Cytotoxicity of structurally-modified chlorins aimed for photodynamic therapy applications

Linares, Irwin Alexander Patiño; Martinelli, Letícia Palombo; Moritz, Milene Nóbrega de Oliveira; Selistre-de-Araújo, Heloísa Sobreiro; Oliveira, Kléber T. de; Perussi, Janice Rodrigues

doi:10.1016/j.jphotochem.2021.113647

Cited by 7 publications

(4 citation statements)

References 43 publications

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“…Chlorins, also known as dihydroporphyrins, are porphyrinic dyes with attractive photophysical characteristics, namely improved absorption in the red region compared to traditional porphyrins [ 177 ]. The preparation of these molecules is usually initiated by derivatizing porphyrins; however, their purification is hampered by the fact that they are critically unstable, either because of the ease of retro-oxidation in porphyrins or because they are not very stable to light, as well as because, generally, multi-step synthesis is necessary, making their preparation even more challenging [ 178 ].…”

Section: N -Heterocyclic-bearing Dyes As Photodynamic Therap...mentioning

confidence: 99%

Photodynamic Therapy: From the Basics to the Current Progress of N-Heterocyclic-Bearing Dyes as Effective Photosensitizers

Lima

Reis

2023

Molecules

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Photodynamic therapy, an alternative that has gained weight and popularity compared to current conventional therapies in the treatment of cancer, is a minimally invasive therapeutic strategy that generally results from the simultaneous action of three factors: a molecule with high sensitivity to light, the photosensitizer, molecular oxygen in the triplet state, and light energy. There is much to be said about each of these three elements; however, the efficacy of the photosensitizer is the most determining factor for the success of this therapeutic modality. Porphyrins, chlorins, phthalocyanines, boron-dipyrromethenes, and cyanines are some of the N-heterocycle-bearing dyes’ classes with high biological promise. In this review, a concise approach is taken to these and other families of potential photosensitizers and the molecular modifications that have recently appeared in the literature within the scope of their photodynamic application, as well as how these compounds and their formulations may eventually overcome the deficiencies of the molecules currently clinically used and revolutionize the therapies to eradicate or delay the growth of tumor cells.

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Section: N -Heterocyclic-bearing Dyes As Photodynamic Therap...mentioning

confidence: 99%

Photodynamic Therapy: From the Basics to the Current Progress of N-Heterocyclic-Bearing Dyes as Effective Photosensitizers

Lima

Reis

2023

Molecules

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“…In PDT applications, chlorins surpass porphyrins, as they exhibit strong absorption at longer wavelengths (650–690 nm), a higher molar absorption coefficient, deeper tumour tissue penetration, low toxicity, and good photostability [ 53 ]. Also, second-generation PS, phthalocyanines have multiple benefits, including light absorption at longer wavelengths, homogeneity, a high extinction coefficient, and high quantum yield in ROS generation.…”

Section: The Main Elements Of Pdt and Melanomamentioning

confidence: 99%

“…There are already several clinically used chlorin-type PSs, namely, Foscan ® , Bremachlorin ® , Photodithazine ® (chlorin e6), and Laserphyrin ® , which are used in the treatment of various types of cancer, including skin cancer [ 53 , 133 ].…”

Section: Porphyrinsmentioning

confidence: 99%

Photosensitizers-Loaded Nanocarriers for Enhancement of Photodynamic Therapy in Melanoma Treatment

et al. 2023

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Malignant melanoma poses a significant global health burden. It is the most aggressive and lethal form of skin cancer, attributed to various risk factors such as UV radiation exposure, genetic modifications, chemical carcinogens, immunosuppression, and fair complexion. Photodynamic therapy is a promising minimally invasive treatment that uses light to activate a photosensitizer, resulting in the formation of reactive oxygen species, which ultimately promote cell death. When selecting photosensitizers for melanoma photodynamic therapy, the presence of melanin should be considered. Melanin absorbs visible radiation similar to most photosensitizers and has antioxidant properties, which undermines the reactive species generated in photodynamic therapy processes. These characteristics have led to further research for new photosensitizing platforms to ensure better treatment results. The development of photosensitizers has advanced with the use of nanotechnology, which plays a crucial role in enhancing solubility, optical absorption, and tumour targeting. This paper reviews the current approaches (that use the synergistic effect of different photosensitizers, nanocarriers, chemotherapeutic agents) in the photodynamic therapy of melanoma.

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“…Furthermore, optimal distribution of the PS within the organism requires stability in solution, easy removal, and synthesis through a cost-effective and practical route [5]. First-and second-generation photosensitizers, such as rhodamine, chlorins, bacteriochlorins, and phthalocyanines, have been widely utilized in PDT [6][7][8][9][10][11]. Thus, Zn (II) phthalocyanines are extremely valuable for PDT due to their high capacity Pharmaceutics 2023, 15, 1892 2 of 18 to absorb light, long triplet lifetimes, high stability, and reduced skin phototoxicity [12].…”

Section: Introductionmentioning

confidence: 99%

New Highly Fluorescent Water Soluble Imidazolium-Perylenediimides: Synthesis and Cellular Response

et al. 2023

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The synthesis and characterization of two new water soluble 2,6-bis(imidazolylmethyl)-4-methylphenoxy-containing perylenediimides, PDI-1 and PDI-2, are described. These compounds demonstrate a high fluorescence quantum yield in water and were investigated as potential photosensitizers for generating reactive oxygen species with applications in anticancer activities. The HeLa cell line (VPH18) was used to evaluate their efficacy. Fluorescence microscopy was employed to confirm the successful internalization of PDI-1 and PDI-2, while confocal microscopy revealed the specific locations of both PDIs within the lysosomes and mitochondria. In vitro studies were conducted to evaluate the anticancer activity of PDI-1 and PDI-2. Remarkably, these photosensitizers demonstrated a significant ability to selectively eliminate cancer cells when exposed to a specific light wavelength. The water solubility, high fluorescence quantum yield, and selective cytotoxicity of these PDIs toward cancer cells highlight their potential as effective agents for targeted photodynamic therapy. In conclusion, the findings presented here provide a strong foundation for the future exploration and optimization of PDI-1 and PDI-2 as effective photosensitizers in photodynamic therapy, potentially leading to improved treatment strategies for cancer patients.

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Cytotoxicity of structurally-modified chlorins aimed for photodynamic therapy applications

Cited by 7 publications

References 43 publications

Photodynamic Therapy: From the Basics to the Current Progress of N-Heterocyclic-Bearing Dyes as Effective Photosensitizers

Photodynamic Therapy: From the Basics to the Current Progress of N-Heterocyclic-Bearing Dyes as Effective Photosensitizers

Photosensitizers-Loaded Nanocarriers for Enhancement of Photodynamic Therapy in Melanoma Treatment

New Highly Fluorescent Water Soluble Imidazolium-Perylenediimides: Synthesis and Cellular Response

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