Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution

Naoto Kojima; Takekuni Morioka; Daisuke Urabe; Masahiro Yano; Yuki Suga; Naoyoshi Maezaki; Ayako Ohashi-Kobayashi; Yasuyuki Fujimoto; Masatomo Maeda; Takao Yamori; Takehiko Yoshimitsu; Tetsuaki Tanaka

doi:10.1016/j.bmc.2010.10.004

Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution

Naoto Kojima, Takekuni Morioka, Daisuke Urabe, Masahiro Yano, Yuki Suga, Naoyoshi Maezaki, Ayako Ohashi-Kobayashi, Yasuyuki Fujimoto, Masatomo Maeda, Takao Yamori, Takehiko Yoshimitsu, Tetsuaki Tanaka

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

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.

Original language	English
Pages (from-to)	8630-8641
Number of pages	12
Journal	Bioorganic and Medicinal Chemistry
Volume	18
Issue number	24
DOIs	https://doi.org/10.1016/j.bmc.2010.10.004
Publication status	Published - Dec 15 2010
Externally published	Yes

Keywords

Annonaceous acetogenins
Antitumor agents
Cell distribution
Convergent synthesis
Fluorescence-labeled analogues

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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Kojima, N., Morioka, T., Urabe, D., Yano, M., Suga, Y., Maezaki, N., Ohashi-Kobayashi, A., Fujimoto, Y., Maeda, M., Yamori, T., Yoshimitsu, T., & Tanaka, T. (2010). Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution. Bioorganic and Medicinal Chemistry, 18(24), 8630-8641. https://doi.org/10.1016/j.bmc.2010.10.004

Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution. / Kojima, Naoto; Morioka, Takekuni; Urabe, Daisuke; Yano, Masahiro; Suga, Yuki; Maezaki, Naoyoshi; Ohashi-Kobayashi, Ayako; Fujimoto, Yasuyuki; Maeda, Masatomo; Yamori, Takao; Yoshimitsu, Takehiko; Tanaka, Tetsuaki.

In: Bioorganic and Medicinal Chemistry, Vol. 18, No. 24, 15.12.2010, p. 8630-8641.

Research output: Contribution to journal › Article › peer-review

Kojima, N, Morioka, T, Urabe, D, Yano, M, Suga, Y, Maezaki, N, Ohashi-Kobayashi, A, Fujimoto, Y, Maeda, M, Yamori, T, Yoshimitsu, T & Tanaka, T 2010, 'Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution', Bioorganic and Medicinal Chemistry, vol. 18, no. 24, pp. 8630-8641. https://doi.org/10.1016/j.bmc.2010.10.004

Kojima, Naoto ; Morioka, Takekuni ; Urabe, Daisuke ; Yano, Masahiro ; Suga, Yuki ; Maezaki, Naoyoshi ; Ohashi-Kobayashi, Ayako ; Fujimoto, Yasuyuki ; Maeda, Masatomo ; Yamori, Takao ; Yoshimitsu, Takehiko ; Tanaka, Tetsuaki. / Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution. In: Bioorganic and Medicinal Chemistry. 2010 ; Vol. 18, No. 24. pp. 8630-8641.

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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.",

keywords = "Annonaceous acetogenins, Antitumor agents, Cell distribution, Convergent synthesis, Fluorescence-labeled analogues",

author = "Naoto Kojima and Takekuni Morioka and Daisuke Urabe and Masahiro Yano and Yuki Suga and Naoyoshi Maezaki and Ayako Ohashi-Kobayashi and Yasuyuki Fujimoto and Masatomo Maeda and Takao Yamori and Takehiko Yoshimitsu and Tetsuaki Tanaka",

note = "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 {\textquoteleft}Cancer{\textquoteright} 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 {\textquoteleft}Creation of Biologically Functional Molecules{\textquoteright} [No. 18032048] from The Ministry of Education, Culture, Sports, Science and Technology, Japan. ",

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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

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Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution

Abstract

Keywords

ASJC Scopus subject areas

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