In vitro production of reactive oxygen species (ROS) by sampangine

Sampangine is an azaoxoaporphine alkaloid with interesting biological activities. Elucidating the mode of action of sampangine is a topic of continuous research. Recently reported cell-based data have indicated heme-dysfunction and subsequent reactive oxygen species production as being responsible f...

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Bibliographic Details
Published in:Medicinal chemistry research 2017-06, Vol.26 (6), p.1170-1175
Main Authors: Nasiri, Hamid R., Hohmann, Katharina, Hatemler, Melissa G., Plodek, Alois, Bracher, Franz, Schwalbe, Harald
Format: Article
Language:English
Subjects:
Binding
Biochemistry
Biological activity
Biomedical and Life Sciences
Biomedicine
Calf thymus
Cell Biology
Cellular manufacture
Cellular structure
Chemical activity
Chemical reduction
Chemical synthesis
Damage assessment
Damage detection
Deoxyribonucleic acid
DNA
DNA damage
Heme
Natural products
Original Research
Oxygen
Pharmacology/Toxicology
Reactive oxygen species
Sampangine
Spectroscopy
Thymus gland
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Summary:Sampangine is an azaoxoaporphine alkaloid with interesting biological activities. Elucidating the mode of action of sampangine is a topic of continuous research. Recently reported cell-based data have indicated heme-dysfunction and subsequent reactive oxygen species production as being responsible for the biological activity of the natural product. By using an in vitro biochemical assay the ability of sampangine to produce reactive oxygen species was confirmed. The production of reactive oxygen species occurred upon mild chemical reduction of sampangine in absence of any cellular components. In an additional structure-activity-relationship study, utilizing synthesized analogs of sampangine, we identified the 1,4-iminoquinone scaffold as the key motif for the observed reactive oxygen species production. To assess the ability of sampangine to induce DNA damage, the direct binding of sampangine to calf thymus—DNA was measured using UV–Visible spectroscopy. No DNA binding was observed when sampangine was tested against calf thymus -DNA up to a ratio of 1:100. This observation rules out the direct involvement of sampangine in DNA binding and damage.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-017-1835-8