authors |
Rocha, DHA; Machado, CM; Sousa, V; Sousa, CFV; Silva, VLM; Silva, AMS; Borges, J; Mano, JF |
nationality |
International |
journal |
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY |
author keywords |
Biomedicine; Cell culture; Nucleobases; One-pot synthesis; Regioselectivity |
keywords |
MICHAEL ADDITION; NUCLEIC-ACIDS; ADENINE; PYRIMIDINE; THYMINE; URACIL; COMBINATION; ALKYLATION; EFFICIENT; POLYMERS |
abstract |
DNA is one of the most exciting biomolecules in nature for developing supramolecular biofunctional nanoarchitectures owing to the highly specific and selective interactions between complementary Watson-Crick base pairing. Herein, simple and one-pot synthetic procedures have been implemented for producing a library of DNA nucleobase derivatives endowed with reactive functional groups for bioconjugation and cross-linking strategies with other (bio)molecules. Purine and pyrimidine molecules have been regioselectively N-H functionalized either via N-alkylation, N-allylation, N-propargylation or Michael-type reactions and structurally characterized. The influence of the reaction conditions was assessed and discussed. The in vitro biocompatibility of the native and nucleobase derivatives was evaluated by culturing them with human fibroblasts, revealing their cytocompatibility. The library of nucleobase derivatives holds great promise for being coupled to different biomolecules, including biopolymeric materials, lipids, and peptides, thus potentially leading to modular supramolecular nanobiomaterials for biomedicine. |
publisher |
WILEY-V C H VERLAG GMBH |
issn |
1434-193X |
isbn |
1099-0690 |
year published |
2021 |
volume |
2021 |
issue |
31 |
beginning page |
4423 |
ending page |
4433 |
digital object identifier (doi) |
10.1002/ejoc.202100786 |
web of science category |
11 |
subject category |
Chemistry, Organic |
unique article identifier |
WOS:000688733800003
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ciceco authors
impact metrics
journal analysis (jcr 2019):
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journal impact factor |
2.889 |
5 year journal impact factor |
2.53 |
category normalized journal impact factor percentile |
67.544 |
dimensions (citation analysis):
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altmetrics (social interaction):
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