Chlorin, Phthalocyanine, and Porphyrin Types Derivatives in Phototreatment of Cutaneous Manifestations: A Review

Annunzio, Sarah Raquel de; Costa, Natalia Caroline Silva; Mezzina, Rafaela Dalbello; Graminha, Márcia Aparecida Silva; Fontana, Carla Raquel

doi:10.3390/ijms20163861

“…Indeed, many drugs used for antitumor photodynamic therapy are based on a porphyrin core [ 79 ]. Recently, these compounds have attracted interest for other areas of application, including photodynamic therapy (PDT) of skin infections, including viral [ 80 ] and other infectious diseases [ 81 ] and in the development of porphyrin nanomaterials in diagnostics and imaging [ 82 ]. The properties of porphyrins and phthalocyanines as antiviral sensitizers are mentioned in a review [ 31 ]; moreover, data on porphyrin analogs as antiviral agents are summarized in a recent focused account [ 39 ].…”

Section: Porphyrins Phtalocyanins and Related Compoundsmentioning

confidence: 99%

Photosensitizing Antivirals

Mariewskaya

¹

,

Tyurin

²

,

Chistov

³

et al. 2021

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Antiviral action of various photosensitizers is already summarized in several comprehensive reviews, and various mechanisms have been proposed for it. However, a critical consideration of the matter of the area is complicated, since the exact mechanisms are very difficult to explore and clarify, and most publications are of an empirical and “phenomenological” nature, reporting a dependence of the antiviral action on illumination, or a correlation of activity with the photophysical properties of the substances. Of particular interest is substance-assisted photogeneration of highly reactive singlet oxygen (1O2). The damaging action of 1O2 on the lipids of the viral envelope can probably lead to a loss of the ability of the lipid bilayer of enveloped viruses to fuse with the lipid membrane of the host cell. Thus, lipid bilayer-affine 1O2 photosensitizers have prospects as broad-spectrum antivirals against enveloped viruses. In this short review, we want to point out the main types of antiviral photosensitizers with potential affinity to the lipid bilayer and summarize the data on new compounds over the past three years. Further understanding of the data in the field will spur a targeted search for substances with antiviral activity against enveloped viruses among photosensitizers able to bind to the lipid membranes.

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“… 34 This type of modification alters the steric and electronic nature of porphyrins giving rise to new molecules that have specific and unique properties, and it also presents a promising alternative for modifying photophysical properties of the compounds: (a) quantum singlet oxygen performance, (b) the range of the therapeutic window, (c) photostability and (d) lipophilicity could be improved. 35 …”

Section: Introductionmentioning

confidence: 99%

Photophysical study and in vitro approach against Leishmania panamensis of dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV)

Espitia-Almeida

¹

,

Díaz‐Uribe

²

,

Vallejo

³

et al. 2021

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Background: Photodynamic therapy activity against different biological systems has been reported for porphyrins. Porphyrin modifications through peripheral groups and/or by metal insertion inside the ring are main alternatives for the improvement of its photo-physical properties. In this study, we synthesized and characterized 5,10,15,20-tetrakis(4-bromophenyl)porphyrin and the dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV). Methods: Metal-free porphyrin was synthesized using the Alder method, while the Sn(IV)-porphyrin complex was prepared by combining metal-free porphyrin with stannous chloride in DMF; the reaction yields were 47% and 64% respectively. Metal-free porphyrin was characterized by UV-Vis, FT-IR, ESI-mass spectrometry and 13C-NMR. Additionally, the Sn(IV) -porphyrin complex was characterized using UV-Vis and FT-IR. Cyclic voltammetry tests in four different solvents. The fluorescence quantum yield (Φf) was measured using fluorescein as a standard, the singlet oxygen quantum yield (ΦD) was estimated using the standard 5,10,15,20-(tetraphenyl)porphyrin (H2TPP) and the quencher of singlet oxygen 1,3-diphenylisobenzofuran (DPBF). Results: UV-Vis assay showed typical Q and Soret bands for porphyrin and its metallo-porphyrin complex. Compounds showed photoluminescence at the visible range of electromagnetic spectrum. The inclusion of the metal in the porphyrin core changed the Φf from 0.15 to 0.05 and the ΦD increased from 0.55 to 0.59. Finally, the effect of the compounds on the viability of L. panamensis was evaluated by means of the MTT test. The results showed that both compounds decreased the viability of the parasite; this inhibitory activity was greater under light irradiation; the porphyrin compound had IC50 of 16.5 μM and the Sn(IV)-porphyrin complex had IC50 of 19.2 μM. Conclusion: The compounds were synthesized efficiently, their characterization was carried out by different spectroscopy techniques and their own signals were evidenced for both structures, both compounds decreased the cell viability of L. panamensis.

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“…34 This type of modification alters the steric and electronic nature of porphyrins giving rise to new molecules that have specific and unique properties, and it also presents a promising alternative for modifying photophysical properties of the compounds: (a) quantum singlet oxygen performance, (b) the range of the therapeutic window, (c) photostability and (d) lipophilicity could be improved. 35 Although, 5,10,15,20-tetrakis(4-bromophenyl)-porphyrin (compound 1) and dicloro-5,10,15,20-tetrakis(4-bromophenyl) porphyrinato Sn (IV) (compound 2) are commercially available, the reports about of its application as sensitizers in PDT are few. Therefore, in this study, we analyzed the photophysical behavior of ( 1) and (2) as regards their potential use in PDT against Leishmania panamensis.…”

Section: Introductionmentioning

confidence: 99%

Photophysical study and in vitro approach against Leishmania panamensis of dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV)

Espitia-Almeida

¹

,

Díaz‐Uribe

²

,

Vallejo

³

et al. 2021

F1000Res

0

View full text Add to dashboard Cite

Background: Photodynamic therapy activity against different biological systems has been reported for porphyrins. Porphyrin modifications through peripheral groups and/or by metal insertion inside the ring are main alternatives for the improvement of its photo-physical properties. In this study, we synthesized and characterized 5,10,15,20-tetrakis(4-bromophenyl)porphyrin and the dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV). Methods: Metal-free porphyrin was synthesized using the Alder method, while the Sn(IV)-porphyrin complex was prepared by combining metal-free porphyrin with stannous chloride in DMF; the reaction yields were 47% and 64% respectively. Metal-free porphyrin was characterized by UV-Vis, FT-IR, ESI-mass spectrometry and 13C-NMR. Additionally, the Sn(IV) -porphyrin complex was characterized using UV-Vis and FT-IR. Cyclic voltammetry tests in four different solvents. The fluorescence quantum yield (Φf) was measured using fluorescein as a standard, the singlet oxygen quantum yield (ΦD) was estimated using the standard 5,10,15,20-(tetraphenyl)porphyrin (H2TPP) and the quencher of singlet oxygen 1,3-diphenylisobenzofuran (DPBF). Results: UV-Vis assay showed typical Q and Soret bands for porphyrin and its metallo-porphyrin complex. Compounds showed photoluminescence at the visible range of electromagnetic spectrum. The inclusion of the metal in the porphyrin core changed the Φf from 0.15 to 0.05 and the ΦD increased from 0.55 to 0.59. Finally, the effect of the compounds on the viability of L. panamensis was evaluated by means of the MTT test. The results showed that both compounds decreased the viability of the parasite; this inhibitory activity was greater under light irradiation; the porphyrin compound had IC50 of 16.5 μM and the Sn(IV)-porphyrin complex had IC50 of 19.2 μM. Conclusion: The compounds were synthesized efficiently, their characterization was carried out by different spectroscopy techniques and their own signals were evidenced for both structures, both compounds decreased the cell viability of L. panamensis.

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Chlorin, Phthalocyanine, and Porphyrin Types Derivatives in Phototreatment of Cutaneous Manifestations: A Review

Cited by 57 publications

References 114 publications

Photosensitizing Antivirals

Photosensitizing Antivirals

Photophysical study and in vitro approach against Leishmania panamensis of dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV)

Photophysical study and in vitro approach against Leishmania panamensis of dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV)

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