A Click Chemistry Approach to Developing Molecularly Targeted DNA Scissors.
DNA damage
DNA triplexes
chemical nuclease
click chemistry
copper
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
15 Dec 2020
15 Dec 2020
Historique:
received:
13
06
2020
revised:
23
07
2020
pubmed:
25
7
2020
medline:
20
2
2021
entrez:
25
7
2020
Statut:
ppublish
Résumé
Nucleic acid click chemistry was used to prepare a family of chemically modified triplex forming oligonucleotides (TFOs) for application as a new gene-targeted technology. Azide-bearing phenanthrene ligands-designed to promote triplex stability and copper binding-were 'clicked' to alkyne-modified parallel TFOs. Using this approach, a library of TFO hybrids was prepared and shown to effectively target purine-rich genetic elements in vitro. Several of the hybrids provide significant stabilisation toward melting in parallel triplexes (>20 °C) and DNA damage can be triggered upon copper binding in the presence of added reductant. Therefore, the TFO and 'clicked' ligands work synergistically to provide sequence-selectivity to the copper cutting unit which, in turn, confers high stabilisation to the DNA triplex. To extend the boundaries of this hybrid system further, a click chemistry-based di-copper binding ligand was developed to accommodate designer ancillary ligands such as DPQ and DPPZ. When this ligand was inserted into a TFO, a dramatic improvement in targeted oxidative cleavage is afforded.
Identifiants
pubmed: 32706904
doi: 10.1002/chem.202002860
doi:
Substances chimiques
Ligands
0
Oligonucleotides
0
Copper
789U1901C5
DNA
9007-49-2
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
16782-16792Subventions
Organisme : H2020 Marie Skłodowska-Curie Actions
ID : H2020-MSCA-ITN-2014-642023
Organisme : Deutsche Forschungsgemeinschaft
ID : 201269156 (SFB1032)
Organisme : Carlsbergfondet
ID : CF15-0675
Organisme : Science Foundation Ireland
ID : 15/CDA/3648
Pays : Ireland
Organisme : Science Foundation Ireland
ID : 17/RC-PhD/3480
Pays : Ireland
Organisme : Science Foundation Ireland
ID : 18/TIDA/6111
Pays : Ireland
Informations de copyright
© 2020 Wiley-VCH GmbH.
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