Spectroscopic and time-resolved fluorescence emission properties of a cationic and an anionic porphyrin in biomimetic media and Candida albicans cells

Novaira, Mercedes; Cormick, M. Paula; Durantini, Edgardo N.

doi:10.1016/j.jphotochem.2012.06.024

Cited by 16 publications

(11 citation statements)

References 28 publications

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“…This partial aggregation of BCS can preclude the photophysical properties of this photosensitizer in aqueous medium . However, the main photodynamic action that leads to microbial death is induced by the photosensitizer that binds to the cells . Data for BCA in PBS is not given due to minimal solubility of this bacteriochlorin in aqueous media.…”

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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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%

“…This uptake can mainly occur as the cell envelope becomes damaged by the photodynamic action. It is even conceivable that a redistribution of the photosensitizer also occurs in the cellular components .…”

Section: Resultsmentioning

confidence: 99%

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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“…Similar results were previously found for porphyrin derivatives bound to microbial cells. 28,30 In solution, the Φ F value of BODIPY 4 was about one order of magnitude lower than BODIPY 3 due to free rotation of the meso-phenyl group. 15 However, the fluorescence intensity of BODIPYs 3 and 4 bound to the cells does not show differences between both BODIPYs.…”

Section: Discussionmentioning

confidence: 96%

Photodynamic inactivation of microorganisms sensitized by cationic BODIPY derivatives potentiated by potassium iodide

Reynoso

Quiroga

Agazzi

et al. 2017

Photochem Photobiol Sci

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The photodynamic inactivation mediated by 1,3,5,7-tetramethyl-8-[4-(N,N,N-trimethylamino)phenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene 3 and 8-[4-(3-(N,N,N-trimethylamino)propoxy)phenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene 4 was investigated on Staphylococcus aureus, Escherichia coli and Candida albicans. In vitro experiments indicated that BODIPYs 3 and 4 were rapidly bound to microbial cells at short incubation periods. Also, fluorescence microscopy images showed green emission of BODIPYs bound to microbial cells. Photosensitized inactivation improved with an increase of the irradiation time. Similar photoinactivation activities were found for both BODIPYs in bacteria. The photoinactivation induced by these BODIPYs was effective for both bacteria. However, the Gram-positive bacterium was inactivated sooner and with a lower concentration of a photosensitizer than the Gram-negative bacterium. After 15 min irradiation, the complete eradication of S. aureus was obtained with 1 μM photosensitizer. A reduction of 4.5 log in the E. coli viability was found when using 5 μM photosensitizer and 30 min irradiation. Also, the last conditions produced a decrease of 4.5 log in C. albicans cells treated with BODIPY 3, while 4 was poorly effective. On the other hand, the effect of the addition of KI on photoinactivation at different irradiation periods and salt concentrations was investigated. A smaller effect was observed in S. aureus because the photosensitizers alone were already very effective. In E. coli, photokilling potentiation was mainly found at longer irradiation periods. Moreover, the photoinactivation of C. albicans mediated by these BODIPYs was increased in the presence of KI. In solution, an increase in the formation of the BODIPY triplet states was observed with the addition of the salt, due to the effect of external heavy atoms. The greater intersystem crossing together with the formation of reactive iodine species induced by BODIPYs may be contributing to enhance the inactivation of microorganisms. Therefore, these BODIPYs represent interesting photosensitizers to inactivate microorganisms. In particular, BODIPY 3 in combination with KI was highly effective as a broad spectrum antimicrobial photosensitizer.

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“…The amount of water in the system was reported as the molar ratio between water and the AOT (W 0 = [H 2 O]/[AOT]). In all experiments, W 0 = 10 was used and the mixtures were sonicated for about 10 s to obtain a clear micellar system (28).…”

Section: Methodsmentioning

confidence: 99%

Tuning the Polarity of Fullerene C₆₀ Derivatives for Enhanced Photodynamic Inactivation^†

Palacios

Durantini

Heredia

et al. 2021

Photochem & Photobiology

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In this article, four novel fulleropyrrolidines derivatives were synthesized to study how the effect of polarity and positive charge distribution can influence the efficacy of photodynamic inactivation treatments to kill bacteria. The design of the photosensitizers was based on DFT calculations that allowed us to estimate the dipolar moment of the molecules. Neutral compounds bearing N-methyl bis-acetoxy-ethyl (1) and bis-hydroxyethyl (2) amine were the starting material to obtain the dicationic analogs N,N-dimethyl bis-methoxyethyl (3), and bis-acetoxy-ethyl) (4) methylammonio. As expected from fullerene C 60 derivatives, compounds 1-4 absorb in the UV region, with a peak at 430 nm, a broader range of absorption up to 710 nm, and exhibit weak fluorescence emission in toluene and reverse micelles. In the biomimetic AOT micellar system, the highest singlet oxygen photosensitization was found for compounds 1, followed by 3, 2, and 4. Whereas 4 was the most effective reducing nitro blue tetrazolium in the presence of β-NADH. The influence of type I and type II mechanism on the photodynamic activity of compounds 3 and 4 was further examined in the presence of Ltryptophan and two reactive oxygen species scavengers. In vitro experiments indicated that the compounds with the highest dipolar moments, 3 (37.19 D) and 4 (38.46 D), inactivated methicillin-resistant Staphylococcus aureus and Escherichia coli bacteria using an energy dose <2.4 J cm −2 . No inactivation was observed for the neutral analogs with the lowest dipolar moments. These findings help to optimize sensitizer structures to improve photodynamic inactivation.

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Spectroscopic and time-resolved fluorescence emission properties of a cationic and an anionic porphyrin in biomimetic media and Candida albicans cells

Cited by 16 publications

References 28 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 inactivation of microorganisms sensitized by cationic BODIPY derivatives potentiated by potassium iodide

Tuning the Polarity of Fullerene C₆₀ Derivatives for Enhanced Photodynamic Inactivation^†

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Spectroscopic and time-resolved fluorescence emission properties of a cationic and an anionic porphyrin in biomimetic media and Candida albicans cells

Cited by 16 publications

References 28 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 inactivation of microorganisms sensitized by cationic BODIPY derivatives potentiated by potassium iodide

Tuning the Polarity of Fullerene C60 Derivatives for Enhanced Photodynamic Inactivation†

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Product

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Tuning the Polarity of Fullerene C₆₀ Derivatives for Enhanced Photodynamic Inactivation^†