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@article{1394832, author = {Sándor, Roman and Slanina, Jiří and Midlik, Adam and Šebrlová, Kristýna and Novotná, Lucie and Čarnecká, Martina and Slaninová, Iva and Táborský, Petr and Táborská, Eva and Peš, Ondřej}, article_location = {Oxford}, article_number = {JAN 2018}, doi = {http://dx.doi.org/10.1016/j.phytochem.2017.10.010}, keywords = {Benzophenanthridine alkaloids; Ene adduct; Hydride transfer; LC-MS; NADH; NADH depletion; Redox cycling; Sanguinarine}, language = {eng}, issn = {0031-9422}, journal = {Phytochemistry}, title = {Sanguinarine is reduced by NADH through a covalent adduct}, volume = {145}, year = {2018} }
TY - JOUR ID - 1394832 AU - Sándor, Roman - Slanina, Jiří - Midlik, Adam - Šebrlová, Kristýna - Novotná, Lucie - Čarnecká, Martina - Slaninová, Iva - Táborský, Petr - Táborská, Eva - Peš, Ondřej PY - 2018 TI - Sanguinarine is reduced by NADH through a covalent adduct JF - Phytochemistry VL - 145 IS - JAN 2018 SP - 77-84 EP - 77-84 PB - Pergamon-Elsevier Science LTD SN - 00319422 KW - Benzophenanthridine alkaloids KW - Ene adduct KW - Hydride transfer KW - LC-MS KW - NADH KW - NADH depletion KW - Redox cycling KW - Sanguinarine N2 - Sanguinarine is a benzo[c]phenanthridine alkaloid with interesting cytotoxic properties, such as induction of oxidative DNA damage and very rapid apoptosis, which is not mediated by p53-dependent signaling. It has been previously documented that sanguinarine is reduced with NADH even in absence of any enzymes while being converted to its dihydro form. We found that the dark blue fluorescent species, observed during sanguinarine reduction with NADH and misinterpreted by Matkar et al. (Arch. Biochem. Biophys. 2008, 477, 43–52) as an anionic form of the alkaloid, is a covalent adduct formed by the interaction of NADH and sanguinarine. The covalent adduct is then converted slowly to the products, dihydrosanguinarine and NAD+, in the second step of reduction. The product of the reduction, dihydrosanguinarine, was continually re-oxidized by the atmospheric oxygen back to sanguinarine, resulting in further reacting with NADH and eventually depleting all NADH molecules. The ability of sanguinarine to diminish the pool of NADH and NADPH is further considered when explaining the sanguinarine-induced apoptosis in living cells. ER -
SÁNDOR, Roman, Jiří SLANINA, Adam MIDLIK, Kristýna ŠEBRLOVÁ, Lucie NOVOTNÁ, Martina ČARNECKÁ, Iva SLANINOVÁ, Petr TÁBORSKÝ, Eva TÁBORSKÁ and Ondřej PEŠ. Sanguinarine is reduced by NADH through a covalent adduct. \textit{Phytochemistry}. Oxford: Pergamon-Elsevier Science LTD, 2018, vol.~145, JAN 2018, p.~77-84. ISSN~0031-9422. Available from: https://dx.doi.org/10.1016/j.phytochem.2017.10.010.
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