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To overcome chemotherapeutic resistance and widen treatment possibilities, new agents with improved or alternative modes of action are highly sought after. Here, we present a click chemistry strategy for developing DNA damaging metallodrugs. The approach involves the development of a series of polyamine ligands where three primary, secondary or tertiary alkyne-amines were selected and \u2018clicked\u2019 using the copper-catalysed azide-alkyne cycloaddition reaction to a 1,3,5-azide mesitylene core to produce a family of compounds we call the \u2018Tri-Click\u2019 (TC) series. From the isolated library, one dominant ligand (TC1) emerged as a high-affinity copper(II) binding agent with potent DNA recognition and damaging properties. Using a range of in vitro biophysical and molecular techniques\u2014including free radical scavengers, spin trapping antioxidants and base excision repair (BER) enzymes\u2014the oxidative DNA damaging mechanism of copper-bound TC1 was elucidated. This activity was then compared to intracellular results obtained from peripheral blood mononuclear cells exposed to Cu(II)\u2013TC1 where use of BER enzymes and fluorescently modified dNTPs enabled the characterisation and quantification of genomic DNA lesions produced by the complex. The approach can serve as a new avenue for the design of DNA damaging agents with unique activity profiles.<\/jats:p>","DOI":"10.1093\/nar\/gkab817","type":"journal-article","created":{"date-parts":[[2021,9,8]],"date-time":"2021-09-08T11:37:07Z","timestamp":1631101027000},"page":"10289-10308","source":"Crossref","is-referenced-by-count":19,"title":["Click and Cut: a click chemistry approach to developing oxidative DNA damaging agents"],"prefix":"10.1093","volume":"49","author":[{"given":"Natasha","family":"McStay","sequence":"first","affiliation":[{"name":"School of Chemical Sciences and National Institute for Cellular Biotechnology, Dublin City University, Glasnevin, Dublin 9, Ireland"},{"name":"Synthesis and Solid-State Pharmaceutical Centre, School of Chemical Sciences, Dublin City University, Glasnevin, Dublin 9, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Creina","family":"Slator","sequence":"additional","affiliation":[{"name":"School of Chemical Sciences and National Institute for Cellular Biotechnology, Dublin City University, Glasnevin, Dublin 9, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vandana","family":"Singh","sequence":"additional","affiliation":[{"name":"Department of Biology and Biological Engineering, Chalmers University of Technology, Gothenburg, Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alex","family":"Gibney","sequence":"additional","affiliation":[{"name":"School of Chemical Sciences and National Institute for Cellular Biotechnology, Dublin City University, Glasnevin, Dublin 9, Ireland"},{"name":"Synthesis and Solid-State Pharmaceutical Centre, School of Chemical Sciences, Dublin City University, Glasnevin, Dublin 9, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4767-4868","authenticated-orcid":false,"given":"Fredrik","family":"Westerlund","sequence":"additional","affiliation":[{"name":"Department of Biology and Biological Engineering, Chalmers University of Technology, Gothenburg, Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8947-1401","authenticated-orcid":false,"given":"Andrew","family":"Kellett","sequence":"additional","affiliation":[{"name":"School of Chemical Sciences and National Institute for Cellular Biotechnology, Dublin City University, Glasnevin, Dublin 9, Ireland"},{"name":"Synthesis and Solid-State Pharmaceutical Centre, School of Chemical Sciences, Dublin City University, Glasnevin, Dublin 9, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2021,9,27]]},"reference":[{"key":"2021100913442088500_B1","doi-asserted-by":"crossref","first-page":"1584","DOI":"10.1093\/nar\/gkx1239","article-title":"Chemistry, mechanism and clinical status of antisense oligonucleotides and duplex RNAs","volume":"46","author":"Shen","year":"2018","journal-title":"Nucleic Acids Res."},{"key":"2021100913442088500_B2","doi-asserted-by":"crossref","first-page":"971","DOI":"10.1039\/C8CS00157J","article-title":"Molecular methods for assessment of non-covalent metallodrug\u2013DNA interactions","volume":"48","author":"Kellett","year":"2019","journal-title":"Chem. 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