Supramolecular Fluorine Magnetic Resonance Spectroscopy Probe Polymer Based on Passerini Bifunctional Monomer

Benoit Couturaud; Zachary H. Houston; Gary J. Cowin; Ivan Prokeš; Jeffrey C. Foster; Kristofer J. Thurecht; Rachel K. O'Reilly

doi:10.1021/acsmacrolett.9b00626

Supramolecular Fluorine Magnetic Resonance Spectroscopy Probe Polymer Based on Passerini Bifunctional Monomer

Benoit Couturaud, Zachary H. Houston, Gary J. Cowin, Ivan Prokeš, Jeffrey C. Foster, Kristofer J. Thurecht, Rachel K. O'Reilly

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

A water-soluble fluorine magnetic resonance spectroscopy host-guest probe, P(HPA-co-AdamCF₃A), was successfully constructed from the facile synthesis of a bifunctional monomer via a quantitative Passerini reaction. Supramolecular complexation with (2-hydroxypropyl)-β-cyclodextrin promoted a change in the chemical environment, leading to modulation of both the relaxation properties as well as chemical shift of the fluorine moieties. This change was used to probe the supramolecular interaction by ¹⁹F MRI spectroscopy and give insight into fluorine probe formulation. This work provides a fundamental basis for an ¹⁹F MR imaging tracer capable of assessing host-guest inclusion and a potential model to follow the fate of a drug delivery system in vivo.

Original language	English
Pages (from-to)	1479-1483
Number of pages	5
Journal	ACS Macro Letters
Volume	8
Issue number	11
DOIs	https://doi.org/10.1021/acsmacrolett.9b00626
State	Published - Nov 19 2019
Externally published	Yes

Funding

This work was supported by the European Union's Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie grant agreement no. 703934, FluoroDendriNostic project. The authors acknowledge the facilities and the scientific and technical assistance of the National Imaging Facility at the Centre for Advanced Imaging University of Queensland. K.J.T. acknowledges the National Health and Medical Research Council for fellowship support (APP1148582). BC acknowledges Maria Galini Faidra Angelerou for fruitful discussions throughout this work. This work was supported by the European Union’s Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie grant agreement no. 703934, FluoroDendriNostic project. The authors acknowledge the facilities and the scientific and technical assistance of the National Imaging Facility at the Centre for Advanced Imaging, University of Queensland. K.J.T. acknowledges the National Health and Medical Research Council for fellowship support (APP1148582). BC acknowledges Maria Galini Faidra Angelerou for fruitful discussions throughout this work.

Funders	Funder number
Centre for Advanced Imaging University of Queensland
Horizon 2020 Framework Programme	703934
National Health and Medical Research Council	APP1148582

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10.1021/acsmacrolett.9b00626

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abstract = "A water-soluble fluorine magnetic resonance spectroscopy host-guest probe, P(HPA-co-AdamCF3A), was successfully constructed from the facile synthesis of a bifunctional monomer via a quantitative Passerini reaction. Supramolecular complexation with (2-hydroxypropyl)-β-cyclodextrin promoted a change in the chemical environment, leading to modulation of both the relaxation properties as well as chemical shift of the fluorine moieties. This change was used to probe the supramolecular interaction by 19F MRI spectroscopy and give insight into fluorine probe formulation. This work provides a fundamental basis for an 19F MR imaging tracer capable of assessing host-guest inclusion and a potential model to follow the fate of a drug delivery system in vivo.",

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AU - Prokeš, Ivan

AU - Foster, Jeffrey C.

AU - Thurecht, Kristofer J.

AU - O'Reilly, Rachel K.

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Supramolecular Fluorine Magnetic Resonance Spectroscopy Probe Polymer Based on Passerini Bifunctional Monomer

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