Sanguinarine is reduced by NADH through a covalent adduct

J 2018

Sanguinarine is reduced by NADH through a covalent adduct

SÁNDOR, Roman, Jiří SLANINA, Adam MIDLIK, Kristýna ŠEBRLOVÁ, Lucie NOVOTNÁ et. al.

Basic information

Original name

Sanguinarine is reduced by NADH through a covalent adduct

Authors

SÁNDOR, Roman (703 Slovakia, belonging to the institution), Jiří SLANINA (203 Czech Republic, belonging to the institution), Adam MIDLIK (703 Slovakia, belonging to the institution), Kristýna ŠEBRLOVÁ (203 Czech Republic, belonging to the institution), Lucie NOVOTNÁ (203 Czech Republic, belonging to the institution), Martina ČARNECKÁ (703 Slovakia, belonging to the institution), Iva SLANINOVÁ (203 Czech Republic, belonging to the institution), Petr TÁBORSKÝ (203 Czech Republic, belonging to the institution), Eva TÁBORSKÁ (203 Czech Republic, belonging to the institution) and Ondřej PEŠ (203 Czech Republic, guarantor, belonging to the institution)

Edition

Phytochemistry, Oxford, Pergamon-Elsevier Science LTD, 2018, 0031-9422

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10608 Biochemistry and molecular biology

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

Impact factor

Impact factor: 2.905

RIV identification code

RIV/00216224:14110/18:00102093

Organization unit

Faculty of Medicine

DOI

http://dx.doi.org/10.1016/j.phytochem.2017.10.010

UT WoS

000423245300009

Keywords in English

Benzophenanthridine alkaloids; Ene adduct; Hydride transfer; LC-MS; NADH; NADH depletion; Redox cycling; Sanguinarine

Abstract

V originále

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.

Links

MUNI/A/0810/2016, interní kód MU

Name: Molekulární a buněčná biologie

Investor: Masaryk University, Category A

MUNI/A/1205/2016, interní kód MU

Name: Příspěvek biochemických metodik ke studiu molekulární podstaty vybraných patologických stavů a onemocnění (Acronym: mopopas)

Investor: Masaryk University, Category A

MUNI/A/1237/2016, interní kód MU

Name: Vývoj metod a instrumentace pro analýzu biologicky významných látek 2017

Investor: Masaryk University, Category A

Citovat

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. 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.

@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.

Detailed Information on Publication Record