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4′‑C‑Trifluoromethyl Modified Oligodeoxynucleotides: Synthesis, Biochemical Studies, and Cellular Uptake Properties

Abstract

Herein, we report the synthesis of 4′-C-trifluoromethyl (4′-CF3) thymidine (T4′-CF3) and its incorporation into oligodeoxynucleotides (ODNs) through solid-supported DNA synthesis. The 4′-CF3 modification leads to a marginal effect on the deoxyribose conformation and a local helix structure perturbation for ODN/RNA duplexes. This type of modification slightly decreases the thermal stability of ODN/RNA duplexes (-1 °C/modification) and renders improved nuclease resistance. Like the well-known phos-phorothioate (PS) modification, heavy 4′-CF3 modifications enable direct cellular uptake of the modi-fied ODNs without any delivery reagents. This work highlights that 4′-CF3 modified ODNs are promis-ing candidates for antisense-based therapeutics, which will, in turn, inspire us to develop more potent modifications for antisense ODNs and siRNAs.

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Supplementary files

Publication details

The article was received on 03 Apr 2019, accepted on 06 May 2019 and first published on 09 May 2019


Article type: Paper
DOI: 10.1039/C9OB00765B
Org. Biomol. Chem., 2019, Accepted Manuscript

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    4′‑C‑Trifluoromethyl Modified Oligodeoxynucleotides: Synthesis, Biochemical Studies, and Cellular Uptake Properties

    Y. Zhou, C. Zang, H. Wang, J. Li, Z. Cui, Q. Li, F. Guo, Z. Yan, X. Wen, Z. Xi and C. Zhou, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB00765B

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