CEBA: A new heterobifunctional reagent for plasmid DNA functionalization by click chemistry
| Autor: | Cristine Gonçalves, Chantal Pichon, Patrick Midoux, Haifei Gao, Delphine Maze |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Azides Fluorophore Guanine Pharmaceutical Science Peptide DNA 02 engineering and technology Alkylation 021001 nanoscience & nanotechnology 030226 pharmacology & pharmacy Combinatorial chemistry Cycloaddition 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine chemistry Alkynes Click chemistry Nucleic acid Click Chemistry 0210 nano-technology Plasmids |
| Zdroj: | International Journal of Pharmaceutics. 601:120566 |
| ISSN: | 0378-5173 |
| DOI: | 10.1016/j.ijpharm.2021.120566 |
| Popis: | Here, we report the synthesis of 3,6,9-trioxaundecan-1-{4-[(2-Chloroethyl)Ethylamino)]-Benzylamino},11-Azide (CEBA). CEBA alkylates the N7 of guanine of DNA thanks its chloroethyl group and can be coupled by a strain-promoted azide-alkyne cycloaddition to an alkynylated molecule. The optimization of the alkylation level of pDNA reveals that the expression of the encoded gene is preserved when it is randomly modified with at most 1 CEBA molecule per 150 bp. We show that the azido group of CEBA allows the linkage via click chemistry of CEBA-pDNA with a fluorophore or a peptide containing a dibenzocyclooctyne (DBCO) function. This new heterobifunctional reagent opens new ways to equip pDNA easily with signal molecules including peptides and nucleic acids without side products providing great interest for non-viral gene therapy. |
| Databáze: | OpenAIRE |
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