Improving the Stability of Maleimide-Thiol Conjugation for Drug Targeting.
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ABSTRACT:
SUBMITTER: Lahnsteiner M
PROVIDER: S-EPMC7756610 | biostudies-literature | 2020 Dec
REPOSITORIES: biostudies-literature
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Improving the Stability of Maleimide-Thiol Conjugation for Drug Targeting.
Lahnsteiner Marianne M Kastner Alexander A Mayr Josef J Roller Alexander A Keppler Bernhard K BK Kowol Christian R CR
Chemistry (Weinheim an der Bergstrasse, Germany) 20201027 68
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 s ...[more]
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