Spectroscopic studies of R(+)-α-lipoic acid--cyclodextrin complexes.
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.
Graduate School of Medicine, Kobe University, Kobe 650-0017, Japan. naoko.ikuta@people.kobe-u.ac.jp.
Naoko
N
Ikuta
College of Science and Engineering, Kanazawa University, Kanazawa 920-1192, Japan. akira.tanaka.621@gmail.com.
Akira
A
Tanaka
College of Science and Engineering, Kanazawa University, Kanazawa 920-1192, Japan. amm21843@gmail.com.
Ayako
A
Otsubo
Department of Pharmaceutical Engineering, School of Pharmacy, Aichi Gakuin University, Nagoya 464-8650, Japan. noriko30@dpc.agu.ac.jp.
Noriko
N
Ogawa
Department of Pharmaceutical Engineering, School of Pharmacy, Aichi Gakuin University, Nagoya 464-8650, Japan. hiromitu@dpc.agu.ac.jp.
Hiromitsu
H
Yamamoto
College of Science and Engineering, Kanazawa University, Kanazawa 920-1192, Japan. peridot@staff.kanazawa-u.ac.jp.
Tomoyuki
T
Mizukami
College of Science and Engineering, Kanazawa University, Kanazawa 920-1192, Japan. ultrasa@staff.kanazawa-u.ac.jp.
Shoji
S
Arai
College of Science and Engineering, Kanazawa University, Kanazawa 920-1192, Japan. mokuno@staff.kanazawa-u.ac.jp.
Masayuki
M
Okuno
Graduate School of Medicine, Kobe University, Kobe 650-0017, Japan. keiji.terao@cyclochem.com.
Keiji
K
Terao
College of Science and Engineering, Kanazawa University, Kanazawa 920-1192, Japan. s-matsugoh@se.kanazawa-u.ac.jp.
Seiichi
S
Matsugo
D003505:Cyclodextrins / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013059:Spectrum Analysis, Raman; D008063:Thioctic Acid / Q000737:chemistry*
D003505:Cyclodextrins; D008063:Thioctic Acid