Synthesis and Antisense Properties of 2′β-F-Arabinouridine Modified Oligonucleotides with 4′-C-OMe Substituent
A novel 2′-F,4′-C-OMe–arabinouridine (araU) was successfully synthesized and introduced into oligonucleotides. The oligonucleotide containing 2′-F,4′-C-OMe–araU exhibited improved nuclease resistance and RNA hybridizing selective ability re...
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| Format: | Article |
| Language: | English |
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MDPI AG
2018-09-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/9/2374 |
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doaj-4708ce6078134fd88abaa9d2e05f5b6e2020-11-24T21:25:02ZengMDPI AGMolecules1420-30492018-09-01239237410.3390/molecules23092374molecules23092374Synthesis and Antisense Properties of 2′β-F-Arabinouridine Modified Oligonucleotides with 4′-C-OMe SubstituentXiao-Yang He0Jing Wang1Dan-Dan Lu2Sheng-Qi Wang3Beijing Institute of Radiation Medicine, Beijing 100850, ChinaSchool of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, ChinaBeijing Institute of Radiation Medicine, Beijing 100850, ChinaBeijing Institute of Radiation Medicine, Beijing 100850, ChinaA novel 2′-F,4′-C-OMe–arabinouridine (araU) was successfully synthesized and introduced into oligonucleotides. The oligonucleotide containing 2′-F,4′-C-OMe–araU exhibited improved nuclease resistance and RNA hybridizing selective ability relative to 2′-F–araU. In particular, when 2′-F,4′-C-OMe–araU inserted into C–H⋯F–C bonding-favorable 5′–uridine–purine–3′ steps, the modified oligonucleotide showed remarkable binding affinity and selectivity to RNA complements. Thus, 2′-F,4′-C-OMe–araU has valuable antisense properties and can be used as novel chemical modification for antisense therapeutic strategy.http://www.mdpi.com/1420-3049/23/9/2374fluorinepseudohydrogen bondarabinonucleotidechemical modification |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Xiao-Yang He Jing Wang Dan-Dan Lu Sheng-Qi Wang |
| spellingShingle |
Xiao-Yang He Jing Wang Dan-Dan Lu Sheng-Qi Wang Synthesis and Antisense Properties of 2′β-F-Arabinouridine Modified Oligonucleotides with 4′-C-OMe Substituent Molecules fluorine pseudohydrogen bond arabinonucleotide chemical modification |
| author_facet |
Xiao-Yang He Jing Wang Dan-Dan Lu Sheng-Qi Wang |
| author_sort |
Xiao-Yang He |
| title |
Synthesis and Antisense Properties of 2′β-F-Arabinouridine Modified Oligonucleotides with 4′-C-OMe Substituent |
| title_short |
Synthesis and Antisense Properties of 2′β-F-Arabinouridine Modified Oligonucleotides with 4′-C-OMe Substituent |
| title_full |
Synthesis and Antisense Properties of 2′β-F-Arabinouridine Modified Oligonucleotides with 4′-C-OMe Substituent |
| title_fullStr |
Synthesis and Antisense Properties of 2′β-F-Arabinouridine Modified Oligonucleotides with 4′-C-OMe Substituent |
| title_full_unstemmed |
Synthesis and Antisense Properties of 2′β-F-Arabinouridine Modified Oligonucleotides with 4′-C-OMe Substituent |
| title_sort |
synthesis and antisense properties of 2′β-f-arabinouridine modified oligonucleotides with 4′-c-ome substituent |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2018-09-01 |
| description |
A novel 2′-F,4′-C-OMe–arabinouridine (araU) was successfully synthesized and introduced into oligonucleotides. The oligonucleotide containing 2′-F,4′-C-OMe–araU exhibited improved nuclease resistance and RNA hybridizing selective ability relative to 2′-F–araU. In particular, when 2′-F,4′-C-OMe–araU inserted into C–H⋯F–C bonding-favorable 5′–uridine–purine–3′ steps, the modified oligonucleotide showed remarkable binding affinity and selectivity to RNA complements. Thus, 2′-F,4′-C-OMe–araU has valuable antisense properties and can be used as novel chemical modification for antisense therapeutic strategy. |
| topic |
fluorine pseudohydrogen bond arabinonucleotide chemical modification |
| url |
http://www.mdpi.com/1420-3049/23/9/2374 |
| work_keys_str_mv |
AT xiaoyanghe synthesisandantisensepropertiesof2bfarabinouridinemodifiedoligonucleotideswith4comesubstituent AT jingwang synthesisandantisensepropertiesof2bfarabinouridinemodifiedoligonucleotideswith4comesubstituent AT dandanlu synthesisandantisensepropertiesof2bfarabinouridinemodifiedoligonucleotideswith4comesubstituent AT shengqiwang synthesisandantisensepropertiesof2bfarabinouridinemodifiedoligonucleotideswith4comesubstituent |
| _version_ |
1725985209611976704 |