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Chemistry","award":["R19-9781"],"award-info":[{"award-number":["R19-9781"]}]},{"name":"INCT-Cat\u00e1lise\/CNPq\/FAPESC","award":["309774\/2020-9"],"award-info":[{"award-number":["309774\/2020-9"]}]},{"name":"INCT-Cat\u00e1lise\/CNPq\/FAPESC","award":["405052\/2021-9"],"award-info":[{"award-number":["405052\/2021-9"]}]},{"name":"INCT-Cat\u00e1lise\/CNPq\/FAPESC","award":["001"],"award-info":[{"award-number":["001"]}]},{"name":"INCT-Cat\u00e1lise\/CNPq\/FAPESC","award":["PPM-00635-18"],"award-info":[{"award-number":["PPM-00635-18"]}]},{"name":"INCT-Cat\u00e1lise\/CNPq\/FAPESC","award":["Rede de Pesquisa e Inova\u00e7\u00e3o para Bioengenharia de Nanossistemas-RED-00282-16"],"award-info":[{"award-number":["Rede de Pesquisa e Inova\u00e7\u00e3o para Bioengenharia de Nanossistemas-RED-00282-16"]}]},{"name":"INCT-Cat\u00e1lise\/CNPq\/FAPESC","award":["R19-9781"],"award-info":[{"award-number":["R19-9781"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In 2021, our research group published the prominent anticancer activity achieved through the successful combination of two redox centres (ortho-quinone\/para-quinone or quinone\/selenium-containing triazole) through a copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. The combination of two naphthoquinoidal substrates towards a synergetic product was indicated, but not fully explored. Herein, we report the synthesis of 15 new quinone-based derivatives prepared from click chemistry reactions and their subsequent evaluation against nine cancer cell lines and the murine fibroblast line L929. Our strategy was based on the modification of the A-ring of para-naphthoquinones and subsequent conjugation with different ortho-quinoidal moieties. As anticipated, our study identified several compounds with IC50 values below 0.5 \u00b5M in tumour cell lines. Some of the compounds described here also exhibited an excellent selectivity index and low cytotoxicity on L929, the control cell line. The antitumour evaluation of the compounds separately and in their conjugated form proved that the activity is strongly enhanced in the derivatives containing two redox centres. Thus, our study confirms the efficiency of using A-ring functionalized para-quinones coupled with ortho-quinones to obtain a diverse range of two redox centre compounds with potential applications against cancer cell lines. Here as well, it literally takes two for an efficient tango!<\/jats:p>","DOI":"10.3390\/molecules28052222","type":"journal-article","created":{"date-parts":[[2023,2,28]],"date-time":"2023-02-28T02:01:51Z","timestamp":1677549711000},"page":"2222","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["It Takes Two to Tango, Part II: Synthesis of A-Ring Functionalised Quinones Containing Two Redox-Active Centres with Antitumour Activities"],"prefix":"10.3390","volume":"28","author":[{"given":"Joyce C.","family":"Oliveira","sequence":"first","affiliation":[{"name":"Institute of Exact Sciences, Department of Chemistry, Universidade Federal de Minas Gerais, UFMG, Belo Horizonte 31270-901, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Renato L.","family":"de Carvalho","sequence":"additional","affiliation":[{"name":"Institute of Exact Sciences, Department of Chemistry, Universidade Federal de Minas Gerais, UFMG, Belo Horizonte 31270-901, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hugo G. S.","family":"Sampaio","sequence":"additional","affiliation":[{"name":"Institute of Exact Sciences, Department of Chemistry, Universidade Federal de Minas Gerais, UFMG, Belo Horizonte 31270-901, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1127-6083","authenticated-orcid":false,"given":"Jo\u00e3o","family":"Honorato","sequence":"additional","affiliation":[{"name":"S\u00e3o Carlos Institute of Physics, Physics and Interdisciplinary Sciences Department, Universidade de S\u00e3o Paulo, USP, S\u00e3o Carlos 13560-970, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0676-3098","authenticated-orcid":false,"given":"Javier A.","family":"Ellena","sequence":"additional","affiliation":[{"name":"S\u00e3o Carlos Institute of Physics, Physics and Interdisciplinary Sciences Department, Universidade de S\u00e3o Paulo, USP, S\u00e3o Carlos 13560-970, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Felipe T.","family":"Martins","sequence":"additional","affiliation":[{"name":"Chemistry Institute, Universidade Federal de Goi\u00e1s, UFG, Goi\u00e2nia 74690-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jo\u00e3o V. M.","family":"Pereira","sequence":"additional","affiliation":[{"name":"Department of Physiology and Pharmacology, Universidade Federal de Cear\u00e1, UFC, Fortaleza 60430-270, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pedro M. S.","family":"Costa","sequence":"additional","affiliation":[{"name":"Department of Physiology and Pharmacology, Universidade Federal de Cear\u00e1, UFC, Fortaleza 60430-270, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudia","family":"Pessoa","sequence":"additional","affiliation":[{"name":"Department of Physiology and Pharmacology, Universidade Federal de Cear\u00e1, UFC, Fortaleza 60430-270, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3324-0601","authenticated-orcid":false,"given":"Rafaela S.","family":"Ferreira","sequence":"additional","affiliation":[{"name":"Biological Sciences Institute, Biochemistry and Immunology Department, Universidade Federal de Minas Gerais, UFMG, Belo Horizonte 31270-901, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria H.","family":"Ara\u00fajo","sequence":"additional","affiliation":[{"name":"Institute of Exact Sciences, Department of Chemistry, Universidade Federal de Minas Gerais, UFMG, Belo Horizonte 31270-901, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6288-7220","authenticated-orcid":false,"given":"Claus","family":"Jacob","sequence":"additional","affiliation":[{"name":"Division of Bioorganic Chemistry, School of Pharmacy, University of Saarland, 66123 Saarbruecken, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1281-5453","authenticated-orcid":false,"given":"Eufr\u00e2nio N.","family":"da Silva J\u00fanior","sequence":"additional","affiliation":[{"name":"Institute of Exact Sciences, Department of Chemistry, Universidade Federal de Minas Gerais, UFMG, Belo Horizonte 31270-901, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,2,27]]},"reference":[{"key":"ref_1","unstructured":"(2022, November 18). 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