title: 6-Triazolyl-6-deoxy-β-cyclodextrin derivatives: synthesis, cellular toxicity, and phase-solubility study.
abstract: Heptakis{6-(4-hydroxymethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy}-β-cyclodextrin (HTβCD) and heptakis{6-(4-sulfonylmethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy}-β-cyclodextrin (STβCD) were prepared using copper(I)-catalyzed azide-alkyne cycloaddition between 6-azido-6-deoxy-β-CD and one of two alkynes, propargyl alcohol, and sodium propargyl sulfonate, respectively. The structures of HTβCD and STβCD were characterized by NMR techniques. NMR interpretations and computer modeling suggested that the limited freedom of rotation of the triazole moieties keeps HTβCD and STβCD rigid and compact. Water solubility tests of HTβCD and STβCD showed that the minimum water solubility of HTβCD and STβCD is at least 20times higher than that of β-CD. MTT assay showed that HTβCD and STβCD did not influence the cell viability under 1mM. A phase-solubility study of prednisolone with the CD derivatives showed increased solubility of prednisolone in the presence of increasing concentrations of HTβCD and STβCD.
authors.affiliation: Graduate School of East-West Medical Science, Kyung Hee University, Gyeonggi-do 449-701, Republic of Korea.
authors.forename: Hoa Thi
authors.initials: HT
authors.lastname: Le
authors.affiliation: Graduate School of East-West Medical Science, Kyung Hee University, Gyeonggi-do 449-701, Republic of Korea.
authors.forename: Hyun Mi
authors.initials: HM
authors.lastname: Jeon
authors.affiliation: Department of Chemistry, College of Life Science and Nano-technology, Hannam University, Daejeon 305-811, Republic of Korea. Electronic address: cwlim@khu.kr.
authors.forename: Choon Woo
authors.initials: CW
authors.lastname: Lim
authors.affiliation: Graduate School of East-West Medical Science, Kyung Hee University, Gyeonggi-do 449-701, Republic of Korea. Electronic address: tw1275@khu.ac.kr.
authors.forename: Tae Woo
authors.initials: TW
authors.lastname: Kim
mesh_terms: D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006367:HeLa Cells; D006801:Humans; D008958:Models, Molecular; D008968:Molecular Conformation; D011789:Quantum Theory; D012995:Solubility; D013329:Structure-Activity Relationship; D047392:beta-Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity*
chemical_list: D047392:beta-Cyclodextrins
keywords: 6-Triazolyl-6-deoxy-β-cyclodextrin derivatives; Copper(I)-catalyzed azide–alkyne cycloaddition; Cyclodextrin; Cyclodextrin click cluster; Phase-solubility study