Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa
Samo za registrovane korisnike
2017
Autori
Aleksić, IvanaŠegan, Sandra B.
Andrić, Filip
Zlatović, Mario
Morić, Ivana
Opsenica, Dejan M.
Šenerović, Lidija
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Izvor:
ACS Chemical Biology, 2017, 12, 5, 1425-1434Izdavač:
- Amer Chemical Soc, Washington
Finansiranje / projekti:
- Izučavanje mikrobiološkog diverziteta i karakterizacija korisnih sredinskih mikroorganizama (RS-MESTD-Basic Research (BR or ON)-173048)
- Sinteza aminohinolina i njihovih derivata kao antimalarika i inhibitora botulinum neurotoksina A (RS-MESTD-Basic Research (BR or ON)-172008)
- European Society of Clinical Microbiology and Infectious Diseases (ESCMID)
Napomena:
- Peer-reviewed manuscript: http://cherry.chem.bg.ac.rs/handle/123456789/3089
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3090
DOI: 10.1021/acschembio.6b01149
ISSN: 1554-8929
PubMed: 28350449
WoS: 000402023300029
Scopus: 2-s2.0-85019737266
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - 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://cherry.chem.bg.ac.rs/handle/123456789/2461 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 VL - 12 IS - 5 SP - 1425 EP - 1434 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", volume = "12", number = "5", pages = "1425-1434", 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 . .