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Triazinylamidophosphate Oligonucleotides: Synthesis and Study of Their Interaction with Cells and DNA-Binding Proteins Full article

Journal Russian Journal of Bioorganic Chemistry
ISSN: 1068-1620
Output data Year: 2021, Volume: 47, Number: 3, Pages: 719-733 Pages count : 15 DOI: 10.1134/S1068162021030110
Tags automated amidophosphite synthesis; Ku-antigen; PARP1; Staudinger’s reaction; triazinylamidophosphate oligonucleotides
Authors Kupryushkin M.S. 1 , Zharkov T.D. 1,2 , Ilina E.S. 1,2 , Markov O.V. 1 , Kochetkova A.S. 1,2 , Akhmetova M.M. 2 , Lomzov A.A. 1 , Pyshnyi D.V. 1 , Lavrik O.I. 1,2 , Khodyreva S.N. 1
Affiliations
1 Institute of Chemical Biology and Fundamental Medicine, Siberian Branch, Russian Academy of Sciences, Novosibirsk, 630090, Russian Federation
2 Novosibirsk National Research State University, Novosibirsk, 630090, Russian Federation

Abstract: Abstract: In this work, representatives of the class of triazinylamidophosphate oligonucleotide derivatives were obtained for the first time. A scheme for the introduction of a modified unit on a solid-phase support during the oxidation step with highly reactive 2-azido-4,6-dichloro[1,3,5]triazine according to the Staudinger reaction was proposed and implemented, followed by the introduction of various aliphatic residues upon treatment with the corresponding amines. A number of model oligonucleotides containing triazinylamidophosphate modification were synthesized. Chemical stability, cellular uptake, and cytotoxicity of the obtained derivatives were studied. The effect of the type of aliphatic substituent in the composition of the oligonucleotides obtained on their resistance to enzymatic hydrolysis in extracts of cultured human cells with different contents of key DNA repair regulatory proteins, Ku-antigen and poly(ADP-ribose) polymerase 1 (PARP1), which are potentially the most effective acceptors of modified oligonucleotides, was studied. © 2021, Pleiades Publishing, Ltd.
Cite: Kupryushkin M.S. , Zharkov T.D. , Ilina E.S. , Markov O.V. , Kochetkova A.S. , Akhmetova M.M. , Lomzov A.A. , Pyshnyi D.V. , Lavrik O.I. , Khodyreva S.N.
Triazinylamidophosphate Oligonucleotides: Synthesis and Study of Their Interaction with Cells and DNA-Binding Proteins
Russian Journal of Bioorganic Chemistry. 2021. V.47. N3. P.719-733. DOI: 10.1134/S1068162021030110 WOS Scopus РИНЦ OpenAlex
Original: Купрюшкин М.С. , Жарков Т.Д. , Ильина Е.С. , Марков О.В. , Кочеткова А.С. , Ахметова М.М. , Ломзов А.А. , Пышный Д.В. , Лаврик О.И. , Ходырева С.Н.
Триазиниламидофосфатные олигонуклеотиды: получение и исследование их взаимодействия с клетками и ДНК-связывающими белками
Биоорганическая химия. 2021. Т.47. №3. С.348-364. DOI: 10.31857/S0132342321030118 РИНЦ OpenAlex
Dates:
Accepted: Oct 28, 2020
Identifiers:
Web of science: WOS:000660549500010
Scopus: 2-s2.0-85107601697
Elibrary: 46807447
OpenAlex: W3166077892
Citing:
DB Citing
Scopus 5
Elibrary 7
Web of science 5
OpenAlex 8
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