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To improve aPDT performance, two Protoporphyrin IX (PpIX) derivatives functionalized with one or two capsaicin fragments were synthesized and biologically evaluated. Their physicochemical, photophysical, and antimicrobial properties were assessed against susceptible and resistant Gram\u2010positive (\n                    <jats:italic>Staphylococcus aureus<\/jats:italic>\n                    ) and Gram\u2010negative (\n                    <jats:italic>Escherichia coli<\/jats:italic>\n                    ) strains. Mono\u2010 and disubstituted capsaicinoid\u2010functionalized derivatives were isolated in 17% and 40% yields, respectively. Structural modification induced minor photophysical changes compared to PpIX, including slightly reduced singlet oxygen generation and photostability. Aggregation studies revealed that PpIX\u2010capsaicin\n                    <jats:bold>1<\/jats:bold>\n                    exhibited a lower tendency to aggregate, whereas PpIX\u2010capsaicin\n                    <jats:bold>2<\/jats:bold>\n                    showed persistent aggregation with coexistence of H\u2010 and J\u2010type species. A significant increase in lipophilicity (Log\n                    <jats:italic>P<\/jats:italic>\n                    ) was observed only for PpIX\u2010capsaicin\n                    <jats:bold>2<\/jats:bold>\n                    . Photoinactivation assays demonstrated superior efficacy of PpIX\u2010capsaicin\n                    <jats:bold>1<\/jats:bold>\n                    against\n                    <jats:italic>S. aureus<\/jats:italic>\n                    , achieving\u2009~3\u2010log reduction, while limited activity was observed against\n                    <jats:italic>E. coli<\/jats:italic>\n                    , likely due to its complex cell envelope. In contrast, PpIX\u2010capsaicin\n                    <jats:bold>2<\/jats:bold>\n                    showed no significant photoactivity. Overall, these findings demonstrate that increased functionalization does not necessarily improve photodynamic performance, highlighting the importance of balanced lipophilicity and aggregation control in photosensitizer design.\n                  <\/jats:p>","DOI":"10.1002\/cmdc.70475","type":"journal-article","created":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T00:55:22Z","timestamp":1788828922000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Effects of Mono\u2010 and Dicapsaicinoid Functionalization on the Physicochemical Properties and Antimicrobial Photodynamic Activity of Protoporphyrin IX"],"prefix":"10.1002","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4491-8836","authenticated-orcid":false,"given":"Ieda Vieira da","family":"Cunha","sequence":"first","affiliation":[{"name":"Institute of Chemistry Federal University of Uberl\u00e2ndia  Uberl\u00e2ndia Minas Gerais 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