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. 2018 May 7:2018:3202719.
doi: 10.1155/2018/3202719. eCollection 2018.

Characterization of α-Glucosidase Inhibitor/Cyclodextrin Complex Prepared by Freeze-Drying

Yutaka Inoue  1 , Sachie Narumi  1 , Akiho Mitsumori  1 , Isamu Murata  1 , Ikuo Kanamoto  1
Affiliations

Characterization of α-Glucosidase Inhibitor/Cyclodextrin Complex Prepared by Freeze-Drying

Yutaka Inoue et al. J Pharm (Cairo). .

Abstract

Miglitol (MT) is an α-glucosidase inhibitor with a postmeal blood glucose level lowering effect that is used to treat type 2 diabetes. In addition, α-cyclodextrin (αCD) has been reported to inhibit increases in postmeal blood glucose. The aim of this study was to prepare a freeze-dried product (FD) composed of MT and αCD or γCD (molar ratio of MT/αCD = 1/1, MT/γCD = 1/1) and to evaluate the physicochemical properties and biological activity of the FD. The PXRD profile of FD exhibited a halo pattern, and characteristic peaks derived from MT, αCD, and γCD were not observed. The TG-DTA results for FD indicated an increased weight loss temperature and the absence of an endothermic peak for MT. The NIR absorption spectrum measurement suggested an intermolecular interaction between MT and αCD or γCD in the FD. 1H-1H NOESY NMR spectroscopy (D2O) revealed an intermolecular interaction in the FD. The results of the α-glucosidase activity inhibition test and the α-amylase activity inhibition test indicated that the FD exhibited the same inhibition rate as MT alone and the effects of MT were not altered by the freeze-drying method.

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Figures

Figure 1
Figure 1
Chemical structures of (a) miglitol, (b) acarbose, (c) αCD, (d) γCD.
Figure 2
Figure 2
PXRD patterns of MT/αCD and MT/γCD systems. (a) MT intact, (b) αCD, (c) γCD, (d) PM (MT/αCD = 1/1), (e) PM (MT/γCD = 1/1), (f) FD (MT/αCD = 1/1), (g) FD (MT/γ CD = 1/1). ■: MT original, ○: αCD original, ▲: γ CD original.
Figure 3
Figure 3
TG curves of MT/αCD and MT/γCD systems. (a) MT, (b) αCD, (c) γCD, (d) PM (MT/αCD = 1/1), (e) PM (MT/γCD = 1/1), (f) FD (MT/αCD = 1/1), (g) FD (MT/γCD = 1/1).
Figure 4
Figure 4
DTA curves of MT/αCD and MT/γCD systems. (a) MT, (b) αCD, (c) γCD, (d) PM (MT/αCD = 1/1), (e) PM (MT/γCD = 1/1), (f) FD (MT/αCD = 1/1), (g) FD (MT/γCD = 1/1).
Figure 5
Figure 5
NIR absorption spectra of MT/αCD systems and second-differentiation NIR absorption spectra of MT/αCD systems ((b) alkyl group, (c) alkyl group, and (d) hydroxy group).
Figure 6
Figure 6
NIR absorption spectra of MT/γCD systems and second-differentiation NIR absorption spectra of MT/γCD systems ((b) alkyl group of MT, (c) hydroxy group of γCD, (d) alkyl group of MT, and (e) hydroxy group of MT).
Figure 7
Figure 7
Proton-NOESY NMR spectra of MT in D2O.
Figure 8
Figure 8
1H-1H -NOESY NMR spectra of MT/αCD system.
Figure 9
Figure 9
1H-1H -NOESY NMR spectra of MT/γCD system.
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