Inclusion complex of GA-13316 with β-cyclodextrin: preparation, characterization, molecular modeling, and in vitro evaluation

Rui Yang; Jing-Bo Chen; Chuan-Fan Xiao; Zhi-Cheng Liu; Zhan-Yong Gao; Sheng-Jiao Yan; Ji-Hong Zhang; Hong-Bin Zhang; Jun Lin

doi:10.1016/j.carbpol.2014.05.021

Inclusion complex of GA-13316 with β-cyclodextrin: preparation, characterization, molecular modeling, and in vitro evaluation

Carbohydr Polym. 2014 Oct 13:111:655-62. doi: 10.1016/j.carbpol.2014.05.021. Epub 2014 May 23.

Authors

Rui Yang¹, Jing-Bo Chen², Chuan-Fan Xiao², Zhi-Cheng Liu³, Zhan-Yong Gao², Sheng-Jiao Yan², Ji-Hong Zhang⁴, Hong-Bin Zhang⁵, Jun Lin⁶

Affiliations

¹ Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China; Faculty of Science, Kunming University of Science and Technology, Kunming 650093, PR China.
² Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
³ Faculty of Science, Kunming University of Science and Technology, Kunming 650093, PR China.
⁴ Faculty of Science, Kunming University of Science and Technology, Kunming 650093, PR China. Electronic address: zhjihong2000@yahoo.com.cn.
⁵ Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China. Electronic address: zhanghb@ynu.edu.cn.
⁶ Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China. Electronic address: linjun@ynu.edu.cn.

PMID: 25037400
DOI: 10.1016/j.carbpol.2014.05.021

Abstract

The inclusion complex of GA-13316 with β-cyclodextrin (β-CD) is one of a unique series of gibberellin derivatives possessed of potential anticancer activities. The complex with β-CD was characterized by means of UV, XRD, DSC, TG, (1)H, and 2D NMR spectroscopy. In addition, we investigated the main aspects of the interaction between GA-13316 and β-CD using both experimental and molecular modeling approaches. The complex still maintained its anticancer activity, as shown by in vitro cell survival assay on the human colon carcinoma cell line (HCT116) and the human lung cancer cell line (H460). The results showed that the use of β-CD could be obviously improved the water solubility and stability of GA-13316, implying that the inclusion complex could be a promising future therapeutic agent.

Keywords: Anticancer; GA-13316; Inclusion complex; Molecular modeling; β-Cyclodextrin.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / administration & dosage*
Antineoplastic Agents / chemistry*
Antineoplastic Agents / pharmacology
Cell Line, Tumor
Colonic Neoplasms / drug therapy
Gibberellins / administration & dosage*
Gibberellins / chemistry*
Gibberellins / pharmacology
Humans
Lung Neoplasms / drug therapy
Magnetic Resonance Spectroscopy
Molecular Docking Simulation
Solubility
beta-Cyclodextrins / chemistry*

Substances

Antineoplastic Agents
Gibberellins
beta-Cyclodextrins
gibberellic acid
betadex