Electrochemical behavior of anthraquinone- and
nitrophenyl-labeled deoxynucleoside triphosphates: a
contribution to development of multipotential redox labeling of
DNA

J 2015

Electrochemical behavior of anthraquinone- and nitrophenyl-labeled deoxynucleoside triphosphates: a contribution to development of multipotential redox labeling of DNA

VIDLÁKOVÁ, Pavlína; Hana PIVOŇKOVÁ; Miroslav FOJTA a Luděk HAVRAN

Základní údaje

Originální název

Electrochemical behavior of anthraquinone- and nitrophenyl-labeled deoxynucleoside triphosphates: a contribution to development of multipotential redox labeling of DNA

Autoři

VIDLÁKOVÁ, Pavlína; Hana PIVOŇKOVÁ; Miroslav FOJTA a Luděk HAVRAN

Vydání

Monatshefte fur Chemie, Wien, Springer-Verlag, 2015, 0026-9247

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10600 1.6 Biological sciences

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 1.131

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14740/15:00081382

Organizační jednotka

Středoevropský technologický institut

Klíčová slova anglicky

Nucleoside triphosphate; DNA labeling; DNA electrochemistry; Anthraquinone; Nitro compounds; Cyclic voltammetry

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 5. 4. 2016 10:54, Mgr. Eva Špillingová

Anotace

V originále

Electrochemical properties of base-modified cytosine or 7-deazaadenine nucleoside triphosphates (dNTPs) bearing electrochemically active anthraquinone or 3-nitrophenyl moieties were studied using cyclic voltammetry with the hanging mercury drop electrode. The anthraquinone moiety in the dNTPs gives well-pronounced reversible quinone/hydroquinone redox signals around -0.40 V (against Ag|AgCl|3M KCl reference electrode), while the nitro group in 3-nitrophenyl exhibits irreversible reduction to hydroxylamine around -0.45 V that can be reversibly oxidized to corresponding nitroso compound close to 0.0 V. Both anthraquinone and hydroxylamine redox groups can be selectively switched off by further electrochemical transformation, depending on negative potential applied and composition of the background electrolyte. Results of this study suggest that both nucleobase and the conjugate label moiety influence remarkably the adsorbability and/or intermolecular interactions taking part at the electrode surface. The potential analytical utilization of these phenomena is discussed. [GRAPHICS] .

Návaznosti

GBP206/12/G151, projekt VaV

Název: Centrum nových přístupů k bioanalýze a molekulární diagnostice

Citovat

VIDLÁKOVÁ, Pavlína; Hana PIVOŇKOVÁ; Miroslav FOJTA a Luděk HAVRAN. Electrochemical behavior of anthraquinone- and nitrophenyl-labeled deoxynucleoside triphosphates: a contribution to development of multipotential redox labeling of DNA. Monatshefte fur Chemie. Wien: Springer-Verlag, 2015, roč. 146, č. 5, s. 839-847. ISSN 0026-9247. Dostupné z: https://doi.org/10.1007/s00706-015-1435-6.

@article{1322763,
   author = {Vidláková, Pavlína and Pivoňková, Hana and Fojta, Miroslav and Havran, Luděk},
   article_location = {Wien},
   article_number = {5},
   doi = {https://doi.org/10.1007/s00706-015-1435-6},
   keywords = {Nucleoside triphosphate; DNA labeling; DNA electrochemistry; Anthraquinone; Nitro compounds; Cyclic voltammetry},
   language = {eng},
   issn = {0026-9247},
   journal = {Monatshefte fur Chemie},
   title = {Electrochemical behavior of anthraquinone- and nitrophenyl-labeled deoxynucleoside triphosphates: a contribution to development of multipotential redox labeling of DNA},
   url = {http://download.springer.com/static/pdf/69/art%253A10.1007%252Fs00706-015-1435-6.pdf?originUrl=http%3A%2F%2Flink.springer.com%2Farticle%2F10.1007%2Fs00706-015-1435-6&token2=exp=1451982145~acl=%2Fstatic%2Fpdf%2F69%2Fart%25253A10.1007%25252Fs00706-015-1435},
   volume = {146},
   year = {2015}
}

TY  - JOUR
ID  - 1322763
AU  - Vidláková, Pavlína - Pivoňková, Hana - Fojta, Miroslav - Havran, Luděk
PY  - 2015
TI  - Electrochemical behavior of anthraquinone- and nitrophenyl-labeled deoxynucleoside triphosphates: a contribution to development of multipotential redox labeling of DNA
JF  - Monatshefte fur Chemie
VL  - 146
IS  - 5
SP  - 839-847
EP  - 839-847
PB  - Springer-Verlag
SN  - 00269247
KW  - Nucleoside triphosphate
KW  - DNA labeling
KW  - DNA electrochemistry
KW  - Anthraquinone
KW  - Nitro compounds
KW  - Cyclic voltammetry
UR  - http://download.springer.com/static/pdf/69/art%253A10.1007%252Fs00706-015-1435-6.pdf?originUrl=http%3A%2F%2Flink.springer.com%2Farticle%2F10.1007%2Fs00706-015-1435-6&token2=exp=1451982145~acl=%2Fstatic%2Fpdf%2F69%2Fart%25253A10.1007%25252Fs00706-015-1435
L2  - http://download.springer.com/static/pdf/69/art%253A10.1007%252Fs00706-015-1435-6.pdf?originUrl=http%3A%2F%2Flink.springer.com%2Farticle%2F10.1007%2Fs00706-015-1435-6&token2=exp=1451982145~acl=%2Fstatic%2Fpdf%2F69%2Fart%25253A10.1007%25252Fs00706-015-1435
N2  - Electrochemical properties of base-modified cytosine or 7-deazaadenine nucleoside triphosphates (dNTPs) bearing electrochemically active anthraquinone or 3-nitrophenyl moieties were studied using cyclic voltammetry with the hanging mercury drop electrode. The anthraquinone moiety in the dNTPs gives well-pronounced reversible quinone/hydroquinone redox signals around -0.40 V (against Ag|AgCl|3M KCl reference electrode), while the nitro group in 3-nitrophenyl exhibits irreversible reduction to hydroxylamine around -0.45 V that can be reversibly oxidized to corresponding nitroso compound close to 0.0 V. Both anthraquinone and hydroxylamine redox groups can be selectively switched off by further electrochemical transformation, depending on negative potential applied and composition of the background electrolyte. Results of this study suggest that both nucleobase and the conjugate label moiety influence remarkably the adsorbability and/or intermolecular interactions taking part at the electrode surface. The potential analytical utilization of these phenomena is discussed. [GRAPHICS] .
ER  -

VIDLÁKOVÁ, Pavlína; Hana PIVOŇKOVÁ; Miroslav FOJTA a Luděk HAVRAN. Electrochemical behavior of anthraquinone- and nitrophenyl-labeled deoxynucleoside triphosphates: a contribution to development of multipotential redox labeling of DNA. \textit{Monatshefte fur Chemie}. Wien: Springer-Verlag, 2015, roč.~146, č.~5, s.~839-847. ISSN~0026-9247. Dostupné z: https://doi.org/10.1007/s00706-015-1435-6.

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