Synthesis, binding and cellular uptake properties of oligodeoxynucleotides containing cationic bicyclo-thymidine residues

Lietard, Jory; Ittig, Damian; Leumann, Christian J. (2011). Synthesis, binding and cellular uptake properties of oligodeoxynucleotides containing cationic bicyclo-thymidine residues. Bioorganic & medicinal chemistry, 19(19), pp. 5869-5875. Amsterdam: Elsevier 10.1016/j.bmc.2011.08.022

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The synthesis and incorporation into oligodeoxynucleotides of two novel derivatives of bicyclothymidine carrying a cationic diaminopropyl or lysine unit in the C(6′)-β position is described. Compared to unmodified DNA these oligonucleotides show Tm-neutral behavior when paired against complementary DNA and are destabilizing when paired against RNA. Unaided uptake experiments of a decamer containing five lys-bcT units into HeLa and HEK293T cells showed substantial internalization with mostly cytosolic distribution which was not observed in the case of an unmodified control oligonucleotide.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Lietard, Jory; Ittig, Damian and Leumann, Christian

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

0968-0896

Publisher:

Elsevier

Language:

English

Submitter:

Christian Leumann

Date Deposited:

04 Oct 2013 14:26

Last Modified:

10 Aug 2015 11:21

Publisher DOI:

10.1016/j.bmc.2011.08.022

Web of Science ID:

000295426400014

BORIS DOI:

10.7892/boris.9416

URI:

https://boris.unibe.ch/id/eprint/9416 (FactScience: 215149)

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