Customizable and Regioselective One-Pot N-H Functionalization of DNA Nucleobases to Create a Library of Nucleobase Derivatives for Biomedical Applications
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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