Synthesis and photodynamic activity of novel non-symmetrical diaryl porphyrins against cancer cell lines

Caruso, Enrico; Cerbara, Monica; Malacarne, M. C.; Marras, Emanuela; Monti, Elena; Gariboldi, Marzia Bruna

doi:10.1016/j.jphotobiol.2019.04.010

Cited by 21 publications

(36 citation statements)

References 38 publications

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“…In this study, a panel of diaryl-porphyrins bearing different substituents, In positions 5 and 15, conferring a different total charge, was considered. Among the neutral PSs, two non-symmetrical diaryl porphyrins bearing one pentafluorophenyl In position 5 differ by the length of the para-bromoalkoxy pendant of the phenyl In position 15, 4C In 1 and 8C In 2, respectively [39]. The neutral porphyrin 3 bears one pendant of 4C, and the symmetrical PS 4 bears two identical pendants of 4C [35].…”

Section: Discussionmentioning

confidence: 99%

“…The neutral porphyrin 3 bears one pendant of 4C, and the symmetrical PS 4 bears two identical pendants of 4C [35]. The four mono-cationic PSs are non-symmetrical, bearing a phenyl (5,6) or a pentafluoro-phenyl (7,8) In position 5 and a pyridinobutoxy-phenyl (5,7) or pyridinooctaoxy-phenyl (6,8) In 15, respectively [35,39]. The three dicationic porphyrins are symmetric and bear a benzyl group as the alkylating group of the pyridyl substituent (9), or alkoxy-linked pyridinium at the end of one 4C (10) or 8C (11) carbon chains [35,38].…”

Section: Discussionmentioning

confidence: 99%

“…The chemical denomination and structure of diaryl-porphyrins used in this study are listed in Table 1 [35,38,39]. Four porphyrins were neutral (1)(2)(3)(4), four were monocationic (5)(6)(7)(8), and three were dicationic (9)(10)(11).…”

Section: Photosensitizersmentioning

confidence: 99%

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Photodynamic Therapy by Diaryl-Porphyrins to Control the Growth of Candida albicans

et al. 2020

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Candida albicans is an opportunistic pathogen that often causes skin infections such as oral thrush, nail fungus, athlete’s foot, and diaper rash. Under particular conditions, C. albicans alters the natural balance of the host microbiota, and as a result, the skin or its accessory structures lose their function and appearance. Conventional antimycotic drugs are highly toxic to host tissues, and long-lasting drug administration induces the arising of resistant strains that make the antimycotic therapy ineffective. Among new antimicrobial approaches to combine with traditional drugs, light-based techniques are very promising. In this study, a panel of dyes was considered for photodynamic therapy (PDT) applications to control the growth of the model strain C. albicans ATCC 14053. The chosen photosensitizers (PSs) belong to the family of synthetic porphyrins, and in particular, they are diaryl-porphyrins. Among these, two monocationic PSs were shown to be particularly efficient in killing C. albicans upon irradiation with light at 410 nm, in a light-dose-dependent manner. The elicited photo-oxidative stress induced the loss of the internal cellular architecture and death. The photodynamic treatment was also successful in inhibiting the biofilm formation of clinical C. albicans strains. In conclusion, this study supports the great potential of diaryl-porphyrins in antimicrobial PDT to control the growth of yeasts on body tissues easily reachable by light sources, such as skin and oral cavity.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Photodynamic Therapy by Diaryl-Porphyrins to Control the Growth of Candida albicans

et al. 2020

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“…A panel of novel diaryl-porphyrins, synthetized by our group and previously tested as antimicrobials [33] antifungals [32] and antitumorals [31,34], was investigated for anti-Pseudomonas activity (Table 1). The neutral and asymmetrical P1 and P2 bear in mesopositions (positions 5 and 15) a pentafluorophenyl group, associated with a C4 or C8 para-bromoalkyloxy-phenyl group, respectively.…”

Section: Panel Of Diaryl-porphyrinsmentioning

confidence: 99%

“…A panel of 13 diaryl-porphyrins previously described [31,33,34] has been used in this study (Table 1). As shown in Figure 1, P1-P6 porphyrins are neutral molecules, P7-P10 are monocationic and P11-P13 di-cationic, respectively.…”

Section: Photosensitizersmentioning

confidence: 99%

Photoinactivation of Pseudomonas aeruginosa Biofilm by Dicationic Diaryl-Porphyrin

Orlandi

Martegani

Bolognese

et al. 2021

IJMS

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In recent years, antimicrobial photodynamic therapy (aPDT) has received increasing attention as a promising tool aimed at both treating microbial infections and sanitizing environments. Since biofilm formation on biological and inert surfaces makes difficult the eradication of bacterial communities, further studies are needed to investigate such tricky issue. In this work, a panel of 13 diaryl-porphyrins (neutral, mono- and di-cationic) was taken in consideration to photoinactivate Pseudomonas aeruginosa. Among cationic photosensitizers (PSs) able to efficiently bind cells, in this study two dicationic showed to be intrinsically toxic and were ruled out by further investigations. In particular, the dicationic porphyrin (P11) that was not toxic, showed a better photoinactivation rate than monocationic in suspended cells. Furthermore, it was very efficient in inhibiting the biofilms produced by the model microorganism Pseudomonas aeruginosa PAO1 and by clinical strains derived from urinary tract infection and cystic fibrosis patients. Since P. aeruginosa represents a target very difficult to inactivate, this study confirms the potential of dicationic diaryl-porphyrins as photo-activated antimicrobials in different applicative fields, from clinical to environmental ones.

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Porphyrin and Phthalocyanine as Materials for Glass Coating—Structure and Properties

Popanda

Środa²

2023

Advances in Material Research and Technology

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Synthesis and photodynamic activity of novel non-symmetrical diaryl porphyrins against cancer cell lines

Cited by 21 publications

References 38 publications

Photodynamic Therapy by Diaryl-Porphyrins to Control the Growth of Candida albicans

Photodynamic Therapy by Diaryl-Porphyrins to Control the Growth of Candida albicans

Photoinactivation of Pseudomonas aeruginosa Biofilm by Dicationic Diaryl-Porphyrin

Porphyrin and Phthalocyanine as Materials for Glass Coating—Structure and Properties

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