Fluorescence of sanguinarine: fundamental characteristics and analysis of interconversion between various forms
Language English Country Germany Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- MeSH
- Anti-Infective Agents MeSH
- Benzophenanthridines chemistry metabolism MeSH
- Fluorescence MeSH
- Spectrometry, Fluorescence MeSH
- Hepatocytes metabolism MeSH
- Isoquinolines chemistry metabolism MeSH
- Cardiotonic Agents MeSH
- Cells, Cultured MeSH
- Humans MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Anti-Infective Agents MeSH
- Benzophenanthridines MeSH
- dihydrosanguinarine MeSH Browser
- Isoquinolines MeSH
- Cardiotonic Agents MeSH
- sanguinarine MeSH Browser
The quaternary isoquinoline alkaloid, sanguinarine (SG) plays an important role in both traditional and modern medicine, exhibiting a wide range of biological activities. Under physiological conditions, there is an equilibrium between the quaternary cation (SG+) and a pseudobase (SGOH) forms of SG. In the gastrointestinal tract, SG is converted to dihydrosanguinarine (DHSG). All forms exhibit bright fluorescence. However, their spectra overlap, which limited the use of powerful techniques based on fluorescence spectroscopy/microscopy. Our experiments using a combination of steady-state and time-resolved techniques enabled the separation of individual components. The results revealed that (a) the equilibrium constant between SG+ and SGOH is pKa = 8.06, while fluorescence of DHSG exhibited no changes in the pH range 5-12, (b) the SGOH has excitation/emission spectra with maxima at 327/418 nm and excited-state lifetime 3.2 ns, the spectra of the SG+ have maxima at 475/590 nm and excited-state lifetime 2.4 ns. The DHSG spectra have maxima at 327/446 nm and 2-exponential decay with components 4.2 and 2.0 ns, (c) NADH is able to convert SG to DHSG, while there is no apparent interaction between NADH and DHSG. These techniques are applicable for monitoring the SG to DHSG conversion in hepatocytes.
References provided by Crossref.org
Fluorescence properties of selected benzo[c]phenanthridines
