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meso-Thiophenium Porphyrins and Their Zn(II) Complexes: A New Category of Cationic Photosensitizers
ACS Medicinal Chemistry Letters ( IF 3.5 ) Pub Date : 2020-09-10 , DOI: 10.1021/acsmedchemlett.0c00266 Zeaul Hoque Mazumdar 1 , Debdulal Sharma 1 , Avinaba Mukherjee 2 , Samita Basu 3 , Pradeep Kumar Shukla 4 , Tarun Jha 5 , Devashish Sengupta 1
ACS Medicinal Chemistry Letters ( IF 3.5 ) Pub Date : 2020-09-10 , DOI: 10.1021/acsmedchemlett.0c00266 Zeaul Hoque Mazumdar 1 , Debdulal Sharma 1 , Avinaba Mukherjee 2 , Samita Basu 3 , Pradeep Kumar Shukla 4 , Tarun Jha 5 , Devashish Sengupta 1
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A new category of cationic meso-thiophenium porphyrins are introduced as possible alternatives to the popular meso-pyridinium porphyrins. Combinations of cationic porphyrins bearing meso-2-methylthiophenium and meso-4-hydroxyphenyl moieties T2(OH)2M (A2B2 type) and T(OH)3M (AB3 type) along with their zinc(II) complexes T2(OH)2MZn and T(OH)3MZn, are reported. The increase in the number of thienyl groups attached to the meso-positions of the porphyrin derivatives (A2B2 frame) has been shown to impart longer fluorescence lifetimes and stronger photocytotoxicity toward A549 lung cancer cells, as evident with T2(OH)2M and its corresponding diamagnetic metal complex T2(OH)2MZn. The photoactivated T2(OH)2MZn imparts an early stage reactive oxygen species (ROS) upregulation and antioxidant depletion in A549 cells and contributes to the strongest oxidative stress-induced cell death mechanism in the series. The DFT calculations of the singlet–triplet energy gap (ΔE) of all the four hydrophilic thiophenium porphyrin derivatives establish the potential applicability of these cationic photosensitizers as PDT agents.
中文翻译：
介孔噻吩卟啉及其 Zn(II) 配合物：一类新的阳离子光敏剂
引入了一类新的阳离子内消旋噻吩卟啉作为流行的内消旋吡啶卟啉的可能替代品。带有内消旋-2-甲基噻吩鎓和内消旋-4-羟基苯基部分T 2 (OH) 2 M（A 2 B 2型）和T(OH) 3 M（AB 3型）以及它们的锌(II)的阳离子卟啉的组合配合物T 2 (OH) 2 MZn和T(OH) 3 MZn，被举报。与卟啉衍生物（A 2 B 2框架）的内消旋位相连的噻吩基数量的增加已被证明可以赋予 A549 肺癌细胞更长的荧光寿命和更强的光细胞毒性，如T 2 (OH) 2 M及其相应的抗磁性金属络合物T 2 (OH) 2 MZn。光活化的T 2 (OH) 2 MZn在 A549 细胞中赋予早期活性氧 (ROS) 上调和抗氧化剂消耗，并有助于该系列中最强的氧化应激诱导的细胞死亡机制。所有四种亲水性噻吩卟啉衍生物的单线态-三线态能隙（Δ E）的 DFT 计算确定了这些阳离子光敏剂作为 PDT 试剂的潜在适用性。
更新日期：2020-10-08
中文翻译：
介孔噻吩卟啉及其 Zn(II) 配合物：一类新的阳离子光敏剂
引入了一类新的阳离子内消旋噻吩卟啉作为流行的内消旋吡啶卟啉的可能替代品。带有内消旋-2-甲基噻吩鎓和内消旋-4-羟基苯基部分T 2 (OH) 2 M（A 2 B 2型）和T(OH) 3 M（AB 3型）以及它们的锌(II)的阳离子卟啉的组合配合物T 2 (OH) 2 MZn和T(OH) 3 MZn，被举报。与卟啉衍生物（A 2 B 2框架）的内消旋位相连的噻吩基数量的增加已被证明可以赋予 A549 肺癌细胞更长的荧光寿命和更强的光细胞毒性，如T 2 (OH) 2 M及其相应的抗磁性金属络合物T 2 (OH) 2 MZn。光活化的T 2 (OH) 2 MZn在 A549 细胞中赋予早期活性氧 (ROS) 上调和抗氧化剂消耗，并有助于该系列中最强的氧化应激诱导的细胞死亡机制。所有四种亲水性噻吩卟啉衍生物的单线态-三线态能隙（Δ E）的 DFT 计算确定了这些阳离子光敏剂作为 PDT 试剂的潜在适用性。
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