A supramolecular fluorine magnetic resonance spectroscopy probe polymer based on Passerini bifunctional monomer

Rachel O'Reilly; Benoit Couturaud; Zachary H Houston; Gary J Cowin; Ivan Prokes; Jeff Foster; Kristofer J. Thurecht

doi:https://doi.org/10.1021/acsmacrolett.9b00626

A supramolecular fluorine magnetic resonance spectroscopy probe polymer based on Passerini bifunctional monomer

Rachel O'Reilly, Benoit Couturaud, Zachary H Houston, Gary J Cowin, Ivan Prokes, Jeff Foster, Kristofer J. Thurecht

Chemistry

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

5 Citations (Scopus)

Abstract

A water soluble fluorine Magnetic Resonance spectroscopy host-guest probe, P(HPA-co-AdamCF3A), was successfully constructed using facile chemistries to synthesize a novel 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 new insight on fluorine probe formulation. This work provides a fundamental basis for
a 19F MRimaging 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
Number of pages	5
Journal	ACS Macro Letters
Volume	8
Issue number	11
DOIs	https://doi.org/10.1021/acsmacrolett.9b00626
Publication status	Published - 15 Oct 2019

Keywords

water soluble fluorine
bifunctional monomer
Passerini reaction
Supramolecular complexation
host-guest chemistry

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https://doi.org/10.1021/acsmacrolett.9b00626

Cite this

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title = "A supramolecular fluorine magnetic resonance spectroscopy probe polymer based on Passerini bifunctional monomer",

abstract = "A water soluble fluorine Magnetic Resonance spectroscopy host-guest probe, P(HPA-co-AdamCF3A), was successfully constructed using facile chemistries to synthesize a novel bifunctional monomer via a quantitative Passerini reaction. Supramolecular complexation with (2-hydroxypropyl)-β-cyclodextrin promoted a change in the chemical environment leading to modulationof both the relaxation properties as well as chemical shift of the fluorine moieties. This change was used to probe the supramolecularinteraction by 19F MRI spectroscopy and give new insight on fluorine probe formulation. This work provides a fundamental basis fora 19F MRimaging tracer capable of assessing host-guest inclusion and a potential model to follow the fate of a drug delivery system invivo.",

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author = "Rachel O'Reilly and Benoit Couturaud and Houston, {Zachary H} and Cowin, {Gary J} and Ivan Prokes and Jeff Foster and Thurecht, {Kristofer J.}",

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doi = "https://doi.org/10.1021/acsmacrolett.9b00626",

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T1 - A supramolecular fluorine magnetic resonance spectroscopy probe polymer based on Passerini bifunctional monomer

AU - O'Reilly, Rachel

AU - Couturaud, Benoit

AU - Houston, Zachary H

AU - Cowin, Gary J

AU - Prokes, Ivan

AU - Foster, Jeff

AU - Thurecht, Kristofer J.

PY - 2019/10/15

Y1 - 2019/10/15

N2 - A water soluble fluorine Magnetic Resonance spectroscopy host-guest probe, P(HPA-co-AdamCF3A), was successfully constructed using facile chemistries to synthesize a novel bifunctional monomer via a quantitative Passerini reaction. Supramolecular complexation with (2-hydroxypropyl)-β-cyclodextrin promoted a change in the chemical environment leading to modulationof both the relaxation properties as well as chemical shift of the fluorine moieties. This change was used to probe the supramolecularinteraction by 19F MRI spectroscopy and give new insight on fluorine probe formulation. This work provides a fundamental basis fora 19F MRimaging tracer capable of assessing host-guest inclusion and a potential model to follow the fate of a drug delivery system invivo.

AB - A water soluble fluorine Magnetic Resonance spectroscopy host-guest probe, P(HPA-co-AdamCF3A), was successfully constructed using facile chemistries to synthesize a novel bifunctional monomer via a quantitative Passerini reaction. Supramolecular complexation with (2-hydroxypropyl)-β-cyclodextrin promoted a change in the chemical environment leading to modulationof both the relaxation properties as well as chemical shift of the fluorine moieties. This change was used to probe the supramolecularinteraction by 19F MRI spectroscopy and give new insight on fluorine probe formulation. This work provides a fundamental basis fora 19F MRimaging tracer capable of assessing host-guest inclusion and a potential model to follow the fate of a drug delivery system invivo.

KW - water soluble fluorine

KW - bifunctional monomer

KW - Passerini reaction

KW - Supramolecular complexation

KW - host-guest chemistry

U2 - https://doi.org/10.1021/acsmacrolett.9b00626

DO - https://doi.org/10.1021/acsmacrolett.9b00626

M3 - Article

SN - 2161-1653

VL - 8

SP - 1479

JO - ACS Macro Letters

JF - ACS Macro Letters

IS - 11

ER -

A supramolecular fluorine magnetic resonance spectroscopy probe polymer based on Passerini bifunctional monomer

Abstract

Keywords

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