A new strategy for preparing molecular imaging and therapy agents using fluorine-rich (fluorous) soluble supports

Journal of the American Chemical Society
Amanda C DonovanJohn F Valliant

Abstract

A convenient new strategy for producing radiolabeled compounds in high effective specific activity was developed using soluble fluorous supports. The reported methodology involves a fluorous linker group that is released from the substrate of interest upon reaction with radioiodine. The desired product can then be selectively separated from unreacted starting material and reaction byproducts using a simple fluorous solid-phase extraction procedure. The utility of this approach was demonstrated by labeling a series of benzoic acid derivatives which are commonly used to prepare molecular imaging agents. All compounds were produced in high radiochemical yields, purities, and effective specific activities. The strategy was further elaborated in that it was used to prepare a small collection of radiolabeled benzamides as a way of demonstrating the potential utility of this method for creating libraries of molecular imaging agents.

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Citations

Jul 31, 2008·Chemical Communications : Chem Comm·Sophie BoldonVéronique Gouverneur
Nov 15, 2008·Chemical Communications : Chem Comm·Wei Zhang, Chun Cai
Nov 2, 2014·Journal of Medicinal Chemistry·Patricia E EdemJohn F Valliant
Feb 12, 2017·Angewandte Chemie·Yiting Gu, Rúben Martín
Jan 20, 2016·Organic & Biomolecular Chemistry·Holisoa RajerisonStéphanie Legoupy
Apr 26, 2012·Chemistry : a European Journal·Ryan W SimmsJohn F Valliant
Jul 30, 2014·Journal of Labelled Compounds & Radiopharmaceuticals·James P K DzandziJohn F Valliant
Sep 12, 2007·Chemical Communications : Chem Comm·Harriet TeareVéronique Gouverneur
Oct 2, 2008·The Journal of Organic Chemistry·Jason W McInteeJohn F Valliant
Jan 17, 2009·Chemical Reviews·Wei Zhang
Sep 8, 2016·Journal of Nuclear Medicine Technology·John F Valliant
May 6, 2020·The Journal of Organic Chemistry·Emmanuelle DubostThomas Cailly
Feb 24, 2015·ACS Medicinal Chemistry Letters·Emilie M F BillaudJean-Michel Chezal

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