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Int. J. Mol. Sci. 2014, 15(11), 20469-20485; doi:10.3390/ijms151120469

Spectroscopic Studies of R(+)-α-Lipoic Acid—Cyclodextrin Complexes

1
Graduate School of Medicine, Kobe University, Kobe 650-0017, Japan
2
College of Science and Engineering, Kanazawa University, Kanazawa 920-1192, Japan
3
Department of Pharmaceutical Engineering, School of Pharmacy, Aichi Gakuin University, Nagoya 464-8650, Japan
4
CycloChem Bio Co., Ltd., Kobe 650-0047, Japan
*
Author to whom correspondence should be addressed.
Received: 8 September 2014 / Revised: 24 October 2014 / Accepted: 29 October 2014 / Published: 7 November 2014
(This article belongs to the Special Issue Bioactive Nanoparticles 2014)
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Abstract

α-Lipoic acid (ALA) has a chiral center at the C6 position, and exists as two enantiomers, R(+)-ALA (RALA) and S(−)-ALA (SALA). RALA is naturally occurring, and is a cofactor for mitochondrial enzymes, therefore playing a major role in energy metabolism. However, RALA cannot be used for pharmaceuticals or nutraceuticals because it readily polymerizes via a 1,2-dithiolane ring-opening when exposed to light or heat. So, it is highly desired to find out the method to stabilize RALA. The purpose of this study is to provide the spectroscopic information of stabilized RALA and SALA through complexation with cyclodextrins (CDs), α-CD, β-CD and γ-CD and to examine the physical characteristics of the resultant complexes in the solid state. The RALA-CD structures were elucidated based on the micro fourier transform infrared (FT-IR) and Raman analyses. The FT-IR results showed that the C=O stretching vibration of RALA appeared at 1717 cm−1 and then shifted on formation of the RALA-CD complexes. The Raman spectra showed that the S–S and C–S stretching vibrations for RALA at 511 cm−1 (S–S), 631 cm−1 (C–S) and 675 cm−1 (C–S) drastically weakened and almost disappeared upon complexation with CDs. Several peaks indicative of O–H vibrations also shifted or changed in intensity. These results indicate that RALA and CDs form host-guest complexes by interacting with one another. View Full-Text
Keywords: cyclodextrin; lipoic acid; microscopic FT-IR; microscopic Raman; raman spectroscopic mapping cyclodextrin; lipoic acid; microscopic FT-IR; microscopic Raman; raman spectroscopic mapping
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. (CC BY 4.0).

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MDPI and ACS Style

Ikuta, N.; Tanaka, A.; Otsubo, A.; Ogawa, N.; Yamamoto, H.; Mizukami, T.; Arai, S.; Okuno, M.; Terao, K.; Matsugo, S. Spectroscopic Studies of R(+)-α-Lipoic Acid—Cyclodextrin Complexes. Int. J. Mol. Sci. 2014, 15, 20469-20485.

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