CEBA: A new heterobifunctional reagent for plasmid DNA functionalization by click chemistry.
Chloroethyl
Click chemistry
DNA conjugation
DNA labelling
Heterobifunctional crosslinking reagent
p-((2-chloroethyl) ethylamino) benzaldehyde
Journal
International journal of pharmaceutics
ISSN: 1873-3476
Titre abrégé: Int J Pharm
Pays: Netherlands
ID NLM: 7804127
Informations de publication
Date de publication:
15 May 2021
15 May 2021
Historique:
received:
19
12
2020
revised:
24
03
2021
accepted:
29
03
2021
pubmed:
5
4
2021
medline:
22
6
2021
entrez:
4
4
2021
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 33812974
pii: S0378-5173(21)00371-9
doi: 10.1016/j.ijpharm.2021.120566
pii:
doi:
Substances chimiques
Alkynes
0
Azides
0
DNA
9007-49-2
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
120566Informations de copyright
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