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; Petr PAROULEK; Michal RÁJECKÝ ; Veronika RÁJECKÁ ; Eva TÁBORSKÁ; R. ERITJA; A. AVINO; S. MAZZINI; R. GARGALLO and Petr TÁBORSKÝ

Edition

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

Other information

Language

English

Type of outcome

Article in a journal

Field of Study

10403 Physical chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

is not subject to a state or trade secret

References:

URL

Impact factor

Impact factor: 3.567

RIV identification code

RIV/00216224:14310/18:00103741

Organization unit

Faculty of Science

DOI

https://doi.org/10.1039/c8cp02681e

UT WoS

000443280900057

EID Scopus

2-s2.0-85052403911

Keywords in English

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

Abstract

In the original language

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

Cite

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://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 = {https://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://doi.org/10.1039/c8cp02681e.

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