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^*

^*Corresponding author for this work

Chemistry

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

5 Citations (Scopus)

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
Early online date	15 Oct 2019
DOIs	https://doi.org/10.1021/acsmacrolett.9b00626
Publication status	Published - 19 Nov 2019

Keywords

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

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10.1021/acsmacrolett.9b00626

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title = "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 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. ",

keywords = "water soluble fluorine, bifunctional monomer, Passerini reaction, Supramolecular complexation, host-guest chemistry",

author = "Benoit Couturaud and Houston, \{Zachary H\} and Cowin, \{Gary J\} and Ivan Proke{\v s} and Foster, \{Jeffrey C\} and Thurecht, \{Kristofer J\} and O'Reilly, \{Rachel K\}",

year = "2019",

month = nov,

day = "19",

doi = "10.1021/acsmacrolett.9b00626",

language = "English",

volume = "8",

pages = "1479--1483",

journal = "ACS Macro Letters",

issn = "2161-1653",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Supramolecular Fluorine Magnetic Resonance Spectroscopy Probe Polymer Based on Passerini Bifunctional Monomer

AU - Couturaud, Benoit

AU - Houston, Zachary H

AU - Cowin, Gary J

AU - Prokeš, Ivan

AU - Foster, Jeffrey C

AU - Thurecht, Kristofer J

AU - O'Reilly, Rachel K

PY - 2019/11/19

Y1 - 2019/11/19

N2 - 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.

AB - 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.

KW - water soluble fluorine

KW - bifunctional monomer

KW - Passerini reaction

KW - Supramolecular complexation

KW - host-guest chemistry

U2 - 10.1021/acsmacrolett.9b00626

DO - 10.1021/acsmacrolett.9b00626

M3 - Letter

C2 - 35651191

SN - 2161-1653

VL - 8

SP - 1479

EP - 1483

JO - ACS Macro Letters

JF - ACS Macro Letters

IS - 11

ER -

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

Abstract

Keywords

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