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While increasing the number of payloads attached to a protein is a proven strategy to enhance the potency of a bioconjugate, the introduction of additional conjugation sites often risks compromising the protein\u2019s targeting properties. In this study, we investigate the potential of 1,3,4-thiadiazole-N-oxides (TNO), a heterocyclic scaffold exhibiting excellent stability in biological media. We demonstrate that this reactive partner undergoes an unprecedented double addition reaction with bicyclo[6.1.0]non-4-yne derivatives. This unique reactivity is harnessed to achieve the site-specific attachment of two probes per conjugation site on a monoclonal antibody. Importantly, this strategy preserves antibody targeting properties, as confirmed by in vivo imaging studies. These findings establish TNO and the Strain-Promoted Alkyne-1,3,4-Thiadiazole-N-Oxide coupling (SPATOC) reaction as valuable new tools in the bioconjugation arsenal, expanding the possibilities for precise and efficient protein modification.<\/jats:p>","DOI":"10.1021\/jacs.6c09261","type":"journal-article","created":{"date-parts":[[2026,8,6]],"date-time":"2026-08-06T10:01:49Z","timestamp":1786010509000},"page":"34615-34625","source":"Crossref","is-referenced-by-count":0,"title":["Unexpected Reactivity\nof 1,3,4-Thiadiazole-\n                    <i>N<\/i>\n                    -oxides with\nStrained Alkynes Enables Enhanced Antibody\nLoading"],"prefix":"10.1021","volume":"148","author":[{"given":"Zoe\u0301","family":"Bonnefoy","sequence":"first","affiliation":[{"name":"Universite\u0301 Bourgogne Europe, CNRS, ICMUB UMR 6302 , ,","place":["Dijon, France, 21000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7718-1629","authenticated-orcid":true,"given":"Mauricio","family":"Da Silva Morais","sequence":"additional","affiliation":[{"name":"Universite\u0301 Bourgogne Europe, CNRS, ICMUB UMR 6302 , ,","place":["Dijon, France, 21000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marie-Jose\u0301","family":"Penouilh","sequence":"additional","affiliation":[{"name":"Universite\u0301 Bourgogne Europe, CNRS, ICMUB UMR 6302 , ,","place":["Dijon, France, 21000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Claron","sequence":"additional","affiliation":[{"name":"Universite\u0301 Bourgogne Europe, CNRS, ICMUB UMR 6302 , ,","place":["Dijon, France, 21000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mathieu","family":"Moreau","sequence":"additional","affiliation":[{"name":"Universite\u0301 Bourgogne Europe, CNRS, ICMUB UMR 6302 , ,","place":["Dijon, France, 21000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yoann","family":"Rousselin","sequence":"additional","affiliation":[{"name":"Universite\u0301 Bourgogne Europe, CNRS, ICMUB UMR 6302 , ,","place":["Dijon, France, 21000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3114-2522","authenticated-orcid":true,"given":"Paul","family":"Fleurat-Lessard","sequence":"additional","affiliation":[{"name":"Universite\u0301 Bourgogne Europe, CNRS, ICMUB UMR 6302 , ,","place":["Dijon, France, 21000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pierre-Simon","family":"Bellaye","sequence":"additional","affiliation":[{"name":"Universite\u0301 Bourgogne Europe, Centre Georges-Franc\u0327ois Leclerc, Unicancer, De\u0301partement de Me\u0301decine Nucle\u0301aire, INSERM, CTM UMR 1231, Equipe Hsp-pathies, INSERM, BioSanD US 58, IMATHERA , ,","place":["Dijon, France, 21000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cindy","family":"Racoeur","sequence":"additional","affiliation":[{"name":"Universite\u0301 Bourgogne Europe, INSERM, CTM UMR 1231 , ,","place":["Dijon, France, 21000"]},{"name":"EPHE, PSL Research University , ,","place":["Paris, France, 75000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7657-5535","authenticated-orcid":true,"given":"Catherine","family":"Paul","sequence":"additional","affiliation":[{"name":"Universite\u0301 Bourgogne Europe, INSERM, CTM UMR 1231 , ,","place":["Dijon, France, 21000"]},{"name":"EPHE, PSL Research University , ,","place":["Paris, France, 75000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9652-4006","authenticated-orcid":true,"given":"Franck","family":"Denat","sequence":"additional","affiliation":[{"name":"Universite\u0301 Bourgogne Europe, CNRS, ICMUB UMR 6302 , ,","place":["Dijon, France, 21000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9854-4409","authenticated-orcid":true,"given":"Victor","family":"Goncalves","sequence":"additional","affiliation":[{"name":"Universite\u0301 Bourgogne Europe, CNRS, ICMUB UMR 6302 , ,","place":["Dijon, France, 21000"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,6]]},"reference":[{"key":"2026081910240225200_cit1","doi-asserted-by":"publisher","first-page":"4895","DOI":"10.1039\/C7CS00184C","article-title":"Inverse electron demand Diels\u2013Alder\nreactions in chemical biology","volume":"46","author":"Oliveira","year":"2017","journal-title":"Chem. 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