Photodynamic inactivation of Escherichia coli by novel meso-substituted porphyrins by 4-(3-N,N,N-trimethylammoniumpropoxy)phenyl and 4-(trifluoromethyl)phenyl groups
Photodynamic inactivation of Escherichia coli by novel meso-substituted porphyrins by 4-(3-N,N,N-trimethylammoniumpropoxy)phenyl and 4-(trifluoromethyl)phenyl groups
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DOI：
10.1039/b513511g
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发表时间：
2006-01-01
影响因子：
3.1
通讯作者：
Durantini, EN
中科院分区：
文献类型：
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作者：
Caminos, DA;Spesia, MB;Durantini, EN
新型阳离子卟啉具有不同的 4-(3-N,N,N-三甲基铵丙氧基)苯基 (A) 和 4-(三氟甲基)苯基 (B) 基团内消旋取代模式，其光动力效应已在带有光氧化底物的溶液中和体外对典型革兰氏阴性细菌大肠杆菌进行了研究。在这些敏化剂中，阳离子基团通过丙氧基间隔基与大环分开。因此，电荷具有高迁移率并且对卟啉的光物理性质的影响最小。这些化合物产生单线态分子氧 O-2( (1)Delta(g))，其量子产率类似于 N,N-二甲基甲酰胺中的 0.41-0.53。在甲醇中，L-色氨酸光分解随着敏化剂中阳离子电荷数量的增加而增加。体外研究表明，阳离子卟啉在大约 5 分钟内即可快速与大肠杆菌细胞结合。发现 A(3)B(3+) 卟啉具有更高的结合力，在三个洗涤步骤后仍与细胞紧密结合。大肠杆菌细胞悬液的光敏灭活遵循以下顺序：A(3)B(3+) > A(4)(4+) >> ABAB(2+) > AB(3)(+)。在这些条件下，发现对作为阴离子敏化剂特征的5,10,15,20-四(4磺基苯基)卟啉(TPPS44-)的影响可以忽略不计。此外，还将这些新型阳离子卟啉的结果与 5,10,15,20-四（4-N,N,N-三甲基铵苯基）卟啉 (TTAP(4+)) 的结果进行了比较，后者是为根除大肠杆菌而建立的标准活性敏化剂。 TTAP(4+)的光动力活性与A(4)(4+)产生的光动力活性非常相似。缺氧条件下的研究表明，氧气对于细菌光动力灭活的作用机制是必需的。生长延迟实验证实了A(3)B(3+)较高的光动力活性。还在琼脂表面固定的大肠杆菌细胞中评估了这些敏化剂的光动力灭活能力。在这些条件下，A(3)B(3+) 卟啉保留了灭活局部细菌细胞的高活性。因此，三阳离子卟啉 A(3)B(3+) 是一种有趣的敏化剂，在液体悬浮液或表面细菌的光动力灭活方面具有潜在的应用前景。
The photodynamic effect of novel cationic porphyrins, with different pattern of meso-substitution by 4-(3-N,N,N-trimethylammoniumpropoxy)phenyl (A) and 4-(trifluoromethyl) phenyl ( B) groups, have been studied in both solution bearing photooxidizable substrates and in vitro on a typical Gram-negative bacterium Escherichia coli. In these sensitizers, the cationic groups are separated from the macrocycle ring by a propoxy spacer. Thus, the charges have a high mobility and a minimal influence on photophysical properties of the porphyrin. These compounds produce singlet molecular oxygen, O-2( (1)Delta(g)), with quantum yields of similar to 0.41-0.53 in N, N-dimethylformamide. In methanol, the L-tryptophan photodecomposition increases with the number of cationic charges in the sensitizer. In vitro investigations show that cationic porphyrins are rapidly bound to E. coli cells in similar to 5 min. A higher binding was found for A(3)B(3+) porphyrin, which is tightly bound to cells still after three washing steps. Photosensitized inactivation of E. coli cellular suspensions follows the order: A(3)B(3+) > A(4)(4+) >> ABAB(2+) > AB(3)(+). Under these conditions, a negligible effect was found for 5,10,15,20-tetra(4sulfonatophenyl) porphyrin (TPPS44-) that characterizes an anionic sensitizer. Also, the results obtained for these new cationic porphyrins were compared with those of 5,10,15,20-tetra(4-N,N,N-trimethylammonium phenyl) porphyrin (TTAP(4+)), which is a standard active sensitizer established to eradicate E. coli. The photodynamic activity of TTAP(4+) is quite similar to that produced by A(4)(4+). Studies in an anoxic condition indicate that oxygen is necessary for the mechanism of action of photodynamic inactivation of bacteria. The higher photodynamic activity of A(3)B(3+) was confirmed by growth delay experiments. Photodynamic inactivation capacities of these sensitizers were also evaluated in E. coli cells immobilized on agar surfaces. Under these conditions, A(3)B(3+) porphyrin retains a high activity to inactivate localized bacterial cells. Therefore, tricationic porphyrin A(3)B(3+) is an interesting sensitizer with potential applications in photodynamic inactivation of bacteria in liquid suspensions or on surfaces.