Phenothiazine-linked nucleosides and nucleotides for redox
labelling of DNA

J 2017

Phenothiazine-linked nucleosides and nucleotides for redox labelling of DNA

SIMONOVA, A.; L. HAVRAN; R. POHL; Miroslav FOJTA; M. HOCEK et al.

Základní údaje

Originální název

Phenothiazine-linked nucleosides and nucleotides for redox labelling of DNA

Autoři

SIMONOVA, A.; L. HAVRAN; R. POHL; Miroslav FOJTA a M. HOCEK

Vydání

ORGANIC & BIOMOLECULAR CHEMISTRY, CAMBRIDGE (ENGLAND), ROYAL SOC CHEMISTRY, 2017, 1477-0520

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.423

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14740/17:00095595

Organizační jednotka

Středoevropský technologický institut

Klíčová slova anglicky

ELECTROCHEMICAL DETECTION; PRIMER EXTENSION; 2'-DEOXYRIBONUCLEOSIDE TRIPHOSPHATES; ENZYMATIC INCORPORATION; OLIGODEOXYNUCLEOTIDES; OLIGONUCLEOTIDES; POLYMERASES; DERIVATIVES; 2'-DEOXYADENOSINE; ANTHRAQUINONE

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 22. 3. 2018 14:06, Mgr. Pavla Foltynová, Ph.D.

Anotace

V originále

Nucleosides and 2'-deoxyribonucleoside triphosphates (dNTPs) bearing phenothiazine (PT) attached to a nucleobase (cytosine or 7-deazaadenine) either directly or through an acetylene linker were prepared through Suzuki or Sonogashira cross-coupling and triphosphorylation, and were studied as building blocks for polymerase construction of modified DNA. The directly PT-substituted dNTPs were better substrates for polymerases than the alkyne-linked dNTPs but all of them were used in enzymatic synthesis of DNA using primer extension, nicking enzyme amplification, PCR or 3'-tail labelling by terminal deoxynucleotidyl transferase. The phenothiazine served as an oxidizable redox label (giving two analytically useful signals of oxidation on electrode) for nucleosides and DNA and was also used in orthogonal combination with previously developed benzofurazane or nitrophenyl labels for redox coding of DNA bases. Therefore, the title PT-linked dNTPs are useful additions to the portfolio of nucleotides for enzymatic synthesis of redox-labelled DNA for electrochemical analysis.

Návaznosti

GBP206/12/G151, projekt VaV

Název: Centrum nových přístupů k bioanalýze a molekulární diagnostice

Citovat

SIMONOVA, A.; L. HAVRAN; R. POHL; Miroslav FOJTA a M. HOCEK. Phenothiazine-linked nucleosides and nucleotides for redox labelling of DNA. ORGANIC & BIOMOLECULAR CHEMISTRY. CAMBRIDGE (ENGLAND): ROYAL SOC CHEMISTRY, 2017, roč. 15, č. 33, s. 6984-6996. ISSN 1477-0520. Dostupné z: https://doi.org/10.1039/c7ob01439b.

@article{1412055,
   author = {Simonova, A. and Havran, L. and Pohl, R. and Fojta, Miroslav and Hocek, M.},
   article_location = {CAMBRIDGE (ENGLAND)},
   article_number = {33},
   doi = {https://doi.org/10.1039/c7ob01439b},
   keywords = {ELECTROCHEMICAL DETECTION; PRIMER EXTENSION; 2'-DEOXYRIBONUCLEOSIDE TRIPHOSPHATES; ENZYMATIC INCORPORATION; OLIGODEOXYNUCLEOTIDES; OLIGONUCLEOTIDES; POLYMERASES; DERIVATIVES; 2'-DEOXYADENOSINE; ANTHRAQUINONE},
   language = {eng},
   issn = {1477-0520},
   journal = {ORGANIC & BIOMOLECULAR CHEMISTRY},
   title = {Phenothiazine-linked nucleosides and nucleotides for redox labelling of DNA},
   url = {http://pubs.rsc.org/en/Content/ArticleLanding/2017/OB/C7OB01439B#!divAbstract},
   volume = {15},
   year = {2017}
}

TY  - JOUR
ID  - 1412055
AU  - Simonova, A. - Havran, L. - Pohl, R. - Fojta, Miroslav - Hocek, M.
PY  - 2017
TI  - Phenothiazine-linked nucleosides and nucleotides for redox labelling of DNA
JF  - ORGANIC & BIOMOLECULAR CHEMISTRY
VL  - 15
IS  - 33
SP  - 6984-6996
EP  - 6984-6996
PB  - ROYAL SOC CHEMISTRY
SN  - 14770520
KW  - ELECTROCHEMICAL DETECTION
KW  - PRIMER EXTENSION
KW  - 2'-DEOXYRIBONUCLEOSIDE TRIPHOSPHATES
KW  - ENZYMATIC INCORPORATION
KW  - OLIGODEOXYNUCLEOTIDES
KW  - OLIGONUCLEOTIDES
KW  - POLYMERASES
KW  - DERIVATIVES
KW  - 2'-DEOXYADENOSINE
KW  - ANTHRAQUINONE
UR  - http://pubs.rsc.org/en/Content/ArticleLanding/2017/OB/C7OB01439B#!divAbstract
L2  - http://pubs.rsc.org/en/Content/ArticleLanding/2017/OB/C7OB01439B#!divAbstract
N2  - Nucleosides and 2'-deoxyribonucleoside triphosphates (dNTPs) bearing phenothiazine (PT) attached to a nucleobase (cytosine or 7-deazaadenine) either directly or through an acetylene linker were prepared through Suzuki or Sonogashira cross-coupling and triphosphorylation, and were studied as building blocks for polymerase construction of modified DNA. The directly PT-substituted dNTPs were better substrates for polymerases than the alkyne-linked dNTPs but all of them were used in enzymatic synthesis of DNA using primer extension, nicking enzyme amplification, PCR or 3'-tail labelling by terminal deoxynucleotidyl transferase. The phenothiazine served as an oxidizable redox label (giving two analytically useful signals of oxidation on electrode) for nucleosides and DNA and was also used in orthogonal combination with previously developed benzofurazane or nitrophenyl labels for redox coding of DNA bases. Therefore, the title PT-linked dNTPs are useful additions to the portfolio of nucleotides for enzymatic synthesis of redox-labelled DNA for electrochemical analysis.
ER  -

SIMONOVA, A.; L. HAVRAN; R. POHL; Miroslav FOJTA a M. HOCEK. Phenothiazine-linked nucleosides and nucleotides for redox labelling of DNA. \textit{ORGANIC \&{} BIOMOLECULAR CHEMISTRY}. CAMBRIDGE (ENGLAND): ROYAL SOC CHEMISTRY, 2017, roč.~15, č.~33, s.~6984-6996. ISSN~1477-0520. Dostupné z: https://doi.org/10.1039/c7ob01439b.

Přehled o publikaci