Benzoquinone and naphthoquinone based redox-active labels for electrochemical detection of modified oligonucleotides on Au electrodes

Benzoquinone and naphthoquinone based redox-active labels for electrochemical detection of modified oligonucleotides on Au electrodes Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039

Output data

Year: 2016, Volume: 57, Number: 3, Pages: 392-395 Pages count : DOI: 10.1016/j.tetlet.2015.12.035

Tags

Quinones; Redox-active labels; Electrochemical reduction; Cyclic voltammetry; Modified oligonucleotides

Authors

Shundrin Leonid A. ^1,2,3 , Irtegova Irina G. ^1,2 , Vasilieva Nadezhda V. ¹ , Khalfina Irina A. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Inst Organ Chem, Academician Lavrentev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Natl Res Univ, Dept Nat Sci, Pirogova Str 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Med Sci, Siberian Branch, Sci Inst Clin & Expt Lymphol, Timakova Str 4, Novosibirsk 630060, Russia

The reaction of 1,4-benzoquinone and 1,4-naphthoquinone with beta-thiopropionic acid yielded 3-[(3,6-dioxocyclohexa-1,4-diene-1-yl)thio]propionic and 3-[(1,4-dioxo-1,4-dihydronaphthalene-2-yl)thio]propionic acids, respectively. These compounds were used to modify oligonucleotides to allow their electrochemical detection on the surface of Au electrodes using cyclic voltammetry. Electrochemical reduction of the corresponding amides, modeling the bonding of the redox-active labels with molecules that are not electrochemically active, was also studied. (C) 2015 Elsevier Ltd. All rights reserved.

Shundrin L.A. , Irtegova I.G. , Vasilieva N.V. , Khalfina I.A.
Benzoquinone and naphthoquinone based redox-active labels for electrochemical detection of modified oligonucleotides on Au electrodes
Tetrahedron Letters. 2016. V.57. N3. P.392-395. DOI: 10.1016/j.tetlet.2015.12.035 WOS Scopus РИНЦ

Published print:

Jan 1, 2016

Web of science	WOS:000369556900039
Scopus	2-s2.0-84953362834
Elibrary	26929366
OpenAlex	W2217904519