2020
DOI: 10.3390/biom10030480
|View full text |Cite
|
Sign up to set email alerts
|

Fluorogenic and Bioorthogonal Modification of RNA Using Photoclick Chemistry

Abstract: A bromoaryltetrazole-modified uridine was synthesized as a new RNA building block for bioorthogonal, light-activated and postsynthetic modification with commercially available fluorescent dyes. It allows “photoclick”-type modifications by irradiation with light (300 nm LED) at internal and terminal positions of presynthesized RNA with maleimide-conjugated fluorophores in good yields. The reaction was evidenced for three different dyes. During irradiation, the emission increases due to the formation of an intri… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1

Citation Types

0
10
0

Year Published

2021
2021
2022
2022

Publication Types

Select...
6

Relationship

1
5

Authors

Journals

citations
Cited by 10 publications
(10 citation statements)
references
References 27 publications
0
10
0
Order By: Relevance
“…The same methodology has been applied to develop tetrazole-modified RNA oligonucleotides, to perform the photo-induced ligation with maleimide conjugated to different fluorescent dyes, as Cy3 and AlexaFluor555. The reaction worked efficiently, even if the yield of adduct depended on the type of probe used; higher amounts of pyrazoline were detected with Alex-aFluor555 (84%) [74]. Despite further optimizations are still required, the advantages of this approach are evident: (1) nucleobase 15 (Fig.…”
Section: Nucleic Acid Labelingmentioning
confidence: 99%
“…The same methodology has been applied to develop tetrazole-modified RNA oligonucleotides, to perform the photo-induced ligation with maleimide conjugated to different fluorescent dyes, as Cy3 and AlexaFluor555. The reaction worked efficiently, even if the yield of adduct depended on the type of probe used; higher amounts of pyrazoline were detected with Alex-aFluor555 (84%) [74]. Despite further optimizations are still required, the advantages of this approach are evident: (1) nucleobase 15 (Fig.…”
Section: Nucleic Acid Labelingmentioning
confidence: 99%
“…[11] The most interesting property of this cycloaddition reaction is its fluorogenicity, which is the result of the generation of the fluorophore pyrazoline as a product. [12] The latter serves as an in situ monitoring system, ensuring the possibility to detect a specific target upon ligation or cross-linking, with no background fluorescence and no need to remove the unreacted substrate. [13] However, pyrazoline fluorescence is affected by structural features and environmental conditions, including a remarkable solvent effect.…”
Section: Introductionmentioning
confidence: 99%
“…Light‐responsive modifications find numerous applications in oligonucleotide research. [ 7 , 26 , 27 , 28 , 29 ] Recent examples investigated RNA folding dynamics,[ 30 , 31 ] regulation of biological processes[ 7 , 32 , 33 ] or labeling strategies. [ 34 , 35 , 36 ] “Photocages”—such as the photolabile 1‐(2‐nitrophenyl)ethyl (NPE) group—temporarily influence or even block the structural or functional behavior of biomolecules.…”
mentioning
confidence: 99%