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由碘化钾增强的阳离子硼二吡咯衍生物敏化的微生物的光动力失活。

Photodynamic inactivation of microorganisms sensitized by cationic BODIPY derivatives potentiated by potassium iodide.

作者信息

Reynoso Eugenia, Quiroga Ezequiel D, Agazzi Maximiliano L, Ballatore María B, Bertolotti Sonia G, Durantini Edgardo N

机构信息

Departamento de Química, Facultad de Ciencias Exactas, Físico-Químicas y Naturales, Universidad Nacional de Río Cuarto, Ruta Nacional 36 Km 601, X5804BYA, Río Cuarto, Córdoba, Argentina.

出版信息

Photochem Photobiol Sci. 2017 Oct 11;16(10):1524-1536. doi: 10.1039/c7pp00204a.

Abstract

The photodynamic inactivation mediated by 1,3,5,7-tetramethyl-8-[4-(N,N,N-trimethylamino)phenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene 3 and 8-[4-(3-(N,N,N-trimethylamino)propoxy)phenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene 4 was investigated on Staphylococcus aureus, Escherichia coli and Candida albicans. In vitro experiments indicated that BODIPYs 3 and 4 were rapidly bound to microbial cells at short incubation periods. Also, fluorescence microscopy images showed green emission of BODIPYs bound to microbial cells. Photosensitized inactivation improved with an increase of the irradiation time. Similar photoinactivation activities were found for both BODIPYs in bacteria. The photoinactivation induced by these BODIPYs was effective for both bacteria. However, the Gram-positive bacterium was inactivated sooner and with a lower concentration of a photosensitizer than the Gram-negative bacterium. After 15 min irradiation, the complete eradication of S. aureus was obtained with 1 μM photosensitizer. A reduction of 4.5 log in the E. coli viability was found when using 5 μM photosensitizer and 30 min irradiation. Also, the last conditions produced a decrease of 4.5 log in C. albicans cells treated with BODIPY 3, while 4 was poorly effective. On the other hand, the effect of the addition of KI on photoinactivation at different irradiation periods and salt concentrations was investigated. A smaller effect was observed in S. aureus because the photosensitizers alone were already very effective. In E. coli, photokilling potentiation was mainly found at longer irradiation periods. Moreover, the photoinactivation of C. albicans mediated by these BODIPYs was increased in the presence of KI. In solution, an increase in the formation of the BODIPY triplet states was observed with the addition of the salt, due to the effect of external heavy atoms. The greater intersystem crossing together with the formation of reactive iodine species induced by BODIPYs may be contributing to enhance the inactivation of microorganisms. Therefore, these BODIPYs represent interesting photosensitizers to inactivate microorganisms. In particular, BODIPY 3 in combination with KI was highly effective as a broad spectrum antimicrobial photosensitizer.

摘要

研究了由1,3,5,7-四甲基-8-[4-(N,N,N-三甲基氨基)苯基]-4,4-二氟-4-硼-3a,4a-二氮杂-s-茚并[1,2-b]噻吩3和8-[4-(3-(N,N,N-三甲基氨基)丙氧基)苯基]-4,4-二氟-4-硼-3a,4a-二氮杂-s-茚并[1,2-b]噻吩4介导的光动力失活对金黄色葡萄球菌、大肠杆菌和白色念珠菌的作用。体外实验表明,硼二吡咯3和4在短时间孵育时能迅速与微生物细胞结合。此外,荧光显微镜图像显示与微生物细胞结合的硼二吡咯发出绿色荧光。随着照射时间的增加,光致敏失活作用增强。两种硼二吡咯对细菌的光失活活性相似。这些硼二吡咯诱导的光失活对两种细菌均有效。然而,革兰氏阳性菌比革兰氏阴性菌更快被失活,且所需光敏剂浓度更低。照射15分钟后,1μM光敏剂可完全根除金黄色葡萄球菌。使用5μM光敏剂并照射30分钟时,大肠杆菌的存活率降低了4.5个对数。同样,在上述条件下,用硼二吡咯3处理的白色念珠菌细胞减少了4.5个对数,而硼二吡咯4的效果较差。另一方面,研究了在不同照射时间和盐浓度下添加碘化钾对光失活的影响。在金黄色葡萄球菌中观察到的影响较小,因为单独的光敏剂已经非常有效。在大肠杆菌中,光杀伤增强主要出现在较长的照射时间。此外,在碘化钾存在下,这些硼二吡咯介导的白色念珠菌光失活作用增强。在溶液中,由于外部重原子的作用,添加盐后观察到硼二吡咯三线态的形成增加。硼二吡咯诱导的更大的系间窜越以及活性碘物种的形成可能有助于增强微生物的失活。因此,这些硼二吡咯是用于使微生物失活的有趣的光敏剂。特别是,硼二吡咯3与碘化钾联合使用作为一种广谱抗菌光敏剂非常有效。

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