Improving the Stability of Maleimide-Thiol Conjugation for Drug Targeting
- Author(s)
- Marianne Lahnsteiner, Alexander Kastner, Josef Mayr, Alexander Roller, Bernhard K. Keppler, Christian R. Kowol
- Abstract
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.
- Organisation(s)
- Department of Inorganic Chemistry, Core Facility Crystal Structure Analysis
- External organisation(s)
- Research Cluster Translational Cancer Therapy Research
- Journal
- Chemistry: A European Journal
- Volume
- 26
- Pages
- 15867-15870
- No. of pages
- 4
- ISSN
- 0947-6539
- DOI
- https://doi.org/10.1002/chem.202003951
- Publication date
- 12-2020
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 301207 Pharmaceutical chemistry, 301206 Pharmacology
- Keywords
- ASJC Scopus subject areas
- Catalysis, Organic Chemistry
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/cd62e564-ee37-4128-9e49-5066ea9f9bc8