Pegylated metal-free and zinc(II) phthalocyanines: synthesis, photophysicochemical properties and in vitro photodynamic activities against head, neck and colon cancer cell lines,Dalton Transactions

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Pegylated metal-free and zinc(II) phthalocyanines: synthesis, photophysicochemical properties and in vitro photodynamic activities against head, neck and colon cancer cell lines
Dalton Transactions ( IF 3.5 ) Pub Date : 2022-06-13 , DOI: 10.1039/d2dt00704e
Berkay Akkoç ₁ , Taylan Samsunlu ₁ , Şeyma Işık _{2,

3} , Mukaddes Özçeşmeci ₁ , Göknur Yaşa Atmaca ₄ , Ali Erdoğmuş ₄ , Müge Serhatlı ₂ , Esin Hamuryudan ₁

Affiliation

In this study, a series of peripherally and non-peripherally tetra-substituted metal-free and zinc(II) phthalocyanines were successfully prepared in good yields by cyclotetramerization of the phthalonitrile derivative bearing a tetraethylene glycol methyl ether group at 3- and 4- positions. All newly synthesized compounds were characterized using spectroscopic methods, such as FT-IR, NMR, mass and UV-Vis spectroscopy. To determine the therapeutic potential of the synthesized phthalocyanines, the effects of the substitution pattern (peripheral and non-peripheral) and central metal atom on the photophysicochemical properties were investigated. When comparing their singlet oxygen generation capabilities (Φ_Δ), metallo-phthalocyanine derivatives with zinc (0.73 for 1b and 0.70 for 2b) showed higher singlet oxygen yield than metal-free derivatives (0.21 for 1a and 0.12 for 2a) in DMSO. The photodynamic therapy activities of the water-soluble phthalocyanines were tested via in vitro studies using the A253, FaDu (head and neck cancer cell lines), and HT29 (colon cancer) cell lines. The strongest photodynamic activity was found in 1b and 2b molecules with a metal core among the four molecules studied. The results suggested that the non-peripherally tetra-substituted 1b molecule was regarded as a suitable photodynamic therapy agent due to its light cytotoxicity and secondary impact induced by ROS production.

中文翻译：

聚乙二醇化无金属和锌 (II) 酞菁：合成、光物理化学性质和针对头、颈和结肠癌细胞系的体外光动力活性

在这项研究中，通过环四聚反应在 3 位和 4 位带有四甘醇甲基醚基的邻苯二甲腈衍生物，成功地制备了一系列外围和非外围四取代的无金属和锌 ( II ) 酞菁。 . 所有新合成的化合物均使用光谱方法进行表征，例如 FT-IR、NMR、质谱和 UV-Vis 光谱。为了确定合成的酞菁的治疗潜力，研究了取代模式（外围和非外围）和中心金属原子对光物理化学性质的影响。当比较它们的单线态氧生成能力 ( Φ _Δ ) 时，金属酞菁衍生物与锌 (0.73 for1b和2b的 0.70 ）在 DMSO 中显示出比无金属衍生物（1a为 0.21 和2a为0.12 ）更高的单线态氧产率。通过使用 A253、FaDu（头颈癌细胞系）和 HT29（结肠癌）细胞系的体外研究测试了水溶性酞菁的光动力治疗活性。在所研究的四种分子中，具有金属核的1b和2b分子中发现了最强的光动力活性。结果表明，非外周四取代的1b分子由于其轻微的细胞毒性和由 ROS 产生引起的二次影响而被认为是一种合适的光动力治疗剂。

更新日期：2022-06-13

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