Photodynamic effect of meso-(aryl)porphyrins and meso-(1-methyl-4-pyridinium)porphyrins on HaCaT keratinocytes

Slomp, Amanda Martinez; Barreira, Sandra M. W.; Carrenho, Luise Zozula Blind; Vandresen, Camila Chevonica; Zattoni, Ingrid Fatima; Lo, S. M.; Dallagnol, Juliana C.C.; Ducatti, Diogo R.B.; Orsato, Alexandre; Duarte, Maria Eugênia R.; Noseda, Miguel D.; Otuki, Michel Fleith; Gonçalves, Alan G.

doi:10.1016/j.bmcl.2016.11.094

Cited by 28 publications

(16 citation statements)

References 38 publications

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“…Slomp's group synthesised a series of cationic porphyrin derivatives and screened their photosensitising activities against HaCaT keratinocytes. The results confirmed that cationic porphyrin PSs exhibited better photosensitivity than derivatives with neutral or negatively charged substituents 32 . Jensen et al 33 then synthesised several cationic porphyrin derivatives possessing -(CH 3 ) 3 þ groups.…”

Section: Functional Group-modified Porphyrin Derivativessupporting

confidence: 67%

Chemical approaches for the enhancement of porphyrin skeleton-based photodynamic therapy

Lin

Zhou

Bai

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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With the development of photodynamic therapy (PDT), remarkable studies have been conducted to generate photosensitisers (PSs), especially porphyrin PSs. A variety of chemical modifications of the porphyrin skeleton have been introduced to improve cellular delivery, stability, and selectivity for cancerous tissues. This review aims to highlight the developments in porphyrin-based structural modifications, with a specific emphasis on the role of PDT in anticancer treatment and the design of PSs to achieve a synergistic effect on multiple targets.

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Section: Functional Group-modified Porphyrin Derivativessupporting

confidence: 67%

Chemical approaches for the enhancement of porphyrin skeleton-based photodynamic therapy

Lin

Zhou

Bai

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Besides, the effect of the metals on the emission profiles has been previously observed for mesoporphyrinic macrocycles upon copper coordination . This behavior is transcendental for potential application of these compounds in PDT, where the main route on singlet oxygen generation relies on the non‐radiative decay . In contrast, only compounds 3 and 4 show higher fluorescence emission intensity than compound 1 , and also the highest fluorescence quantum yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin and (Zn²⁺, Mn²⁺, Sn²⁺, Ni²⁺, Al³⁺, V³⁺)‐Derivatives: Photophysical and DFT study

et al. 2019

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A novel family of porphyrins based on 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin (1) and six metallo‐derivatives (Zn2+(2), Sn2+(3), Mn2+ (4), Ni2+ (5), Al3+ (6) and V3+ (7)) were synthesized via the Alder‐cols method (synthesis yield between 59%‐75%) and characterized through 1H‐ and 13C‐ NMR, MALDI‐TOF mass spectrometry and FT‐IR assay. Photophysical study was carried out by UV‐Vis and fluorescence spectrophotometry with the aim of assessing their potential as dye sensitizers for photodynamic therapy (PDT). In this regard, fluorescence quantum yield values are between 0.002‐0.38, being the macrocycle 3, the porphyrin with the highest fluorescence quantum yield while the derivative 7 showed the lowest value. Quantum chemical calculations were carried out to study the molecular structure of the porphyrins and to get insight of the luminescent process for 1, which is the free metal system and 3 which includes Sn2+ as metal center. Results indicated that the emissive states involve the transitions with LLCT character for 1, while for 3 it is ML–LCT. This fact evidenced the metal effects on their photophysical properties. Finally, optical and spectroscopic properties and besides, DFT study suggest that 3 could be used as sensitizer in photodynamic therapy applications.

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“…In comparison, among anionic, neutral with polar groups and neutral hydrophobic porphyrins, only cationic meso-(1-methyl-4-pyridinium)porphyrins were shown to be PDT-efficient and were proposed to be used as PSs for psoriasis treatment. Amongst the cationic PSs, the most efficient were those with two and more charges, especially the dicationic cis-isomer, and those with methylpyridinium groups directly attached to the meso carbon of the porphyrin ring (Slomp et al 2017). Finally, two new derivatives of pyropheophorbide-a (PPa) have been synthesised and their PDT activity on SKOV3 ovarian cancer cells studied.…”

Section: Lipophilicity and Cellular Uptakementioning

confidence: 99%

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

2017

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Photodynamic therapy (PDT) combines a photosensitiser, light and molecular oxygen to induce oxidative stress that can be used to kill pathogens, cancer cells and other highly proliferative cells. There is a growing number of clinically approved photosensitisers and applications of PDT, whose main advantages include the possibility of selective targeting, localised action and stimulation of the immune responses. Further improvements and broader use of PDT could be accomplished by designing new photosensitisers with increased selectivity and bioavailability. Porphyrin-based photosensitisers with amphiphilic properties, bearing one or more positive charges, are an effective tool in PDT against cancers, microbial infections and, most recently, autoimmune skin disorders. The aim of the review is to present some of the recent examples of the applications and research that employ this specific group of photosensitisers. Furthermore, we will highlight the link between their structural characteristics and PDT efficiency, which will be helpful as guidelines for rational design and evaluation of new PSs.

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Photodynamic effect of meso-(aryl)porphyrins and meso-(1-methyl-4-pyridinium)porphyrins on HaCaT keratinocytes

Cited by 28 publications

References 38 publications

Chemical approaches for the enhancement of porphyrin skeleton-based photodynamic therapy

Chemical approaches for the enhancement of porphyrin skeleton-based photodynamic therapy

Synthesis and Characterization of 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin and (Zn²⁺, Mn²⁺, Sn²⁺, Ni²⁺, Al³⁺, V³⁺)‐Derivatives: Photophysical and DFT study

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

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Photodynamic effect of meso-(aryl)porphyrins and meso-(1-methyl-4-pyridinium)porphyrins on HaCaT keratinocytes

Cited by 28 publications

References 38 publications

Chemical approaches for the enhancement of porphyrin skeleton-based photodynamic therapy

Chemical approaches for the enhancement of porphyrin skeleton-based photodynamic therapy

Synthesis and Characterization of 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin and (Zn2+, Mn2+, Sn2+, Ni2+, Al3+, V3+)‐Derivatives: Photophysical and DFT study

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

Contact Info

Product

Resources

About

Synthesis and Characterization of 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin and (Zn²⁺, Mn²⁺, Sn²⁺, Ni²⁺, Al³⁺, V³⁺)‐Derivatives: Photophysical and DFT study