Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution
| Autor: | Naoto Kojima, Tetsuaki Tanaka, Takekuni Morioka, Takao Yamori, Naoyoshi Maezaki, Daisuke Urabe, Yuki Suga, Ayako Ohashi-Kobayashi, Masahiro Yano, Masatomo Maeda, Takehiko Yoshimitsu, Yasuyuki Fujimoto |
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| Rok vydání: | 2010 |
| Předmět: |
Acetogenins
Stereochemistry Clinical Biochemistry Convergent synthesis Pharmaceutical Science Alkyne Antineoplastic Agents Biochemistry Chemical synthesis chemistry.chemical_compound Polyketide Cell Line Tumor Drug Discovery Humans Tissue Distribution Molecular Biology Cell Proliferation Fluorescent Dyes chemistry.chemical_classification Organic Chemistry Biological activity Fluorescence Mitochondria chemistry Acetogenin Benzethonium Molecular Medicine Lactone |
| Zdroj: | Bioorganic & Medicinal Chemistry. 18:8630-8641 |
| ISSN: | 0968-0896 |
| DOI: | 10.1016/j.bmc.2010.10.004 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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