Modulating the phototoxicity and selectivity of a porphyrazine towards epidermal tumor cells by coordination with metal ions.

IF 2.7 3区 化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY
Photochemical & Photobiological Sciences Pub Date : 2024-09-01 Epub Date: 2024-09-06 DOI:10.1007/s43630-024-00629-z
Pedro A Pinheiro, Gabriel F M Pereira, Leandro O Cunha, Julia P S C Leal, Meiry E Alvarenga, Felipe T Martins, Heveline Silva, Jorge L S Milani, Thiago T Tasso
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引用次数: 0

Abstract

Porphyrazines (Pzs) are porphyrin derivatives that show potential application as photosensitizers for photodynamic therapy (PDT), but are still far less explored in the literature. In this work, we evaluate how the photophysics and phototoxicity of the octakis(trifluoromethylphenyl)porphyrazine (H2Pz) against tumor cells can be modulated by coordination with Mg(II), Zn(II), Cu(II) and Co(II) ions. Fluorescence and singlet oxygen quantum yields for the Pzs were measured in organic solvents and in soy phosphatidylcholine (PC) liposomes suspended in water. While H2Pz and the respective complexes with Cu(II) and Co(II) showed very low efficiency to fluoresce and to produce 1O2, the Mg(II) and Zn(II) complexes showed significantly higher quantum yields in organic solvents. The fluorescence of these two Pzs in the liposomes was sensitive to the fluidity of the membrane, showing potential use as viscosity markers. The cytotoxicity of the compounds was tested in HaCaT (normal) and A431 (tumor) cells using soy PC liposomes as drug carriers. Despite the low 1O2 quantum yields in water, the Mg(II) and Zn(II) complexes showed IC50 values against A431 cells in the nanomolar range when activated with low doses of red LED light. Their phototoxicity was ca. three times higher for the tumor cells compared to the normal ones, showing promising application as photosensitizers for PDT protocols. Considering that H2Pz and the respective Co(II) and Cu(II) complexes were practically non-phototoxic to the cells, we demonstrate the importance of the central metal ion in the modulation of the photodynamic activity of porphyrazines.

Abstract Image

通过与金属离子配位调节卟吩嗪对表皮肿瘤细胞的光毒性和选择性。
卟嗪(Pzs)是一种卟啉衍生物,具有作为光动力疗法(PDT)光敏剂的潜在应用前景,但文献中对它的研究还远远不够。在这项工作中,我们评估了八(三氟甲基苯基)卟吩(H2Pz)对肿瘤细胞的光物理和光毒性如何通过与 Mg(II)、Zn(II)、Cu(II) 和 Co(II) 离子配位来调节。在有机溶剂和悬浮于水中的大豆磷脂酰胆碱(PC)脂质体中测量了 Pzs 的荧光和单线态氧量子产率。在有机溶剂中,H2Pz 以及与 Cu(II) 和 Co(II) 的各自配合物的荧光效率和产生 1O2 的效率都很低,而 Mg(II) 和 Zn(II) 配合物的量子产率则明显较高。这两种 Pz 在脂质体中的荧光对膜的流动性很敏感,显示出作为粘度标记物的潜在用途。使用大豆 PC 脂质体作为药物载体,在 HaCaT(正常)和 A431(肿瘤)细胞中测试了化合物的细胞毒性。尽管 Mg(II) 和 Zn(II) 复合物在水中的 1O2 量子产率较低,但在低剂量红色 LED 光的激活下,它们对 A431 细胞的 IC50 值在纳摩尔范围内。与正常细胞相比,它们对肿瘤细胞的光毒性大约高出三倍,这表明它们有望作为光敏剂应用于光导治疗方案。考虑到 H2Pz 以及相应的 Co(II) 和 Cu(II) 复合物对细胞几乎没有光毒性,我们证明了中心金属离子在调节卟吩嗪光动力活性中的重要性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Photochemical & Photobiological Sciences
Photochemical & Photobiological Sciences 生物-生化与分子生物学
CiteScore
5.60
自引率
6.50%
发文量
201
审稿时长
2.3 months
期刊介绍: A society-owned journal publishing high quality research on all aspects of photochemistry and photobiology.
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