Structure–activity relationship of porphyrin-induced photoinactivation with membrane function in bacteria and erythrocytes,Photochemical & Photobiological Sciences

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Structure–activity relationship of porphyrin-induced photoinactivation with membrane function in bacteria and erythrocytes
Photochemical & Photobiological Sciences ( IF 2.7 ) Pub Date : 2018-06-05 00:00:00 , DOI: 10.1039/c8pp00092a
Hisato Kato _{1,

2,

3} , Keiko Komagoe _{3,

4,

5,

6} , Tsuyoshi Inoue _{3,

5,

6,

7,

8} , Kazufumi Masuda _{2,

3,

9} , Takashi Katsu _{1,

2,

3}

Affiliation

We analyzed the structure–activity relationship of porphyrins with the photoinactivation of membrane function in bacteria and erythrocytes. The porphyrins tested were protoporphyrin (PP), mesoporphyrin (MP), deuteroporphyrin (DP), hematoporphyrin (HP), coproporphyrin (CP) and uroporphyrin (UP), along with hematoporphyrin derivative (HPD) and photofrin (PF). These porphyrins dissipated membrane potential of Staphylococcus aureus cells depending on the degrees of respiratory inhibition and K⁺ leakage. The dysfunction of bacterial membrane was caused within minutes and in the order of PP ∼ MP > DP > HPD ≫ HP > PF > CP ∼ UP. For bovine erythrocytes, these porphyrins induced leakage of K⁺ and inhibition of the enzyme acetylcholinesterase, which is located on the outer layer of the erythrocyte membrane, in the same order as that observed in bacteria. At high concentrations of PP, MP, DP and HPD, hemolysis (the lysis of erythrocytes with liberation of hemoglobin) was also induced. We found that the degree of photoinactivation of membrane function was closely associated with porphyrin-induced morphological changes in bovine erythrocytes, forming a crenated form from the normal discoid, which is the index of the amount of porphyrins in the outer layer of the cytoplasmic membrane. Furthermore, the degree of morphological changes was related with the octanol/water partition coefficients of porphyrins. These results strongly supported that porphyrins located in the outer layer of cytoplasmic membrane inactivated the cell membrane function by photo-irradiation, and the strength of photoinactivation by porphyrins depended on their affinity to the cell membrane.

中文翻译：

细菌和红细胞中卟啉诱导的光失活与膜功能的结构-活性关系

我们分析了卟啉与细菌和红细胞中膜功能的光失活之间的结构-活性关系。测试的卟啉是原卟啉（PP），中卟啉（MP），氘卟啉（DP），血卟啉（HP），辅卟啉（CP）和尿卟啉（UP），以及血卟啉衍生物（HPD）和光敏蛋白（PF）。这些卟啉消散了金黄色葡萄球菌细胞的膜电位，这取决于呼吸抑制和K ⁺渗漏的程度。细菌膜的功能障碍是在数分钟内引起的，并且顺序为PP〜MP> DP> HPD≫ HP> PF> CP〜UP。对于牛红细胞，这些卟啉可导致K ^+的渗漏并以与细菌中观察到的相同顺序抑制位于红细胞膜外层的乙酰胆碱酯酶。在高浓度的PP，MP，DP和HPD时，也会引起溶血（红细胞溶解并释放血红蛋白）。我们发现，膜功能的光失活程度与卟啉诱导的牛红细胞形态变化密切相关，从正常的盘状体形成锯齿状，这是细胞质膜外层中卟啉量的指数。此外，形态变化的程度与卟啉的辛醇/水分配系数有关。

更新日期：2018-06-05

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