Synthesis, Crystal Structures, Genotoxicity, and Antifungal and Antibacterial Studies of Ni(II) and Cd(II) Pyrazole Amide Coordination Complexes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of the Ligands
2.2. Synthesis of the Complexes
2.3. FT-IR Spectroscopy
2.4. X-ray Crystallography
2.5. Antibacterial Activity
2.6. Antifungal Activity
2.7. Antifungal Activity on Mycelial Growth of Fusarium oxysporum f. sp. Albinidis
2.8. Genotoxicity
3. Experimental Section
3.1. Materials and Instrumentation
3.2. Synthesis Section
3.2.1. Synthesis of Ethyl 1,5-Dimethyl-1H-pyrazole-3-carboxylate
3.2.2. Synthesis of 1,5-Dimethyl-1H-pyrazole-3-carboxylic Acid (A1)
3.2.3. Synthesis of 1,5-Dimethyl-1H-pyrazol-3-carbonyl Chloride (A2)
3.2.4. Synthesis of 1,5-Dimethyl-N-phenyl-1H-pyrazole-3-carboxamide (L1)
3.2.5. Synthesis of 1,5-Dimethyl-N-propyl-1H-pyrazole-3-carboxamide (L2)
3.2.6. Synthesis of [Ni(L1)2](ClO4)2 (C1)
3.2.7. Synthesis of [Cd2(L2)2]Cl4 (C2)
3.3. X-ray Crystallographic Studies
4. Biological Activity
4.1. Microorganisms and Culture Media
4.2. Measurement of Antibacterial and Antifungal Activities
4.3. Antifungal Activity on Mycelial Growth of Fusarium oxysporum
4.4. Genotoxicity Effect
4.5. Statistical Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compound | C (mmol/L) | Inhibition Zone (mm) | Ref. | |||
---|---|---|---|---|---|---|
E. coli [n] | Li. Innocua [p] | Ps. Aeruginosa [n] | S. Aureus [p] | |||
L1 | 27.8 | 9.20 ± 0.53 * | 7.94 ± 0.40 * | 9.17 ± 1.04 * | 8.17 ± 0.76 * | This work |
C1 | 7.98 | 9.65 ± 0.28 * | 10.20 ± 0.28 * | 10.15 ± 0.28 * | 10.6 ± 0.28 * | This work |
L2 | 33.1 | 9.30 ± 0.17 * | 8.33 ± 1.15 * | 9.17 ± 0.85 * | 7.10 ± 1.56 * | This work |
C2 | 7.88 | 16.10 ± 0.28 * | 14 ± 0.28 * | 14.7 ± 0.57 * | 12.8 ± 0.28 * | This work |
Gentamicin | 1.25 | 29.9 ± 0.28 | 30.10 ± 0.28 | 27.75 ± 0.35 | 32.85 ± 0.70 | This work |
[Cd2(dmamp)2 (NCS)2]n | --- | 9.2 | -- | 13.1 | -- | [37] |
[Ni(btbepa)CH3OH(H2O)](ClO4)2 | -- | 28 | -- | -- | 27 | [6] |
H3O[Ni(dmptr)3](ClO4)3 | 4.62 | 12 ± 0.38 | -- | -- | 12 ± 0.25 | [32] |
[Cd(dmptr)2 Cl2] | 7.85 | 27 ± 0.25 | -- | -- | 27 ± 0.19 | [32] |
[Cd(htcd)(SCN)]SCN | -- | 22 | -- | -- | 24 | [39] |
[NiL3](ClO4)2 | 3.49 | 8 ± 0.8 | 9 ± 0.35 | 9 ± 0.95 | 8 ± 0.35 | [38] |
CdL2Cl2 | 5.25 | 14 ± 0.75 | 11 ± 0.5 | 12 ± 0.3 | 11 ± 0.5 | [38] |
Ni(ClO4)2·6H2O | 8.2 | 0 | 0 | 0 | 0 | [38] |
CdCl2·H2O | 14.9 | 11 ± 0.3 | 0 | 8 ± 0.2 | 0 | [38] |
Compound | C (mmol/L) | Inhibition Zone (mm) | Ref. | ||
---|---|---|---|---|---|
G.candidum | A. niger | P. crustosum | |||
L1 | 27.87 | 13.9 ± 0.1 * | 10.25 ± 0.75 * | 8.8 ± 0.2 * | This work |
C1 | 7.98 | 15.5 ± 0.71 * | 19 ± 1.41 * | 22 ± 1.41 | This work |
L2 | 33.11 | 12.5 ± 0.6 * | 9.85 ± 0.65 * | 8.25 ± 0.25 * | This work |
C2 | 7.88 | 20 ± 1.41 * | 24.5 ± 0.71 * | 26 ± 2.83 * | This work |
Cycloheximide | 21.33 | 22.8 ± 0.2 | 22.7 ± 0.5 | 22.6 ± 0.6 | This work |
Cycloheximide (lower concentration) | 10.66 | 22 ± 0.8 | 22 ± 0.7 | 22 ± 0.6 | This work |
[Ni(IND)2(Gly)(H2O) 2]Cl | -- | 22.7 ± 0.03 | -- | -- | [41] |
Cd(bdade)(NCS)2 | -- | -- | 18.44 | -- | [42] |
[Ni(psi)2SO4] | -- | -- | 10 | -- | [43] |
[Ni(CH3COO)2(Tyr)2] Tyr = Tyrosine | -- | -- | 23 | -- | [45] |
[NiL3](ClO4)2 | 3.49 | 0 | 9 | 9 ± 0.1 | [38] |
CdL2Cl2 | 5.25 | 14 ± 0.2 | 14 ± 0.8 | 15 ± 0.45 | [38] |
Ni(ClO4)2·6H2O | 8.2 | 0 | 0 | 0 | [38] |
CdCl2·H2O | 14.9 | 10 ± 0.1 | 6 ± 0.3 | 5 ± 0.2 | [38] |
Compound | Sample Volumes (µL) | C (µmol/L) | Inhibition (%) | Ref. |
---|---|---|---|---|
L1 | 50 | 92.9 | 46.3 ± 2.5 * | This work |
150 | 278.7 | 50 ± 4.5 | ||
C1 | 50 | 26.6 | 43.8 ± 3.3 | This work |
150 | 79.8 | 62.5 ± 2.2 * | ||
L2 | 50 | 110.35 | 50 ± 7.8 * | This work |
150 | 331.05 | 57.5 ± 6.6 | ||
C2 | 50 | 26.3 | 87.5 ± 3.3 * | This work |
150 | 78.9 | 96.3 ± 1.3 * | ||
Cycloheximide | 50 | 71.1 | 35 ± 3.3 | This work |
150 | 213.3 | 55 ± 2.5 | ||
250 | 355.5 | 66.7 ± 2.9 | ||
Cd(dmptr)2 Cl2 | 200 | 104.6 | 50 | [32] |
(H3O)[Ni(dmptr)3](ClO4)3 | 200 | 29.41 | 38 | [32] |
[Ni(btbepa)CH3OH(H2O)](ClO4)2 | 200 | 68.8 | 44 | [6] |
NiL3(ClO4)2 | 150 | 66.42 | 35 | [38] |
CdL2Cl2 | 150 | 97.75 | 51 | [38] |
Co2(HL2)L2Cl3 | 150 | 81.1 | 97 | [38] |
Cu2(HL’2)Cl2 | 150 | 158.02 | 97 | [44] |
Ni(ClO4)2·6H2O | 150 | 164.07 | 8 | [38] |
CdCl2·H2O | 150 | 298.01 | 12 | [38] |
Compound | L1 | C1 | C2 |
---|---|---|---|
Empirical formula | C12 H13 N3 O | C26 H34 Cl2 N6 Ni O12 | C38 H68 Cd4 Cl8 N12 O6 |
Formula weight | 215.25 | 752.20 | 1522.24 |
T (K) | 293(2) | 293(2) | 293(2) |
Wavelength (Å) | 0.71073 | 0.71073 | 0.71073 |
Crystal system | Orthorhombic | Monoclinic | Orthorhombic |
Space group | Pbca | P21/n | Pca21 |
Unit cell dimensions (Å,°) | a = 10.4982(4) | a = 10.6244(6) | a = 16.7846(3) |
b = 9.8653(4) | b = 13.0110(7) | b = 16.4470(3) | |
c = 21.4838(9) | c = 11.8231(7) | c = 20.9709(3) | |
α = 90 | α = 90 | α = 90 | |
β = 90 | β = 96.503(6) | β = 90 | |
γ = 90 | γ = 90 | γ = 90 | |
V (Å3) | 2225.04(15) | 1623.84(16) | 5789.16(16) |
Z | 8 | 2 | 4 |
Density (calculated) (g/cm3) | 1.285 | 1.538 | 1.747 |
Absorption coefficient (mm−1) | 0.085 | 0.832 | 1.869 |
F(000) | 912 | 780 | 3024 |
Crystal size (mm3) | 0.32 × 0.15 × 0.12 | 0.35 × 0.30 × 0.20 | 0.40 × 0.25 × 0.20 |
θrange for data collection (°) | 2.988 to 26.193 | 2.902 to 26.232 | 2.893 to 26.187 |
Reflections collected | 16410 | 11040 | 39165 |
Independent reflections | 2215 [R(int) = 0.0480] | 3199 [R(int) = 0.0253] | 11,407 [R(int) = 0.0185] |
Completeness to θ 25.242° (%) | 99.2 | 98.9 | 98.9 |
Max. and min. transmission | 1.00000 and 0.82569 | 1.00000 and 0.88273 | 1.00000 and 0.66350 |
Data/restraints/parameters | 2215/0/147 | 3199/99/273 | 11407/43/721 |
Goodness-of-fit on F2 | 1.086 | 1.045 | 1.070 |
Final R indices [I > 2s(I)] | R1 = 0.0441, wR2 = 0.1216 | R1 = 0.0374, wR2 = 0.1059 | R1 = 0.0188, wR2 = 0.0486 |
R indices (all data) | R1 = 0.0488, wR2 = 0.1254 | R1 = 0.0398, wR2 = 0.1079 | R1 = 0.0197, wR2 = 0.0490 |
Absolute structure parameter | . | . | 0.31(2) |
Δρ(max, min)(e.Å−3) | 0.187, −0.170 | 0.411, −0.289 | 0.528, −0.371 |
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El Mahdaoui, A.; Radi, S.; Draoui, Y.; El Massaoudi, M.; Ouahhoud, S.; Asehraou, A.; Bentouhami, N.E.; Saalaoui, E.; Benabbes, R.; Robeyns, K.; et al. Synthesis, Crystal Structures, Genotoxicity, and Antifungal and Antibacterial Studies of Ni(II) and Cd(II) Pyrazole Amide Coordination Complexes. Molecules 2024, 29, 1186. https://doi.org/10.3390/molecules29051186
El Mahdaoui A, Radi S, Draoui Y, El Massaoudi M, Ouahhoud S, Asehraou A, Bentouhami NE, Saalaoui E, Benabbes R, Robeyns K, et al. Synthesis, Crystal Structures, Genotoxicity, and Antifungal and Antibacterial Studies of Ni(II) and Cd(II) Pyrazole Amide Coordination Complexes. Molecules. 2024; 29(5):1186. https://doi.org/10.3390/molecules29051186
Chicago/Turabian StyleEl Mahdaoui, Amal, Smaail Radi, Youssef Draoui, Mohamed El Massaoudi, Sabir Ouahhoud, Abdeslam Asehraou, Nour Eddine Bentouhami, Ennouamane Saalaoui, Redouane Benabbes, Koen Robeyns, and et al. 2024. "Synthesis, Crystal Structures, Genotoxicity, and Antifungal and Antibacterial Studies of Ni(II) and Cd(II) Pyrazole Amide Coordination Complexes" Molecules 29, no. 5: 1186. https://doi.org/10.3390/molecules29051186