title: Preparation, characterization and in vitro biological evaluation of (1:2) phenoxodiol-β-cyclodextrin complex.
abstract: Phenoxodiol is an isoflavone analogue that possesses potent anticancer properties. However, the poor water solubility of phenoxodiol limits its overall efficacy as an anticancer agent. To overcome this, β-cyclodextrin was used to encapsulate phenoxodiol. The phenoxodiol-β-cyclodextrin complex was prepared via a modified co-evaporation method and characterized by1H NMR and X-ray crystallography, revealing a 1:2 stoichiometry. The 2D ROESY NMR spectroscopy suggested the limited motion of phenoxodiol within the cavity of β-cyclodextrin while the X-ray crystal data displays by far the best 'ship-in-a-bottle' case of 1:2 inclusion complex. The aqueous solubility of the phenoxodiol in β-cyclodextrin had improved and the in vitro biological evaluation revealed enhanced anti-proliferative activity against three cancer cell lines. Additionally, the toxicity of the complex against normal human cell line was 2.5 times lower. These data indicates that the encapsulation of phenoxodiol into β-cyclodextrin leads to an improvement in its overall water solubility and biological activity.
authors.affiliation: School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.
authors.forename: Eugene M H
authors.initials: EM
authors.lastname: Yee
authors.affiliation: School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.
authors.forename: James M
authors.initials: JM
authors.lastname: Hook
authors.affiliation: Mark Wainwright Analytical Centre, The University of New South Wales, UNSW, Sydney, Australia.
authors.forename: Mohan M
authors.initials: MM
authors.lastname: Bhadbhade
authors.affiliation: Children's Cancer Institute Australia, Lowy Cancer Research Centre, The University of New South Wales, Sydney, Australia; ARC Centre of Excellence in Convergent Bio-Nano Science and Technology, Australian Centre for NanoMedicine, The University of New South Wales, NSW, Sydney, Australia.
authors.forename: Orazio
authors.initials: O
authors.lastname: Vittorio
authors.affiliation: Mark Wainwright Analytical Centre, The University of New South Wales, UNSW, Sydney, Australia.
authors.forename: Rhiannon P
authors.initials: RP
authors.lastname: Kuchel
authors.affiliation: Children's Cancer Institute Australia, Lowy Cancer Research Centre, The University of New South Wales, Sydney, Australia; ARC Centre of Excellence in Convergent Bio-Nano Science and Technology, Australian Centre for NanoMedicine, The University of New South Wales, NSW, Sydney, Australia.
authors.forename: Miriam B
authors.initials: MB
authors.lastname: Brandl
authors.affiliation: School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia; Mark Wainwright Analytical Centre, The University of New South Wales, UNSW, Sydney, Australia.
authors.forename: Richard D
authors.initials: RD
authors.lastname: Tilley
authors.affiliation: School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.
authors.forename: David StC
authors.initials: DS
authors.lastname: Black
authors.affiliation: School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia. Electronic address: n.kumar@unsw.edu.au.
authors.forename: Naresh
authors.initials: N
authors.lastname: Kumar
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry; D045744:Cell Line, Tumor; D006801:Humans; D007529:Isoflavones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D012995:Solubility; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D007529:Isoflavones; D047392:beta-Cyclodextrins; C471183:phenoxodiol
keywords: Anti-cancer; Cyclodextrin complex; Isoflavene; Phenoxodiol; X-ray crystal structure