TY - JOUR
T1 - Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution
AU - Kojima, Naoto
AU - Morioka, Takekuni
AU - Urabe, Daisuke
AU - Yano, Masahiro
AU - Suga, Yuki
AU - Maezaki, Naoyoshi
AU - Ohashi-Kobayashi, Ayako
AU - Fujimoto, Yasuyuki
AU - Maeda, Masatomo
AU - Yamori, Takao
AU - Yoshimitsu, Takehiko
AU - Tanaka, Tetsuaki
N1 - Funding Information:
In vitro antiproliferative activities of fluorescence-labeled solamins and natural solamin against human cancer cell lines were examined by the Screening Committee of New Anticancer Agents supported by a Grant-in-Aid for Scientific Research on Priority Area ‘Cancer’ from The Ministry of Education, Culture, Sports, Science and Technology, Japan. We acknowledge financial support in the form of a Grant-in-Aid for Young Scientists (B) [No. 21790113], a Grant-in-Aid for Scientific Research (B) [No. 22390021], and a Grant-in Aid for Scientific Research on Priority Area ‘Creation of Biologically Functional Molecules’ [No. 18032048] from The Ministry of Education, Culture, Sports, Science and Technology, Japan.
PY - 2010/12/15
Y1 - 2010/12/15
N2 - 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.
AB - 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.
KW - Annonaceous acetogenins
KW - Antitumor agents
KW - Cell distribution
KW - Convergent synthesis
KW - Fluorescence-labeled analogues
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U2 - 10.1016/j.bmc.2010.10.004
DO - 10.1016/j.bmc.2010.10.004
M3 - Article
C2 - 21074443
AN - SCOPUS:78649450946
VL - 18
SP - 8630
EP - 8641
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
SN - 0968-0896
IS - 24
ER -