合成新型吡喃黄基染料，作为抗菌光动力灭活的理想光敏剂

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2024-10-17 DOI:10.1016/j.dyepig.2024.112495

Paula Araújo, Patrícia Correia, Nuno Mateus, Victor de Freitas, Iva Fernandes, Luís Cruz, Joana Oliveira

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引用次数: 0

摘要

最近，有人描述了氨基取代染料在针对细菌生长的光动力疗法中有趣的光敏特性。在本研究中，两种新型吡喃黄基染料，即 4′-二甲基氨基-10-(4''-(二甲基氨基)苯基)吡喃黄基（4′,4″N(Me)2PyF）和 6-溴-4′-二甲基氨基-10-(4''-(二甲基氨基)苯基)吡喃黄基（6Br4′、4″N(Me)2PyF)的光性质。由于吡喃环上多了一个二甲基氨基苯基基团，并插入了一个溴原子，母黄烷的光谱特性发生了变化，导致吸收带红移、摩尔消光系数升高和荧光发射。这两种吡喃黄基染料都显示出明显的单线态氧产生，光毒性研究证明了它们的光活性性质，经过 15 分钟的照射（22.5 J/cm2）后，金黄色葡萄球菌 ATCC 29213 的细胞活力降低了 >3log。可以进一步探索这种方法，为抗菌剂光动力灭活开发新的解决方案，从而有可能解决与抗菌剂耐药性有关的问题。

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Synthesis of novel pyranoflavylium-based dyes as promising photosensitizers for antimicrobial photodynamic inactivation

Amino-substituted dyes have recently been described for their interesting photosensitizing properties in photodynamic therapy against bacterial growth. In the present study, two novel pyranoflavylium-based dyes namely 4′-dimethylamino-10-(4''-(dimethylamino)phenyl)pyranoflavylium (4′,4″N(Me)₂PyF) and 6-Bromo-4′-dimethylamino-10-(4''-(dimethylamino)phenyl)pyranoflavylium (6Br4′,4″N(Me)₂PyF) were synthesized through the reactions between salicylaldehyde and acetophenone derivatives to improve the photo-properties of 5-hydroxy-4′-dimethylaminoflavylium (5OH4′N(Me)₂F), a non-photoactivated flavylium salt previously reported due to the presence of a hydroxyl group in its structure. The presence of a pyranic ring with an additional dimethylaminophenyl group and the insertion of a bromine atom changed the spectroscopic properties of the parent flavylium, causing a red shift of the absorption band, higher molar extinction coefficient, and fluorescence emission. Both pyranoflavylium dyes showed appreciable singlet oxygen production, and phototoxicity studies demonstrated their photoactivable nature, leading to a reduction of >3log in cellular viability of S. aureus ATCC 29213 after 15 min of irradiation (22.5 J/cm²).

In conclusion, this study describes a chemical strategy to extend π-conjugation, converting a non-active flavylium dye into photoactivable ones. This approach could be further explored to develop novel solutions for antimicrobial photodynamic inactivation, potentially addressing issues related to antimicrobial resistance.

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

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.