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 | |
| Publication status | Published - Dec 15 2010 |
| Externally published | Yes |
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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
Cite this
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
}
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
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
UR - http://www.scopus.com/inward/record.url?scp=78649450946&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=78649450946&partnerID=8YFLogxK
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 -