Photophysical characterization of a bisacridinium-diphenylporphyrin conjugate

Ruani, Federica; Edo-Osagie, Amy; Rouville, Henri‐Pierre Jacquot de; Heitz, Valérie; Ventura, Barbara; Armaroli, Nicola

doi:10.1142/s1088424623500396

Cited by 1 publication

(1 citation statement)

References 31 publications

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“…The molar absorption coefficient of the Soret band of IP-H-OH 2+ (ε = 3.0 × 10 5 M −1 cm −1 ) and its fluorescence quantum yield (ϕ F = 0.11) in ethanol are also comparable to the values of other cationic di-imidazolyl porphyrins. [43] The relatively low fluorescence quantum yields are consistent with those of other neutral and cationic 5,15-di-arylporphyrins [44].…”

Section: Photophysical and Photochemical Studiessupporting

confidence: 69%

Photodynamic inactivation of E. coli with cationic imidazolyl-porphyrin photosensitizers and their synergic combination with antimicrobial cinnamaldehyde

Silva,

Aroso,

Dabrowski

et al. 2024

Photochem Photobiol Sci

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Bacterial infections are a global health concern, particularly due to the increasing resistance of bacteria to antibiotics. 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 (logP) values of this class of photosensitizers on PDI efficacy of Escherichia coli. The derivative with logP = –0.5, IP-H-OH2+, achieved a remarkable 3 log CFU reduction of E. coli at 100 nM with only 1.36 J/cm2 light dose at 415 nm, twice as effective as the second-best porphyrin IP-H-Me2+, of logP = –1.35. We relate the rapid uptake of IP-H-OH2+ by E. coli to improved PDI and the very low uptake of a fluorinated derivative, IP-H-CF32+, logP ≈ 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 E. coli (7 log CFU reduction), using 50 nM of IP-H-OH2+ and just 1.36 J/cm2 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. Graphical Abstract

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Section: Photophysical and Photochemical Studiessupporting

confidence: 69%