Exceptional fluorescence properties of some quaternary benzo[c]phenanthridine alkaloids.

Authors

SLANINOVÁ Iva SLANINA Jiří GREGOROVÁ Jana URBANOVÁ Jana TÁBORSKÝ Petr HAMMEROVÁ Jindřiška TÁBORSKÁ Eva

Year of publication 2009
Type Article in Proceedings
Conference Book of Abstract of Conference of Functional Molecules from Natural Sources
MU Faculty or unit

Faculty of Medicine

Citation
Field Morphological specializations and cytology
Keywords benzo[c]phenanthridine alkaloids; fluorescence; fluorescence spectroscopy; fluorescence microscopy; flow cytometry; DNA probe;
Description Quaternary benzo[c]phenanthridine alkaloids (QBAs) are a small group of isoquinoline alkaloids occurring mainly in families Papaveraceae, Ranunculaceae and Rutaceae. The most common sanguinarine and chelerythrine are known by their significant and variable biological effects. Some plants contain other QBA (sanguilutine, sanguirubine, chelilutine, chelirubine, and macarpine), that are due to their low content and occurrence named as minor QBA. Among the minor QBAs chelirubine (CHR), macarpine (MA) and sanguirubine (SR) have shown very remarkable photoluminescence properties. Additionally, luminescence properties of all these alkaloids, similarly like sanguinarine (SA), are dependent on presence of double-stranded DNA. The most remarkable changes in emission spectra were observed in case of chelirubine, sanguirubine and macarpine [1]. These properties predetermine using some of these alkaloids as specific fluorescent probes applicable for fluorescent microscopy and flow cytometry. All tested alkaloids immediately enter living cells and MA, CHR and SA bound DNA and stain nuclei [2]. MA showed the best DNA staining properties. Fluorescence microscopy of MA stained cells reveals nuclear architecture and clearly defines chromosomes and apoptotic fragments in living cells. Moreover MA can rapidly report the cellular DNA content of living cells at a resolution level adequate for cell cycle analysis. QBAs were excitable by common argon lasers (488 nm) emitting at the range 575 - 755 nm (i.e. fluorescence detectors FL2-5). Spectral characteristics of MA allow simultaneous surface immunophenotyping.
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