Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Antifungal Activity
2.3. Antibacterial Activity
2.4. Cytotoxicity and Selective Index
3. Materials and Methods
3.1. Antifungal Activity
3.1.1. Microorganisms and Media
3.1.2. Antifungal Susceptibility Testing
3.1.3. Fungal Growth Inhibition Percentage Determination
3.2. Antituberculosis and Antibacterial Activity
3.3. Cytotoxicity on VERO Cell Line
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Structure | Hybrid | R1 | R2 | R3 | R4 | Ca | Cn | Afu | Afl | Ani |
---|---|---|---|---|---|---|---|---|---|---|
| 7a | OMe | H | H | - | 125 | 62.5 | i | i | i |
7b | Me | H | H | - | 62.5 | 62.5 | i | i | i | |
7c | H | H | Me | - | 62.5 | 15.6 | 62.5 | 62.5 | 62.5 | |
7d | H | Cl | H | - | 62.5 | 15.6 | 62.5 | 62.5 | 62.5 | |
| 7e | OMe | H | H | Bu | i | 250 | i | i | i |
7f | Me | H | H | Bu | 250 | 125 | i | i | i | |
7g | H | Cl | H | Bu | 250 | 62.5 | i | i | i | |
7h | H | H | H | Bn | i | 250 | 250 | 250 | 250 | |
AmpB | 0.78 | 0.25 | 0.50 | 0.50 | 0.50 |
Comp. | Concentration in µg/mL | MIC in µg/mL | ||||||
---|---|---|---|---|---|---|---|---|
250 | 125 | 62.50 | 31.25 | 15.62 | 7.81 | 3.90 | ||
7a | 100 | 100 | 100 | 43.6 ± 3.86 | 18.60 ± 8.59 | 4.72 ± 1.39 | 0 | 62.5 |
7b | 100 | 100 | 100 | 92.58 ± 4.81 | 67.84 ± 5.66 | 57.14 ± 4.93 | 12.54 ± 0.36 | 31.25 |
7c | 100 | 100 | 100 | 100 | 100 | 53.45 ± 4.42 | 48.41 ± 4.63 | 15.62 |
7d | 100 | 100 | 100 | 100 | 100 | 67.59 ± 9.19 | 0 | 15.62 |
7e | 100 | 62.46 ± 0.30 | 41.46 ± 0.58 | 38.79 ± 3.79 | 29.92 ± 6.13 | 17.19 ± 0.91 | 8.23 ± 3.18 | 250 |
7f | 100 | 100 | 49.28 ± 3.20 | 24.91 ± 0.15 | 19.01 ± 3.40 | 9.34 ± 2.90 | 0 | 62.5 |
7g | 100 | 94.15 ± 4.15 | 90.90 ± 7.60 | 50.44 ± 2.09 | 30.94 ± 5.61 | 25.50 ± 5.35 | 0 | 250 |
7h | 100 | 76.77 ± 1.91 | 48.99 ± 3.00 | 46.84 ±5.32 | 35.32 ± 2.02 | 22.76 ± 2.87 | 2.52 ± 0.56 | 250 |
AmpB | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 0.25 |
Hybrid | MICs in µg/mL (µM) | ||||
---|---|---|---|---|---|
E. coli | K. pneumoniae | S. aureus | M. bovis BCG | M. tuberculosis H37Rv | |
7a | 100 (231) | 100 (231) | 100 (231) | 50 (115) | 20 (46) |
7b | 200 (480) | 50 (120) | 2 (5) | 50 (120) | 10 (24) |
7c | 200 (480) | 200 (480) | 100 (240) | 200 (480) | 200 (480) |
7d | 100 (229) | 200 (457) | 100 (229) | 50 (114) | 50 (114) |
7e | 200 (462) | 100 (231) | 100 (231) | 50 (115) | 50 (115) |
7f | 200 (478) | 200 (478) | 200 (478) | 200 (478) | 100 (239) |
7g | 200 (228) | 100 (114) | 100 (114) | 100 (228) | 100 (228) |
7h | 100 (228) | 100 (228) | 20 (47) | 50 (114) | 50 (114) |
chloramphenicol | 20 (62) | 20 (62) | 20 (62) | nd | nd |
isoniazid | nd | nd | nd | 0.05 (0.36) | 0.05 (0.36) |
Hybrid | Selectivity Index (SI) (SI = LC50/MIC) | |||||
---|---|---|---|---|---|---|
Cytotoxicity LC50-Vero cells | E. coli | K. pneumoniae | S. aureus | M. bovis BCG | M. tuberculosis H37Rv | |
7a | 277 ± 14.6 | 2.77 | 2.77 | 2.77 | 5.54 | 13.9 |
7b | 234 ± 4 | 1.17 | 4.68 | 117 | 4.68 | 23.4 |
7c | 268 ± 5.69 | 1.34 | 1.34 | 2.68 | 1.34 | 1.34 |
7d | 189 ± 14.5 | 1.89 | 0.94 | 1.89 | 3.78 | 3.78 |
7e | 125 ± 22 | 0.62 | 1.25 | 1.25 | 2.5 | 2.50 |
7f | 150 ± 12.2 | 0.75 | 0.75 | 0.75 | 0.75 | 1.50 |
7g | 144 ± 8.9 | 1.44 | 1.44 | 1.44 | 1.44 | 1.44 |
7h | 235 ± 6.5 | 2.35 | 2.35 | 11.8 | 4.70 | 4.70 |
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Share and Cite
Insuasty, D.; Vidal, O.; Bernal, A.; Marquez, E.; Guzman, J.; Insuasty, B.; Quiroga, J.; Svetaz, L.; Zacchino, S.; Puerto, G.; et al. Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids. Antibiotics 2019, 8, 239. https://doi.org/10.3390/antibiotics8040239
Insuasty D, Vidal O, Bernal A, Marquez E, Guzman J, Insuasty B, Quiroga J, Svetaz L, Zacchino S, Puerto G, et al. Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids. Antibiotics. 2019; 8(4):239. https://doi.org/10.3390/antibiotics8040239
Chicago/Turabian StyleInsuasty, Daniel, Oscar Vidal, Anthony Bernal, Edgar Marquez, Juan Guzman, Braulio Insuasty, Jairo Quiroga, Laura Svetaz, Susana Zacchino, Gloria Puerto, and et al. 2019. "Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids" Antibiotics 8, no. 4: 239. https://doi.org/10.3390/antibiotics8040239