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Fork- and Comb-like Lipophilic Structures: Different Chemical Approaches to the Synthesis of Oligonucleotides with Multiple Dodecyl Residues Full article

Journal International Journal of Molecular Sciences
, E-ISSN: 1422-0067
Output data Year: 2023, Volume: 24, Number: 19, Article number : 14637, Pages count : DOI: 10.3390/ijms241914637
Tags lipophilic oligonucleotides; phosphoryl guanidine; triazinyl phosphoramidate; conjugates; delivery
Authors Zharkov T.D. 1 , Mironova E.M. 1 , Markov O.V. 1 , Zhukov S. 1 , Khodyreva S.N. 1 , Kupryushkin M.S. 1
Affiliations
1 Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of RAS, Lavrentiev Ave. 8, 630090 Novosibirsk, Russia

Funding (2)

1 МИНИСТЕРСТВО НАУКИ И ВЫСШЕГО ОБРАЗОВАНИЯ РОССИЙСКОЙ ФЕДЕРАЦИИ ПФНИ РФ (2021-2030) 0245-2021-0007
2 Russian Science Foundation РНФ №19-14-00204 (продление)

Abstract: Lipophilic oligonucleotide conjugates represent a powerful tool for nucleic acid cellular delivery, and many methods for their synthesis have been developed over the past few decades. In the present study, a number of chemical approaches for the synthesis of different fork- and comb-like dodecyl-containing oligonucleotide structures were performed, including use of non-nucleotide units and different types of phosphate modifications such as alkyl phosphoramidate, phosphoryl guanidine, and triazinyl phosphoramidate. The influence of the number of introduced lipophilic residues, their mutual arrangement, and the type of formed modification backbone on cell penetration was evaluated. The results obtained indicate great potential in the developed chemical approaches, not only for the synthesis of complex oligonucleotide structures but also for the fine-tuning of their properties
Cite: Zharkov T.D. , Mironova E.M. , Markov O.V. , Zhukov S. , Khodyreva S.N. , Kupryushkin M.S.
Fork- and Comb-like Lipophilic Structures: Different Chemical Approaches to the Synthesis of Oligonucleotides with Multiple Dodecyl Residues
International Journal of Molecular Sciences. 2023. V.24. N19. 14637 . DOI: 10.3390/ijms241914637 WOS Scopus OpenAlex
Dates:
Published print: Sep 27, 2023
Identifiers:
Web of science: WOS:001081466000001
Scopus: 2-s2.0-85174748159
OpenAlex: W4387139031
Citing:
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OpenAlex 5
Scopus 2
Web of science 3
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