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Photoinactivation of Escherichia coli with Water-Soluble Ammonium-Substituted Phthalocyanines
ACS Applied Bio Materials ( IF 4.6 ) Pub Date : 2020-06-10 , DOI: 10.1021/acsabm.0c00128 Sara R D Gamelas 1 , Ana T P C Gomes 2 , Maria Amparo F Faustino 1 , Augusto C Tomé 1 , João P C Tomé 3 , Adelaide Almeida 2 , Leandro M O Lourenço 1
ACS Applied Bio Materials ( IF 4.6 ) Pub Date : 2020-06-10 , DOI: 10.1021/acsabm.0c00128 Sara R D Gamelas 1 , Ana T P C Gomes 2 , Maria Amparo F Faustino 1 , Augusto C Tomé 1 , João P C Tomé 3 , Adelaide Almeida 2 , Leandro M O Lourenço 1
Affiliation
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Zinc(II) phthalocyanines (Pcs) peripherally decorated with 2,4,6-tris(dimethylaminomethyl)phenoxy groups (Pcs 1 and 3) and the corresponding quaternized derivatives (Pcs 2 and 4) were synthesized and their photodynamic inactivation (PDI) efficiency against recombinant bioluminescent Escherichia coli was examined. The photophysical data revealed that the presence of the ammonium units on the Pc structures promotes a redshift of the absorption bands when compared with the corresponding nonquaternized ones. The ammonium-substituted Pcs 2 and 4 showed excellent stability in dimethylformamide, moderate photostability, and increased efficiency to generate singlet oxygen (1O2). The water-soluble photosensitizers 2 and 4 at 5.0 μM exhibited a high photodynamic inactivation (PDI) efficiency against planktonic bioluminescent E. coli, reaching the detection limit of the methodology (a decrease of ∼4 log in the bioluminescence signal) after 210 min and 150 min under red light, delivered at a fluence rate of 135 mW·cm–2, respectively. Moreover, for the first time, it was accessed with the combined action of KI with ammonium-substituted Pcs. The addition of potassium iodide significantly improved the efficacy of Pc 2, which could reach the same inactivation rate after a short period of 5 min under the same irradiation conditions. The use of KI potentiates the PDI efficacy probably because of the generation of additional highly cytotoxic species during the photodynamic process which begins with the reaction of 1O2 with KI producing peroxyiodide species. The results of this work show that Pcs 2 and 4, with or without KI, can be considered as promising Pc dyes for the PDI of Gram-negative bacteria.
中文翻译：
水溶性铵取代酞菁对大肠杆菌的光灭活
合成了外围装饰有 2,4,6-三(二甲基氨基甲基)苯氧基 (Pcs 1和3 ) 的锌 (II) 酞菁 (Pcs) 和相应的季铵化衍生物 (Pcs 2和4 ) 及其光动力灭活 (PDI) 效率对重组生物发光大肠杆菌进行了检测。光物理数据表明，与相应的非季铵化结构相比，Pc 结构上铵单元的存在促进了吸收带的红移。铵取代的 Pcs 2和4在二甲基甲酰胺中表现出优异的稳定性，中等的光稳定性，并提高了产生单线态氧（1 O 2）的效率。5.0 μM的水溶性光敏剂2和4对浮游生物发光大肠杆菌表现出高光动力灭活 (PDI) 效率，在 210 分钟后达到该方法的检测限（生物发光信号减少 ∼4 log）和在红光下 150 分钟，分别以 135 mW·cm –2的通量率传输。此外，它首次通过 KI 与铵取代的 Pcs 的联合作用获得。碘化钾的加入显着提高了Pc 2的疗效, 在相同的辐照条件下, 短时间 5 min 后即可达到相同的灭活率。KI 的使用增强了 PDI 的功效，这可能是因为在光动力过程中产生了额外的高细胞毒性物质，该过程始于1 O 2与 KI 反应产生过氧化碘物质。这项工作的结果表明，无论是否含有 KI，Pcs 2和4都可以被认为是用于革兰氏阴性菌 PDI 的有前景的 Pc 染料。
更新日期：2020-07-20
中文翻译：
水溶性铵取代酞菁对大肠杆菌的光灭活
合成了外围装饰有 2,4,6-三(二甲基氨基甲基)苯氧基 (Pcs 1和3 ) 的锌 (II) 酞菁 (Pcs) 和相应的季铵化衍生物 (Pcs 2和4 ) 及其光动力灭活 (PDI) 效率对重组生物发光大肠杆菌进行了检测。光物理数据表明，与相应的非季铵化结构相比，Pc 结构上铵单元的存在促进了吸收带的红移。铵取代的 Pcs 2和4在二甲基甲酰胺中表现出优异的稳定性，中等的光稳定性，并提高了产生单线态氧（1 O 2）的效率。5.0 μM的水溶性光敏剂2和4对浮游生物发光大肠杆菌表现出高光动力灭活 (PDI) 效率，在 210 分钟后达到该方法的检测限（生物发光信号减少 ∼4 log）和在红光下 150 分钟，分别以 135 mW·cm –2的通量率传输。此外，它首次通过 KI 与铵取代的 Pcs 的联合作用获得。碘化钾的加入显着提高了Pc 2的疗效, 在相同的辐照条件下, 短时间 5 min 后即可达到相同的灭活率。KI 的使用增强了 PDI 的功效，这可能是因为在光动力过程中产生了额外的高细胞毒性物质，该过程始于1 O 2与 KI 反应产生过氧化碘物质。这项工作的结果表明，无论是否含有 KI，Pcs 2和4都可以被认为是用于革兰氏阴性菌 PDI 的有前景的 Pc 染料。
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