Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa
Аутори
Aleksić, IvanaŠegan, Sandra B.
Andrić, Filip
Zlatović, Mario
Morić, Ivana
Opsenica, Dejan M.
Šenerović, Lidija
Чланак у часопису (Рецензирана верзија)
Метаподаци
Приказ свих података о документуАпстракт
Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC) gt 400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean to...pological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.
Извор:
ACS Chemical Biology, 2017, 12, 5, 1425-1434Издавач:
- Amer Chemical Soc, Washington
Финансирање / пројекти:
- Изучавање микробиолошког диверзитета и карактеризација корисних срединских микроорганизама (RS-MESTD-Basic Research (BR or ON)-173048)
- Синтеза аминохинолина и њихових деривата као антималарика и инхибитора ботулинум неуротоксина А (RS-MESTD-Basic Research (BR or ON)-172008)
- European Society of Clinical Microbiology and Infectious Diseases (ESCMID)
Напомена:
- This is the peer-reviewed version of the following article: Aleksić, I.; Šegan, S.; Andrić, F.; Zlatović, M.; Moric, I.; Opsenica, D. M.; Senerovic, L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia Marcescens and Pseudomonas Aeruginosa. ACS Chemical Biology 2017, 12 (5), 1425–1434. https://doi.org/10.1021/acschembio.6b01149
- Supplementary material: https://imagine.imgge.bg.ac.rs/handle/123456789/2227
Повезане информације:
- Друга верзија
https://doi.org/10.1002/app.54663 - Друга верзија
https://imagine.imgge.bg.ac.rs/handle/123456789/1092
DOI: 10.1021/acschembio.6b01149
ISSN: 1554-8929
WoS: 000402023300029
Scopus: 2-s2.0-85019737266
Институција/група
Institut za molekularnu genetiku i genetičko inženjerstvoTY - JOUR AU - Aleksić, Ivana AU - Šegan, Sandra B. AU - Andrić, Filip AU - Zlatović, Mario AU - Morić, Ivana AU - Opsenica, Dejan M. AU - Šenerović, Lidija PY - 2017 UR - https://imagine.imgge.bg.ac.rs/handle/123456789/2226 AB - Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC) gt 400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species. PB - Amer Chemical Soc, Washington T2 - ACS Chemical Biology T1 - Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa EP - 1434 IS - 5 SP - 1425 VL - 12 DO - 10.1021/acschembio.6b01149 ER -
@article{ author = "Aleksić, Ivana and Šegan, Sandra B. and Andrić, Filip and Zlatović, Mario and Morić, Ivana and Opsenica, Dejan M. and Šenerović, Lidija", year = "2017", abstract = "Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC) gt 400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.", publisher = "Amer Chemical Soc, Washington", journal = "ACS Chemical Biology", title = "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa", pages = "1434-1425", number = "5", volume = "12", doi = "10.1021/acschembio.6b01149" }
Aleksić, I., Šegan, S. B., Andrić, F., Zlatović, M., Morić, I., Opsenica, D. M.,& Šenerović, L.. (2017). Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa. in ACS Chemical Biology Amer Chemical Soc, Washington., 12(5), 1425-1434. https://doi.org/10.1021/acschembio.6b01149
Aleksić I, Šegan SB, Andrić F, Zlatović M, Morić I, Opsenica DM, Šenerović L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa. in ACS Chemical Biology. 2017;12(5):1425-1434. doi:10.1021/acschembio.6b01149 .
Aleksić, Ivana, Šegan, Sandra B., Andrić, Filip, Zlatović, Mario, Morić, Ivana, Opsenica, Dejan M., Šenerović, Lidija, "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa" in ACS Chemical Biology, 12, no. 5 (2017):1425-1434, https://doi.org/10.1021/acschembio.6b01149 . .