An efficient synthetic access to new uracil-alditols bearing a porphyrin unit and biological assessment in prostate cancer cells

Dias, Cristina J.; Sardo, Inês; Moura, Nuno M. M.; Felgueiras, Juliana; Neves, Maria G. P. M. S.; Fardilha, Margarida; Faustino, Maria A. F.

doi:10.1016/j.dyepig.2019.107996

Cited by 14 publications

(8 citation statements)

References 56 publications

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“…Photodynamic therapy (PDT) has been used as an effective approach to treat several types of cancer, namely nonmelanoma skin cancers (NMSC), 1 bladder, 2 breast, 3 lung, and prostate cancer, 4 among others. 5−8 Essentially, the PDT action requires light irradiation at a specific wavelength of a photosensitizer (PS) that in the presence of dioxygen ( 3 O 2 ) leads to the formation of cytotoxic reactive oxygen species (ROS) that are responsible for the cell death.…”

Section: ■ Introductionmentioning

confidence: 99%

Comparison of the Photodynamic Action of Porphyrin, Chlorin, and Isobacteriochlorin Derivatives toward a Melanotic Cell Line

Castro

Ramos

Mesquita

et al. 2021

ACS Appl. Bio Mater.

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Melanoma is the most dangerous form of skin cancer, with an abrupt growth of its incidence over the last years. It is extremely resistant to traditional treatments such as chemotherapy and radiotherapy, but therapies for this cancer are gaining attention. Photodynamic therapy (PDT) is considered an effective modality to treat several types of skin cancers and can offer the possibility to treat one of the most aggressive ones: melanoma. In this work, the effect of PDT on a melanotic cell line (B16F10 cells) was assessed by exposing cultured cells to 5,10,15-tris(pentafluorophenyl)-20-(4pyridyl)porphyrin (PS1) and to its chlorin (PS2) and isobacteriochlorin (PS3) corresponding derivatives and red LED light (λ = 660 ± 20 nm). The PDT effect in the cells' viability was measured using the MTT assay. The cell apoptosis was quantified by flow cytometry, and the subcellular localization of the photosensitizer was determined by fluorescence microscopy. In addition, the ability of PS2 to generate superoxide radicals was qualitatively assessed by tyrosine nitration. The results show that the efficiency of the PDT process is dependent on the structure of the PS and on their ability to produce singlet oxygen. Besides that, the photoactivation efficiency is highly dependent on the cellular sublocalization of the PS and on its cellular uptake and singlet oxygen production. We also found that the resistant cell line B16F10 has distinctive chlorin, isobacteriochlorin, or porphyrin-specific resistance profiles. Furthermore, it is shown that the highly fluorescent chlorin derivative PS2 can also be considered in imaging diagnostics.

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Section: ■ Introductionmentioning

confidence: 99%

Comparison of the Photodynamic Action of Porphyrin, Chlorin, and Isobacteriochlorin Derivatives toward a Melanotic Cell Line

Castro

Ramos

Mesquita

et al. 2021

ACS Appl. Bio Mater.

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“…In fact, PDT efficiency can be enhanced by improving intracellular targeting ability of a PS [17]. One of the approaches to reach this selectivity is based on the synthesis of porphyrins bearing targeting moieties, like carbohydrate units [13,15,19,[23][24][25][26], cyclodextrins [13,[27][28][29][30], human serum albumin and monoclonal antibodies [13,[31][32][33], among others. Other moieties that merit attention are based on triazoles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Photodynamic Activity against Bladder Cancer Cells of Novel Triazole-Porphyrin Derivatives

et al. 2020

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Novel triazole-porphyrin derivatives (TZ-PORs) were synthesized through the Heck reaction and then incorporated into polyvinylpyrrolidone (PVP) micelles. After verifying that this incorporation did not compromise the photophysical and chemical features of TZ-PORs as photosensitizers, the phototoxicity of the formulations towards cancer cells was screened. Biological studies show high photodynamic activity of all PVP-TZ-POR formulations against a bladder cancer cell line with a particular highlight to PVP-TZ-POR 7e and 7f that are able to significantly reduce HT-1376 cell viability, while they had no effect on control ARPE-19 cells.

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“…Nevertheless, most porphyrins are weak emitters, have solubility issues, and tend to aggregate in water [ 10 , 11 ], thus hampering most cases for their application in biomedicine. Porphyrinoids’ functionalization with hydrophilic units [ 12 , 13 , 14 , 15 ] is an elegant synthetic strategy used to overcome porphyrins’ low solubility. Nanotechnological development, is also encouraging the use of different nanoparticles such as gold nanoparticles (AuNP), as porphyrinoid carriers to improve imaging and photodynamic capabilities [ 16 , 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Merging Porphyrins with Gold Nanorods: Self Assembly Construct to High Fluorescent Polyelectrolyte Microcapsules

Serra

Vallejo

et al. 2022

Nanomaterials

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Dual probe porphyrin-gold nanorod polyelectrolyte microcapsules were developed to explore the enhancing effects of a plasmonic interface of self-assembled gold nanoparticles in the fluorescence emission from porphyrins loaded into the capsules’ core. An analysis of fluorescence lifetime imaging microscopy (FLIM) data reports a notable 105–106-fold increase in the maximum detected photon rates from diffraction-limited spots and an overall six-fold increase in fluorescence as averaged over the whole microcapsule area. Large emission enhancements were correlated with decreases in fluorescence lifetimes. The microcapsule’s design proved effective in achieving high fluorescent hybrids and may shed light on new possibilities for advanced materials imaging applications.

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An efficient synthetic access to new uracil-alditols bearing a porphyrin unit and biological assessment in prostate cancer cells

Cited by 14 publications

References 56 publications

Comparison of the Photodynamic Action of Porphyrin, Chlorin, and Isobacteriochlorin Derivatives toward a Melanotic Cell Line

Comparison of the Photodynamic Action of Porphyrin, Chlorin, and Isobacteriochlorin Derivatives toward a Melanotic Cell Line

Synthesis, Characterization and Photodynamic Activity against Bladder Cancer Cells of Novel Triazole-Porphyrin Derivatives

Merging Porphyrins with Gold Nanorods: Self Assembly Construct to High Fluorescent Polyelectrolyte Microcapsules

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