Naturally occurring quaternary benzo[c]phenanthridine alkaloids
selectively stabilize G-quadruplexes

J 2018

Naturally occurring quaternary benzo[c]phenanthridine alkaloids selectively stabilize G-quadruplexes

JAROŠOVÁ, Petra, Petr PAROULEK, Michal RÁJECKÝ, Veronika RÁJECKÁ, Eva TÁBORSKÁ et. al.

Basic information

Original name

Naturally occurring quaternary benzo[c]phenanthridine alkaloids selectively stabilize G-quadruplexes

Authors

JAROŠOVÁ, Petra (203 Czech Republic, belonging to the institution), Petr PAROULEK (203 Czech Republic, belonging to the institution), Michal RÁJECKÝ (203 Czech Republic, belonging to the institution), Veronika RÁJECKÁ (203 Czech Republic, belonging to the institution), Eva TÁBORSKÁ (203 Czech Republic, belonging to the institution), R. ERITJA (724 Spain), A. AVINO (724 Spain), S. MAZZINI (380 Italy), R. GARGALLO (724 Spain) and Petr TÁBORSKÝ (203 Czech Republic, guarantor, belonging to the institution)

Edition

Physical Chemistry Chemical Physics, CAMBRIDGE, Royal Society of Chemistry, 2018, 1463-9076

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10403 Physical chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 3.567

RIV identification code

RIV/00216224:14310/18:00103741

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1039/c8cp02681e

UT WoS

000443280900057

Keywords in English

HUMAN TELOMERIC DNA; ANTIPROLIFERATIVE ACTIVITY; PROMOTER REGION; SMALL MOLECULES; DRUG DESIGN; K+ SOLUTION; IN-VIVO; BINDING; BENZOPHENANTHRIDINE; OLIGONUCLEOTIDES

Abstract

V originále

In this work, the interaction of six natural benzo[c]phenanthridine alkaloids (macarpine, sanguilutine, sanguirubine, chelerythrine, sanguinarine and chelirubine) with parallel and antiparallel G-quadruplex DNA structures was studied. HT22 corresponding to the end of human telomeres and the modified promoter oncogene c-kit21 and Pu22 sequences have been used. Spectroscopically-monitored melting experiments and fluorescence titrations, competitive dialysis and nuclear magnetic resonance spectroscopy were used for this purpose. The results showed that these alkaloids stabilized G-quadruplex structures in terms of increments of T-m values (from 15 to 25 degrees C) with high selectivity over duplexes and unfolded DNA. The mode of binding was mainly by stacking on the terminal G-tetrads with stoichiometries of 1:2 (DNA:ligand). The presence of non-specific electrostatic interactions was also observed. Overall, the results pointed to a strong stabilization of G-quadruplex structures by these alkaloids.

Links

LH12176, research and development project

Name: Benzofenanthridinové alkaloidy - studium účinků na celulární a molekulární úrovni (Acronym: KBF)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

JAROŠOVÁ, Petra, Petr PAROULEK, Michal RÁJECKÝ, Veronika RÁJECKÁ, Eva TÁBORSKÁ, R. ERITJA, A. AVINO, S. MAZZINI, R. GARGALLO and Petr TÁBORSKÝ. Naturally occurring quaternary benzo[c]phenanthridine alkaloids selectively stabilize G-quadruplexes. Physical Chemistry Chemical Physics. CAMBRIDGE: Royal Society of Chemistry, 2018, vol. 20, No 33, p. 21772-21782. ISSN 1463-9076. Available from: https://dx.doi.org/10.1039/c8cp02681e.

@article{1439376,
   author = {Jarošová, Petra and Paroulek, Petr and Rájecký, Michal and Rájecká, Veronika and Táborská, Eva and Eritja, R. and Avino, A. and Mazzini, S. and Gargallo, R. and Táborský, Petr},
   article_location = {CAMBRIDGE},
   article_number = {33},
   doi = {http://dx.doi.org/10.1039/c8cp02681e},
   keywords = {HUMAN TELOMERIC DNA; ANTIPROLIFERATIVE ACTIVITY; PROMOTER REGION; SMALL MOLECULES; DRUG DESIGN; K+ SOLUTION; IN-VIVO; BINDING; BENZOPHENANTHRIDINE; OLIGONUCLEOTIDES},
   language = {eng},
   issn = {1463-9076},
   journal = {Physical Chemistry Chemical Physics},
   title = {Naturally occurring quaternary benzo[c]phenanthridine alkaloids selectively stabilize G-quadruplexes},
   url = {http://pubs.rsc.org/en/Content/ArticleLanding/2018/CP/C8CP02681E#!divAbstract},
   volume = {20},
   year = {2018}
}

TY  - JOUR
ID  - 1439376
AU  - Jarošová, Petra - Paroulek, Petr - Rájecký, Michal - Rájecká, Veronika - Táborská, Eva - Eritja, R. - Avino, A. - Mazzini, S. - Gargallo, R. - Táborský, Petr
PY  - 2018
TI  - Naturally occurring quaternary benzo[c]phenanthridine alkaloids selectively stabilize G-quadruplexes
JF  - Physical Chemistry Chemical Physics
VL  - 20
IS  - 33
SP  - 21772-21782
EP  - 21772-21782
PB  - Royal Society of Chemistry
SN  - 14639076
KW  - HUMAN TELOMERIC DNA
KW  - ANTIPROLIFERATIVE ACTIVITY
KW  - PROMOTER REGION
KW  - SMALL MOLECULES
KW  - DRUG DESIGN
KW  - K+ SOLUTION
KW  - IN-VIVO
KW  - BINDING
KW  - BENZOPHENANTHRIDINE
KW  - OLIGONUCLEOTIDES
UR  - http://pubs.rsc.org/en/Content/ArticleLanding/2018/CP/C8CP02681E#!divAbstract
N2  - In this work, the interaction of six natural benzo[c]phenanthridine alkaloids (macarpine, sanguilutine, sanguirubine, chelerythrine, sanguinarine and chelirubine) with parallel and antiparallel G-quadruplex DNA structures was studied. HT22 corresponding to the end of human telomeres and the modified promoter oncogene c-kit21 and Pu22 sequences have been used. Spectroscopically-monitored melting experiments and fluorescence titrations, competitive dialysis and nuclear magnetic resonance spectroscopy were used for this purpose. The results showed that these alkaloids stabilized G-quadruplex structures in terms of increments of T-m values (from 15 to 25 degrees C) with high selectivity over duplexes and unfolded DNA. The mode of binding was mainly by stacking on the terminal G-tetrads with stoichiometries of 1:2 (DNA:ligand). The presence of non-specific electrostatic interactions was also observed. Overall, the results pointed to a strong stabilization of G-quadruplex structures by these alkaloids.
ER  -

JAROŠOVÁ, Petra, Petr PAROULEK, Michal RÁJECKÝ, Veronika RÁJECKÁ, Eva TÁBORSKÁ, R. ERITJA, A. AVINO, S. MAZZINI, R. GARGALLO and Petr TÁBORSKÝ. Naturally occurring quaternary benzo[c]phenanthridine alkaloids selectively stabilize G-quadruplexes. \textit{Physical Chemistry Chemical Physics}. CAMBRIDGE: Royal Society of Chemistry, 2018, vol.~20, No~33, p.~21772-21782. ISSN~1463-9076. Available from: https://dx.doi.org/10.1039/c8cp02681e.

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