title: Reversing the Cytotoxicity of Bile Acids by Supramolecular Encapsulation.
abstract: Supramolecular encapsulation has been developed into a powerful tool in clearance of toxic substances and hazardous waste from living body and external environments. Herein we tested the special efficacy of tyramine-modified β-cyclodextrin (1) in inhibiting and reversing of the inherent cytotoxicity of deoxycholic acid (DCA). The decarboxylation from tyrosine to tyramine in 1 is crucial to the mutual electrostatic communication, ultimately leading to great enhancement in binding affinity and molecular selectivity toward bile acids. As a result, the DCA-mediated cytotoxicity could be largely eliminated by the biocompatible 1. Meanwhile, the excess DCA could be rapidly excreted by 1 via rat urinary clearance, thus facilitating the decrease of DCA concentration in blood. This study presents a proof of principle that the supramolecular encapsulation with functional cyclodextrin derivatives can efficiently modulate the cell progression and remove the cytotoxic DCA, which provides a practical approach to prevent or treat bile acid-involved diseases.
authors.affiliation: Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, P. R. China.
authors.forename: Ying-Ming
authors.initials: YM
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, P. R. China.
authors.forename: Xun
authors.initials: X
authors.lastname: Xu
authors.affiliation: Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, P. R. China.
authors.forename: Qilin
authors.initials: Q
authors.lastname: Yu
authors.affiliation: Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, P. R. China.
authors.forename: Yao-Hua
authors.initials: YH
authors.lastname: Liu
authors.affiliation: Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, P. R. China.
authors.forename: Yu-Hui
authors.initials: YH
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, P. R. China.
authors.forename: Li-Xia
authors.initials: LX
authors.lastname: Chen
authors.affiliation: Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, P. R. China.|Collaborative Innovation Center of Chemical Science and Engineering , Tianjin 300071, P. R. China.
authors.forename: Yu
authors.identifier: 0000-0001-8723-1896
authors.initials: Y
authors.lastname: Liu
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects*; D003840:Deoxycholic Acid / Q000097:blood / Q000737:chemistry / Q000494:pharmacology* / Q000652:urine; D005260:Female; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D051379:Mice; D008807:Mice, Inbred BALB C; D051381:Rats
chemical_list: D003840:Deoxycholic Acid