Vicinal Diol-Tethered Nucleobases as Targets for DNA Redox
Labeling with Osmate Complexes

J 2020

Vicinal Diol-Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes

HAVRANOVA-VIDLAKOVA, P.; M. KROMER; V. SYKOROVA; M. TREFULKA; Miroslav FOJTA et al.

Základní údaje

Originální název

Vicinal Diol-Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes

Autoři

HAVRANOVA-VIDLAKOVA, P.; M. KROMER; V. SYKOROVA; M. TREFULKA; Miroslav FOJTA; L. HAVRAN a M. HOCEK

Vydání

Chembiochem, WEINHEIM, WILEY-VCH, 2020, 1439-4227

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10608 Biochemistry and molecular biology

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.164

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14740/20:00120577

Organizační jednotka

Středoevropský technologický institut

Klíčová slova anglicky

DNA; electrochemistry; nucleotides; osmium; redox labeling

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 5. 5. 2022 15:41, Mgr. Pavla Foltynová, Ph.D.

Anotace

V originále

Six-valent osmium (osmate) complexes with nitrogenous ligands have previously been used for the modification and redox labeling of biomolecules involving vicinal diol moieties (typically, saccharides or RNA). In this work, aliphatic (3,4-dihydroxybutyl and 3,4-dihydroxybut-1-ynyl) or cyclic (6-oxo-6-(cis-3,4-dihydroxypyrrolidin-1-yl)hex-2-yn-1-yl, PDI) vicinal diols are attached to nucleobases to functionalize DNA for subsequent redox labeling with osmium(VI) complexes. The diol-linked 2 '-deoxyribonucleoside triphosphates were used for the polymerase synthesis of diol-linked DNA, which, upon treatment with K2OsO3 and bidentate nitrogen ligands, gave the desired Os-labeled DNA, which were characterized by means of the gel-shift assay and ESI-MS. Through ex situ square-wave voltammetry at a basal plane pyrolytic graphite electrode, the efficiency of modification/labeling of individual diols was evaluated. The results show that the cyclic cis-diol (PDI) was a better target for osmylation than that of the flexible aliphatic ones (alkyl- or alkynyl-linked). The osmate adduct-specific voltammetric signal obtained for Os-VI-treated DNA decorated with PDI showed good proportionality to the number of PDI per DNA molecule. The Os-VI reagents (unlike OsO4) do not attack nucleobases; thus offering specificity of modification on the introduced glycol targets.

Citovat

HAVRANOVA-VIDLAKOVA, P.; M. KROMER; V. SYKOROVA; M. TREFULKA; Miroslav FOJTA; L. HAVRAN a M. HOCEK. Vicinal Diol-Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes. Chembiochem. WEINHEIM: WILEY-VCH, 2020, roč. 21, 1-2, s. 171-180. ISSN 1439-4227. Dostupné z: https://doi.org/10.1002/cbic.201900388.

@article{1621399,
   author = {HavranovaandVidlakova, P. and Kromer, M. and Sykorova, V. and Trefulka, M. and Fojta, Miroslav and Havran, L. and Hocek, M.},
   article_location = {WEINHEIM},
   article_number = {1-2},
   doi = {https://doi.org/10.1002/cbic.201900388},
   keywords = {DNA; electrochemistry; nucleotides; osmium; redox labeling},
   language = {eng},
   issn = {1439-4227},
   journal = {Chembiochem},
   title = {Vicinal Diol-Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes},
   url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cbic.201900388},
   volume = {21},
   year = {2020}
}

TY  - JOUR
ID  - 1621399
AU  - Havranova-Vidlakova, P. - Kromer, M. - Sykorova, V. - Trefulka, M. - Fojta, Miroslav - Havran, L. - Hocek, M.
PY  - 2020
TI  - Vicinal Diol-Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes
JF  - Chembiochem
VL  - 21
IS  - 1-2
SP  - 171-180
EP  - 171-180
PB  - WILEY-VCH
SN  - 14394227
KW  - DNA
KW  - electrochemistry
KW  - nucleotides
KW  - osmium
KW  - redox labeling
UR  - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cbic.201900388
N2  - Six-valent osmium (osmate) complexes with nitrogenous ligands have previously been used for the modification and redox labeling of biomolecules involving vicinal diol moieties (typically, saccharides or RNA). In this work, aliphatic (3,4-dihydroxybutyl and 3,4-dihydroxybut-1-ynyl) or cyclic (6-oxo-6-(cis-3,4-dihydroxypyrrolidin-1-yl)hex-2-yn-1-yl, PDI) vicinal diols are attached to nucleobases to functionalize DNA for subsequent redox labeling with osmium(VI) complexes. The diol-linked 2 '-deoxyribonucleoside triphosphates were used for the polymerase synthesis of diol-linked DNA, which, upon treatment with K2OsO3 and bidentate nitrogen ligands, gave the desired Os-labeled DNA, which were characterized by means of the gel-shift assay and ESI-MS. Through ex situ square-wave voltammetry at a basal plane pyrolytic graphite electrode, the efficiency of modification/labeling of individual diols was evaluated. The results show that the cyclic cis-diol (PDI) was a better target for osmylation than that of the flexible aliphatic ones (alkyl- or alkynyl-linked). The osmate adduct-specific voltammetric signal obtained for Os-VI-treated DNA decorated with PDI showed good proportionality to the number of PDI per DNA molecule. The Os-VI reagents (unlike OsO4) do not attack nucleobases; thus offering specificity of modification on the introduced glycol targets.
ER  -

HAVRANOVA-VIDLAKOVA, P.; M. KROMER; V. SYKOROVA; M. TREFULKA; Miroslav FOJTA; L. HAVRAN a M. HOCEK. Vicinal Diol-Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes. \textit{Chembiochem}. WEINHEIM: WILEY-VCH, 2020, roč.~21, 1-2, s.~171-180. ISSN~1439-4227. Dostupné z: https://doi.org/10.1002/cbic.201900388.

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