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  Synthesis, gene silencing, and molecular modeling studies of 4 '-C-aminomethyl-2 '-O-methyl modified small interfering RNAs.

Gore, K. R., Nawale, G. N., Harikrishna, S., Chittoor, V. G., Pandey, S. K., Höbartner, C., et al. (2012). Synthesis, gene silencing, and molecular modeling studies of 4 '-C-aminomethyl-2 '-O-methyl modified small interfering RNAs. Journal of Organic Chemistry, 77(7), 3233-3245. doi:10.1021/jo202666m.

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Datensatz-Permalink: https://hdl.handle.net/11858/00-001M-0000-000F-88AE-D Versions-Permalink: https://hdl.handle.net/11858/00-001M-0000-0027-C686-C
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 Urheber:
Gore, K. R., Autor
Nawale, G. N., Autor
Harikrishna, S., Autor
Chittoor, V. G., Autor
Pandey, S. K., Autor
Höbartner, C.1, Autor           
Patankar, S., Autor
Pradeepkumar, P. I., Autor
Affiliations:
1Research Group of Nucleic Acid Chemistry, MPI for biophysical chemistry, Max Planck Society, ou_578605              

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 Zusammenfassung: The linear syntheses of 4′-C-aminomethyl-2′-O-methyl uridine and cytidine nucleoside phosphoramidites were achieved using glucose as the starting material. The modified RNA building blocks were incorporated into small interfering RNAs (siRNAs) by employing solid phase RNA synthesis. Thermal melting studies showed that the modified siRNA duplexes exhibited slightly lower Tm (1 °C/modification) compared to the unmodified duplex. Molecular dynamics simulations revealed that the 4′-C-aminomethyl-2′-O-methyl modified nucleotides adopt South-type conformation in a siRNA duplex, thereby altering the stacking and hydrogen-bonding interactions. These modified siRNAs were also evaluated for their gene silencing efficiency in HeLa cells using a luciferase-based reporter assay. The results indicate that the modifications are well tolerated in various positions of the passenger strand and at the 3′ end of the guide strand but are less tolerated in the seed region of the guide strand. The modified siRNAs exhibited prolonged stability in human serum compared to unmodified siRNA. This work has implications for the use of 4′-C-aminomethyl-2′-O-methyl modified nucleotides to overcome some of the challenges associated with the therapeutic utilities of siRNAs.

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Sprache(n): eng - English
 Datum: 2012-02-282012-04-06
 Publikationsstatus: Erschienen
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 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: DOI: 10.1021/jo202666m
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Titel: Journal of Organic Chemistry
Genre der Quelle: Zeitschrift
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Seiten: - Band / Heft: 77 (7) Artikelnummer: - Start- / Endseite: 3233 - 3245 Identifikator: -