Chlorophyllin Derivatives as Photosensitizers: Synthesis and Photodynamic Properties

Fernandes, Adjaci Uchôa; Konopko, Aaron M.; Baptista, Maurı́cio S.

doi:10.5935/0103-5053.20150290

Cited by 15 publications

(22 citation statements)

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“…Although few studies have indicated the potential use of E-141ii to promote aPDI of S. aureus , its capability of acting successfully as a PS against an MRSA strain is demonstrated here for the first time. Despite demanding a higher concentration to photoinactivate the MRSA, the present findings demonstrated that the E-141ii can be applied to efficiently photoinactivate both MRSA and MSSA under red-light illumination as successfully applications using E-141ii and other chlorophyll derivatives typically apply concentrations in the 1.0 to 100.0 µM range, depending on the light dose and wavelength [ 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 32 , 33 ]. We also verified that MRSA was less susceptible to aPDI than MSSA at p < 0.05 (paired sample t -test) as presented in Figure 4 , requiring a higher concentration of E-141ii to inhibit bacterial growth.…”

Section: Resultsmentioning

confidence: 98%

“…However, despite its potential as a PS for photoinactivation, metal-free sodium chlorophyllin (E-140ii) is the chlorophyll derivative most applied in aPDI. The rare use of E-141ii in aPDI may be related to a premise that E-141ii could not work as a PS because of the lack of long-lived excited state due to the presence of the paramagnetic Cu 2+ in its chemical structure [ 23 ]. Sciuti et al reported that E-141ii does not have an electronic population in long-lived excited states, as a triplet state, and has no fluorescence, exhibiting a rapid deexcitation of the first excited singlet state (~25 ps) due to the internal conversion process [ 39 ].…”

Section: Resultsmentioning

confidence: 99%

“…It is important to point out that E-141ii is a natural green colorant derived from chlorophyll authorized as a food additive in several countries (for instance, Europe, United States, and Brazil) [ 19 , 20 , 21 , 22 ]. As a food additive, E-141ii is a non-toxic compound, and it also presents a high extinction coefficient in the photodynamic therapy window (600–700 nm range), which is a desired feature of a good PS for medical applications [ 23 ]. Furthermore, in contrast to chlorophyll, E-141ii is water-soluble and stable to oxidation.…”

Section: Introductionmentioning

confidence: 99%

“…There are only a few reports on the antibacterial photoactivity of E-141ii [ 5 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ]. Lopez-Carballo et al tested the aPDI efficacy of E-141ii against Gram-positive and Gram-negative bacteria when incorporated into gelatin films [ 24 ].…”

Section: Introductionmentioning

confidence: 99%

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Photodynamic Inactivation of Methicillin-Resistant Staphylococcus aureus by a Natural Food Colorant (E-141ii)

et al. 2020

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This study evaluates the photosensitizing effectiveness of sodium copper chlorophyllin, a natural green colorant commonly used as a food additive (E-141ii), to inactivate methicillin-sensitive and methicillin-resistant Staphylococcus aureus under red-light illumination. Antimicrobial photodynamic inactivation (aPDI) was tested on a methicillin-sensitive reference strain (ATCC 25923) and a methicillin-resistant Staphylococcus aureus strain (GenBank accession number Mh087437) isolated from a clinical sample. The photoinactivation efficacy was investigated by exposing the bacterial strains to different E-141ii concentrations (0.0, 1.0, 2.5, 5.0, 10.0, and 20.0 µM) and to red light (625 nm) at 30 J cm−2. The results showed that E-141ii itself did not prevent bacterial growth for all tested concentrations when cultures were placed in the dark. By contrast, E-141ii photoinactivated both methicillin-sensitive Staphylococcus aureus (MSSA) and methicillin-resistant Staphylococcus aureus (MRSA) under red-light illumination. However, different dose responses were observed for MSSA and MRSA. Whilst the MSSA growth was inhibited to the detection limit of the method with E-141ii at 2.5 µM, >10 µM concentrations were required to inhibit the growth of MRSA. The data also suggest that E-141ii can produce reactive oxygen species (ROS) via Type I reaction by electron transfer from its first excited singlet state to oxygen molecules. Our findings demonstrate that the tested food colorant has great potential to be used in aPDI of MRSA.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Photodynamic Inactivation of Methicillin-Resistant Staphylococcus aureus by a Natural Food Colorant (E-141ii)

et al. 2020

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“…Furthermore, photobleaching of chlorophyllin was investigated 30 as well as that of chlorophyllin sodium copper salt which was found to be temperature dependent. 31 The purpose of this experiment is to use derivative of chlorophyllin sodium copper salt photosensitizer 32 shown in Figure 2 as a thermally and photochemical stable substitute of commercially available chlorophyllin sodium copper salt for the decomposition of diclofenac potassium as a model pharmaceutical contaminant present in water.…”

Section: Introductionmentioning

confidence: 99%

Photosensitizer Using Visible Light

Alzamly

Alawadhi

Ahmed

et al. 2018

Int J Innov Educ Res

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In this experiment, the visible light reactive photosensitizer (PS) derived from chlorophyllin sodium copper salt has been synthesized via a simple synthetic route. The enhanced photocatalytic activity for the decomposition of the pharmaceutical compound Diclofenac Potassium available as Voltfast sachets under visible light irradiation was demonstrated by comparing the photocatalytic decomposition of Diclofenac Potassium in the presence and absence of the new synthesized visible light photosensitizer under the same photocatalytic conditions. Based on the experimental results, higher activity was achieved for the sample composed of the new synthesized visible light photosensitizer. The photosensitized sample using the new derivative of chlorophyllin sodium copper salt exhibited approximately 21 times higher rate when compared with that of Chlorophyllin sodium copper salt sample. This photocatalytic activity can be attributed to the enhanced visible light harvesting of the new derivative of Chlorophyllin sodium copper salt.

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Synthesis of a poly(ethylene glycol) galloyl sensitizer tip for an ’all‐in‐one' photodynamic device

Ghogare

Greer

2016

Journal of Biophotonics

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This paper describes the synthesis of a specialized silica tip for an optical fiber device capable of delivering all components necessary for photodynamic therapy. Oxygen, light and a cleavable tripolyethylene glycol (PEG)-galloyl pheophorbide sensitizer are simultaneously delivered by the silica tip, where the tip was synthesized in six steps. A comparison of synthetic steps to reach PEGylated sensitizers bound to fluorinated silica and a previously reported Teflon/polyvinyl alcohol (PVA) nanocomposite ( Ghosh, G. et al. J. Phys. Chem. B 2015, 119, 4155- 4164) was made. The hydrolytic stability of the attached PEGs and the extent to which the PEG groups enhance solubility will also be discussed. The new triPEG-galloyl sensitizer has the potential for use in intraoperative pointsource photodynamic therapy which aims for precision treatment of residual disease. Schematic of the synthesis of a photoactive silica surface. It is composed of fluorinated silica connected to a photo-releasable sensitizer with short-chain PEGs.

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Chlorophyllin Derivatives as Photosensitizers: Synthesis and Photodynamic Properties

Cited by 15 publications

References 0 publications

Photodynamic Inactivation of Methicillin-Resistant Staphylococcus aureus by a Natural Food Colorant (E-141ii)

Photodynamic Inactivation of Methicillin-Resistant Staphylococcus aureus by a Natural Food Colorant (E-141ii)

Photosensitizer Using Visible Light

Synthesis of a poly(ethylene glycol) galloyl sensitizer tip for an ’all‐in‐one' photodynamic device

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