Department of Chemistry, Gauhati University, Guwahati, Assam, 781014, India.
Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore, 560012, India.
ChemMedChem. 2024 Nov 4;19(21):e202400376. doi: 10.1002/cmdc.202400376. Epub 2024 Sep 12.
In recent years, Sn(IV) porphyrins have proven to be excellent choice as photosensitizers for photodynamic therapy. This work reports the synthesis, characterization and photodynamic activity of four high-valent fluorinated Sn(IV) porphyrins having different numbers of F-atoms in the peripheral of meso-phenyl groups viz. (Dichloro)meso-tetrakis(4-fluorophenylporphyrinato)stannic(IV), [Sn(IV)FTPP(Cl)] or Sn1; (Dichloro)meso-tetrakis(2,4-difluorophenylporphyrinato)stannic(IV), [Sn(IV)2,4-FTPP(Cl)] or Sn2; (Dichloro)meso-tetrakis(2,6-difluorophenylporphyrinato)stannic(IV), [Sn(IV)2,6-FTPP(Cl)] or Sn3 and (Dichloro)meso-tetrakis(4-trifluoromethylphenylporphyrinato)stannic(IV), [Sn(IV)CFTPP(Cl)] or Sn4. The solid-state structure of Sn1 has been determined by single crystal X-ray diffraction analysis. The increasing number of F-atoms attached to the meso-phenyl positions of the porphyrin framework results in increase of their lipophilicity, singlet oxygen quantum yield (Φ) and photocytotoxicity in A549 (human lung adenocarcinoma cells), MCF-7 and MDA-MB-231 (human breast adenocarcinoma) cells. Sn4 predominantly localize in the mitochondria of A549 cells. The light-induced cell death by the Sn(IV) porphyrins in A549 cells occur primarily via apoptosis.
近年来，Sn(IV)卟啉已被证明是光动力治疗的优秀光敏剂选择。本工作报道了四种具有不同数目氟原子的高氧化态氟化 Sn(IV)卟啉的合成、表征和光动力活性，这些氟原子位于间苯基的外围：（二氯）间四（4-氟苯基卟啉基）锡(IV)，[Sn(IV)FTPP(Cl)]或 Sn1；（二氯）间四（2,4-二氟苯基卟啉基）锡(IV)，[Sn(IV)2,4-FTPP(Cl)]或 Sn2；（二氯）间四（2,6-二氟苯基卟啉基）锡(IV)，[Sn(IV)2,6-FTPP(Cl)]或 Sn3；（二氯）间四（4-三氟甲基苯基卟啉基）锡(IV)，[Sn(IV)CFTPP(Cl)]或 Sn4。Sn1 的固态结构已通过单晶 X 射线衍射分析确定。卟啉骨架中连接到间苯基位置的氟原子数目增加，导致其亲脂性、单线态氧量子产率（Φ）和在 A549（人肺腺癌细胞）、MCF-7 和 MDA-MB-231（人乳腺癌）细胞中的光细胞毒性增加。Sn4 主要定位于 A549 细胞的线粒体中。Sn(IV)卟啉在 A549 细胞中引起的光诱导细胞死亡主要通过细胞凋亡发生。
