Inclusion complex of α-lipoic acid and modified cyclodextrins

Maeda, Hideko; Onodera, Tomoko

doi:10.1007/s10847-010-9767-7

Cited by 20 publications

(29 citation statements)

References 18 publications

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“…ZHENG, W. TANG 1 , R. KONG AND X. ZHU 1 * the melting point (58.6°) [8] . Due to its low solubility in water, there are some limitations of LA in the practical application.…”

Section: Inclusion Complex Of α-Lipoic Acid Containing Alkalizer For mentioning

confidence: 99%

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Inclusion Complex of alpha-Lipoic Acid Containing Alkalizer for Improving the Solubility and Stability Prepared by Co-grinding

Zheng¹,

Tang²,

Kong³

et al. 2017

pharmaceutical-sciences

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Zheng, et al.: Inclusion Complex of α-Lipoic Acid Containing AlkalizerThe inclusion complex was prepared by co-grinding α-lipoic acid with hydroxypropyl-β-cyclodextrin and alkalizer to enhance the solubility and stability of α-lipoic acid. Lipoic acid was chosen as a model drug because of its poor and pH-dependent aqueous solubility. Sodium carbonate and sodium bicarbonate were chosen as the pH regulators. Furthermore, the study investigated the proportion of alkalizer, hydroxypropyl-β-cyclodextrin and α-lipoic acid. Although the micronization has little effect on the solubility of the drug, the formation of amorphous form has an important effect of inclusion complexes. X-ray powder diffractometry and differential scanning calorimetry were used to assess the phase change of the drugs. The in vitro dissolution test indicates that the alkalizer plays a positive factor for the drug dissolution rate enhancement. The intermolecular interactions in the inclusion complexes were investigated using Fourier transform infrared spectroscopy. It was found that the drug frequency of the C=O band decreased or disappeared when the alkalizer was added. Thermal stability experiments showed that the inclusion complex have better stability after adding alkalizer. The solubility of α-lipoic acid can be increased 40 times when the ratio of α-lipoic acid and sodium carbonate is 1:1.2 in the ternary inclusion complex. It was evident that the inclusion compounds with alkalizer can improved the solubility and stability of α-lipoic acid significantly.

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“…ZHENG, W. TANG 1 , R. KONG AND X. ZHU 1 * the melting point (58.6°) [8] . Due to its low solubility in water, there are some limitations of LA in the practical application.…”

Section: Inclusion Complex Of α-Lipoic Acid Containing Alkalizer For mentioning

confidence: 99%

“…Due to its low solubility in water, there are some limitations of LA in the practical application. It is necessary to produce a product, which has higher solubility and stability [7][8][9][10] .…”

Section: Inclusion Complex Of α-Lipoic Acid Containing Alkalizer For mentioning

confidence: 99%

Inclusion Complex of alpha-Lipoic Acid Containing Alkalizer for Improving the Solubility and Stability Prepared by Co-grinding

Zheng¹,

Tang²,

Kong³

et al. 2017

pharmaceutical-sciences

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“…The formation of inclusion complex between SBE-β-CD and small molecule drug is of great interest in different science fields. Due to relative nonpolarity of the internal cavity, SBE-β-CD as a host can accommodate hydrophobic molecules of various sizes as guests, such as 2-(2-nitrovinyl) furan (G-0), 7 repaglinide, 8 α-lipoic acid, 9 voriconazole, 10 rutin, 11 chenodeoxycholate, 12 and flavonoids. 13 However, the inclusion behavior of SBE-β-CD with perphenazine (PPH) has not been described so far.…”

Section: Introductionmentioning

confidence: 99%

Study on the Inclusion Behavior of Sulfobutylether-β-Cyclodextrin with Perphenazine by Flow Injection Chemiluminescence

Shen¹,

Lv²,

Song³

2013

Bulletin of the Korean Chemical Society

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The inclusion behavior of sulfobutylether-β-cyclodextrin (SBE-β-CD) with perphenazine (PPH) was first studied by flow injection (FI)-chemiluminescence (CL) analysis with proposed lg[(I 0 -I s )/I s ] = lgK P-CD + nlg[C PPH ] model and molecular docking. Results showed that a 1:1 complex of SBE-β-CD/PPH could online form, with the formation constant K P-CD of 2.57 × 10 7 L mol −1 at 298 K. The thermodynamic parameters showed that the inclusion behavior of SBE-β-CD/PPH was a spontaneous process by hydrophobic interaction. The molecular docking results revealed PPH entered into the larger cavity of SBE-β-CD with two hydrogen bonds. Based on the linear relationship of the decrement of luminol/SBE-β-CD/PPH CL intensity against the logarithm of PPH concentration ranging from 0.03 to 30.0 ng mL, the present FI-CL analysis using luminol/ SBE-β-CD/PPH system was successfully applied to PPH determination in biological fluids and tablets with recoveries from 94.5 to 105.6% and RSDs less than 2.6% (n = 5).

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“…The effect of -CD on the solubility and stability of LA were recently investigated (Maeda et al, 2010;Takahashi et al, 2011), but no crystal structure of the complex has been determined so far.…”

Section: Introductionmentioning

confidence: 99%

Structure of the inclusion complex of β-cyclodextrin with lipoic acid from laboratory powder diffraction data

Rácz

Borodi

Pop

et al. 2012

Acta Crystallogr B Struct Sci

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The crystal structure of the inclusion complex of β-cyclodextrin with lipoic acid was determined from laboratory powder diffraction data. Thermogravimetric data was used to estimate the number of water molecules in the crystal structure. Lipoic acid is included in β-cyclodextrin through its primary face with the five-membered ring reaching the center plane of the cyclodextrin cavity and its fatty acid chain adopting a bent conformation. Lipoic acid and β-cyclodextrin form a channel-like packing which is stabilized by guest-host hydrogen bonding and close contacts, host-host intermolecular interactions and hydrogen bonding involving the water molecules.

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Inclusion complex of α-lipoic acid and modified cyclodextrins

Cited by 20 publications

References 18 publications

Inclusion Complex of alpha-Lipoic Acid Containing Alkalizer for Improving the Solubility and Stability Prepared by Co-grinding

Inclusion Complex of alpha-Lipoic Acid Containing Alkalizer for Improving the Solubility and Stability Prepared by Co-grinding

Study on the Inclusion Behavior of Sulfobutylether-β-Cyclodextrin with Perphenazine by Flow Injection Chemiluminescence

Structure of the inclusion complex of β-cyclodextrin with lipoic acid from laboratory powder diffraction data

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