Comparison of thermoresponsive Diels-Alder linkers for the release of payloads from magnetic nanoparticles via hysteretic heating

Investigation into the use of thermally reversible Diels-Alder chemistry coupled with magnetic iron oxide nanoparticles has grown over the last decade. This technology has been used for a variety of applications such as thermoresponsive materials, catalytic chemistry, and drug delivery systems. In t...

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Autores principales:	Julien H. Arrizabalaga, Jonathan S. Casey, Jeffrey C. Becca, Lasse Jensen, Daniel J. Hayes
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2021
Materias:	Diels-alder Click chemistry Alternating magnetic field Controlled release Iron oxide Magnetic nanoparticles Physical and theoretical chemistry QD450-801 Chemical technology TP1-1185
Acceso en línea:	https://doaj.org/article/923ff00a5c274d8fa9c8c35a81c6b0d8
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spelling	oai:doaj.org-article:923ff00a5c274d8fa9c8c35a81c6b0d82021-11-26T04:42:19ZComparison of thermoresponsive Diels-Alder linkers for the release of payloads from magnetic nanoparticles via hysteretic heating2666-934X10.1016/j.jciso.2021.100034https://doaj.org/article/923ff00a5c274d8fa9c8c35a81c6b0d82021-12-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S2666934X21000337https://doaj.org/toc/2666-934XInvestigation into the use of thermally reversible Diels-Alder chemistry coupled with magnetic iron oxide nanoparticles has grown over the last decade. This technology has been used for a variety of applications such as thermoresponsive materials, catalytic chemistry, and drug delivery systems. In this study, we evaluate two distinct thermally labile Diels-Alder linkers for the release of payloads from the surface of magnetic iron oxide nanoparticles. Density functional theory (DFT) computational predictions of the Gibbs free energy and enthalpy reaction barriers were performed and revealed a dramatic difference in reverse energy barriers between the two linkers. These thiophene-based cycloadducts were then synthesized, conjugated to the surface of iron oxide nanoparticles, and characterized by NMR and ESI-MS. The results of the modeling were confirmed when the functionalized nanoparticles were subjected to immersion heating and the payload release rates observed were in agreement with the DFT calculations. Similarly, AMF-RF hysteretic heating of the functionalized nanoparticles revealed payload release rates that correlated with the DFT calculations and the data from the heat immersion studies. Together, these results indicate that these distinct thermally labile Diels-Alder linkers can be used to fine-tune the kinetics of payload release from nanoparticles.Julien H. ArrizabalagaJonathan S. CaseyJeffrey C. BeccaLasse JensenDaniel J. HayesElsevierarticleDiels-alderClick chemistryAlternating magnetic fieldControlled releaseIron oxideMagnetic nanoparticlesPhysical and theoretical chemistryQD450-801Chemical technologyTP1-1185ENJCIS Open, Vol 4, Iss , Pp 100034- (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Diels-alder Click chemistry Alternating magnetic field Controlled release Iron oxide Magnetic nanoparticles Physical and theoretical chemistry QD450-801 Chemical technology TP1-1185
spellingShingle	Diels-alder Click chemistry Alternating magnetic field Controlled release Iron oxide Magnetic nanoparticles Physical and theoretical chemistry QD450-801 Chemical technology TP1-1185 Julien H. Arrizabalaga Jonathan S. Casey Jeffrey C. Becca Lasse Jensen Daniel J. Hayes Comparison of thermoresponsive Diels-Alder linkers for the release of payloads from magnetic nanoparticles via hysteretic heating
description	Investigation into the use of thermally reversible Diels-Alder chemistry coupled with magnetic iron oxide nanoparticles has grown over the last decade. This technology has been used for a variety of applications such as thermoresponsive materials, catalytic chemistry, and drug delivery systems. In this study, we evaluate two distinct thermally labile Diels-Alder linkers for the release of payloads from the surface of magnetic iron oxide nanoparticles. Density functional theory (DFT) computational predictions of the Gibbs free energy and enthalpy reaction barriers were performed and revealed a dramatic difference in reverse energy barriers between the two linkers. These thiophene-based cycloadducts were then synthesized, conjugated to the surface of iron oxide nanoparticles, and characterized by NMR and ESI-MS. The results of the modeling were confirmed when the functionalized nanoparticles were subjected to immersion heating and the payload release rates observed were in agreement with the DFT calculations. Similarly, AMF-RF hysteretic heating of the functionalized nanoparticles revealed payload release rates that correlated with the DFT calculations and the data from the heat immersion studies. Together, these results indicate that these distinct thermally labile Diels-Alder linkers can be used to fine-tune the kinetics of payload release from nanoparticles.
format	article
author	Julien H. Arrizabalaga Jonathan S. Casey Jeffrey C. Becca Lasse Jensen Daniel J. Hayes
author_facet	Julien H. Arrizabalaga Jonathan S. Casey Jeffrey C. Becca Lasse Jensen Daniel J. Hayes
author_sort	Julien H. Arrizabalaga
title	Comparison of thermoresponsive Diels-Alder linkers for the release of payloads from magnetic nanoparticles via hysteretic heating
title_short	Comparison of thermoresponsive Diels-Alder linkers for the release of payloads from magnetic nanoparticles via hysteretic heating
title_full	Comparison of thermoresponsive Diels-Alder linkers for the release of payloads from magnetic nanoparticles via hysteretic heating
title_fullStr	Comparison of thermoresponsive Diels-Alder linkers for the release of payloads from magnetic nanoparticles via hysteretic heating
title_full_unstemmed	Comparison of thermoresponsive Diels-Alder linkers for the release of payloads from magnetic nanoparticles via hysteretic heating
title_sort	comparison of thermoresponsive diels-alder linkers for the release of payloads from magnetic nanoparticles via hysteretic heating
publisher	Elsevier
publishDate	2021
url	https://doaj.org/article/923ff00a5c274d8fa9c8c35a81c6b0d8
work_keys_str_mv	AT julienharrizabalaga comparisonofthermoresponsivedielsalderlinkersforthereleaseofpayloadsfrommagneticnanoparticlesviahystereticheating AT jonathanscasey comparisonofthermoresponsivedielsalderlinkersforthereleaseofpayloadsfrommagneticnanoparticlesviahystereticheating AT jeffreycbecca comparisonofthermoresponsivedielsalderlinkersforthereleaseofpayloadsfrommagneticnanoparticlesviahystereticheating AT lassejensen comparisonofthermoresponsivedielsalderlinkersforthereleaseofpayloadsfrommagneticnanoparticlesviahystereticheating AT danieljhayes comparisonofthermoresponsivedielsalderlinkersforthereleaseofpayloadsfrommagneticnanoparticlesviahystereticheating
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Comparison of thermoresponsive Diels-Alder linkers for the release of payloads from magnetic nanoparticles via hysteretic heating

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