Department of Industrial Microbiology and Biotechnology, Faculty of Biology and Environmental Protection, University of Lodz, 90-237 Lodz, Poland.
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, 90-151 Lodz, Poland.
Int J Mol Sci. 2023 Sep 6;24(18):13722. doi: 10.3390/ijms241813722.
One of the main challenges of medicinal chemistry is the search for new substances with antimicrobial potential that could be used in the fight against pathogenic microorganisms. Therefore, the antimicrobial activity of newly synthesized compounds is still being investigated. Carbazole-containing compounds appear to be promising antibacterial, antifungal, and antiviral agents. The aim of this study was to examine the antimicrobial potential and toxicity of newly synthesized isomeric fluorinated 4-[4-(benzylamino)butoxy]-9-carbazole derivatives. Their antimicrobial activity against bacteria and fungi was tested according to CLSI guidelines. Similarly to previously studied carbazole-containing compounds, the tested derivatives showed the ability to effectively inhibit the growth of Gram-positive bacteria. The addition of carbazole derivatives , , and at the concentration of 16 µg/mL caused the inhibition of growth by over 60%. The MIC value of compounds - and - was 32 µg/mL for strains. Gram-negative strains of and were found to be more resistant to the tested carbazole derivatives. cells treated with compounds and at a concentration of 64 µg/mL resulted in a greater-than-40% reduction in bacterial growth. In the case of the strain, all compounds in the highest concentration that we tested limited growth by 35-42%. Moreover, an over-60% inhibition of fungal growth was observed in the cultures of and incubated with 64 µg/mL of compounds or and or , respectively. The hemolysis of red blood cells after their incubation with the tested carbazole derivatives was in the range of 2-13%. In the case of human fibroblast cells, the toxicity of the tested compounds was higher. Derivative , functionalized with fluorine in position 2 and its hydrobromide, was the least toxic. The obtained results indicated the antimicrobial potential of the tested 4-[4-(benzylamino)butoxy]-9-carbazole derivatives, especially against strains; therefore, it is worth further modifying these structures, in order to enhance their activity against pathogenic microorganisms.
药用化学面临的主要挑战之一是寻找具有抗菌潜力的新物质，这些物质可用于对抗病原微生物。因此，新合成化合物的抗菌活性仍在研究中。含咔唑的化合物似乎是很有前途的抗菌、抗真菌和抗病毒药物。本研究旨在研究新合成的异构氟化 4-[4-(苄基氨基)丁氧基]-9-咔唑衍生物的抗菌潜力和毒性。根据 CLSI 指南测试了它们对细菌和真菌的抗菌活性。与之前研究过的含咔唑的化合物类似，测试的衍生物表现出有效抑制革兰氏阳性菌生长的能力。在浓度为 16μg/ml 时，咔唑衍生物 、 、和 的添加导致 生长抑制超过 60%。化合物 - 和 - 的 MIC 值为 32μg/ml ，针对 株。革兰氏阴性菌 和 对测试的咔唑衍生物更为耐药。在浓度为 64μg/ml 时，用化合物 和 处理的 细胞导致细菌生长减少超过 40%。在 株的情况下，我们测试的最高浓度的所有化合物均将生长限制在 35-42%。此外，在浓度为 64μg/ml 时，化合物 或 或 分别孵育的 和 真菌培养物中观察到真菌生长抑制超过 60%。用测试的咔唑衍生物孵育后，红细胞溶血率在 2-13%范围内。在人成纤维细胞的情况下，测试化合物的毒性更高。在 2 位氟化的衍生物 及其氢溴酸盐具有最低毒性。研究结果表明，测试的 4-[4-(苄基氨基)丁氧基]-9-咔唑衍生物具有抗菌潜力，特别是针对 株；因此，值得进一步修饰这些结构，以提高它们对病原微生物的活性。
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