Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents

Scanone, Ana Coral; Gsponer, Natalia Soledad; Alvarez, M. Gabriela; Durantini, Edgardo N.

doi:10.1016/j.pdpdt.2018.09.017

Cited by 28 publications

(48 citation statements)

References 35 publications

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“…Considering the p K A values of spermine , the acid‐base equilibria of the amine groups should be shifted to the protonated form. Therefore, a high percentage of the amine groups can acquire positive charges by protonation in water, increasing the interaction with the cell envelope . Moreover, it was previously demonstrated that photosensitizers with basic amine groups are as effective as those with intrinsic positive charges to inactivate microorganisms .…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, both the presence of positive charges and the amphiphilic character appear to play an important role in the molecular structure of effective photosensitizers to eradicate microorganisms . In this sense, spermine is a polyamine that is found as a polycation in a biological medium, converting BCS into an effective photosensitizer to kill microorganisms.…”

Section: Resultsmentioning

confidence: 99%

“…Bacterial suspensions in PBS (1 mL, ~10 8 CFU/mL) were incubated with the corresponding bacteriochlorin at different concentrations for 30 minutes in the dark at 37°C . The bacteriochlorins were added from stock solutions in DMF (0.5 mM).…”

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Bacteriochlorin‐bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms

Ballatore

Milanesio

Fujita

et al. 2019

Journal of Biophotonics

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A novel bacteriochlorin bearing two spermine units (BCS) was synthesized from 3, 8,18,13 ). The synthesis involved the Suzuki coupling of BC-Br 3,13 to obtain a bacteriochlorin-dibenzaldehyde (BCA), which was subjected to reductive amination with spermine. The resulting bacteriochlorin BCS presents a strong near-infrared absorption band at 747 nm, emits at 750 nm with fluorescence quantum yield of 0.14, and generates singlet molecular oxygen, O 2 ( 1 Δ g ), with a quantum yield of 0.27. Photokilling capacities mediated by BCS were evaluated in microbial cells. The viability of Staphylococcus aureus decreased 7 logs when cells were incubated with 1 μM BCS and irradiated for 15 minutes. Comparable photocytotoxic effect was obtained with Escherichia coli, when cells were treated for 30 minutes with visible light. BCS was also an effective photosensitizer to inactivate Candida albicans. In addition, this bacteriochlorin was able to eradicate bacteria at short incubation times. The structure of BCS contains eight basic amino groups that, when protonated in water, increase the binding to the cell envelope. In summary, the readily accessible bacteriochlorin BCS was highly effective at low concentrations as a broad-spectrum antimicrobial photosensitizer.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Bacteriochlorin‐bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms

Ballatore

Milanesio

Fujita

et al. 2019

Journal of Biophotonics

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“…Recently, a mixed porphyrin formulation, containing mono-, di-, tri-, and tetra-Py(+)-Me, was shown to control C. albicans In plasma and In whole blood efficiently [46]. Thus, porphyrins, widely investigated to photoinactivate bacteria, represent a family of promising photo-antifungals [47]. Among porphyrins, novel diaryl-porphyrins were active against Bacillus subtilis, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa [35,38].…”

Section: Discussionmentioning

confidence: 99%

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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“…In this sense, it is interesting to develop porphyrins asymmetrically substituted in the meso positions by two different structures (A and B). In these compounds, structure A has a functional group that allows covalent attachment to other molecules, while B is substituted by groups that allows changing the properties of the tetrapyrrolic macrocycle [5,6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Porphyrins with ABAB Symmetry from Dipyrromethanes as Potential Phototherapeutic Agents

Boarini

Pérez

Milanesio

et al. 2020

The 24th International Electronic Conference on Synthetic Organic Chemistry

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Asymmetrically meso-substituted porphyrins were synthesized with ABAB symmetry patterns. The approach required the formation of dipyrromethanes, which were obtained from the condensation of an aldehyde (pentafluorobenzaldehyde, 4-nitrobenzaldehyde or N,Ndiphenylaminobenzaldehyde) with a large excess of pyrrole (1:47 aldehyde/pyrrole mol ratio), catalyzed by trifluoroacetic acid in 70-94% yields. Then, acid catalyzed condensation of these dipyrromethanes with an aldehyde (N,N-dimethylaminobenzaldehyde, 4-carboxymethyl benzaldehyde or N-ethyl-3-carbazolecarbaldehyde) (1:1 mol ratio) in dichloromethane, followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone affords the diseased porphyrins in 10-42% yields. These ABAB-porphyrins are interesting starting materials to obtain photoactive molecular structures as potential phototherapeutic agents.

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Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents

Cited by 28 publications

References 35 publications

Bacteriochlorin‐bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms

Bacteriochlorin‐bis(spermine) conjugate affords an effective photodynamic action to eradicate microorganisms

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

Synthesis of Porphyrins with ABAB Symmetry from Dipyrromethanes as Potential Phototherapeutic Agents

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