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A Fluorescent Kinase Inhibitor that Exhibits Diagnostic Changes in Emission upon Binding

Journal article
Authors Cassandra L. Fleming
Patrick A Sandoz
Tord Inghardt
Björn Önfelt
Morten Grøtli
Joakim Andréasson
Published in Angewandte Chemie - International Edition
Volume 58
Issue 42
Pages 15000-15004
ISSN 1433-7851
Publication year 2019
Published at Department of Chemistry and Molecular Biology
Pages 15000-15004
Language en
Keywords fluorescence, inhibitors, kinase, solvatochromism
Subject categories Chemical Sciences


© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The development of a fluorescent LCK inhibitor that exhibits favourable solvatochromic properties upon binding the kinase is described. Fluorescent properties were realised through the inclusion of a prodan-derived fluorophore into the pharmacophore of an ATP-competitive kinase inhibitor. Fluorescence titration experiments demonstrate the solvatochromic properties of the inhibitor, in which dramatic increase in emission intensity and hypsochromic shift in emission maxima are clearly observed upon binding LCK. Microscopy experiments in cellular contexts together with flow cytometry show that the fluorescence intensity of the inhibitor correlates with the LCK concentration. Furthermore, multiphoton microscopy experiments demonstrate both the rapid cellular uptake of the inhibitor and that the two-photon cross section of the inhibitor is amenable for excitation at 700 nm.

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