title: Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution.
abstract: The convergent synthesis of fluorescence-labeled solamin, an antitumor Annonaceous acetogenin, was accomplished by two asymmetric alkynylations of 2,5-diformyl tetrahydrofuran with an alkyne tagged with fluorescent groups and another alkyne with an α,β-unsaturated γ-lactone. Assay for the growth inhibitory activity against human cancer cell lines revealed that the probe with the fluorescent groups at the end of the hydrocarbon chain may have the same mode of action as natural acetogenins. The merged fluorescence of dansyl-labeled solamin and MitoTracker Red suggests that Annonaceous acetogenins localize in the mitochondria.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. kojima@phs.osaka-u.ac.jp
authors.forename: Naoto
authors.initials: N
authors.lastname: Kojima
authors.forename: Takekuni
authors.initials: T
authors.lastname: Morioka
authors.forename: Daisuke
authors.initials: D
authors.lastname: Urabe
authors.forename: Masahiro
authors.initials: M
authors.lastname: Yano
authors.forename: Yuki
authors.initials: Y
authors.lastname: Suga
authors.forename: Naoyoshi
authors.initials: N
authors.lastname: Maezaki
authors.forename: Ayako
authors.initials: A
authors.lastname: Ohashi-Kobayashi
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Fujimoto
authors.forename: Masatomo
authors.initials: M
authors.lastname: Maeda
authors.forename: Takao
authors.initials: T
authors.lastname: Yamori
authors.forename: Takehiko
authors.initials: T
authors.lastname: Yoshimitsu
authors.forename: Tetsuaki
authors.initials: T
authors.lastname: Tanaka
mesh_terms: D054378:Acetogenins / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D001558:Benzethonium; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D006801:Humans; D008928:Mitochondria / Q000378:metabolism; D014018:Tissue Distribution
chemical_list: D054378:Acetogenins; D000970:Antineoplastic Agents; D005456:Fluorescent Dyes; D001558:Benzethonium