Discovery of novel 3-(piperazin-1-yl)propan-2-ol decorated carbazole derivatives as new membrane-targeting antibacterial agents

Ding, Yao; Gao, Xiaofei; Wang, Na; Long, Zhou-Qing; Liu, Hongwu; Xie, Jiao; Liu, Shi‐Tao; Qi, Pu-Ying; Zhou, Xiang; Liu, Liwei; Yang, Song

doi:10.1016/j.arabjc.2023.104991

Cited by 2 publications

(2 citation statements)

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“…The binding energy values of DC1, DC2, DC3, and streptomycin were 6.5, 6.2, 6.1, and 5.3 kcal/mol, respectively [ 15 ]. Ding et al [ 16 ] received novel carbazole derivatives containing a 3-(piperazin-1-yl) propan-2-ol moiety, and evaluated their potential against plant bacterial pathogens. The EC50 of compound A9 against Xanthomonas oryzae and Xanthomonas axonopodis demonstrated the values of 6.80 and 6.37 µg/ml, respectively.…”

Section: Discussionmentioning

confidence: 99%

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Antimicrobial Activity and Toxicity of Newly Synthesized 4-[4-(benzylamino)butoxy]-9H-carbazole Derivatives

Niedziałkowska,

Felczak,

Głowacka

et al. 2023

IJMS

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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]-9H-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 2, 4, and 8 at the concentration of 16 µg/mL caused the inhibition of S. aureus growth by over 60%. The MIC value of compounds 2–5 and 7–10 was 32 µg/mL for Staphylococcus strains. Gram-negative strains of E. coli and P. aeruginosa were found to be more resistant to the tested carbazole derivatives. E. coli cells treated with compounds 3 and 8 at a concentration of 64 µg/mL resulted in a greater-than-40% reduction in bacterial growth. In the case of the P. aeruginosa 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 C. albicans and A. flavus incubated with 64 µg/mL of compounds 2 or 7 and 1 or 4, 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 1, 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]-9H-carbazole derivatives, especially against S. aureus strains; therefore, it is worth further modifying these structures, in order to enhance their activity against pathogenic microorganisms.

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Section: Discussionmentioning

confidence: 99%

“…It was found that compound A9 showed an ability to damage the bacterial cell membrane, which resulted in a leak of cytoplasmic components. At the same time, this compound was characterized by a low phytotoxicity, which could enable its practical use in plant protection against bacterial pathogens [ 16 ].…”

Section: Discussionmentioning

confidence: 99%