Comparison of thermally actuated retro-diels-alder release groups for nanoparticle based nucleic acid delivery

Journal of Colloid and Interface Science
Mohammad Abu-LabanDaniel J Hayes

Abstract

The present study explores alternate pericyclic chemistries for tethering amine-terminal biomolecules onto silver nanoparticles. Employing the versatile tool of the retro-Diels-Alder (rDA) reaction, three thermally-labile cycloadducts are constructed that cleave at variable temperature ranges. While the reaction between furan and maleimide has widely been reported, the current study also evaluates the reverse reaction kinetics between thiophene-maleimide, and pyrrole-maleimide cycloadducts. Density Functional Theorem (DFT) calculations used to model and plan the experiments, predict energy barriers for the thiophene-maleimide reverse reaction to be greatest, and the pyrrole-maleimide barriers the lowest. Based on the computational analyses, it is projected that the cycloreversion rate would occur slowest with the thiophene, followed by furan, and finally pyrrole would yield the promptest release. These thermally-responsive linkers, characterized by Electrospray Ionization Mass Spectrometry, 1H and 13C NMR, are thiol-linked to silver nanoparticles and conjugate single stranded siRNA mimics with 5' fluorescein tag. Second harmonic generation spectroscopy (SHG) and fluorescence spectroscopy are used to measure release and rate of ...Continue Reading

References

Apr 6, 2004·Angewandte Chemie·Koji KumamotoHiyoshizo Kotsuki
Apr 13, 2006·Chemical Reviews·Kenneth B Eisenthal
Jun 3, 2006·Nucleic Acids Research·Ted C ChuMatthew Levy
Jul 17, 2007·Bioconjugate Chemistry·Austin M DerfusSangeeta N Bhatia
Oct 11, 2008·Oligonucleotides·Robyn P HickersonRoger L Kaspar
Jan 15, 2009·Journal of the American Chemical Society·Faith C BomanFranz M Geiger
Aug 7, 2010·The Journal of Physical Chemistry. a·A H Pakiari, Z Jamshidi
Oct 13, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Shuji YamashitaTakuro Niidome
Jun 5, 2012·Nature Nanotechnology·Hyukjin LeeDaniel G Anderson
Jan 1, 2011·Current Protocols in Chemical Biology·Stanislav I PresolskiM G Finn
Feb 19, 2013·The Journal of Physical Chemistry. B·Benjamin DoughtyKenneth B Eisenthal
Apr 30, 2013·Journal of Controlled Release : Official Journal of the Controlled Release Society·Jing LiDavid Oupický
Jul 25, 2013·The Journal of Organic Chemistry·Kate E Horner, Peter B Karadakov
Oct 24, 2013·Nature Materials·Rosemary KanastyDaniel Anderson
Nov 1, 2013·Langmuir : the ACS Journal of Surfaces and Colloids·Grazia Gonella, Hai-Lung Dai
Jun 25, 2014·ACS Nano·Alejandro ManjavacasPeter Nordlander
Jun 26, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Wen GaoYoungnam Cho
Jul 12, 2014·Chemical Research in Toxicology·Darja GramecMarija Sollner Dolenc
Jul 24, 2014·BioMed Research International·M S MohamedSamar S Fathallah
Jan 7, 2015·Nature Nanotechnology·Mark L BrongersmaPeter Nordlander
Aug 28, 2015·Langmuir : the ACS Journal of Surfaces and Colloids·Raju R KumalLouis H Haber
Nov 18, 2015·Chemical Research in Toxicology·Chaitanya K JaladankiPrasad V Bharatam
Nov 29, 2015·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·Manuel Gregoritza, Ferdinand P Brandl
Aug 16, 2016·The Journal of Physical Chemistry Letters·Mohammad Sharifian GhHai-Lung Dai
Oct 13, 2016·Chembiochem : a European Journal of Chemical Biology·Rachel A P ValenzuelaPeter A Beal
Nov 12, 2016·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Samuel M CohenSean V Taylor
Mar 7, 2018·Beilstein Journal of Organic Chemistry·Imane NekkaaFerenc Fülöp

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Citations

Mar 27, 2020·Journal of Colloid and Interface Science·Jonathan S CaseyDaniel J Hayes
May 4, 2021·Chemical Reviews·Ramya KumarTheresa M Reineke
May 25, 2021·International Journal of Pharmaceutics·Adeolu Oluwasanmi, Clare Hoskins
Mar 27, 2020·ACS Applied Materials & Interfaces·Lili YaoKuang Sheng

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