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.
| Original language | English |
|---|---|
| Pages (from-to) | 15867-15870 |
| Number of pages | 4 |
| Journal | Chemistry: A European Journal |
| Volume | 26 |
| Issue number | 68 |
| DOIs | |
| Publication status | Published - 4 Dec 2020 |
Funding
This work was supported by the Austrian Science Fund (FWF) project AP32886 (to C. Kowol). Many thanks to Dr. Katharina Pallitsch, University of Vienna, for helpful discussions.
Austrian Fields of Science 2012
- 301207 Pharmaceutical chemistry
- 301206 Pharmacology
Keywords
- bioconjugation
- bioorganic chemistry
- drug delivery
- maleimide
- retro-Michael reactions
- TRANSCYCLIZATION
- STABILIZATION
- CLEAVAGE
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