Improving the Stability of Maleimide-Thiol Conjugation for Drug Targeting.

Maleimides are essential compounds for drug conjugation reactions via thiols to antibodies, peptides and other targeting units. However, one main drawback is the occurrence of thiol exchange reactions with, for example, glutathione resulting in loss of the targeting ability. A new strategy to overcome such retro-Michael exchange processes of maleimide-thiol conjugates by stabilization of the thiosuccinimide via a transcyclization reaction is presented. This reaction enables the straightforward synthesis of stable maleimide-thiol adducts essential in drug-conjugation applications. © 2020 The Authors. Published by Wiley-VCH GmbH.

Citation

Marianne Lahnsteiner, Alexander Kastner, Josef Mayr, Alexander Roller, Bernhard K Keppler, Christian R Kowol. Improving the Stability of Maleimide-Thiol Conjugation for Drug Targeting. Chemistry (Weinheim an der Bergstrasse, Germany). 2020 Dec 04;26(68):15867-15870

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PMID: 32871016

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