santiago 9170022, Chile
3
Department of Biology, CEM, Universidad of Chile, Las Palmeras 3425, Santiago 7800003, Chile
4
Department of Physics, Universidad de Chile, Beauchef 850, Santiago 8370448, Chile
5
Department of Pharmacological and Toxicological Chemistry, Universidad of Chile, Sergio Livingston 1007, Santiago 8380492, Chile
*
Authors to whom correspondence should be addressed.
Academic Editor: Bernard Martel
Received: 14 September 2016 / Revised: 14 October 2016 / Accepted: 19 October 2016 / Published: 29 October 2016
(This article belongs to the Special Issue Cyclodextrin Chemistry)
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Abstract

Cyclodextrin (CD) molecules form inclusion compounds (ICs), generating dimers that are capable of encapsulating molecules derived from long-chain hydrocarbons. The aim of this study is to evaluate the structural changes experienced by ICs in solution with increasing temperatures. For this, a nuclear magnetic resonance (1H-NMR) titration was performed to determinate the stoichiometric α-cyclodextrin (α-CD):octylamine (OA) 2:1 and binding constant (k = 2.16 M−2) of ICs. Solution samples of α-CD-OA ICs conjugated with gold nanoparticles (AuNPs) were prepared, and 1H-NMR spectra at different temperatures were recorded. Comparatively, 1H-NMR spectra of the sample irradiated with a laser with tunable wavelengths, with plasmons of conjugated AuNPs, were recorded. In this work, we present evidence of the disassembly of ICs conjugated with AuNPs. Thermal studies demonstrated that, at 114 °C, there are reversible rearrangements of the host and guests in the ICs in a solid state. Migration movements of the guest molecules from the CD cavity were monitored via temperature-dependent 1H-NMR, and were verified comparing the chemical shifts of octylamine dissolved in deuterated dimethylsulfoxide (DMSO-d6) with the OA molecule included in α-CD dissolved in the same solvent. It was observed that, at 117 °C, OA exited the α-CD cavity. CD IC dimer disassembly was also observed when the sample was irradiated with green laser light. View Full-Text
Keywords: inclusion compounds; cyclodextrin; octylamine; gold nanoparticles; photothermal effects inclusion compounds; cyclodextrin; octylamine; gold nanoparticles; photothermal effects
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MDPI and ACS Style

Silva, N.; Moris, S.; Díaz, M.; Yutronic, N.; Lang, E.; Chornik, B.; Kogan, M.J.; Jara, P. Evidence of the Disassembly of α-Cyclodextrin-octylamine Inclusion Compounds Conjugated to Gold Nanoparticles via Thermal and Photothermal Effects. Molecules 2016, 21, 1444.

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