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Designing kinetically stable aryltrifluoroborates as 18 F‐capture agents for PET imaging
Author(s) -
Liu Zhibo,
Li Ying,
Ting Richard,
Perrin David M.
Publication year - 2015
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3403
Subject(s) - chemistry , biomolecule , nucleophile , aqueous solution , radiosynthesis , combinatorial chemistry , fluoride , ion , computational chemistry , organic chemistry , inorganic chemistry , biochemistry , catalysis , microbiology and biotechnology , in vivo , biology
One‐step 18 F‐radiolabeling of peptides and other large biomolecules has been challenged by a critical gap in chemical compatibility between fluoride anion, which is unreactive as a nucleophile in water, and large biomolecules such as peptides that are insoluble in dry solvents. Traditionally, this disparity has been overcome through the preliminary synthesis of an 18 F‐labeled radioprosthetic group that is appended to peptides following at least one additional step. Ideally, however, peptides should be labeled in a single aqueous step. Hence, we proposed the use of arylboronic acids as captors of aqueous 18 F‐fluoride ion to simplify the radiosynthesis of 18 F‐aryltrifluoroborate bioconjugates. Yet, the use of aryltrifluoroborates as radioprosthetic groups can only be considered if kinetically stable ones can be designed. Herein, we discuss the kinetic and thermodynamic parameters review our previous use of a Hammett analysis that can inform the design of kinetically stable 18 F‐labeled aryltrifluoroborates for use as novel radioprosthetic groups. Copyright © 2014 John Wiley & Sons, Ltd.