A new sulfonic-substituted Zinc(II)-Porphyrin with high aqueous solubility: Synthesis, photophysical properties and application in porcine cell-imaging

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2025-02-28 DOI:10.1016/j.dyepig.2025.112736

Meng-yan Chai , Thayalan Rajeshkumar , Hui Su , Fu-jie Zhao , Zhi Wang , Wei-ping Yin , Song Jiang , Guo-xing Liu , Li-jie Liu , Xin Zheng , Li-xia Xie , Sheng-qiang Guo , Yu-qiang Xiang , Laurent Maron , Cao-yuan Niu

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Abstract

The poor aqueous solubility of porphyrins and metalloporphyrins has long impeded their applications in biological systems. In this study, we report the synthesis of a novel porphyrin derivative—ZnTSPP—achieved by introducing four sulfonic acid groups onto a single porphyrin molecule. The photophysical properties were comprehensively characterized via UV–Vis absorption and fluorescence emission spectroscopy in deionized water, phosphate-buffered saline (PBS), and fetal bovine serum (FBS). ZnTSPP exhibits intense absorption in both the Soret and Q bands and displays a reversible pH response. Density Functional Theory (DFT) calculations further corroborate the pH-dependent formation of J- and H-aggregates. Additionally, cellular imaging studies performed on pig kidney epithelial cells (LLC-PK1) demonstrate that ZnTSPP is not only pH-responsive but also an efficient singlet oxygen generator. These attributes position ZnTSPP as a promising agent for biomedical imaging and photodynamic therapy.

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长期以来，卟啉和金属卟啉的水溶性较差，阻碍了它们在生物系统中的应用。在本研究中，我们报告了通过在单个卟啉分子上引入四个磺酸基团而合成的新型卟啉衍生物-ZnTSPP。在去离子水、磷酸盐缓冲盐水（PBS）和胎牛血清（FBS）中，通过紫外-可见吸收和荧光发射光谱对其光物理性质进行了全面表征。ZnTSPP 在 Soret 波段和 Q 波段都表现出强烈的吸收，并显示出可逆的 pH 值响应。密度泛函理论（DFT）计算进一步证实了 J- 和 H-聚集体的形成与 pH 值有关。此外，在猪肾上皮细胞（LLC-PK1）上进行的细胞成像研究表明，ZnTSPP 不仅具有 pH 响应性，还是一种高效的单线态氧发生器。这些特性使 ZnTSPP 成为一种很有前景的生物医学成像和光动力疗法制剂。

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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.