Quaternary protoberberine alkaloids and their interactions with
DNA

J 2019

Quaternary protoberberine alkaloids and their interactions with DNA

JAROŠOVÁ, Petra, Roman SÁNDOR, Andrea SLANINKOVÁ, Marek VIDO, Ondřej PEŠ et. al.

Basic information

Original name

Quaternary protoberberine alkaloids and their interactions with DNA

Authors

JAROŠOVÁ, Petra (203 Czech Republic, belonging to the institution), Roman SÁNDOR (703 Slovakia, belonging to the institution), Andrea SLANINKOVÁ (703 Slovakia, belonging to the institution), Marek VIDO (703 Slovakia, belonging to the institution), Ondřej PEŠ (203 Czech Republic, belonging to the institution) and Petr TÁBORSKÝ (203 Czech Republic, guarantor, belonging to the institution)

Edition

Chemical Papers, CHAM, SPRINGER INTERNATIONAL PUBLISHING AG, 2019, 0366-6352

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10406 Analytical chemistry

Country of publisher

Switzerland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 0.963 in 2017

RIV identification code

RIV/00216224:14310/19:00112242

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1007/s11696-019-00857-z

UT WoS

000488930200010

Keywords in English

Protoberberine alkaloids; Non-canonical structures; G-quadruplex; dsDNA; Competitive dialysis; CD; Melting temperatures; Mass spectrometry

Abstract

V originále

The G-quadruplex DNA is commonly present in several protooncogenic-DNA promoters and participates in many important biological processes such as replication, transcription, and translation. Because of their supposed role in cancer, G-quadruplex DNA is often studied as a target for anti-cancer drugs. Quaternary protoberberine and tetrahydroprotoberberine alkaloids (corysamine, coptisine, stylopine), which are supposed to selectively bind these structures, have been compared in terms of stability with selected types of DNA. Influence of selected alkaloids on the stability of double-stranded DNA and non-canonical forms of DNA was observed by determining association constants of alkaloid-DNA complexes using spectroscopic methods-molecular absorption spectrometry, fluorescence spectrometry, and mass spectrometry. Furthermore, the effect of given alkaloids on the melting temperature of these DNA structures was determined using CD spectrometry. Competitive dialysis and electrospray mass spectrometry were performed for affinity comparison of certain alkaloids to different DNA structures including G-quadruplexes. These experiments have proven that corysamine and coptisine prefer interaction with G-quadruplexes in comparison to dsDNA and ssDNA, whereas tetrahydroprotoberberine alkaloid stylopine does not interact with any DNA whatsoever.

Links

ED1.1.00/02.0068, research and development project

Name: CEITEC - central european institute of technology

MUNI/A/0976/2018, interní kód MU

Name: Příspěvek chemických a biochemických metodik ke studiu molekulární podstaty vybraných patologických stavů a onemocnění

Investor: Masaryk University, Category A

MUNI/A/1286/2017, interní kód MU

Name: Vývoj metod a instrumentace pro analýzu biologicky významných látek 2018

Investor: Masaryk University, Category A

Citovat

JAROŠOVÁ, Petra, Roman SÁNDOR, Andrea SLANINKOVÁ, Marek VIDO, Ondřej PEŠ and Petr TÁBORSKÝ. Quaternary protoberberine alkaloids and their interactions with DNA. Chemical Papers. CHAM: SPRINGER INTERNATIONAL PUBLISHING AG, 2019, vol. 73, No 12, p. 2965-2973. ISSN 0366-6352. Available from: https://dx.doi.org/10.1007/s11696-019-00857-z.

@article{1601606,
   author = {Jarošová, Petra and Sándor, Roman and Slaninková, Andrea and Vido, Marek and Peš, Ondřej and Táborský, Petr},
   article_location = {CHAM},
   article_number = {12},
   doi = {http://dx.doi.org/10.1007/s11696-019-00857-z},
   keywords = {Protoberberine alkaloids; Non-canonical structures; G-quadruplex; dsDNA; Competitive dialysis; CD; Melting temperatures; Mass spectrometry},
   language = {eng},
   issn = {0366-6352},
   journal = {Chemical Papers},
   title = {Quaternary protoberberine alkaloids and their interactions with DNA},
   url = {https://link.springer.com/article/10.1007%2Fs11696-019-00857-z},
   volume = {73},
   year = {2019}
}

TY  - JOUR
ID  - 1601606
AU  - Jarošová, Petra - Sándor, Roman - Slaninková, Andrea - Vido, Marek - Peš, Ondřej - Táborský, Petr
PY  - 2019
TI  - Quaternary protoberberine alkaloids and their interactions with DNA
JF  - Chemical Papers
VL  - 73
IS  - 12
SP  - 2965-2973
EP  - 2965-2973
PB  - SPRINGER INTERNATIONAL PUBLISHING AG
SN  - 03666352
KW  - Protoberberine alkaloids
KW  - Non-canonical structures
KW  - G-quadruplex
KW  - dsDNA
KW  - Competitive dialysis
KW  - CD
KW  - Melting temperatures
KW  - Mass spectrometry
UR  - https://link.springer.com/article/10.1007%2Fs11696-019-00857-z
L2  - https://link.springer.com/article/10.1007%2Fs11696-019-00857-z
N2  - The G-quadruplex DNA is commonly present in several protooncogenic-DNA promoters and participates in many important biological processes such as replication, transcription, and translation. Because of their supposed role in cancer, G-quadruplex DNA is often studied as a target for anti-cancer drugs. Quaternary protoberberine and tetrahydroprotoberberine alkaloids (corysamine, coptisine, stylopine), which are supposed to selectively bind these structures, have been compared in terms of stability with selected types of DNA. Influence of selected alkaloids on the stability of double-stranded DNA and non-canonical forms of DNA was observed by determining association constants of alkaloid-DNA complexes using spectroscopic methods-molecular absorption spectrometry, fluorescence spectrometry, and mass spectrometry. Furthermore, the effect of given alkaloids on the melting temperature of these DNA structures was determined using CD spectrometry. Competitive dialysis and electrospray mass spectrometry were performed for affinity comparison of certain alkaloids to different DNA structures including G-quadruplexes. These experiments have proven that corysamine and coptisine prefer interaction with G-quadruplexes in comparison to dsDNA and ssDNA, whereas tetrahydroprotoberberine alkaloid stylopine does not interact with any DNA whatsoever.
ER  -

JAROŠOVÁ, Petra, Roman SÁNDOR, Andrea SLANINKOVÁ, Marek VIDO, Ondřej PEŠ and Petr TÁBORSKÝ. Quaternary protoberberine alkaloids and their interactions with DNA. \textit{Chemical Papers}. CHAM: SPRINGER INTERNATIONAL PUBLISHING AG, 2019, vol.~73, No~12, p.~2965-2973. ISSN~0366-6352. Available from: https://dx.doi.org/10.1007/s11696-019-00857-z.

Detailed Information on Publication Record