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

Gomes, Ana T. P. C.; Fernandes, Rosa; Ribeiro, Carlos; Tomé, João P. C.; Neves, Maria G. P. M. S.; Silva, Fernando de Carvalho da; Ferreira, Vı́tor F.; Cavaleiro, José A. S.

doi:10.3390/molecules25071607

Cited by 12 publications

(13 citation statements)

References 69 publications

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“…VPD was selected as the monomer to prepare PVP formulations due to their already reported features, namely, pharmacokinetic and pharmacological properties, non-toxicity, and water-solubility of the obtained micelles [ 96 ]. This strategy allows to improve the hydrophilicity of biologically active drugs and is being efficiently used to solubilize neutral porphyrin-base PS in water with positive effects in photodynamic processes [ 97 , 98 , 99 , 100 ]. Moreover, this carrier demonstrated to be non-toxic for both normal and cancer cells after PDT treatment [ 100 ].…”

Section: Resultsmentioning

confidence: 99%

“…This strategy allows to improve the hydrophilicity of biologically active drugs and is being efficiently used to solubilize neutral porphyrin-base PS in water with positive effects in photodynamic processes [ 97 , 98 , 99 , 100 ]. Moreover, this carrier demonstrated to be non-toxic for both normal and cancer cells after PDT treatment [ 100 ]. However, to the best of our knowledge, this approach has not been used with benzoporphyrin-type derivatives.…”

Section: Resultsmentioning

confidence: 99%

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Unraveling the Photodynamic Activity of Cationic Benzoporphyrin-Based Photosensitizers against Bladder Cancer Cells

et al. 2021

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In this study, we report the preparation of new mono-charged benzoporphyrin complexes by reaction of the appropriate neutral benzoporphyrin with (2,2′-bipyridine)dichloroplatinum(II) and of the analogs’ derivatives synthesized through alkylation of the neutral scaffold with iodomethane. All derivatives were incorporated into polyvinylpyrrolidone (PVP) micelles. The ability of the resultant formulations to generate reactive oxygen species was evaluated, mainly the singlet oxygen formation. Then, the capability of the PVP formulations to act as photosensitizers against bladder cancer cells was assessed. Some of the studied formulations were the most active photosensitizers causing a decrease in HT-1376 cells’ viability. This creates an avenue to further studies related to bladder cancer cells.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Unraveling the Photodynamic Activity of Cationic Benzoporphyrin-Based Photosensitizers against Bladder Cancer Cells

et al. 2021

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“…Next, 130 was submitted to a metallation reaction with Zn(OAc) 2, giving rise to 2‐bromo‐5,10,15,20‐tetraphenylporphyrinatozinc (II) 131 , which in turn undergoes a Heck coupling reaction with 4‐vinyl‐1,2,3‐triazoles 88 . Finally, the demetallation of 132 using trifluoroacetic acid (TFA) furnishes β‐substituted triazole‐porphyrins 133 in quantitative yields [93] . Importantly, singlet oxygen generation studies have revealed that all PVP‐ 133 formulations presented superior ability of producing ROS than PVP‐TPP, which is used as reference.…”

Section: Synthetic Strategies Toward 123‐triazole Derivativesmentioning

confidence: 99%

“…Importantly, singlet oxygen generation studies have revealed that all PVP‐ 133 formulations presented superior ability of producing ROS than PVP‐TPP, which is used as reference. In addition, the photodynamic effect of such formulations was evaluated in human bladder cancer cells (HT‐1376 cell line), and the results have shown that those are effective for PDT [93] …”

Section: Synthetic Strategies Toward 123‐triazole Derivativesmentioning

confidence: 99%

Bioactive 1,2,3‐Triazoles: An Account on their Synthesis, Structural Diversity and Biological Applications

Forezi

Lima

Amaral

et al. 2021

The Chemical Record

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The triazole heterocycle is a privileged scaffold in medicinal chemistry, since its structure is present in a large number of biologically active molecules, including several drugs currently in the market. Due to their vast applications, a wide variety of methods are described for their preparation, such as the 1,3‐dipolar cycloaddition and processes involving diazo compounds and diazo transfer reactions. Considering the significant number of contributions from our research group to this chemistry in recent decades, in this account we discuss both the development of new methods for the synthesis of 1,2,3‐triazoles and the preparation of new triazole‐functionalized biologically active molecules using classical approaches.

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“…Photodynamic therapy (PDT) is a non-invasive approach to treat oncological and non-oncological diseases (Figueira et al, 2014;Kwiatkowski et al, 2018;Mesquita et al, 2018a,b;Gazzi et al, 2019;Negri et al, 2019;Castro et al, 2020;Gomes et al, 2020;Lee et al, 2020). PDT is a clinically approved treatment based on the activation of a photosensitizer (PS) by the light of a specific wavelength, in the presence of molecular oxygen to produce reactive oxygen species (ROS), resulting in neoplastic cell death (Agostinis et al, 2011;Bogoeva et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Hybrid Nanoparticles as an Efficient Porphyrin Delivery System for Cancer Cells to Enhance Photodynamic Therapy

Silva

Castro

Botteon

et al. 2021

Front. Bioeng. Biotechnol.

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Photodynamic therapy (PDT) is a potential non-invasive approach for application in oncological diseases, based on the activation of a photosensitizer (PS) by light at a specific wavelength in the presence of molecular oxygen to produce reactive oxygen species (ROS) that trigger the death tumor cells. In this context, porphyrins are interesting PS because they are robust, have high chemical, photo, thermal, and oxidative stability, and can generate singlet oxygen (1O2). However, porphyrins exhibit low solubility and a strong tendency to aggregate in a biological environment which limits their clinical application. To overcome these challenges, we developed hybrid nanostructures to immobilize 5,10,15,20-tetrakis[(4-carboxyphenyl) thio-2,3,5,6-tetrafluorophenyl] (P), a new third-generation PS. The biological effect of this system was evaluated against bladder cancer (BC) cells with or without light exposition. The nanostructure composed of lipid carriers coated by porphyrin-chitosan (P-HNP), presented a size of ca. 130 nm and low polydispersity (ca. 0.25). The presence of the porphyrin-chitosan (P-chitosan) on lipid nanoparticle surfaces increased the nanoparticle size, changed the zeta potential to positive, decreased the recrystallization index, and increased the thermal stability of nanoparticles. Furthermore, P-chitosan incorporation on nanoparticles increased the stability and enhanced the self-organization of the system and the formation of spherical structures, as observed by small-angle X-ray scattering (SAXS) analysis. Furthermore, the immobilization process maintained the P photoactivity and improved the photophysical properties of PS, minimizing its aggregation in the cell culture medium. In the photoinduction assays, the P-HNP displayed high phototoxicity with IC50 3.2-folds lower than free porphyrin. This higher cytotoxic effect can be correlated to the high cellular uptake of porphyrin immobilized, as observed by confocal images. Moreover, the coated nanoparticles showed mucoadhesive properties interesting to its application in vivo. Therefore, the physical and chemical properties of nanoparticles may be relevant to improve the porphyrin photodynamic activity in BC cells.

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

Cited by 12 publications

References 69 publications

Unraveling the Photodynamic Activity of Cationic Benzoporphyrin-Based Photosensitizers against Bladder Cancer Cells

Unraveling the Photodynamic Activity of Cationic Benzoporphyrin-Based Photosensitizers against Bladder Cancer Cells

Bioactive 1,2,3‐Triazoles: An Account on their Synthesis, Structural Diversity and Biological Applications

Hybrid Nanoparticles as an Efficient Porphyrin Delivery System for Cancer Cells to Enhance Photodynamic Therapy

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