The Aqueous Solubility and Thermal Stability of α-Lipoic Acid Are Enhanced by Cyclodextrin

被引：38
作者：
Takahashi, Hideki [1 ]
Bungo, Yuri [1 ]
Mikuni, Katsuhiko [1 ]
机构：
[1] Ensuiko Sugar Refining Co Ltd, Carbohydrate Res Lab, Kanazawa Ku, Yokohama, Kanagawa 2360004, Japan
来源：
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 2011年 / 75卷 / 04期
关键词：
alpha-lipoic acid; cyclodextrin; complex; solubility; stability; CONTROLLED-TRIAL ALADIN; SYMPTOMATIC DIABETIC POLYNEUROPATHY; THIOCTIC ACID; DIHYDROLIPOIC ACID; BETA-CYCLODEXTRIN; ANTIOXIDANT; COMPLEXES; NEUROPATHY;
D O I：
10.1271/bbb.100596
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
We investigated the effects of various cyclodextrins (CDs) on the aqueous solubility and thermal stability of alpha-lipoic acid, a compound with low water solubility. alpha-CD, beta-CD, and gamma-CD had little effect on the aqueous solubility of alpha-lipoic acid. In contrast, 6-O-alpha-maltosyl-CDs increased it in a concentration-dependent manner, 6-O-alpha-maltosyl-beta-CD enhancing solubility the most. The thermal stability of alpha-lipoic acid in the solid state was improved by the addition of G2-beta-CD (R), a commercial product of 6-O-alpha-maltosyl-/3-CD. The thermal stability of alpha-lipoic acid was also improved by the addition of beta-CD. Analysis by differential scanning calorimetry showed that G243-CD (R), a mixture of maltosyl-beta-CDs, and beta-CD efficiently formed complexes with alpha-lipoic acid. These results suggest that the sizes and shapes of these beta-CD compounds are compatible with complexation with alpha-lipoic acid. Moreover, both the formation of an aqueous complex with G2-beta-CD (R) and an insoluble complex with beta-CD increased the thermal stability of alpha-lipoic acid.
引用
收藏
页码：633 / 637
页数：5
相关论文
共 23 条
  • [1] Carofiglio T, 2002, EUR J ORG CHEM, V2002, P1191
  • [2] Effects of alpha-lipoic acid on microcirculation in patients with peripheral diabetic neuropathy
    Haak, E
    Usadel, KH
    Kusterer, K
    Amini, P
    Frommeyer, R
    Tritschler, HJ
    Haak, T
    [J]. EXPERIMENTAL AND CLINICAL ENDOCRINOLOGY & DIABETES, 2000, 108 (03) : 168 - 174
  • [3] Higuchi T., 1965, Adv. Anal. Chem. Instrum., V4, P117, DOI DOI 10.1016/S0076-6879(82)87029-8
  • [4] HOWARD SC, 1981, J CHROMATOGR, V208, P129
  • [5] Thermodynamic analysis of the binding of a hepatoprotectant drug, thioctic acid, by β-cyclodextrin
    Junquera, E
    Aicart, E
    [J]. JOURNAL OF PHARMACEUTICAL SCIENCES, 1999, 88 (06) : 626 - 631
  • [6] KOIKE M, 1960, J BIOL CHEM, V235, P1931
  • [7] Inclusion complex of α-lipoic acid and modified cyclodextrins
    Maeda, Hideko
    Onodera, Tomoko
    Nakayama, Hirokazu
    [J]. JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2010, 68 (1-2) : 201 - 206
  • [8] Antioxidant and prooxidant activities of α-lipoic acid and dihydrolipoic acid
    Moini, H
    Packer, L
    Saris, NEL
    [J]. TOXICOLOGY AND APPLIED PHARMACOLOGY, 2002, 182 (01) : 84 - 90
  • [9] Sulfur-centered radical formation from the antioxidant dihydrolipoic acid
    Mottley, C
    Mason, RP
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (46) : 42677 - 42683
  • [10] OKADA Y, 1988, CHEM PHARM BULL, V36, P2176
123