{"title":"Structurally similar porphyrins and porphyrazines perform differently under green or red light irradiation against non-melanoma skin tumor cells","authors":"Gustavo Wander Streit, Heveline Silva, Thiago Teixeira Tasso, Gilson DeFreitas-Silva","doi":"10.1016/j.dyepig.2024.112527","DOIUrl":null,"url":null,"abstract":"<div><div>A porphyrin (H<sub>2</sub>P) and a porphyrazine (H<sub>2</sub>Pz) and their respective zinc complexes (ZnP and ZnPz), with the substituent <em>N</em>-ethylpyridyl-3-yl, were synthesized and their photophysical and phototoxic properties were compared. These substances showed high solubility in water due to the cationic moieties and without notable aggregation in this solvent. Photophysical studies showed that H<sub>2</sub>P and H<sub>2</sub>Pz have fluorescence quantum yields (Φ<sub>F</sub>) of 2.04 % and 0.48 % in water, respectively, that, upon metalation, decreases to 1.4 % for the metalloporphyrin (ZnP) and increases to 6.1 % for the metalloporphyrazine (ZnPz). Regarding the singlet oxygen production efficiency (Φ<sub>Δ</sub>) of the substances in water, a considerable increase from 16.2 % to 41 % was obtained for the porphyrin upon coordination to zinc, while the porphyrazines practically do not produce singlet oxygen (<1 %) in this solvent. When tested against human squamous cell carcinoma cells (A-431) and immortalized human keratinocytes (HaCaT), the toxicity of all compounds increased using green (520 ± 5 nm) and red (625 ± 5 nm) radiation when compared to the non-irradiated cells, however, phototoxicity was higher for the porphyrins using green light, while the porphyrazines performed better under red radiation. Furthermore, porphyrins had a higher phototoxic index than porphyrazines and greater selectivity for A-431 cancer cells compared to HaCaT cells. To the best of our knowledge, this is the first work that compares the photophysical response and in vitro anticancer activity of porphyrins and porphyrazines with the same substituent.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112527"},"PeriodicalIF":4.1000,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Dyes and Pigments","FirstCategoryId":"88","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S014372082400593X","RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
A porphyrin (H2P) and a porphyrazine (H2Pz) and their respective zinc complexes (ZnP and ZnPz), with the substituent N-ethylpyridyl-3-yl, were synthesized and their photophysical and phototoxic properties were compared. These substances showed high solubility in water due to the cationic moieties and without notable aggregation in this solvent. Photophysical studies showed that H2P and H2Pz have fluorescence quantum yields (ΦF) of 2.04 % and 0.48 % in water, respectively, that, upon metalation, decreases to 1.4 % for the metalloporphyrin (ZnP) and increases to 6.1 % for the metalloporphyrazine (ZnPz). Regarding the singlet oxygen production efficiency (ΦΔ) of the substances in water, a considerable increase from 16.2 % to 41 % was obtained for the porphyrin upon coordination to zinc, while the porphyrazines practically do not produce singlet oxygen (<1 %) in this solvent. When tested against human squamous cell carcinoma cells (A-431) and immortalized human keratinocytes (HaCaT), the toxicity of all compounds increased using green (520 ± 5 nm) and red (625 ± 5 nm) radiation when compared to the non-irradiated cells, however, phototoxicity was higher for the porphyrins using green light, while the porphyrazines performed better under red radiation. Furthermore, porphyrins had a higher phototoxic index than porphyrazines and greater selectivity for A-431 cancer cells compared to HaCaT cells. To the best of our knowledge, this is the first work that compares the photophysical response and in vitro anticancer activity of porphyrins and porphyrazines with the same substituent.
期刊介绍：
Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied.
Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media.
The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.
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