Methods for the synthesis of oligonucleotides containing reactive electrophilic groups

Kachalova, Anna V.; Zubin, E. M.; Oretskaya, T. S.

doi:10.1070/rc2002v071n12abeh000742

Cited by 18 publications

(8 citation statements)

References 46 publications

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“…In general, pH-sensitive conjugates of oligonucleotides containing a hydrazone bond are synthesized through the interaction between fully unprotected aldehyde-containing oligonucleotides and hydrazides of small molecules, antibodies, peptides, proteins, and others (see, e.g., [ 27 , 28 , 29 ]). To that end, oligonucleotides with aldehyde group at various positions of the chain (5′- or 3′-end, heterocyclic base as well as 1′- or 2′-position of ribose) are obtained by several ways: (1) via 1,2-diols followed by oxidation with periodate (see, e.g., [ 30 , 31 , 32 , 33 ]); (2) by synthesizing oligonucleotides with an aldehyde group protected with substituted 1,3-propanediols, which are removed during mild acid treatment (see, e.g., [ 34 , 35 , 36 ]); (3) using oligonucleotides with masked AP-site (see, e.g., [ 37 , 38 , 39 ]); (4) through special aldehyde-succinimide modifiers (see, e.g., [ 40 , 41 , 42 ]).…”

Section: Introductionmentioning

confidence: 99%

A Versatile Solid-Phase Approach to the Synthesis of Oligonucleotide Conjugates with Biodegradable Hydrazone Linker

et al. 2021

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One of the ways to efficiently deliver various drugs, including therapeutic nucleic acids, into the cells is conjugating them with different transport ligands via labile or stable bonds. A convenient solid-phase approach for the synthesis of 5′-conjugates of oligonucleotides with biodegradable pH-sensitive hydrazone covalent bonds is proposed in this article. The approach relies on introducing a hydrazide of the ligand under aqueous/organic media to a fully protected support-bound oligonucleotide containing aldehyde function at the 5′-end. We demonstrated the proof-of-principle of this approach by synthesizing 5′-lipophilic (e.g., cholesterol and α-tocopherol) conjugates of modified siRNA and non-coding RNAs imported into mitochondria (antireplicative RNAs and guide RNAs for Mito-CRISPR/system). The developed method has the potential to be extended for the synthesis of pH-sensitive conjugates of oligonucleotides of different types (ribo-, deoxyribo-, 2′-O-methylribo-, and others) with ligands of different nature.

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Section: Introductionmentioning

confidence: 99%

A Versatile Solid-Phase Approach to the Synthesis of Oligonucleotide Conjugates with Biodegradable Hydrazone Linker

et al. 2021

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“…The ODN conjugation through oxime bond formation is achieved by coupling ODN-aldehyde with aminooxymodified target molecule or vice-versa [84]. The oxime bonds are stable over a pH range but can still be hydrolysed under forcing conditions.…”

Section: Conjugation Via Reductive Amination Hydrazone or Oxime Linkagementioning

confidence: 99%

Chemical Strategies for Oligonucleotide-Conjugates Synthesis

Defrancq

Singh²,

Spinelli

2008

COC

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Oligonucleotide conjugates have found numerous applications in the field of diagnostics and therapeutics. Structurally diverse oligonucleotide conjugates have been prepared and evaluated for various applications. Research efforts have focused on the development of synthetic procedures to accomplish efficient oligonucleotide conjugation with different target molecules. Both on-support and solution-phase coupling procedures have been used to conjugate oligonucleotides. This review gives an account of major synthetic approaches available to prepare covalent oligonucleotide conjugates with diverse target molecules.

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“…Therefore, the use of linkers is the only possible approach to the attachment of electrophilic groups at the C(2 H ) atom of the nucleoside. A recently published review 109 devoted to the preparation of modified oligonucleotides containing electrophilic groups describes the synthesis of nucleosides containing…”

Section: Synthesis Of Nucleosides Containing Electrophilic Groupsmentioning

confidence: 99%

Nucleosides and oligonucleotides containing 2'-reactive groups: synthesis and applications

Zatsepin¹,

Романова²,

Oretskaya³

2004

Russ. Chem. Rev.

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The known methods for the synthesis of 2 The known methods for the synthesis of 2 H -functional--functionalised nucleosides, oligonucleotides and their conjugates are sys-ised nucleosides, oligonucleotides and their conjugates are systematised. The applications of 2 tematised. The applications of 2 H -modified nucleosides and -modified nucleosides and oligonucleotides are discussed. The bibliography includes 451 oligonucleotides are discussed. The bibliography includes 451 references references. .

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Methods for the synthesis of oligonucleotides containing reactive electrophilic groups

Cited by 18 publications

References 46 publications

A Versatile Solid-Phase Approach to the Synthesis of Oligonucleotide Conjugates with Biodegradable Hydrazone Linker

A Versatile Solid-Phase Approach to the Synthesis of Oligonucleotide Conjugates with Biodegradable Hydrazone Linker

Chemical Strategies for Oligonucleotide-Conjugates Synthesis

Nucleosides and oligonucleotides containing 2'-reactive groups: synthesis and applications

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