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We disclosed recently that some <jats:italic>N<\/jats:italic>\u2010linked tetrazole\u2010saccharinates bind selectively to copper, forming complexes that are highly cytotoxic towards cancer cells. Because tetrazole\u2010saccharinates are photolabile, due to the photoreactivity of tetrazoles, we proposed thiadiazolyl\u2010saccharinates as an alternative. Herein we describe the synthesis, structure, and monomeric photochemistry of a sulphanyl\u2010bridged thiadiazolyl\u2010saccharinate, 3\u2010[(5\u2010methyl\u20101,3,4\u2010thiadiazol\u20102\u2010yl)sulphanyl]\u20101,2\u2010benzothiazole 1,1\u2010dioxide (MTSB). The monomeric structure, charge density analysis, and characteristic infrared spectrum of MTSB were investigated theoretically, using quantum chemical calculations, and also experimentally, using matrix\u2010isolation infrared spectroscopy. The crystal structure was investigated by combining X\u2010ray crystallography with infrared and Raman spectroscopies. Results show that the structure of isolated MTSB is similar to that found in the crystal, with an S\u22c5\u22c5\u22c5N interaction clearly contributing to the structure of the molecule and of the crystal. Matrix irradiation revealed a high photostability of MTSB, compared to parent tetrazole\u2010saccharinates and to the 5\u2010methyl\u20101,3,4\u2010thiadiazole building block, emphasizing the photostabilizing effect of the saccharyl system. Finally, in vitro toxicity assays of MTSB showed a copper concentration\u2010dependent toxicity against cancer cells, without affecting normal cells. In particular, MTSB was most effective towards the hepatic (HepG2), neuroblastoma (SH\u2010SY5), and lymphoma cell lines (U937). Thus, MTSB represents a promising lead for cancer chemotherapy based on chelating agents.<\/jats:p>","DOI":"10.1002\/chem.201705319","type":"journal-article","created":{"date-parts":[[2017,12,28]],"date-time":"2017-12-28T07:28:42Z","timestamp":1514446122000},"page":"3251-3262","source":"Crossref","is-referenced-by-count":12,"title":["Synthesis, Structure, and Cytotoxicity of a New Sulphanyl\u2010Bridged Thiadiazolyl\u2010Saccharinate Conjugate: The Relevance of S\u22c5\u22c5\u22c5N Interaction"],"prefix":"10.1002","volume":"24","author":[{"given":"L\u00edlia I. L.","family":"Cabral","sequence":"first","affiliation":[{"name":"Department of Chemistry and Pharmacy, F.C.T. 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