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首页> 外文期刊>Archiv der Pharmazie >Physicochemical properties and photodynamic activity of novel derivatives of triarylmethane and thiazine
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Physicochemical properties and photodynamic activity of novel derivatives of triarylmethane and thiazine

机译：三芳基甲烷和噻嗪新型衍生物的理化性质和光动力活性

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Triarylmethane and thiazine dyes have attracted attention as anticancer and antimicrobial agents, due to their structural features and selective localizations. Although these dyes have been initially explored in the context of photodynamic therapy, some of these such as New Fuchsin and Azure B have still not been extensively investigated. For this reason, we evaluated the chemical stability, aggregation effect, and lipophilicity, as well as the photodynamic activity against LM-2 murine mammary carcinoma cells of five new brominated dyes of triarylmethane and thiazine. These cationic compounds were obtained at high purities and unequivocally characterized by conventional techniques. The introduction of bromine atoms into the chromophoric system of New Fuchsin and Azure B dyes gave rise to a moderate bathochromic shift and increased the lipophilicity, thereby improving their photophysical and photochemical properties for biomedical applications. Moreover, the in vitro photodynamic activity demonstrated that, as the degree of bromination increased, the phototoxicity remained unchanged or decreased. The lower efficiency to inactivate cultured tumor cells may be attributed to the formation of the colorless carbinol pseudobase and aggregation effects for triarylmethane and thiazine dyes, respectively. A promising strategy to reverse the biological activity decrease observed might be the design of third-generation photosensitizers. The chemical stability, aggregation effect, and lipophilicity, as well as the photodynamic activity of five new brominated dyes of New Fuchsin and Azure B were evaluated. These compounds presented a moderate bathochromic shift and increased lipophilicity, but their photocytotoxicity remained unchanged or decreased. This behavior may be attributed to the instability or aggregation of the compounds, which could be reversed through the design of third-generation photosensitizers.
机译：三芳基甲烷和噻嗪染料由于其结构特征和选择性定位而作为抗癌剂和抗微生物剂备受关注。尽管这些染料最初是在光动力疗法的背景下进行探索的，但其中的一些染料如新品红和天青B仍未得到广泛研究。因此，我们评估了五种新的三芳基甲烷和噻嗪溴化染料的化学稳定性，聚集作用和亲脂性，以及对LM-2鼠乳癌细胞的光动力活性。这些阳离子化合物以高纯度获得，并通过常规技术明确表征。将溴原子引入新品红和天蓝色B染料的发色体系中会引起适度的红移并增加亲脂性，从而改善其在生物医学应用中的光物理和光化学性质。此外，体外光动力活性表明，随着溴化程度的增加，光毒性保持不变或降低。使培养的肿瘤细胞失活的效率较低可能分别归因于无色甲醇假碱基的形成以及三芳基甲烷和噻嗪染料的聚集作用。逆转观察到的生物活性下降的一种有前途的策略可能是第三代光敏剂的设计。评价了五种新品红和天蓝色B的化学稳定性，聚集效应和亲脂性，以及五种新溴化染料的光动力活性。这些化合物呈现出适度的红移和亲脂性，但它们的光细胞毒性保持不变或降低。此行为可能归因于化合物的不稳定性或聚集，这可以通过设计第三代光敏剂来解决。

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