Catalytic, Theoretical, and Biological Investigations of Ternary Metal (II) Complexes Derived from L-Valine-Based Schiff Bases and Heterocyclic Bases
Abstract
:1. Introduction
2. Materials and Methods
2.1. Experimental Section
2.1.1. Reagents and Characterization
2.1.2. Preparation of Potassium (E)-2-((5-bromo-2-hydroxy benzylidene)amino)-3-methylbutanoate (HL)
2.2. Preparation of Complexes
2.2.1. Preparation of [Co(L)(phen)] (1a)
2.2.2. Preparation of [Ni(L)(phen)] (1b)
2.2.3. Preparation of [Cu(L)(phen)] (1c)
2.2.4. Preparation of [Zn(L)(phen)] (1d)
2.2.5. Preparation of [Co(L)(bpy)] (1e)
2.2.6. Preparation of [Ni(L)(bpy)] (1f)
2.2.7. Preparation of [Cu(L)(bpy)] (1g)
2.2.8. Preparation of [Zn(L)(bpy)] (1h)
2.3. In Vitro MTT Assay
2.4. Molecular Modeling
2.5. Computational Analysis
2.6. The General Process for the Synthesis of β-Amino Carbonyl Derivative
3. Results and Discussion
3.1. Results and Discussion
3.2. Spectral Characterization
3.2.1. FT-IR Spectral Analysis
3.2.2. UV–Visible Spectral Analysis
3.2.3. Mass Spectral Analysis
3.2.4. Thermal Analysis
3.2.5. EPR Spectral Analysis
3.2.6. XRD Analysis
3.3. Electrochemical Studies
3.3.1. Reduction Process
3.3.2. Oxidation Process
3.4. Catalytic Activity
3.5. Theoretical Studies
3.5.1. Geometry Optimization
3.5.2. Molecular Orbital Analysis
3.6. Molecular Docking Studies
Validation of the Active Site of Thymidylate Synthase
3.7. Biological Evaluation
3.7.1. In Vitro Antibacterial Assay
3.7.2. In Vitro Anticancer Activity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Abbreviations
bpy | 2,2′-Bipyridyl |
DMF | N,N-Dimethylformamide |
DPPH | 2,2′-Diphenyl-1-picrylhydrazyl |
DMEM | Dulbecco’s Modified Eagle’s Medium |
DFT | Density functional theory |
EPR | Electron paramagnetic resonance spectroscopy |
ESI-MS | Electrospray ionization mass spectroscopy |
FBS | Fetal bovine serum |
FMO | Frontier molecular orbital |
HOMO | Highest occupied molecular orbital |
IC50 | 50% of inhibitory concentration |
LUMO | Lowest unoccupied molecular orbital |
MTT | 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyltetrazolium bromide |
NHDF | Nontumorigenic human dermal fibroblasts |
OPLS | Optimized potentials for liquid simulations |
PDB | Protein data bank |
phen | 1,10-Phenanthroline |
RMSD | Root mean square deviation |
TBAP | Tetra(n-butyl)ammonium perchlorate |
UV–Vis | Ultraviolet–visible |
XRD | X-ray diffraction |
MCF-7 | Michigan Cancer Foundation |
HeLa | Henrietta Lacks |
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Complexes | Formula | Color | Mol.Wt. gm/mol | M.p. (°C) | Yield (%) | Found (calc.) (%) | ||
---|---|---|---|---|---|---|---|---|
C | H | N | ||||||
[Co(L)(phen)] 1a | C24H20BrCoN3O3 | Brown | 537.08 | >300 | 80 | 53.63 (53.65) | 3.72 (3.75) | 7.81 (7.82) |
[Ni(L)(phen)] 1b | C24H20BrN3NiO3 | Pale green | 536.92 | >300 | 80 | 53.66 (53.68) | 3.73 (3.75) | 7.80 (7.82) |
[Cu(L)(phen)] 1c | C24H20BrCuN3O3 | green | 541.78 | >300 | 88 | 53.19 (53.20) | 3.70 (3.72) | 7.72 (7.75) |
[Zn(L)(phen)] 1d | C24H20BrN3O3Zn | Pale yellow | 543.28 | >300 | 67 | 52.98 (53.02) | 3.69 (3.71) | 7.72 (7.73) |
[Co(L)(bpy)] 1e | C22H20BrCoN3O3 | Brown | 513.03 | >300 | 84 | 51.46 (51.48) | 3.92 (3.93) | 8.18 (8.19) |
[Ni(L)(bpy)] 1f | C22H20BrN3NiO3 | Pale green | 512.89 | >300 | 79 | 51.49 (51.51) | 3.91 (3.93) | 8.17 (8.19) |
[Cu(L)(bpy)] 1g | C22H20BrCuN3O3 | green | 517.69 | >300 | 83 | 51.00 (51.02) | 3.88 (3.89) | 8.09 (8.11) |
[Zn(L)(bpy) ] 1h | C22H20BrN3O3Zn | Pale yellow | 519.38 | >300 | 67 | 50.81 (50.84) | 3.86 (3.88) | 8.06 (8.09) |
Complexes | FT-IR Spectral Data (cm−1) | UV–Visible Spectral Data (λmax/nm (ε/M−1cm−1dm3) | |||||
---|---|---|---|---|---|---|---|
ν(-C=N-) | νas(COO) | νs(COO) | ν(M-O) | ν(M-N) | d-d | Charge Transfer | |
HL | 1643 | 1594 | 1405 | -- | -- | -- | 409 (500), 353 (180), 264 (1590) |
[Co(L)(phen)] 1a | 1636 | 1587 | 1371 | 549 | 457 | 494 (152) 634 (58) | 228 (33,895) (π–π*) 269 (25,834) (n–π*) 337 (1209) (LMCT) |
[Ni(L)(phen)] 1b | 1612 | 1586 | 1380 | 542 | 460 | 623 (6) | 254 (57,302) (π–π*) 288 (36,331) (n–π*) 389 (3657) (LMCT) |
[Cu(L)(phen)] 1c | 1611 | 1562 | 1356 | 554 | 486 | 637 (17) | 259 (864,222) (π–π*) 284 (58,665) (n–π*) 372 (1502) (LMCT) |
[Zn(L)(phen)] 1d | 1622 | 1557 | 1376 | 549 | 502 | -- | 270 (35,064) (π–π*) 292 (9154) (n–π*) 373 (4019) (LMCT |
[Co(L)(bpy)] 1e | 1623 | 1575 | 1369 | 562 | 488 | 463 (127) 619 (65) | 249 (19,579)(π–π*) 301 (8048) (n–π*) 389 (854) (LMCT) |
[Ni(L)(bpy)] 1f | 1634 | 1570 | 1379 | 542 | 485 | 625 (4) | 238 (4056) (π–π*) 298 (2094) (n–π*) 379 (920) (LMCT) |
[Cu(L)(bpy)] 1g | 1594 | 1568 | 1358 | 553 | 461 | 642 (24) | 240 (13,846) (π–π*) 300 (11,085) (n–π*) 375 (144) (LMCT |
[Zn(L3)(bpy)] 3h | 1635 | 1577 | 1370 | 548 | 497 | -- | 274 (20,198) (π–π*) 294 (16,748) (n–π*) 374 (8425) (LMCT) |
Complexes | Epc (V) | Epa (V) | ∆Ep (V) | Ipc (μA) | Ipa (μA) | Ipc/Ipa |
---|---|---|---|---|---|---|
[Co(L)(phen)] 1a | −0.71 | +1.19 | 1.90 | 57.63 | −1138 | 0.050 |
[Ni(L)(phen)] 1b | −0.71 | +1.12 | 1.83 | 54.50 | −694 | 0.078 |
[Cu(L)(phen)] 1c | −0.54 | -- | -- | 8.90 | -- | -- |
[Zn(L)(phen)] 1d | NA * | NA | -- | -- | -- | -- |
[Co(L)(bpy)] 1e | −0.66 | +1.30 | 1.96 | 62.97 | −2015 | 0.031 |
[Ni(L)(bpy)] 1f | −0.58 | +1.17 | 1.75 | 35.40 | −1174 | 0.030 |
[Cu(L)(bpy)] 1g | −0.58 | -- | -- | 29.55 | -- | -- |
[Zn(L)(bpy)] 1h | NA | NA | -- | -- | -- | -- |
S.No | Catalyst | Deri- vative | Concentration of Substituted Phenanthroline Metal Salts | ||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
0.0367 mmol | 0.0735 mmol | 0.1103 mmol | |||||||||||||
CR | MR | CR | MR | CR | MR | ||||||||||
T | Y | T | Y | T | Y | T | Y | T | Y | T | Y | ||||
1 | Substituted phenanthroline metal (II) salts | 1a | 2a | 85 | 65 | 40 | 75 | 75 | 76 | 30 | 82 | 65 | 88 | 20 | 97 |
2b | 95 | 64 | 45 | 71 | 85 | 74 | 35 | 79 | 75 | 86 | 25 | 94 | |||
2c | 75 | 66 | 35 | 75 | 70 | 77 | 30 | 82 | 60 | 92 | 20 | 90 | |||
2d | 65 | 73 | 30 | 80 | 60 | 83 | 25 | 84 | 50 | 91 | 15 | 93 | |||
2e | 55 | 76 | 25 | 80 | 45 | 88 | 20 | 87 | 40 | 90 | 10 | 95 | |||
2 | 1b | 2a | 95 | 62 | 50 | 71 | 85 | 74 | 40 | 80 | 75 | 86 | 30 | 94 | |
2b | 105 | 60 | 55 | 73 | 95 | 71 | 45 | 74 | 85 | 83 | 35 | 91 | |||
2c | 85 | 61 | 45 | 72 | 80 | 75 | 40 | 80 | 70 | 90 | 30 | 88 | |||
2d | 75 | 71 | 40 | 78 | 70 | 78 | 35 | 77 | 60 | 88 | 25 | 89 | |||
2e | 65 | 72 | 35 | 76 | 55 | 82 | 30 | 85 | 50 | 86 | 20 | 91 | |||
3 | 1c | 2a | 105 | 60 | 60 | 69 | 95 | 70 | 50 | 78 | 85 | 82 | 40 | 92 | |
2b | 115 | 57 | 65 | 70 | 105 | 67 | 55 | 71 | 95 | 80 | 45 | 88 | |||
2c | 95 | 59 | 55 | 68 | 90 | 72 | 50 | 77 | 80 | 82 | 40 | 90 | |||
2d | 85 | 67 | 50 | 79 | 80 | 76 | 45 | 78 | 70 | 82 | 35 | 89 | |||
2e | 75 | 72 | 45 | 76 | 65 | 82 | 40 | 85 | 60 | 86 | 30 | 91 | |||
4 | 1d | 2a | 115 | 59 | 70 | 64 | 105 | 69 | 60 | 72 | 95 | 80 | 50 | 90 | |
2b | 125 | 57 | 75 | 70 | 115 | 67 | 65 | 71 | 105 | 80 | 55 | 88 | |||
2c | 105 | 59 | 55 | 65 | 90 | 70 | 50 | 75 | 80 | 80 | 40 | 88 | |||
2d | 95 | 65 | 50 | 77 | 80 | 73 | 45 | 75 | 70 | 81 | 35 | 88 | |||
2e | 75 | 70 | 45 | 72 | 65 | 79 | 40 | 83 | 60 | 82 | 30 | 90 |
S.No | Catalyst | Deri- vative | Concentration of Substituted Pyridine Metal Salts | ||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
0.0384 mmol | 0.0769 mmol | 0.1154 mmol | |||||||||||||
CR | MR | CR | MR | CR | MR | ||||||||||
T | Y | T | Y | T | Y | T | Y | T | Y | T | Y | ||||
1 | Substituted 2,2-bipyidyl metal (II) salts | 1e | 2a | 75 | 68 | 35 | 78 | 70 | 79 | 20 | 85 | 55 | 91 | 15 | 96 |
2b | 85 | 67 | 40 | 74 | 80 | 77 | 25 | 82 | 65 | 89 | 20 | 92 | |||
2c | 65 | 69 | 30 | 79 | 65 | 80 | 20 | 85 | 50 | 95 | 15 | 95 | |||
2d | 55 | 76 | 25 | 83 | 55 | 86 | 15 | 87 | 40 | 94 | 10 | 97 | |||
4e | 45 | 79 | 20 | 84 | 40 | 91 | 10 | 90 | 30 | 93 | 05 | 98 | |||
2 | 1f | 2a | 85 | 65 | 45 | 74 | 75 | 77 | 30 | 83 | 65 | 89 | 25 | 92 | |
2b | 95 | 63 | 50 | 77 | 85 | 73 | 35 | 77 | 75 | 86 | 30 | 90 | |||
2c | 75 | 64 | 40 | 75 | 70 | 78 | 30 | 83 | 60 | 93 | 25 | 91 | |||
2d | 65 | 74 | 35 | 81 | 60 | 81 | 25 | 81 | 50 | 91 | 20 | 89 | |||
2e | 55 | 75 | 30 | 79 | 45 | 85 | 20 | 88 | 40 | 89 | 15 | 91 | |||
3 | 1g | 2a | 95 | 63 | 55 | 71 | 85 | 73 | 40 | 81 | 75 | 85 | 35 | 90 | |
2b | 105 | 60 | 60 | 73 | 95 | 70 | 45 | 74 | 85 | 83 | 40 | 89 | |||
2c | 85 | 62 | 50 | 71 | 80 | 75 | 40 | 80 | 70 | 85 | 35 | 89 | |||
2d | 75 | 70 | 45 | 82 | 70 | 79 | 25 | 81 | 60 | 86 | 30 | 90 | |||
2e | 65 | 75 | 40 | 79 | 55 | 85 | 30 | 88 | 50 | 89 | 25 | 92 | |||
4 | 1h | 2a | 105 | 63 | 65 | 68 | 95 | 72 | 50 | 75 | 85 | 85 | 45 | 91 | |
2b | 115 | 61 | 70 | 73 | 105 | 71 | 55 | 74 | 95 | 83 | 50 | 90 | |||
2c | 95 | 62 | 50 | 65 | 80 | 73 | 40 | 78 | 70 | 84 | 35 | 89 | |||
2d | 85 | 69 | 45 | 77 | 70 | 76 | 35 | 81 | 60 | 86 | 30 | 92 | |||
2e | 65 | 73 | 40 | 72 | 55 | 82 | 30 | 87 | 60 | 85 | 25 | 90 |
Catalyst | Percentage of Recyclability of Catalyst | |||
---|---|---|---|---|
First Cycle | Second Cycle | Third Cycle | Fourth Cycle | |
1a | 91 | 91 | 90 | 89 |
1b | 89 | 89 | 87 | 87 |
1c | 87 | 87 | 87 | 85 |
1d | 92 | 91 | 91 | 90 |
1e | 90 | 89 | 89 | 88 |
1f | 88 | 88 | 88 | 86 |
1g | 90 | 89 | 89 | 88 |
1h | 89 | 88 | 88 | 86 |
Bond Angle (deg) B3LYP/LACVP++ | |||||||
---|---|---|---|---|---|---|---|
[Co(L)(phen)] 1a | [Ni(L)(phen)] 1b | [Cu(L)(phen)] 1c | [Zn(L1)(phen)] 1d | ||||
N(18)-Co(1)-N(8) | 84.536 | N(18)-Ni(1)-N(8) | 85.326 | N(18)-Cu(1)-N(8) | 81.547 | N(18)-Zn(1)-N(8) | 79.945 |
N(18)-Co(1)-N(4) | 171.246 | N(18)-Ni(1)-N(4) | 153.435 | N(18)-Cu(1)-N(4) | 154.944 | N(18)-Zn(1)-N(4) | 151.161 |
N(18)-Co(1)-O(3) | 85.923 | N(18)-Ni(1)-O(3) | 86.310 | N(18)-Cu(1)-O(3) | 85.065 | N(18)-Zn(1)-O(3) | 81.925 |
N(18)-Co(1)-O(2) | 98.447 | N(18)-Ni(1)-O(2) | 113.717 | N(18)-Cu(1)-O(2) | 108.729 | N(18)-Zn(1)-O(2) | 113.265 |
N(8)-Co(1)-N(4) | 98.118 | N(8)-Ni(1)-N(4) | 94.750 | N(8)-Cu(1)-N(4) | 95.945 | N(8)-Zn(1)-N(4) | 98.121 |
N(8)-Co(1)-O(3) | 126.249 | N(8)-Ni(1)-O(3) | 156.955 | N(8)-Cu(1)-O(3) | 149.119 | N(8)-Zn(1)-O(3) | 135.705 |
N(8)-Co(1)-O(2) | 101.038 | N(8)-Ni(1)-O(2) | 94.179 | N(8)-Cu(1)-O(2) | 95.100 | N(8)-Zn(1)-O(2) | 103.250 |
N(4)-Co(1)-O(3) | 84.163 | N(4)-Ni(1)-O(3) | 83.387 | N(4)-Cu(1)-O(3) | 82.697 | N(4)-Zn(1)-O(3) | 79.707 |
N(4)-Co(1)-O(2) | 92.301 | N(4)-Ni(1)-O(2) | 92.797 | N(4)-Cu(1)-O(2) | 94.313 | N(4)-Zn(1)-O(2) | 95.274 |
O(3)-Co(1)-O(2) | 123.606 | O(3)-Ni(1)-O(2) | 108.843 | O(3)-Cu(1)-O(2) | 112.778 | O(3)-Zn(1)-O(2) | 121.039 |
Bond distance (Å) | |||||||
Co(1)-N(18) | 1.870 | Ni(1)-N(18) | 1.836 | Cu(1)-N(18) | 1.934 | Zn(1)-N(18) | 2.029 |
Co(1)-N(8) | 1.918 | Ni(1)-N(8) | 1.884 | Cu(1)-N(8) | 2.059 | Zn(1)-N(8) | 2.049 |
Co(1)-N(4) | 1.871 | Ni(1)-N(4) | 1.845 | Cu(1)-N(4) | 1.912 | Zn(1)-N(4) | 2.004 |
Co(1)-O(3) | 1.837 | Ni(1)-O(3) | 1.822 | Cu(1)-O(3) | 1.882 | Zn(1)-O(3) | 1.937 |
Co(1)-O(2) | 1.918 | Ni(1)-O(2) | 2.014 | Cu(1)-O(2) | 1.932 | Zn(1)-O(2) | 1.873 |
Bond Angle (deg) B3LYP/LACVP++ | |||||||
---|---|---|---|---|---|---|---|
[Co(L)(bpy)] 1e | [Ni(L)(bpy)] 1f | [Cu(L)(bpy)] 1g | [Zn(L)(bpy)] 1h | ||||
N(16)-Co(1)-N(8) | 83.244 | N(16)-Ni(1)-N(8) | 78.400 | N(16)-Cu(1)-N(8) | 80.539 | N(16)-Zn(1)-N(8) | 78.477 |
N(16)-Co(1)-N(4) | 172.888 | N(16)-Ni(1)-N(4) | 120.752 | N(16)-Cu(1)-N(4) | 152.716 | N(16)-Zn(1)-N(4) | 151.914 |
N(16)-Co(1)-O(3) | 86.817 | N(16)-Ni(1)-O(3) | 79.803 | N(16)-Cu(1)-O(3) | 85.620 | N(16)-Zn(1)-O(3) | 82.922 |
N(16)-Co(1)-O(2) | 97.946 | N(16)-Ni(1)-O(2) | 105.384 | N(16)-Cu(1)-O(2) | 113.072 | N(16)-Zn(1)-O(2) | 112.970 |
N(8)-Co(1)-N(4) | 99.500 | N(8)-Ni(1)-N(4) | 158.557 | N(8)-Cu(1)-N(4) | 96.460 | N(8)-Zn(1)-N(4) | 98.792 |
N(8)-Co(1)-O(3) | 125.104 | N(8)-Ni(1)-O(3) | 87.110 | N(8)-Cu(1)-O(3) | 148.646 | N(8)-Zn(1)-O(3) | 134.815 |
N(8)-Co(1)-O(2) | 101.888 | N(8)-Ni(1)-O(2) | 88.367 | N(8)-Cu(1)-O(2) | 97.421 | N(8)-Zn(1)-O(2) | 104.122 |
N(4)-Co(1)-O(3) | 83.670 | N(4)-Ni(1)-O(3) | 87.159 | N(4)-Cu(1)-O(3) | 81.407 | N(4)-Zn(1)-O(3) | 79.510 |
N(4)-Co(1)-O(2) | 92.045 | N(4)-Ni(1)-O(2) | 94.828 | N(4)-Cu(1)-O(2) | 94.212 | N(4)-Zn(1)-O(2) | 94.892 |
O(3)-Co(1)-O(2) | 122.850 | O(3)-Ni(1)-O(2) | 162.290 | O(3)-Cu(1)-O(2) | 117.930 | O(3)-Zn(1)-O(2) | 121.051 |
Bond distance (Å) | |||||||
Co(1)-N(16) | 1.855 | Ni(1)-N(16) | 2.289 | Cu(1)-N(16) | 1.929 | Zn(1)-N(16) | 2.026 |
Co(1)-N(8) | 1.897 | Ni(1)-N(8) | 1.865 | Cu(1)-N(8) | 2.002 | Zn(1)-N(8) | 2.030 |
Co(1)-N(4) | 1.880 | Ni(1)-N(4) | 1.790 | Cu(1)-N(4) | 1.928 | Zn(1)-N(4) | 2.013 |
Co(1)-O(3) | 1.840 | Ni(1)-O(3) | 1.805 | Cu(1)-O(3) | 1.890 | Zn(1)-O(3) | 1.933 |
Co(1)-O(2) | 1.917 | Ni(1)-O(2) | 1.804 | Cu(1)-O(2) | 1.938 | Zn(1)-O(2) | 1.873 |
Complexes | HOMO (eV) | LUMO (eV) | ΔE (eV) | χ | η | σ | Pi | S | ω | ΔN Max |
---|---|---|---|---|---|---|---|---|---|---|
[Co(L)(phen)] 1a | −5.19 | −2.11 | 3.07 | 3.65 | 1.54 | 0.65 | −3.65 | 0.33 | 10.24 | −2.38 |
[Ni(L)(phen)] 1b | −4.72 | −2.38 | 2.34 | 3.55 | 1.17 | 0.85 | −3.55 | 0.43 | 7.36 | −3.03 |
[Cu(L)(phen)] 1c | −4.90 | −2.52 | 2.38 | 3.71 | 1.19 | 0.84 | −3.71 | 0.42 | 8.18 | −3.11 |
[Zn(L)(phen)] 1d | −4.87 | −2.67 | 2.21 | 3.77 | 1.10 | 0.91 | −3.77 | 0.45 | 7.85 | −3.41 |
[Co(L)(bpy)] 1e | −5.23 | −2.13 | 3.10 | 3.68 | 1.55 | 0.64 | −3.68 | 0.32 | 10.52 | −2.37 |
[Ni(L)(bpy)] 1f | −4.38 | −2.01 | 2.37 | 3.19 | 1.19 | 0.84 | −3.19 | 0.42 | 6.05 | −2.69 |
[Cu(L)(bpy)] 1g | −4.92 | −2.58 | 2.34 | 3.75 | 1.17 | 0.85 | −3.75 | 0.43 | 8.25 | −3.20 |
[Zn(L)(bpy)] 1h | −4.90 | −2.66 | 2.25 | 3.78 | 1.12 | 0.89 | −3.78 | 0.45 | 8.02 | −3.37 |
Complexes | Docking Score kcal.mol−1 | Active Sites with a Mode of Interaction | ||
---|---|---|---|---|
H-bond | Π–π Stacking | Hydrophobic Interactions (Cutoff at 5Å) | ||
[Co(L)(phen)] 1a | −5.700 | -- | PHE 225 | PHE 80, PHE 91, ILE 108, TRP 109, TYR 135, LEU 192, CYS 195, LEU 221, VAL 223, PRO 224, PHE 225, TYR 258 |
[Ni(L)(phen)] 1b | −5.615 | -- | PHE 225 | PHE 80, PHE 91, ILE 108, TRP 109, TYR 135, LEU 192, CYS 195, LEU 221, VAL 223, PRO 224, PHE 225, TYR 258 |
[Cu(L)(phen)] 1c | −5.791 | ASN 226 | PHE 225 | PHE 80, PHE 91, ILE 108, TRP 109, TYR 135, LEU 192, PRO 193, PRO 194, CYS 195, VAL 223, PHE 225, VAL 238, TYR 258 |
[Zn(L)(phen)] 1d | −5.367 | ASN 226 | -- | PHE 80, PHE 91, ILE 108, TRP 109, TYR 135, LEU 192, CYS 195, LEU 221, VAL 223, PHE 225, TYR 258 |
[Co(L)(bpy)] 1e | −5.49 | ASN 226 | -- | PHE 80, TRP 90, LEU 101, ALA 111 ILE 108, TRP 109, ALA 111, TYR 135, LEU 192, CYS 195, LEU 221, VAL 223, PHE 225 |
[Ni(L)(bpy)] 1f | −4.97 | -- | TRP 109 | PHE 80, TRP 90, LEU 101, ALA 111 ILE 108, TRP 109, ALA 111, TYR 135, LEU 192, PRO 193, PRO 194, CYS 195, LEU 221, VAL 223, PHE 225 |
[Cu(L)(bpy)] 1g | −5.026 | -- | PHE 225 | PHE 80, PHE 91, ILE 108, TRP 109, ALA 111, TYR 135, LEU 192, CYS 195, LEU 221, VAL 223, PRO 224, PHE 225, TYR 258 |
[Zn(L)(bpy)] 1h | −5.223 | ASN 226 | -- | PHE 80, PHE 91, ILE 108, TRP 109, TYR 135, LEU 192, CYS 195, LEU 221, VAL 223, PHE 225, TYR 258 |
Complexes | Inhibition Zone Measured (mm) | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
Escherichia coli | Klebsiella pneumonia | Staphylococcus aureus | ||||||||||
Concentration (µL/mL) | ||||||||||||
5 | 10 | 15 | 20 | 5 | 10 | 15 | 20 | 5 | 10 | 15 | 20 | |
[Co(L)(phen)] 1a | 7.5 ± 0.6 | 8.7 ± 0.4 | 9.8 ± 0.3 | 10.6 ± 0.4 | -- | -- | 7.6 ± 0.5 | 8.7 ± 0.1 | -- | 7.6 ± 0.5 | 8.5 ± 0.3 | 9.3 ± 0.4 |
[Ni(L)(phen)] 1b | 8.0 ± 0.4 | 9.1 ± 1.2 | 10.9 ± 0.4 | 13.6 ± 0.6 | 8.3 ± 0.7 | 9.6 ± 0.6 | 10.8 ± 1.2 | 13.9 ± 0.8 | 7.2 ± 0.2 | 9.0 ± 0.2 | 10.6 ± 0.6 | 12.3 ± 0.4 |
[Cu(L)(phen)] 1c | 9.8 ± 0.4 | 12.1 ± 0.2 | 13.6 ± 0.4 | 14.6 ± 0.7 | 8.9 ± 0.8 | 10.3 ± 0.7 | 11.8 ± 0.1 | 12.6 ± 0.3 | 10.6 ± 0.9 | 12.8 ± 0.6 | 14.5 ± 0.9 | 15.8 ± 0.2 |
[Zn(L)(phen)] 1d | 7.8 ± 0.6 | 8.8 ± 0.5 | 10.2 ± 0.6 | 12.4 ± 0.5 | 8.2 ± 0.6 | 9.7 ± 1.3 | 10.8 ± 1.1 | 12.8 ± 0.8 | 7.6 ± 0.5 | 8.8 ± 0.7 | 10.2 ± 0.8 | 11.8 ± 0.6 |
[Co(L)(bpy)] 1e | 7.2 ± 0.6 | 8.3 ± 0.4 | 9.3 ± 0.3 | 10.2 ± 0.4 | -- | -- | 9.6 ± 0.5 | 10.7 ± 0.1 | -- | -- | 8.3 ± 0.3 | 9.1 ± 0.4 |
[Ni(L)(bpy)] 1f | 7.7 ± 0.4 | 8.4 ± 1.2 | 9.5 ± 0.6 | 12.2 ± 0.4 | 8.8 ± 0.6 | 10.2 ± 0.8 | 12.7 ± 1.3 | 14.7 ± 0.8 | 7.4 ± 0.4 | 9.3 ± 0.6 | 10.9 ± 0.6 | 12.8 ± 0.4 |
[Cu(L)(bpy)] 1g | 9.5 ± 1.2 | 11.6 ± 0.5 | 12.8 ± 0.9 | 13.6 ± 0.4 | 9.2 ± 0.1 | 10.9 ± 0.6 | 12.2 ± 0.8 | 13.8 ± 0.4 | 10.8 ± 0.7 | 13.3 ± 0.8 | 14.5 ± 0.8 | 15.6 ± 0.9 |
[Zn(L)(bpy)] 1h | 7.4 ± 0.6 | 8.6 ± 0.5 | 9.6 ± 0.6 | 11.4 ± 0.5 | 8.8 ± 0.4 | 10.2 ± 1.1 | 11.8 ± 1.2 | 13.7 ± 0.8 | 7.9 ± 0.5 | 9.2 ± 0.4 | 10.8 ± 0.8 | 13.2 ± 0.6 |
S. No | Complexes | Cell lines Tested | |||
---|---|---|---|---|---|
IC50 (μM) * | |||||
A549 | HeLa | MCF-7 | NHDF | ||
1. | [Cu(L)(phen)] 1c | 25.95 ± 1.82 | 26.26 ± 1.06 | 17.13 ± 0.74 | 86.46 |
2. | [Cu(L)(bpy)] 1g | 39.18 ± 0.43 | 43.14 ± 0.65 | 33.18 ± 1.14 | 71.73 |
3. | cisplatin | 17.91 ± 0.12 | 16.13 ± 0.16 | 13.01 ± 0.44 | 94.12 |
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Sasikumar, G.; Subramani, A.; Tamilarasan, R.; Rajesh, P.; Sasikumar, P.; Albukhaty, S.; Mohammed, M.K.A.; Karthikeyan, S.; Al-aqbi, Z.T.; Al-Doghachi, F.A.J.; et al. Catalytic, Theoretical, and Biological Investigations of Ternary Metal (II) Complexes Derived from L-Valine-Based Schiff Bases and Heterocyclic Bases. Molecules 2023, 28, 2931. https://doi.org/10.3390/molecules28072931
Sasikumar G, Subramani A, Tamilarasan R, Rajesh P, Sasikumar P, Albukhaty S, Mohammed MKA, Karthikeyan S, Al-aqbi ZT, Al-Doghachi FAJ, et al. Catalytic, Theoretical, and Biological Investigations of Ternary Metal (II) Complexes Derived from L-Valine-Based Schiff Bases and Heterocyclic Bases. Molecules. 2023; 28(7):2931. https://doi.org/10.3390/molecules28072931
Chicago/Turabian StyleSasikumar, Gopalakrishnan, Annadurai Subramani, Ramalingam Tamilarasan, Punniyamurthy Rajesh, Ponnusamy Sasikumar, Salim Albukhaty, Mustafa K. A. Mohammed, Subramani Karthikeyan, Zaidon T. Al-aqbi, Faris A. J. Al-Doghachi, and et al. 2023. "Catalytic, Theoretical, and Biological Investigations of Ternary Metal (II) Complexes Derived from L-Valine-Based Schiff Bases and Heterocyclic Bases" Molecules 28, no. 7: 2931. https://doi.org/10.3390/molecules28072931