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Inclusion complex of GA-13315 with cyclodextrins: Preparation, characterization, inclusion mode and properties

Yang, Rui, Chen, Jing-Bo, Dai, Xiao-Yang, Huang, Rong, Xiao, Chuan-Fan, Gao, Zhan-Yong, Yang, Bo, Yang, Li-Juan, Yan, Sheng-Jiao, Hong-Bin Zhang,, Qing, Chen, Lin, Jun
Carbohydrate polymers 2012 v.89 no.1 pp. 89-97
X-ray diffraction, beta-cyclodextrin, cytotoxicity, doxorubicin, gibberellic acid, nuclear magnetic resonance spectroscopy, scanning electron microscopy, water solubility
GA-13315 (13-chlorine-3,15-dioxy-gibberllic acid methyl ester) was semi-synthesized by GA₃ (gibberellic acid) as a potential anticancer drug. To pursue its promising application, cyclodextrin was used for forming complexes to overcome its drawbacks such as poor water solubility and stability. So, GA-13315/CD complexes were prepared with native β-cyclodextrin and its derivatives (hydroxypropyl-β-cyclodextrin (HPβCD)) and their inclusion complexation behavior, characterization and binding ability in both solution and the solid state was studied by means of UV, XRD, DSC, SEM, ¹H and 2D NMR spectroscopy. Furthermore, preliminary in vitro cytotoxicity assay showed that the complexes still maintain antitumor activities, compared with GA-13315 or adriamycin (ADM, positive control) as the positive control. The results showed that the water solubility and stability of GA-13315 were obviously improved in the inclusion complex with cyclodextrins, suggesting the inclusion complexes as promising future therapeutic agents.