Gebze Technical University, Department of Chemistry, 41400, Gebze, Kocaeli, Turkey.
Laboratory and Veterinary Health, Technical Science Vocational School, Mersin University, TR-33343 Mersin, Turkey.
Dalton Trans. 2024 Oct 1;53(38):16005-16017. doi: 10.1039/d4dt02115k.
In this study, new peripherally substituted symmetric zinc and magnesium phthalocyanines (4 and 5) were successfully prepared by cyclotetramerization of the tetrahydropyrimidone (THPM)-linked phthalonitrile 3. The identity of the compounds were confirmed primarily through spectroscopic analysis including NMR, FT-IR, UV-Vis and MALDI-TOF mass spectroscopy. The photophysical and photochemical properties of the synthesized phthalocyanines (Pcs) were examined using UV-Vis absorption and fluorescence emission spectroscopy techniques. The quantum yields of singlet oxygen were found to be 0.50 and 0.33 for compounds 4 and 5 in DMSO, respectively. In addition to photo-physicochemical properties, the enhanced biological activities of compounds 4 and 5 were investigated using a range of biological assays, namely, antibiofilm, microbial cell viability, antioxidant, DNA cleavage, antimicrobial and photodynamic antimicrobial assays. The maximum DPPH inhibition of 4 and 5 was detected as 40.46% and 25.76% at 100 mg L, respectively. Fragmentation of the DNA molecule was observed at concentrations of 25 mg L, 50 mg L and 100 mg L for 4 and 5. Additionally, effective inhibition of microbial cell viability was observed with the targeted Pcs. The antibiofilm properties of these compounds were found to be concentration-dependent. The biofilm inhibition activities of 4 and 5 were found to be 96.01% and 92.04% for , while they were 95.42% and 91.27%, for , respectively. The antimicrobial activities of 4 and 5 on different microorganisms were evaluated using the microdilution assay. In the case of photodynamic antimicrobial treatment, the newly synthesized Pcs showed more effective antimicrobial inhibition compared to the control. These findings suggest that compounds 4 and 5 can be used as promising photodynamic antimicrobial agents for the treatment of many diseases, particularly infectious diseases.
在这项研究中，通过四氢嘧啶（THPM）连接的苯并二氮杂腈 3 的环三聚反应，成功制备了新的外围取代的对称锌和镁酞菁（4 和 5）。通过包括 NMR、FT-IR、UV-Vis 和 MALDI-TOF 质谱在内的光谱分析初步确认了化合物的身份。通过使用 UV-Vis 吸收和荧光发射光谱技术研究了合成酞菁（Pcs）的光物理和光化学性质。发现化合物 4 和 5 在 DMSO 中的单线态氧量子产率分别为 0.50 和 0.33。除了光物理化学性质外，还通过一系列生物测定研究了化合物 4 和 5 的增强生物活性，即抗生物膜、微生物细胞活力、抗氧化、DNA 切割、抗菌和光动力抗菌测定。在 100 mg L 时，4 和 5 的最大 DPPH 抑制率分别检测为 40.46%和 25.76%。在 25 mg L、50 mg L 和 100 mg L 的浓度下观察到 DNA 分子的片段化。此外，目标 Pcs 有效地抑制了微生物细胞活力。这些化合物的抗生物膜特性被发现是浓度依赖性的。化合物 4 和 5 的生物膜抑制活性分别为 96.01%和 92.04%，而它们分别为 95.42%和 91.27%。使用微量稀释法评估了 4 和 5 对不同微生物的抗菌活性。在光动力抗菌治疗的情况下，新合成的 Pcs 显示出比对照更有效的抗菌抑制作用。这些发现表明，化合物 4 和 5 可作为有前途的光动力抗菌剂用于治疗许多疾病，特别是传染病。
Zotero 插件