title: Novel water-soluble fisetin/cyclodextrins inclusion complexes: Preparation, characterization, molecular docking and bioavailability.
abstract: Novel water-soluble inclusion complexes for fisetin (FIT) were developed by introducing β-cyclodextrin (β-CD) and γ-CD. Properties of the obtained complexes, as well as the interactions between each component, were systematically investigated in both solution and solid states by means of ESI-MS, NMR, FT-IR, XRD, DSC, SEM etc. All characterization information demonstrated that FIT/CDs inclusion complexes were formed, and exhibited different spectroscopic features and properties from FIT. A complex with 1:1 stoichiometry of FIT and CDs was confirmed with Job's method. Meanwhile, as supported by molecular modeling calculations, we suggested that phenyl group (C ring) of FIT molecule was included in the CDs cavity from the wide side. Moreover, the water solubility of FIT/CDs was successfully improved from 2.8 mg/mL (in ethanol aqueous solution) to 4.5 mg/mL (FIT/β-CD complex) and 7.8 mg/mL (FIT/γ-CD complex), and higher thermal stability results were shown by thermal analysis for those complexes. Notably, the inclusion complexes displayed almost two times higher cytotoxicity compared to free FIT against Hela and MCF-7 cells. These results suggested that FIT/CDs complexes could be potentially useful in food industry and healthcare area.
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
authors.forename: Jian-Qiang
authors.initials: JQ
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
authors.forename: Kun-Ming
authors.initials: KM
authors.lastname: Jiang
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
authors.forename: Kun
authors.initials: K
authors.lastname: An
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
authors.forename: Si-Hao
authors.initials: SH
authors.lastname: Ren
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China. Electronic address: xgxie@ynu.edu.cn.
authors.forename: Xiao-Guang
authors.initials: XG
authors.lastname: Xie
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China. Electronic address: jinyi@ynu.edu.cn.
authors.forename: Yi
authors.initials: Y
authors.lastname: Jin
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China; Advanced Analysis and Measurement Center, Yunnan University, Kunming 650091, China. Electronic address: linjun@ynu.edu.cn.
authors.forename: Jun
authors.initials: J
authors.lastname: Lin
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001682:Biological Availability; D049109:Cell Proliferation / Q000187:drug effects; D003505:Cyclodextrins / Q000737:chemistry* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology*; D044948:Flavonols; D006367:HeLa Cells; D006801:Humans; D061986:MCF-7 Cells; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D010316:Particle Size; D012995:Solubility; D013499:Surface Properties; D013696:Temperature; D014867:Water / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D003505:Cyclodextrins; D005419:Flavonoids; D044948:Flavonols; D014867:Water; C017875:fisetin
keywords: Antitumor activity; Cyclodextrins; Fisetin; Inclusion complex; Molecular modeling