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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\u2010Michael exchange processes of maleimide\u2013thiol conjugates by stabilization of the thiosuccinimide via a transcyclization reaction is presented. This reaction enables the straightforward synthesis of stable maleimide\u2013thiol adducts essential in drug\u2010conjugation applications.<\/jats:p>","DOI":"10.1002\/chem.202003951","type":"journal-article","created":{"date-parts":[[2020,9,1]],"date-time":"2020-09-01T16:19:15Z","timestamp":1598977155000},"page":"15867-15870","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":82,"title":["Improving the Stability of Maleimide\u2013Thiol Conjugation for Drug Targeting"],"prefix":"10.1002","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0466-5865","authenticated-orcid":false,"given":"Marianne","family":"Lahnsteiner","sequence":"first","affiliation":[{"name":"Faculty of Chemistry Institute of Inorganic Chemistry University of Vienna  Waehringer Strasse 42 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4678-9997","authenticated-orcid":false,"given":"Alexander","family":"Kastner","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Institute of Inorganic Chemistry University of Vienna  Waehringer Strasse 42 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Josef","family":"Mayr","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Institute of Inorganic Chemistry University of Vienna  Waehringer Strasse 42 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander","family":"Roller","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Institute of Inorganic Chemistry University of Vienna  Waehringer Strasse 42 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0877-1822","authenticated-orcid":false,"given":"Bernhard K.","family":"Keppler","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Institute of Inorganic Chemistry University of Vienna  Waehringer Strasse 42 1090 Vienna Austria"},{"name":"Research Cluster \u201eTranslational Cancer Therapy Research\u201c  Waehringer Strasse 42 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8311-1632","authenticated-orcid":false,"given":"Christian R.","family":"Kowol","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Institute of Inorganic Chemistry University of Vienna  Waehringer Strasse 42 1090 Vienna Austria"},{"name":"Research Cluster \u201eTranslational Cancer Therapy Research\u201c  Waehringer Strasse 42 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,10,27]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.8b00252"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1158\/1078-0432.CCR-12-0290"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1158\/1535-7163.MCT-11-0727"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/nbt.2108"},{"key":"e_1_2_2_5_1","unstructured":"\u00a0"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jconrel.2015.09.032"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1038\/nbt.2968"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201609733"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201609733"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc5005262"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00775-017-1450-7"},{"key":"e_1_2_2_11_1","unstructured":"\u00a0"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201601126"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.6b03448"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8RA02138D"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201508118"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201508118"},{"key":"e_1_2_2_16_1","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201306241"},{"key":"e_1_2_2_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201306241"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/bc400245v"},{"key":"e_1_2_2_19_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms13128"},{"key":"e_1_2_2_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202000837"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202000837"},{"key":"e_1_2_2_21_1","volume-title":"Bioconjugate techniques","author":"Hermanson G. 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