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邻、间、对位取代基对阳离子吡啶二氢噻唑酞菁体外光动力抗菌化疗活性的影响。

The implications of ortho-, meta- and para- directors on the in-vitro photodynamic antimicrobial chemotherapy activity of cationic pyridyl-dihydrothiazole phthalocyanines.

机构信息

Department of Chemistry, Institute for Nanotechnology Innovation, Rhodes University, Grahamstown 6140, South Africa.

Department of Chemistry, Institute for Nanotechnology Innovation, Rhodes University, Grahamstown 6140, South Africa.

出版信息

Photodiagnosis Photodyn Ther. 2022 Sep;39:103029. doi: 10.1016/j.pdpdt.2022.103029. Epub 2022 Jul 21.

DOI:10.1016/j.pdpdt.2022.103029
PMID:35872353
Abstract

Cationic Zn phthalocyanine complexes were derived by alkylation reaction of tetra-(pyridinyloxy) phthalocyanines (Pcs) at the ortho, meta, and para positions to form Zn (II) tetrakis 3-(4-(2-pyridin-1-ium-1-yl) butyl)-2-mercapto-4,5-dihydrothiazol-3-ium phthalocyanine (2), Zn (II) tetrakis 3-(4-(3-pyridin-1-ium-1-yl) butyl)-2-mercapto-4,5-dihydrothiazol-3-ium phthalocyanine (4) and Zn (II) tetrakis 3-(4-(4-pyridin-1-ium-1-yl) butyl)-2-mercapto-4,5-dihydrothiazol-3-ium phthalocyanine (6). The photophysicochemical behaviors of the Pc complexes were assessed. The meta and para-substituted complexes gave high singlet oxygen quantum yields. The cationic Pcs demonstrated good planktonic antibacterial activity against Staphylococcus aureus and Escherichia coli with the high log reduction values of 9.29 and 8.55, respectively. The cationic complexes also showed a significant decrease in the viability of in vitro biofilms after photo-antimicrobial chemotherapy at 100 µM for both Staphylococcus aureus and Escherichia coli biofilms.

摘要

通过对邻位、间位和对位的四-(吡啶氧基)酞菁进行烷基化反应,得到了阳离子锌酞菁配合物,形成了 Zn(II)四-3-(4-(2-吡啶基-1-基-1-基)丁基)-2-巯基-4,5-二氢噻唑-3- 基)酞菁(2)、Zn(II)四-3-(4-(3-吡啶基-1-基-1-基)丁基)-2-巯基-4,5-二氢噻唑-3-基)酞菁(4)和 Zn(II)四-3-(4-(4-吡啶基-1-基-1-基)丁基)-2-巯基-4,5-二氢噻唑-3-基)酞菁(6)。评估了酞菁配合物的光物理化学行为。间位和对位取代的配合物具有较高的单线态氧量子产率。阳离子酞菁对金黄色葡萄球菌和大肠杆菌具有良好的浮游态抗菌活性,log 减少值分别为 9.29 和 8.55。阳离子配合物在 100 μM 时对金黄色葡萄球菌和大肠杆菌生物膜进行光抗菌化疗后,生物膜的体外活性显著降低。

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