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

M. S. Kupryushkin, T. D. Zharkov, E. S. Ilina, O. V. Markov, A. S. Kochetkova, M. M. Akhmetova, A. A. Lomzov, D. V. Pyshnyi, O. I. Lavrik, S. N. Khodyreva

Результат исследования: Научные публикации в периодических изданияхстатьярецензирование

Аннотация

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.

Язык оригиналаанглийский
Страницы (с-по)719-733
Число страниц15
ЖурналRussian Journal of Bioorganic Chemistry
Том47
Номер выпуска3
DOI
СостояниеОпубликовано - мая 2021

Предметные области OECD FOS+WOS

  • 1.06 БИОЛОГИЧЕСКИЕ НАУКИ
  • 1.04 ХИМИЧЕСКИЕ НАУКИ
  • 1.06.CQ БИОХИМИЯ И МОЛЕКУЛЯРНАЯ БИОЛОГИЯ

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