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Among a wide variety of chemi-\/bioluminescent systems, one of the most well-known and studied systems is that of marine imidazopyrazinones, such as Coelenterazine and Cypridina luciferin. Due to the increasing usefulness of their chemi-\/bioluminescent reactions in terms of imaging and sensing applications, among others, significant effort has been made over the years by researchers to develop new derivatives with enhanced properties. Herein, we report the synthesis and chemiluminescent characterization of a novel dibrominated Coelenterazine analog. This novel compound consistently showed superior luminescence, in terms of total light output and emission lifetime, to natural imidazopyrazinones and commercially available analogs in aprotic media, while being capable of yellow light emission. Finally, this new compound showed enhanced chemiluminescence in an aqueous solution when triggered by superoxide anion, showing potential to be used as a basis for optimized probes for reactive oxygen species. In conclusion, bromination of the imidazopyrazinone scaffold appears to be a suitable strategy for obtaining Coelenterazines with enhanced properties.<\/jats:p>","DOI":"10.3390\/ijms23158490","type":"journal-article","created":{"date-parts":[[2022,8,1]],"date-time":"2022-08-01T02:06:42Z","timestamp":1659319602000},"page":"8490","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Comparative Investigation of the Chemiluminescent Properties of a Dibrominated Coelenterazine Analog"],"prefix":"10.3390","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0895-1380","authenticated-orcid":false,"given":"Jo\u00e3o","family":"Sousa","sequence":"first","affiliation":[{"name":"Centro de Investiga\u00e7\u00e3o em Qu\u00edmica (CIQUP), Instituto de Ci\u00eancias Moleculares (IMS), Departamento de Geoci\u00eancias, Ambiente e Ordenamento do Territ\u00f3rio, Faculdade de Ci\u00eancias, Universidade do Porto, Rua do Campo Alegre s\/n, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9152-7865","authenticated-orcid":false,"given":"Carla M.","family":"Magalh\u00e3es","sequence":"additional","affiliation":[{"name":"Centro de Investiga\u00e7\u00e3o em Qu\u00edmica (CIQUP), Instituto de Ci\u00eancias Moleculares (IMS), Departamento de Geoci\u00eancias, Ambiente e Ordenamento do Territ\u00f3rio, Faculdade de Ci\u00eancias, Universidade do Porto, Rua do Campo Alegre s\/n, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0138-4929","authenticated-orcid":false,"given":"Patricia","family":"Gonz\u00e1lez-Berdullas","sequence":"additional","affiliation":[{"name":"Centro de Investiga\u00e7\u00e3o em Qu\u00edmica (CIQUP), Instituto de Ci\u00eancias Moleculares (IMS), Departamento de Geoci\u00eancias, Ambiente e Ordenamento do Territ\u00f3rio, Faculdade de Ci\u00eancias, Universidade do Porto, Rua do Campo Alegre s\/n, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8478-3441","authenticated-orcid":false,"given":"Joaquim C. G.","family":"Esteves da Silva","sequence":"additional","affiliation":[{"name":"Centro de Investiga\u00e7\u00e3o em Qu\u00edmica (CIQUP), Instituto de Ci\u00eancias Moleculares (IMS), Departamento de Geoci\u00eancias, Ambiente e Ordenamento do Territ\u00f3rio, Faculdade de Ci\u00eancias, Universidade do Porto, Rua do Campo Alegre s\/n, 4169-007 Porto, Portugal"},{"name":"LACOMEPHI, GreenUPorto, Departamento de Geoci\u00eancias, Ambiente e Ordenamento do Territ\u00f3rio, Faculdade de Ci\u00eancias, Universidade do Porto, Rua do Campo Alegre s\/n, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5647-8455","authenticated-orcid":false,"given":"Lu\u00eds","family":"Pinto da Silva","sequence":"additional","affiliation":[{"name":"Centro de Investiga\u00e7\u00e3o em Qu\u00edmica (CIQUP), Instituto de Ci\u00eancias Moleculares (IMS), Departamento de Geoci\u00eancias, Ambiente e Ordenamento do Territ\u00f3rio, Faculdade de Ci\u00eancias, Universidade do Porto, Rua do Campo Alegre s\/n, 4169-007 Porto, Portugal"},{"name":"LACOMEPHI, GreenUPorto, Departamento de Geoci\u00eancias, Ambiente e Ordenamento do Territ\u00f3rio, Faculdade de Ci\u00eancias, Universidade do Porto, Rua do Campo Alegre s\/n, 4169-007 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2022,7,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2286","DOI":"10.1002\/cphc.201600270","article-title":"Chemiluminescence and Bioluminescence as an Excitation Source in the Photodynamic Therapy of Cancer: A Critical Review","volume":"17","year":"2016","journal-title":"Chem. 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