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Exploiting double exchange Diels-Alder cycloadditions for immobilization of peptide nucleic acids on gold nanoparticles

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Abstract
The generation of PNA-decorated gold nanoparticles (AuNPs) has revealed to be more difficult as compared to the generation of DNA-functionalized ones. The less polar nature of this artificial nucleic acid system and the associated tendency of the neutral poly-amidic backbone to aspecifically adsorb onto the gold surface rather than forming a covalent bond through gold-thiol interaction, combined with the low solubility of PNAs itself, form the main limiting factors in the functionalization of AuNP. Here, we provide a convenient methodology that allows to easily conjugate PNAs to AuNP. Positively charged PNAs containing a masked furan moiety were immobilized via a double exchange Diels-Alder cycloaddition onto masked maleimide-functionalized AuNPs in a one-pot fashion. Conjugated PNA strands retain their ability to selectively hybridize with target DNA strands. Moreover, the duplexes resulting from hybridization can be detached through a retro-Diels-Alder reaction, thus allowing straightforward catch-and-release of specific nucleic acid targets.
Keywords
MOLECULES, PNA, gold nanoparticles, AuNP, gold nanocluster, reversible diels-alder, controlled release, peptide nucleic acids

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MLA
Cadoni, Enrico, et al. “Exploiting Double Exchange Diels-Alder Cycloadditions for Immobilization of Peptide Nucleic Acids on Gold Nanoparticles.” FRONTIERS IN CHEMISTRY, vol. 8, 2020.
APA
Cadoni, E., Rosa-Gastaldo, D., Manicardi, A., Mancin, F., & Madder, A. (2020). Exploiting double exchange Diels-Alder cycloadditions for immobilization of peptide nucleic acids on gold nanoparticles. FRONTIERS IN CHEMISTRY, 8.
Chicago author-date
Cadoni, Enrico, Daniele Rosa-Gastaldo, Alex Manicardi, Fabrizio Mancin, and Annemieke Madder. 2020. “Exploiting Double Exchange Diels-Alder Cycloadditions for Immobilization of Peptide Nucleic Acids on Gold Nanoparticles.” FRONTIERS IN CHEMISTRY 8.
Chicago author-date (all authors)
Cadoni, Enrico, Daniele Rosa-Gastaldo, Alex Manicardi, Fabrizio Mancin, and Annemieke Madder. 2020. “Exploiting Double Exchange Diels-Alder Cycloadditions for Immobilization of Peptide Nucleic Acids on Gold Nanoparticles.” FRONTIERS IN CHEMISTRY 8.
Vancouver
1.
Cadoni E, Rosa-Gastaldo D, Manicardi A, Mancin F, Madder A. Exploiting double exchange Diels-Alder cycloadditions for immobilization of peptide nucleic acids on gold nanoparticles. FRONTIERS IN CHEMISTRY. 2020;8.
IEEE
[1]
E. Cadoni, D. Rosa-Gastaldo, A. Manicardi, F. Mancin, and A. Madder, “Exploiting double exchange Diels-Alder cycloadditions for immobilization of peptide nucleic acids on gold nanoparticles,” FRONTIERS IN CHEMISTRY, vol. 8, 2020.
@article{8658545,
  abstract     = {The generation of PNA-decorated gold nanoparticles (AuNPs) has revealed to be more difficult as compared to the generation of DNA-functionalized ones. The less polar nature of this artificial nucleic acid system and the associated tendency of the neutral poly-amidic backbone to aspecifically adsorb onto the gold surface rather than forming a covalent bond through gold-thiol interaction, combined with the low solubility of PNAs itself, form the main limiting factors in the functionalization of AuNP. Here, we provide a convenient methodology that allows to easily conjugate PNAs to AuNP. Positively charged PNAs containing a masked furan moiety were immobilized via a double exchange Diels-Alder cycloaddition onto masked maleimide-functionalized AuNPs in a one-pot fashion. Conjugated PNA strands retain their ability to selectively hybridize with target DNA strands. Moreover, the duplexes resulting from hybridization can be detached through a retro-Diels-Alder reaction, thus allowing straightforward catch-and-release of specific nucleic acid targets.},
  articleno    = {4},
  author       = {Cadoni, Enrico and Rosa-Gastaldo, Daniele and Manicardi, Alex and Mancin, Fabrizio and Madder, Annemieke},
  issn         = {2296-2646},
  journal      = {FRONTIERS IN CHEMISTRY},
  keywords     = {MOLECULES,PNA,gold nanoparticles,AuNP,gold nanocluster,reversible diels-alder,controlled release,peptide nucleic acids},
  language     = {eng},
  pages        = {7},
  title        = {Exploiting double exchange Diels-Alder cycloadditions for immobilization of peptide nucleic acids on gold nanoparticles},
  url          = {http://dx.doi.org/10.3389/fchem.2020.00004},
  volume       = {8},
  year         = {2020},
}

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