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. 2023 Jun 12;28(12):4716.
doi: 10.3390/molecules28124716.

A Comparative Evaluation of the Photosensitizing Efficiency of Porphyrins, Chlorins and Isobacteriochlorins toward Melanoma Cancer Cells

Kelly A D F Castro  1   2 , Nuno M M Moura  2 , Mário M Q Simões  2 , Mariana M Q Mesquita  2 , Loyanne C B Ramos  1 , Juliana C Biazzotto  1 , José A S Cavaleiro  2 , M Amparo F Faustino  2 , Maria Graça P M S Neves  2 , Roberto S da Silva  1
Affiliations

A Comparative Evaluation of the Photosensitizing Efficiency of Porphyrins, Chlorins and Isobacteriochlorins toward Melanoma Cancer Cells

Kelly A D F Castro et al. Molecules. .

Abstract

Skin cancer is one of the cancers that registers the highest number of new cases annually. Among all forms of skin cancer, melanoma is the most invasive and deadliest. The resistance of this form of cancer to conventional treatments has led to the employment of alternative/complementary therapeutic approaches. Photodynamic therapy (PDT) appears to be a promising alternative to overcome the resistance of melanoma to conventional therapies. PDT is a non-invasive therapeutic procedure in which highly reactive oxygen species (ROS) are generated upon excitation of a photosensitizer (PS) when subjected to visible light of an adequate wavelength, resulting in the death of cancer cells. In this work, inspired by the efficacy of tetrapyrrolic macrocycles to act as PS against tumor cells, we report the photophysical characterization and biological assays of isobacteriochlorins and their corresponding chlorins and porphyrins against melanoma cancer cells through a photodynamic process. The non-tumoral L929 fibroblast murine cell line was used as the control. The results show that the choice of adequate tetrapyrrolic macrocycle-based PS can be modulated to improve the performance of PDT.

Keywords: chlorin; isobacteriochlorin; melanoma; photodynamic therapy; photosensitizer; porphyrin; skin cancer.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of porphyrins, chlorins, and isobacteriochlorins studied in this work.
Figure 2
Figure 2
Near IR emission spectra of singlet oxygen produced by ZnPc, Por1, Chl1, Iso1, Por2, Chl2, and Iso2 in DMF (λexc = 660 nm) with an OD = 0.1.
Figure 3
Figure 3
Cytotoxicity (dark) and photocytotoxicity (5.4 J/cm2) of Chl1 (A,B) and Iso1 (C,D) against L929 (A,C) and B16F10 (B,D) cells after irradiation (λ = 660 nm; light dose of 5.4 J/cm2). The results are presented as mean ± standard deviation. Significant differences relative to control cell cultures are presented with an # and relative to irradiated and non-irradiated by *. Statistical significance: # p < 0.05, * p < 0.05, *** p < 0.001, and **** p < 0.0001.
Figure 4
Figure 4
Cytotoxicity (dark) and photocytotoxicity (5.4 J/cm2) of Por2 (A,B), Chl2 (C,D), and Iso2 (E,F) against L929 (A,C,E) and B16F10 (B,D,F) cells after red light irradiation (λ = 660 nm; light dose of 5.4 J/cm2). The results are presented as mean ± standard deviation. Significant differences relative to irradiated and non-irradiated by *. Statistical significance: * p < 0.05, ** p < 0.01; *** p < 0.001, and **** p < 0.0001.
Figure 5
Figure 5
Fluorescence microscopy images of B16F10 cells treated with chlorins (Chl1 and Chl2) and isobacteriochlorins (Iso1 and Iso2). From left to right: blue fluorescence (Hoechst 33342), green fluorescence (Rhodamine 123), red fluorescence (Chl1, Iso1, Chl2, and Iso2) and merged images.
See this image and copyright information in PMC

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