Antimicrobial Activity of Pyrazinamide Coordination Frameworks Synthesized by Mechanochemistry
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Characterization
2.2. Shelf and Thermal Stability of Compounds 2, 3, and 5
2.3. Antimicrobial Activity of the Compounds
3. Experimental Details
3.1. Reagents
3.2. Synthesis of the Compounds
3.3. General Characterization
3.4. Single Crystal X-ray Diffraction Studies (SCXRD)
3.5. Antibacterial Activity Assays
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compound | Symmetry Operation | D–H⋯A | d(D-H) (Å) | d(H⋯A) (Å) | d(D⋯A) (Å) | (DHA) (°) |
---|---|---|---|---|---|---|
1 | 1 − x,1 − y, 1 − z | N3–H7⋯O3W | 0.86 | 2.50 | 3.193(8) | 138 |
1 − x,1 − y, 1 − z | N3–H7⋯O5 | 0.86 | 2.42 | 3.163(8) | 144 | |
x, y, z | N3–H8⋯O7 | 0.86 | 2.08 | 2.937(8) | 172 | |
2 − x, 1 − y, 1 − z | N6–H9⋯O5 | 0.86 | 2.41 | 3.231(8) | 161 | |
2 − x, ½ + y, ½ − z | N6–H10⋯O4 | 0.86 | 2.07 | 2.913(7) | 166 | |
x, y, z | O3W–H11W⋯O4 | 0.75(6) | 2.06(7) | 2.781(8) | 162(9) | |
1 − x,1 − y, 1 − z | O3W–H12W⋯O8 | 0.76(7) | 2.05(7) | 2.810(8) | 177(7) | |
2 | 1 − x, 2 − y, − z | N3–H1N⋯O8 | 0.77(2) | 2.15(3) | 2.889(2) | 159(2) |
2 − x, 1 − y, 1 − z | O1w–H1w⋯O2 | 0.86(3) | 1.94(3) | 2.7773(18) | 166(2) | |
x, 1 + y, z | N3–H2N⋯O4 | 0.89(3) | 2.54(2) | 3.368(2) | 155(2) | |
x, 1 + y, z | N3–H2N⋯O5 | 0.89(3) | 2.41(3) | 3.228(2) | 153(2) | |
x, y, z | O1w–H2w⋯O6 | 0.81(3) | 1.87(3) | 2.6723(19) | 169(3) | |
1 + x, y, 1 + z | N6–H3N⋯N2 | 0.81(3) | 2.23(2) | 3.008(2) | 163(2) | |
1 − x, 1 − y, 1 − z | O2w–H3w⋯O3 | 0.75(3) | 2.28(3) | 2.9714(18) | 155(3) | |
1 − x, 1 − y, 1 − z | O2w–H3w⋯O4 | 0.75(3) | 2.51(3) | 3.186(2) | 150(3) | |
2 − x, 2 − y, 1 − z | N6–H4N⋯O7 | 0.87(3) | 2.20(3) | 2.880(2) | 135(2) | |
1 − x, 1 − y, 1 − z | O2w–H4w⋯O2 | 0.89(3) | 1.84(3) | 2.7278(17) | 178(3) | |
3 | x, y, z | N3–H1N⋯N2 | 0.90(5) | 2.44(8) | 2.733(7) | 100(6) |
2 − x 1 − y, 1 − z | N3–H1N⋯N2 | 0.90(5) | 2.44(8) | 3.150(7) | 137(6) | |
1 − x, 1 − y, 2 − z | N3–H2N⋯O1 | 0.90(6) | 2.02(6) | 2.888(7) | 164(6) | |
4 | x, − y, 1 − z | N3–H1N⋯N2 | 0.81(8) | 2.48(8) | 3.118(8) | 136(7) |
2 − x, 1 − y, 1 − z | N3–H2N⋯O1 | 0.79(8) | 2.10(8) | 2.883(8) | 177(8) |
Compounds | E. coli | S. aureus | M. smegmatis | |||
---|---|---|---|---|---|---|
MIC * (µg/mL) | MBC * (µg/mL) | MIC ** (µg/mL) | MBC * (µg/mL) | MIC ** (µg/mL) | MBC * (µg/mL) | |
Pyrazinamide | >62.5 | 250 | >250 | 500 | >62.5 | 125 |
(1) | >62.5 | 500 | >250 | 500 | >62.5 | 62.5 |
Zn(NO3)2 | >62.5 | 500 | >250 | 500 | >62.5 | 62.5 |
(2) | >62.5 | 500 | >250 | 500 | >62.5 | 125 |
Mn(NO3)2 | >62.5 | 500 | >250 | 500 | >62.5 | 125 |
(3) | 15.63 | 31.25 | 62.5 | 125 | 15.63 | 31.25 |
(5) | 7.81 | 31.25 | 62.5 | 125 | 7.81 | 31.25 |
AgNO3 | 7.81 | 31.25 | 62.5 | 125 | 7.81 | 7.81 |
Positive control | <0.49 (NOR) | Nd | 0.98 (VAN) | Nd | <0.49 (VAN) | Nd |
Negative control (DMSO) | 62.5 | Nd | 250 | Nd | 62.5 | Nd |
Pyrazinamide (PYR) | Metal Salt (M) | Molar Ratio (PYR:M) | Time | Resulting Compound |
---|---|---|---|---|
0.0907 g (0.74 mmol) | Zn(NO3)2⋅6H2O 0.1105 g (0.37 mmol) | 2:1 | 10 min | (1) |
0.0992 g (0.81 mmol) | Mn(NO3)2⋅4H2O 0.1036 g (0.41 mmol) | 2:1 | 15 min | (2) |
0.1183 g (0.96 mmol) | AgNO3 0.0829 g (0.49 mmol) | 2:1 | (3) | |
0.0840 g (0.68 mmol) | AgNO3 0.1171 g (0.69 mmol) | 1:1 | (5) |
2 | 3 | 4 | |
---|---|---|---|
Chemical formula | C10H10N6O2Mn⋅2H2O⋅2NO3 | C10H10N6O2Ag⋅NO3 | C10H10N6O2Ag⋅NO3 |
Formula weight | 461.23 | 416.12 | 416.12 |
Temperature (K) | 293 | 293 | 293 |
Wavelength (Å) | 0.71073 | 0.71073 | 0.71073 |
Crystal form, color | Block, colorless | Block, colorless | Plate, colorless |
Crystal size (mm) | 0.17 × 0.08 × 0.03 | 0.14 × 0.10 × 0.10 | 0.12 × 0.12 × 0.10 |
Crystal system | Triclinic | Monoclinic | Monoclinic |
Space group | P | P21/m | P2/c |
a (Å) | 6.9866(3) | 3.6132(11) | 3.5903(4) |
b (Å) | 9.2273(4) | 27.735(8) | 6.7181(6) |
c (Å) | 14.1882(5) | 6.6273(19) | 27.610(3) |
α (°) | 90.584(3) | 90.00 | 90.00 |
β (°) | 99.285(2) | 94.007(9) | 91.149(5) |
γ (°) | 101.460(2) | 90.00 | 90.00 |
V (Å3) | 883.85(6) | 662.5(3) | 665.81(11) |
Z | 2 | 2 | 2 |
d (mg.m−3) | 1.733 | 2.086 | 2.076 |
µ (mm−1) | 0.820 | 1.564 | 1.556 |
F(000) | 470 | 412 | 412 |
θ range (°) | 2.630–30.976 | 3.081–26.510 | 2.952–26.563 |
Reflections collected/unique | 15432/5513 | 4443/1381 | 5186/1374 |
Rint | 0.0349 | 0.0470 | 0.0301 |
GOF | 1.020 | 1.132 | 1.217 |
Final R indices [I > 2σ(I)] | R1 = 0.0357, wR2 = 0.0892 | R1 = 0.0630, wR2 = 0.1316 | R1 = 0.0577, wR2 = 0.1256 |
Indices all data | R1 = 0.0476, wR2 = 0.0938 | R1 = 0.0780, wR2 = 0.1372 | R1 = 0.0620, wR2 = 0.1273 |
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Quaresma, S.; Alves, P.C.; Rijo, P.; Duarte, M.T.; André, V. Antimicrobial Activity of Pyrazinamide Coordination Frameworks Synthesized by Mechanochemistry. Molecules 2021, 26, 1904. https://doi.org/10.3390/molecules26071904
Quaresma S, Alves PC, Rijo P, Duarte MT, André V. Antimicrobial Activity of Pyrazinamide Coordination Frameworks Synthesized by Mechanochemistry. Molecules. 2021; 26(7):1904. https://doi.org/10.3390/molecules26071904
Chicago/Turabian StyleQuaresma, Sílvia, Paula C. Alves, Patrícia Rijo, M. Teresa Duarte, and Vânia André. 2021. "Antimicrobial Activity of Pyrazinamide Coordination Frameworks Synthesized by Mechanochemistry" Molecules 26, no. 7: 1904. https://doi.org/10.3390/molecules26071904