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Multi-drug resistance (MDR) is a considerable challenge, and novel approaches are needed to treat bacterial infections. Photodynamic inactivation (PDI) of microorganisms is increasingly recognized as an effective method to inactivate a broad spectrum of bacteria and overcome resistance mechanisms. This study presents the synthesis of a new cationic 5,15-di-imidazolyl porphyrin derivative and the impact of n-octanol\/water partition coefficient (log<jats:italic>P<\/jats:italic>) values of this class of photosensitizers on PDI efficacy of <jats:italic>Escherichia coli<\/jats:italic>. The derivative with log<jats:italic>P<\/jats:italic>\u2009=\u2009\u20130.5, <jats:bold>IP-H-OH<\/jats:bold><jats:sup><jats:bold>2+<\/jats:bold><\/jats:sup>, achieved a remarkable 3 log CFU reduction of <jats:italic>E. coli<\/jats:italic> at 100\u00a0nM with only 1.36\u00a0J\/cm<jats:sup>2<\/jats:sup> light dose at 415\u00a0nm, twice as effective as the second-best porphyrin <jats:bold>IP-H-Me<\/jats:bold><jats:sup><jats:bold>2+<\/jats:bold><\/jats:sup>, of log<jats:italic>P<\/jats:italic>\u2009=\u2009\u20131.35. We relate the rapid uptake of <jats:bold>IP-H-OH<\/jats:bold><jats:sup><jats:bold>2+<\/jats:bold><\/jats:sup> by <jats:italic>E. coli<\/jats:italic> to improved PDI and the very low uptake of a fluorinated derivative, <jats:bold>IP-H-CF<\/jats:bold><jats:sub><jats:bold>3<\/jats:bold><\/jats:sub><jats:sup><jats:bold>2+<\/jats:bold><\/jats:sup>, log<jats:italic>P<\/jats:italic> \u2248 1, to its poor performance. Combination of PDI with cinnamaldehyde, a major component of the cinnamon plant known to alter bacteria cell membranes, offered synergic inactivation of <jats:italic>E. coli<\/jats:italic> (7 log CFU reduction), using 50\u00a0nM of <jats:bold>IP-H-OH<\/jats:bold><jats:sup><jats:bold>2+<\/jats:bold><\/jats:sup> and just 1.36\u00a0J\/cm<jats:sup>2<\/jats:sup> light dose. The success of combining PDI with this natural compound broadens the scope of therapies for MDR infections that do not add drug resistance. In vivo studies on a mouse model of wound infection showed the potential of cationic 5,15-di-imidazolyl porphyrins to treat clinically relevant infected wounds.<\/jats:p>\n                <jats:p><jats:bold>Graphical Abstract<\/jats:bold><\/jats:p>","DOI":"10.1007\/s43630-024-00581-y","type":"journal-article","created":{"date-parts":[[2024,5,12]],"date-time":"2024-05-12T13:01:38Z","timestamp":1715518898000},"page":"1129-1142","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Photodynamic inactivation of E. coli with cationic imidazolyl-porphyrin photosensitizers and their synergic combination with antimicrobial cinnamaldehyde"],"prefix":"10.1007","volume":"23","author":[{"given":"Madalena F. 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