Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents

Pérez, M. E.; Durantini, Javier E.; Reynoso, Eugenia; Alvarez, M. Gabriela; Milanesio, M. Elisa; Durantini, Edgardo N.

doi:10.3390/molecules26195877

Cited by 18 publications

(22 citation statements)

References 55 publications

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“…•− ) [423,424]; similar findings have been obtained when using KI with cationic BOD-IPY derivatives [425] or porphyrin-Schiff base conjugates bearing basic amino groups [426]. Potassium thiocyanate and potassium selenocyanate could also form reactive species, such as the sulfur trioxide radical anion and selenocyanogen (SeCN) 2 , respectively [427].…”

Section: Addition Of Inorganic Saltssupporting

confidence: 59%

Antimicrobial Photodynamic Therapy: Latest Developments with a Focus on Combinatory Strategies

et al. 2021

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Antimicrobial photodynamic therapy (aPDT) has become a fundamental tool in modern therapeutics, notably due to the expanding versatility of photosensitizers (PSs) and the numerous possibilities to combine aPDT with other antimicrobial treatments to combat localized infections. After revisiting the basic principles of aPDT, this review first highlights the current state of the art of curative or preventive aPDT applications with relevant clinical trials. In addition, the most recent developments in photochemistry and photophysics as well as advanced carrier systems in the context of aPDT are provided, with a focus on the latest generations of efficient and versatile PSs and the progress towards hybrid-multicomponent systems. In particular, deeper insight into combinatory aPDT approaches is afforded, involving non-radiative or other light-based modalities. Selected aPDT perspectives are outlined, pointing out new strategies to target and treat microorganisms. Finally, the review works out the evolution of the conceptually simple PDT methodology towards a much more sophisticated, integrated, and innovative technology as an important element of potent antimicrobial strategies.

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Section: Addition Of Inorganic Saltssupporting

confidence: 59%

Antimicrobial Photodynamic Therapy: Latest Developments with a Focus on Combinatory Strategies

et al. 2021

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“…The PDI of E. coli sensitized by PZnTEP was also evaluated in presence of KI. This inorganic salt has shown impressive bacterial killing when combined with PDI [ 26 , 27 , 39 , 40 , 41 , 42 ]. The improved therapy results from the formation of a triiodide anion after reaction of iodide anion with traces amounts of O 2 ( 1 Δ g ) ( Scheme S1 ) [ 26 , 43 ].…”

Section: Resultsmentioning

confidence: 99%

“…The improved therapy results from the formation of a triiodide anion after reaction of iodide anion with traces amounts of O 2 ( 1 Δ g ) ( Scheme S1 ) [ 26 , 43 ]. In this work, we incubated E. coli with 100 mM KI; this concentration was selected because no toxicity was found herein ( Figure 5 B, treatment 5) and previous studies [ 27 ]. Also, this inorganic salt was not toxic for E. coli exposed to irradiation for 15 and 30 min ( Figure S5 , treatments 4 and 5).…”

Section: Resultsmentioning

confidence: 99%

“…Cells were exposed for different time intervals (15 and 30 min, which represent 81 and 162 J/cm 2 , respectively) to white light (90 mW/cm 2 , Figure S2B,C ). For PDI tests of E. coli in presence of KI, before adding PZnTEP (1.0 µM) the cell suspensions (2mL, 10 8 CFU/mL) were previously treated with 100 mM KI for 30 min at 37 °C in the dark [ 27 ]. KI was added from an aqueous 1.0 M solution.…”

Section: Methodsmentioning

confidence: 99%

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Antimicrobial Photosensitizing Material Based on Conjugated Zn(II) Porphyrins

et al. 2022

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The widespread use of antibiotics has led to a considerable increase in the resistance of microorganisms to these agents. Consequently, it is imminent to establish new strategies to combat pathogens. An alternative involves the development of photoactive polymers that represent an interesting strategy to kill microbes and maintain aseptic surfaces. In this sense, a conjugated polymer (PZnTEP) based on Zn(II) 5,10,15,20-tetrakis-[4-(ethynyl)phenyl]porphyrin (ZnTEP) was obtained by the homocoupling reaction of terminal alkyne groups. PZnTEP exhibits a microporous structure with high surface areas allowing better interaction with bacteria. The UV-visible absorption spectra show the Soret and Q bands of PZnTEP red-shifted by about 18 nm compared to those of the monomer. Also, the conjugate presents the two red emission bands, characteristic of porphyrins. This polymer was able to produce singlet molecular oxygen and superoxide radical anion in the presence of NADH. Photocytotoxic activity sensitized by PZnTEP was investigated in bacterial suspensions. No viable Staphylococcus aureus cells were detected using 0.5 µM PZnTEP and 15 min irradiation. Under these conditions, complete photoinactivation of Escherichia coli was observed in the presence of 100 mM KI. Likewise, no survival was detected for E. coli incubated with 1.0 µM PZnTEP after 30 min irradiation. Furthermore, polylactic acid surfaces coated with PZnTEP were able to kill efficiently these bacteria. This surface can be reused for at least three photoinactivation cycles. Therefore, this conjugated photodynamic polymer is an interesting antimicrobial photoactive material for designing and developing self-sterilizing surfaces.

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“…Emission spectrum of the broadband radiation source is shown in Figure S1. The projector was placed vertically with the light beam focused on the 96-well microtiter plate lid, producing a fluence rate of 90 mW/cm 2 [16,17].…”

Section: Instrumentationmentioning

confidence: 99%

Photodynamic Effect of 5,10,15,20-Tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]chlorin towards the Human Pathogen Candida albicans under Different Culture Conditions

et al. 2021

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Photocytotoxic activity sensitized by 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]chlorin (TAPC) was investigated in Candida albicans under different culture conditions. Planktonic cells incubated with 2.5 μM TAPC were eradicated after 5 min irradiation with white light. Studies in the presence of reactive oxygen species scavengers indicated the involvement of mainly a type II mechanism. Furthermore, cell growth of C. albicans was suppressed in the presence of 5 μM TAPC. A decrease in pseudohyphae survival of 5 log was found after 30 min irradiation. However, the photokilling of this virulence factor reached a 1.5 log reduction in human serum. The uptake of TAPC by pseudohyphae decreased in serum due to the interaction of TAPC with albumin. The binding constant of the TAPC-albumin complex was ~104 M−1, while the bimolecular quenching rate constant was ~1012 s−1 M−1, indicating that this process occurred through a static process. Thus, the photoinactivation of C. albicans was considerably decreased in the presence of albumin. A reduction of 2 log in cell survival was observed using 4.5% albumin and 30 min irradiation. The results allow optimizing the best conditions to inactivate C. albicans under different culture conditions.

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Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents

Cited by 18 publications

References 55 publications

Antimicrobial Photodynamic Therapy: Latest Developments with a Focus on Combinatory Strategies

Antimicrobial Photodynamic Therapy: Latest Developments with a Focus on Combinatory Strategies

Antimicrobial Photosensitizing Material Based on Conjugated Zn(II) Porphyrins

Photodynamic Effect of 5,10,15,20-Tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]chlorin towards the Human Pathogen Candida albicans under Different Culture Conditions

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