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Reversible Lysine Modification on Proteins by Using Functionalized Boronic Acids
Author(s) -
Cal Pedro M. S. D.,
Frade Raquel F. M.,
Cordeiro Carlos,
Gois Pedro M. P.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500127
Subject(s) - bioorthogonal chemistry , conjugate , polyethylene glycol , chemistry , lysine , peg ratio , combinatorial chemistry , bioconjugation , azide , boronic acid , paclitaxel , biochemistry , pegylation , cytotoxicity , phenylboronic acid , amino acid , click chemistry , organic chemistry , in vitro , cancer , biology , mathematical analysis , mathematics , finance , economics , genetics , catalysis
Iminoboronates have been utilized to successfully install azide and alkyne bioorthogonal functions on proteins, which may then be further reacted with their bioorthogonal counterparts. These constructs were also used to add polyethylene glycol (PEG) to insulin, a modification which has been shown to be reversible in the presence of fructose. Finally, iminoboronates were used to assemble a folic acid/paclitaxel small‐molecule/drug conjugate in situ with an IC 50 value of 20.7 n M against NCI‐H460 cancer cells and negligible cytotoxicity against the CRL‐1502 noncancer cells.