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Phthalocyanine–sulfonamide conjugates: Synthesis and photodynamic inactivation of Gram-negative and Gram-positive bacteria
European Journal of Medicinal Chemistry ( IF 6.0 ) Pub Date : 2018-05-09 , DOI: 10.1016/j.ejmech.2018.05.009
Raquel Nunes da Silva , Ângela Cunha , Augusto C. Tomé

Phthalocyanines bearing four or eight sulfonamide units were synthesized and their efficiency in the photodynamic inactivation of Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) bacteria was evaluated. Conjugates with simpler sulfonamide units (N,N-diethylbenzenesulfonamide, N-isopropylbenzenesulfonamide and N-(4-methoxyphenyl)benzenesulfonamide) caused stronger inactivation than those with heterocyclic groups (N-(thiazol-2-yl)benzenesulfonamide) or long alkyl chains (N-dodecylbenzenesulfonamide) in both bacteria. Furthermore, the encapsulation of the phthalocyanine–sulfonamide conjugates within polyvinylpyrrolidone micelles, used as drug delivery vehicles, in general showed to enhance the inactivation efficiency. The results show that encapsulated phthalocyanine–sulfonamide conjugates are a promising class of photosensitizers to be used in photodynamic antimicrobial therapy.



中文翻译:

酞菁-磺酰胺偶联物:革兰氏阴性和革兰氏阳性细菌的合成和光动力灭活

合成了带有四个或八个磺酰胺单元的酞菁类,并评估了它们在革兰氏阴性(大肠杆菌)和革兰氏阳性(金黄色葡萄球菌)细菌的光动力失活中的效率。与具有杂环基团(N-(噻唑-2-基)苯磺酰胺)或较长烷基链的磺酰胺单元(NN-二乙基苯磺酰胺,N-异丙基苯磺酰胺和N-(4-甲氧基苯基)苯磺酰胺)相比,结合物引起的灭活作用更强。ñ-十二烷基苯磺酰胺)。此外,酞菁-磺酰胺共轭物在聚乙烯吡咯烷酮胶束中的包封(用作药物传递载体)通常可以提高灭活效率。结果表明,封装的酞菁-磺酰胺共轭物是一种有前途的光敏剂,可用于光动力抗菌治疗。

更新日期:2018-05-09
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