Domingos Carolina V, Silva Madalena F C, Eusébio M Ermelinda S, Maria Teresa M R, Pires João R A, da Silva Gabriela J, Aroso Rafael T, Pereira Mariette M
CQC-IMS, Department of Chemistry, University of Coimbra, Rua Larga, 3004-535, Coimbra, Portugal.
Bio4Plas - Biopolimeros, Lda. Zona Industrial Lote 61, 3064-197 Cantanhede, Portugal.
J Mater Chem B. 2025 Aug 22. doi: 10.1039/d5tb01354b.
The global rise of multidrug-resistant (MDR) bacteria highlights the urgent need for alternative strategies to prevent their spread, particularly in healthcare environments. Here, we report the synthesis and evaluation of a novel mono-cationic -imidazolyl porphyrin (3) and its integration into biodegradable poly(lactic acid) (PLA) films, resulting in potentially effective, reusable, and broad-spectrum photodynamic antibacterial surfaces. The porphyrin was prepared using a mixed aldehyde condensation followed by microwave-assisted methylation, reducing reaction time to just 1 minute with near-quantitative yield. PLA films containing porphyrin 3 (+PLA-3) were successfully prepared and fully characterized, showing exceptional photostability and minimal leaching in aqueous environments, even under prolonged light exposure. Notably, cationic +PLA-3 exhibited superior material stability compared to analogous PLA films incorporating tetra-cationic porphyrins, attributed to the improved amphiphilic balance of the mono-cationic photosensitizer. Antibacterial studies confirmed that cationic +PLA-3 films achieved complete photodynamic inactivation (7 log CFU reduction) of both Gram-positive () and Gram-negative () bacteria under blue LED irradiation. They also demonstrated great effectiveness against clinical multidrug-resistant strains, including MRSA, , , , and , reaching total inactivation under light doses up to 23.5 J cm. Reusability tests confirmed full retention of antibacterial efficacy after up to 11 irradiation cycles, totalling 258.5 J cm. These results position cationic +PLA-3 as a promising candidate for use in self-disinfecting surfaces with potential to reduce nosocomial infection risks and environmental impact in healthcare settings.
多重耐药(MDR)细菌在全球范围内的增多凸显了采取替代策略来防止其传播的迫切需求,尤其是在医疗环境中。在此,我们报告了一种新型单阳离子咪唑基卟啉(3)的合成与评估,并将其整合到可生物降解的聚乳酸(PLA)薄膜中,从而得到了具有潜在高效、可重复使用且广谱的光动力抗菌表面。该卟啉通过混合醛缩合反应制备,随后进行微波辅助甲基化反应,反应时间缩短至仅1分钟,产率接近定量。成功制备并全面表征了含有卟啉3的PLA薄膜(+PLA-3),其在水环境中表现出优异的光稳定性和极少的浸出,即使在长时间光照下也是如此。值得注意的是,与包含四阳离子卟啉的类似PLA薄膜相比,阳离子型+PLA-3表现出更高的材料稳定性,这归因于单阳离子光敏剂两亲平衡的改善。抗菌研究证实,阳离子型+PLA-3薄膜在蓝色LED照射下对革兰氏阳性菌()和革兰氏阴性菌()均实现了完全的光动力灭活(减少7个对数CFU)。它们对包括耐甲氧西林金黄色葡萄球菌(MRSA)、、、和在内的临床多重耐药菌株也显示出很强的有效性,在高达23.5 J/cm²的光剂量下达到完全灭活。可重复使用性测试证实,在多达11个照射循环(总计258.5 J/cm²)后,抗菌效果完全保持。这些结果表明,阳离子型+PLA-3有望成为用于自消毒表面的候选材料,有可能降低医疗环境中的医院感染风险和环境影响。