Theoretical and Experimental Studies of Phosphonium Ionic Liquids as Potential Antibacterials of MDR Acinetobacter baumannii
Abstract
:1. Introduction
2. Materials and Methods
2.1. QSAR Modeling of Antioxidant Activity
2.1.1. Dataset
2.1.2. QSAR
Descriptors
2.2. Biology
2.2.1. Antibacterial Activity Evaluation
2.2.2. Antioxidant Activity Evaluation
3. Results
3.1. Regression Model to Predict the Antioxidant Activity
N | Method | Training Set a | Test Set a | ||
---|---|---|---|---|---|
q2 | MAEc | q2 | MAE | ||
1 | Transformer CNN | 0.77 ± 0.02 | 0.3 ± 0.01 | 0.75 ± 0.05 | 0.28 ± 0.02 |
2 | Transformer CNF | 0.76 ± 0.02 | 0.3 ± 0.01 | 0.77 ± 0.04 | 0.28 ± 0.02 |
3 | RF | 0.73 ± 0.02 | 0.32 ± 0.01 | 0.72 ± 0.04 | 0.3 ± 0.02 |
4 | Consensusb | 0.77 ± 0.02 | 0.29 ± 0.01 | 0.77 ± 0.04 | 0.27 ± 0.02 |
3.2. Selection of Compounds with the Help of In Silico Tools
3.3. Synthesis of PILs
3.3.1. Initial Materials and Structure Confirmation
3.3.2. Synthesis of Ionic Liquids
- Octyl(triphenyl)phosphonium bromide (PPh3C8–Br), CASRN 42036-78-2.Colorless solid, m.p.: 61–63 °C.1H NMR (400 MHz, DMSO-d6): σ = 0.81 (t, 3H, CH3), 1.19 (m, 8H, CH2), 1.48 (m, 4H, PCH2CH2CH2CH2), 3.56 (m, 2H, PCH2), 7.76–7.84 (m, 15H, Ar–H).
- Decyl(triphenyl)phosphonium bromide (PPh3C10–Br), CASRN 32339-43-8.White solid, m.p.: 86–88 °C.1H NMR (400 MHz, DMSO-d6): σ = 0.83 (t, 3H, CH3), 1.2 (m, 12H, CH2), 1.46 (m, 4H, PCH2CH2CH2CH2), 3.6 (m, 2H, PCH2), 7.8–7.9 (m, 15H, Ar–H).
- Dodecyl(triphenyl)phosphonium bromide (PPh3C12–Br), CASRN 15510-55-1.White solid, m.p.: 89–92 °C.1H NMR (400 MHz, DMSO-d6): σ = 0.83 (t, 3H, CH3), 1.2 (m, 16H, CH2), 1.46 (m, 4H, PCH2CH2CH2CH2), 3.6 (m, 2H, PCH2), 7.8–7.9 (m, 15H, Ar–H).
- Octyl(tributyl)phosphonium bromide (PBu3C8–Br), CARSN 57702-65-5.Liquid.1H NMR (400 MHz, CDCl3): σ = 0.86 (t, 3H, CH3), 0.96 (t, 9H, CH2CH2CH2CH3), 1.24 (m, 8H, CH2), 1.51 (m, 16H, PCH2CH2CH2CH2), 2.44 (m, 8H, PCH2).
- Decyl(tributyl)phosphonium bromide (Pbu3C10–Br), CASRN 99045-50-8.Viscous liquid.1H NMR (400 MHz, CDCl3): σ = 0.85 (t, 3H, CH3), 0.96 (t, 9H, CH2CH2CH2CH3), 1.24 (m, 12H, CH2), 1.51 (m, 16H, PCH2CH2CH2CH2), 2.43 (m, 8H, PCH2).
- Dodecyl(tributyl)phosphonium bromide (Pbu3C12–Br), CASRN 15294-63-0.White solid, m.p.: 30–32 °C.1H NMR (400 MHz, CDCl3): σ = 0.86 (t, 3H, CH3), 0.96 (t, 9H, CH2CH2CH2CH3), 1.24 (m, 16H, CH2), 1.52 (m, 16H, PCH2CH2CH2CH2), 2.44 (m, 8H, PCH2).
3.4. In Vitro Evaluation of the Activity of the PILs
3.4.1. Antibacterial Activity
N | Compound | Compound Content on a Disk (µmoles) | |||
---|---|---|---|---|---|
0.01 | 0.05 | 0.25 | 1.25 | ||
1 | PPh3C8–Br | 8.1 ± 0.3 | 12.3 ± 0.6 | 15.5 ± 0.3 | 17.3 ± 0.6 |
2 | PPh3C10–Br | 20.4 ± 0.9 | 25.4 ± 0.3 | 28.6 ± 0.9 | 31.5 ± 0.6 |
3 | PPh3C12–Br | 26.2 ± 0.6 | 30.1 ± 0.6 | 34.4 ± 0.9 | 41.8 ± 0.9 |
4 | Pbu3C8–Br | 14.5 ± 0.3 | 18.8 ± 0.3 | 22.3 ± 0.6 | 26.1 ± 0.3 |
5 | Pbu3C10–Br | 20.7 ± 0.3 | 25.4 ± 0.6 | 31.3 ± 0.3 | 34.2 ± 0.3 |
6 | Pbu3C12–Br | 26.1 ± 0.6 | 30.3 ± 0.3 | 33.2 ± 0.6 | 36.6 ± 0.6 |
7 | Ampicillin, oxacillin, ceftriaxone | 6 ± 0.3 | 6 ± 0.3 | 6 ± 0.3 | 6 ± 0.3 |
3.4.2. Antioxidant Activity
N | Compound | Inhibition Fate of MDA, % |
---|---|---|
1 | PPh3C8–Br | 31.5 ± 2.0 |
2 | PPh3C10–Br | 34.2 ± 1.2 |
3 | PPh3C12–Br | 33.3 ± 1.5 |
4 | PPh3C8–Br | 31.5 ± 2.0 |
5 | PPh3C10–Br | 34.2 ± 1.2 |
6 | PBu3C12–Br | 33.1 ± 2.2 |
Ionol a | 31.4 ± 2.5 | |
1% DMSO b | 14 ± 0.5 |
4. Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Abbreviations
AOA | Antioxidant activity |
CDK | Chemistry Development Kit |
CFU | Colony-forming unit |
CNF | Convolutional neural fingerprint |
CNN | Convolutional neural network |
ILs | Ionic liquids |
MAE | Mean absolute error |
MDR | Multidrug-resistant |
OCHEM | Online chemical database and modeling environment |
PILs | Phosphonium ionic liquids |
QSAR | Quantitative structure–activity relationship |
RF | Random forest |
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PILs | Compound | Molecular Weight | Chemical Structure | Chemical Name |
---|---|---|---|---|
1 | PPh3C8–Br | 455.41 | | Octyl(triphenyl)phosphonium bromide |
2 | PPh3C10–Br | 483.46 | | Decyl(triphenyl)phosphonium bromide |
3 | PPh3C12–Br | 511.52 | | Dodecyl(triphenyl)phosphonium bromide |
4 | PBu3C8–Br | 395.4 | | Octyl(tributyl)phosphonium bromide |
5 | PBu3C10–Br | 423.49 | | Decyl(tributyl)phosphonium bromide |
6 | PBu3C12–Br | 451.55 | | Dodecyl(tributyl)phosphonium bromide |
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Metelytsia, L.O.; Hodyna, D.M.; Semenyuta, I.V.; Kovalishyn, V.V.; Rogalsky, S.P.; Derevianko, K.Y.; Brovarets, V.S.; Tetko, I.V. Theoretical and Experimental Studies of Phosphonium Ionic Liquids as Potential Antibacterials of MDR Acinetobacter baumannii. Antibiotics 2022, 11, 491. https://doi.org/10.3390/antibiotics11040491
Metelytsia LO, Hodyna DM, Semenyuta IV, Kovalishyn VV, Rogalsky SP, Derevianko KY, Brovarets VS, Tetko IV. Theoretical and Experimental Studies of Phosphonium Ionic Liquids as Potential Antibacterials of MDR Acinetobacter baumannii. Antibiotics. 2022; 11(4):491. https://doi.org/10.3390/antibiotics11040491
Chicago/Turabian StyleMetelytsia, Larysa O., Diana M. Hodyna, Ivan V. Semenyuta, Vasyl V. Kovalishyn, Sergiy P. Rogalsky, Kateryna Yu Derevianko, Volodymyr S. Brovarets, and Igor V. Tetko. 2022. "Theoretical and Experimental Studies of Phosphonium Ionic Liquids as Potential Antibacterials of MDR Acinetobacter baumannii" Antibiotics 11, no. 4: 491. https://doi.org/10.3390/antibiotics11040491