Design of Novel Oligomeric Mixed Ligand Complexes: Preparation, Biological Applications and the First Example of Their Nanosized Scale
Abstract
:1. Introduction
2. Results and Discussion
2.1. Infrared Spectra
2.2. Mass Spectra
2.3. UV-Vis Spectra
2.4. Magnetic Measurements
2.5. Thermal Analysis
2.6. In Silico Predictions
2.7. Biological Activity
2.8. Anticancer Activity
2.9. Synthesis of Nanosized Coordinated Complexes
3. Materials and Methods
3.1. Materials
3.2. Instrumentation
3.3. Synthesis of Ternary Metal Complexes
3.3.1. Synthesis of Divalent Metal Complexes of Co, Ni, Cu or Zn
3.3.2. Synthesis of Trivalent Metal Complexes of Cr or Fe
3.3.3. Synthesis of Nanosized Coordination Polymers
3.4. In Silico Predictions
3.4.1. Bioactivity Predictions Using Molinspiration
3.4.2. Physicochemical and Pharmacokinetic Predictions Using Swiss ADME
3.5. Biological Tests
3.5.1. Cell Culture
3.5.2. Cytotoxicity Evaluation Using Viability Assay
3.6. Antimicrobial Assay
4. Conclusions
Author Contributions
Acknowledgments
Conflicts of Interest
References
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No. | Monomeric Unit | Color | Mol. Wt. | pH | Magnetic Moment | C% cal/found | H% cal./found | N% cal./found | S% cal./found | M% cal./found |
---|---|---|---|---|---|---|---|---|---|---|
1 | H2(Co(HNTA)(GluH)(SO4)) | Pink | 493.268 | 3.3 | 6.49 | 26.76/25.98 | 3.65/3.57 | 5.68/4.99 | 6.49/7.50 | 11.95/12.00 |
2 | H2(Ni(HNTA)(GluH)(SO4)) | Green | 493.028 | 4 | 2.99 | 26.77/25.98 | 3.65/3.85 | 5.68/4.86 | 6.49/7.55 | 11.90/11.75 |
3 | H2(Cu(HNTA)(GluH)(SO4)) | Blue | 497.881 | 4.4 | 1.16 | 26.51/26.96 | 3.62/2.95 | 5.62/5.38 | 6.43/5.74 | 12.76/12.87 |
4 | H2(Zn(HNTA)(GluH)(SO4)) | White | 499.744 | 2.3 | diamagnetic | 26.41/26.50 | 3.60/3.32 | 5.60/5.31 | 6.40/6.70 | 14.09/14.56 |
5 | H(Cr(HNTA)(GluH)(SO4)) | Blue violet | 486.331 | 3 | 4.96 | 27.14/27.49 | 3.70/3.70 | 5.75/5.26 | 6.58/8.21 | 10.69/10.49 |
6 | H(Fe(HNTA)(GluH)(SO4)) | Paige | 490.182 | 3 | 4.16 | 26.93/26.86 | 3.67/3.65 | 5.71/5.40 | 6.53/7.50 | 13.39/13.62 |
No. | Ligands and Oligomers | υ (OH) | υ (NH3+) | υ (COOH) | υ (COO−) | υ (C–N) | υ (M–N) | υ (M–O) | ν1 (SO4) | ν2 (SO4) | ν3 (SO4) | ν4 (SO4) |
---|---|---|---|---|---|---|---|---|---|---|---|---|
NTA | 3434 | - | 1725 | 1575 (as) 1530 (s) | 1206 | - | - | - | - | - | - | |
Glu | 3434 | 3062 | 1728 | 1641 (as) 1418 (s) | 1242 | - | - | - | - | - | - | |
1 | (H2(Co(HNTA)(GluH)(SO4)))n | 3417 | 3048 | - | 1587 (as) 1455–1421 (s) | 1026 | 551 | 395 | 989 | 446 | 1026 1177 1102 | 551 633 |
2 | (H2(Ni(HNTA)(GluH)(SO4)))n | 3395 | 3056 | - | 1589 (as) 1462–1414 (s) | 1088 | 556 | 343 | 981 | 443 | 1064–1088 1185 1122 | 564 626 669 |
3 | H2(Cu(HNTA)(GluH)(SO4)))n | 3424 | 3193 | - | 1597–1567 (as) 1435–1418 (s) | 1048 | 552 | 332 | 983 | 467 | 1048 1193 1102 | 596 604 641 |
4 | (H2(Zn(HNTA)(GluH)(SO4)))n | 3452 | 3048 | 1724 | 1622–1584 (as) 1461–1406 (s) | 1064 | 557 | 318 | 988 | 477 | 1064 1169 1153 | 570 627 677 |
5 | (H(Cr(HNTA)(GluH)(SO4)))n | 3450 | 3056 | - | 1644 (as) 1435–1387 (s) | 1051 | 550 | 330 | 995 | 479 | 1051 1185 1104 | 598 620 653 |
6 | (H(Fe(HNTA)(GluH)(SO4)))n | 3445 | 3080 | - | 1628–1548 (as) 1445 (s) | 1044 | 556 | 320 | 997 | 482 | 1072 1169 1104 | 588 629 661 |
No. | Oligomers | Monomer Mol. Wt. | Monomer m/z | m/z |
---|---|---|---|---|
1 | (H2(Co(HNTA)(GluH)(SO4)))n | 493.268 | 497 | 1678 |
2 | (H2(Ni(HNTA)(GluH)(SO4)))n | 493.028 | 499 | 1321 |
3 | (H2(Cu(HNTA)(GluH)(SO4)))n | 497.881 | 495 | 1217 |
4 | (H2(Zn(HNTA)(GluH)(SO4)))n | 499.744 | 509 | 1307 |
5 | (H(Cr(HNTA)(GluH)(SO4)))n | 486.331 | 499 | 1627 |
6 | (H(Fe(HNTA)(GluH)(SO4)))n | 490.182 | 425 | 2402 |
No. | Oligomers | Mol. Wt. | TGA Range (°C) | Mass Loss (%) | Total Mass Loss (%) | Assignment | ||
---|---|---|---|---|---|---|---|---|
Fou. | Calc. | Fou. | Calc. | |||||
1 | (H2(Co(HNTA) (GluH)(SO4)))n | 493.268 | 25–150 | 10.50 | 10.34 | 74.20 | 75.41 | H2S+NH3 |
150–441 | 37.50 | 38.72 | Maleic acid+glycine | |||||
441–779 | 23.00 | 23.11 | 2CO2+C2H2 | |||||
779–868 | 3.20 | 3.24 | CH4 | |||||
Above 868 | 25.80 | 24.92 | Residue | CoSO2 | ||||
2 | (H2(Ni(HNTA) (GluH)(SO4)))n | 493.028 | 25–127 | 10.00 | 10.34 | 70.50 | 72.20 | H2S+NH3 |
127–429 | 22.00 | 23.53 | Maleic acid | |||||
429–779 | 38.50 | 37.53 | Glycine+3CO+C2H2 | |||||
Above 779 | 29.50 | 28.13 | Residue | NiSO3 | ||||
3 | (H2(Cu(HNTA) (GluH)(SO4)))n | 497.881 | 25–200 | 7.00 | 6.8 | 73.50 | 74.69 | H2S |
200–664 | 66.50 | 67.89 | Maleic acid+ glycine+ CH4+2CO2+C2H2 +NH3 | |||||
Above 664 | 26.50 | 25.62 | Residue | CuSO2 | ||||
4 | (H2(Zn(HNTA) (GluH)(SO4)))n | 499.744 | 25–135 | 10.00 | 10.21 | 73.00 | 74.44 | H2S + NH3 |
135–500 | 63.00 | 64.23 | Maleic acid + glyciene + 2CO2 + C2H2+ CH4 | |||||
Above 500 | 26.90 | 25.89 | Residue | ZnSO4 | ||||
5 | (H(Cr(HNTA) (GluH)(SO4)))n | 486.331 | 25–100 | 7.00 | 6.99 | 70.50 | 71.26 | H2S |
100–212 | 6.50 | 6.79 | NH3 +CH4 | |||||
212–650 | 57.00 | 56.55 | Maleic acid + Glycine + 3CO | |||||
Above 650 | 29.50 | 30.43 | Residue | CrSO4 | ||||
6 | H(Fe(HNTA) (GluH)(SO4)) | 490.182 | 25–122 | 7.00 | 6.94 | 77.00 | 75.9 | H2S |
122–400 | 41.00 | 39.99 | Glycine + 2CO2 + NH3 + CH4 | |||||
400–650 | 29.00 | 28.97 | Maleic acid + C2H2 | |||||
Above 650 | 23.00 | 24.45 | Residue | FeSO4 |
No. | GPCR Ligand | Ion Channel Modulator | Kinase Inhibitor | Nuclear Receptor Ligand | Protease Inhibitor | Enzyme Inhibitor |
---|---|---|---|---|---|---|
1 | 0.04 | 0.21 | −0.00 | 0.01 | 0.47 | 0.50 |
2 | 0.04 | 0.21 | −0.00 | 0.01 | 0.47 | 0.50 |
3 | 0.04 | 0.21 | −0.00 | 0.01 | 0.47 | 0.50 |
4 | 0.40 | 0.21 | −0.00 | 0.01 | 0.47 | 0.54 |
5 | 0.04 | 0.21 | −0.00 | 0.01 | 0.47 | 0.50 |
6 | 0.45 | 0.21 | −0.00 | 0.01 | 0.47 | 0.53 |
No. | Monomeric Unit | Mol. wt. | Fraction Csp3 a | HBA b | HBD c | Molar Refractivity | Water Solubility | TPSA d |
---|---|---|---|---|---|---|---|---|
1 | H2(Co(HNTA)(GluH)(SO4)) | 493.268 | 0.58 | 19 | 7 | 100.09 | Yes | 364.14 |
2 | H2(Ni(HNTA)(GluH)(SO4)) | 493.028 | 0.57 | 19 | 7 | 100.15 | Yes | 364.16 |
3 | H2(Cu(HNTA)(GluH)(SO4)) | 497.881 | 0.55 | 19 | 7 | 100.15 | Yes | 364.17 |
4 | H2(Zn(HNTA)(GluH)(SO4)) | 499.744 | 0.56 | 19 | 7 | 100.11 | Yes | 364.13 |
5 | H(Cr(HNTA)(GluH)(SO4)) | 486.331 | 0.54 | 19 | 7 | 100.13 | Yes | 364.15 |
6 | H(Fe(HNTA)(GluH)(SO4)) | 490.182 | 0.55 | 19 | 7 | 100.15 | Yes | 364.17 |
No. | Monomeric Unit | GI abs a | BBB Permeant b | P-Gpsubstrate c | CYP1A2 Inhibitor d | Log Kp e |
---|---|---|---|---|---|---|
1 | H2(Co(HNTA)(GluH)(SO4)) | Low | No | Yes | No | −16.21 |
2 | H2(Ni(HNTA)(GluH)(SO4)) | Low | No | Yes | No | −16.21 |
3 | H2(Cu(HNTA)(GluH)(SO4)) | Low | No | Yes | No | −16.24 |
4 | H2(Zn(HNTA)(GluH)(SO4)) | Low | No | Yes | No | −16.25 |
5 | H(Cr(HNTA)(GluH)(SO4)) | Low | No | Yes | No | −16.17 |
6 | H(Fe(HNTA)(GluH)(SO4)) | Low | No | Yes | No | −16.19 |
No. | Cpd. | S. pneum. (+ve) | B. Subtilis (+ve) | P. Aerug. (−ve) | E. coli (−ve) | A. fumig. | S. raceme. | G. candi. | C. albic. |
---|---|---|---|---|---|---|---|---|---|
Amphotericin B | NA | NA | NA | NA | 23.7 ± 0.1 (0.24) | 19.7 ± 0.2 (3.9) | 28.7 ± 0.2 (0.015) | 25.4 ± 0.1 (0.12) | |
Ampicillin | 23.8 ± 0.2 (0.24 ) | 32.4 ± 0.3 (0.007 ) | NA | NA | NA | NA | NA | ||
Gentamicin | NA | NA | 17.3 ± 0.1 (15.63 ) | 19.9 ± 0.3 (3.9 ) | NA | NA | NA | NA | |
1 | (H2(Co(HNTA) (GluH)(SO4)))n | NA | 12.3 ± 0.37 | NA | 13.6 ± 0.58 | 13.4 ± 0.63 | 11.6 ± 0.58 | 12.6 ± 0.25 | 10.6 ± 0.44 |
2 | (H2(Ni(HNTA) (GluH)(SO4)))n | 22.0 ± 0.29 (1.95) | 26.1 ± 0.44 (0.24) | 22.9 ± 0.58 (7.81) | 21.9 ± 0.72 (1.95) | 20.3 ± 0.58 (3.9) | 19.4 ± 0.44(31.25) | 22.3 ± 0.63 (3.9) | 18.4 ± 0.44 (125) |
3 | (H2(Cu(HNTA) (GluH)(SO4)))n | 20.9 ± 0.44 (1.95) | 23.8 ± 0.17 (0.24) | 22.3 ± 0.17 (0.98) | 25.2 ± 0.63 (0.12) | 24.8 ± 0.58 (0.12) | 23.8 ± 0.58 (0.24) | 24.2 ± 0.44 (0.24) | 20.9 ± 0.37 (1.95) |
4 | (H2(Zn(HNTA) (GluH)(SO4)))n | 18.2 ± 0.63 (15.63) | 19.3 ± 0.72 (7.81) | NA | 11.8 ± 0.58 (500) | 18.4 ± 0.58 (15.63) | 15.2 ± 0.58 (62.5) | 15.9 ± 0.08 (62.5) | 9.8 ± 0.44 (NA) |
5 | (H(Cr(HNTA) (GluH)(SO4)))n | 14.5 ± 0.44 (62.5) | 22.3 ± 0.37 (0.98) | NA | 11.6 ± 0.25 (125) | 17.2 ± 0.63 (31.25) | 16.8 ± 0.44 (31.25) | 18.3 ± 0.44 (15.63) | NA |
6 | (H(Fe(HNTA) (GluH)(SO4)))n | 24.7 ± 0.58 (0.12) | 28.2 ± 0.58 (0.015) | 22.8 ± 0.44 (0.49) | 24.4 ± 0.63 (0.24) | 24.4 ± 0.37 (0.24) | 17.2 ± 0.72 (31.25) | 25.3 ± 0.44 (0.12) | 19.9 ± 0.77 (3.9) |
No. | Oligomers | Sample Conc. (µg/mL) | MCF-7 Viability% | IC50 (µg/mL) | HCT-116 Viability (µg/mL) | IC50 (µg/mL) | HepG-2 Viability% | IC50 (µg/mL) |
---|---|---|---|---|---|---|---|---|
1 | (H2(Co(HNTA) (GluH)(SO4)))n | 50 | 64.28 | >50 | 68.57 | >50 | 60.86 | >50 |
25 | 72.73 | 82.46 | 78.13 | |||||
12.5 | 89.42 | 93.12 | 91.48 | |||||
6.25 | 94.54 | 98.78 | 97.24 | |||||
3.125 | 98.16 | 100 | 100 | |||||
1.56 | 100 | 100 | 100 | |||||
0 | 100 | 100 | 100 | |||||
2 | (H2(Ni(HNTA) (GluH)(SO4)))n | 50 | 49.84 | 49.7 ± 0.23 | 57.42 | >50 | 46.18 | 44.8 ± 0.24 |
25 | 63.51 | 69.78 | 64.39 | |||||
12.5 | 71.62 | 83.14 | 80.61 | |||||
6.25 | 82.94 | 92.65 | 91.74 | |||||
3.125 | 91.05 | 98.78 | 96.52 | |||||
1.56 | 97.48 | 100 | 99.06 | |||||
0 | 100 | 100 | 100 | |||||
3 | (H2(Cu(HNTA) (GluH)(SO4)))n | 50 | 24.32 | 11.5 ± 0.09 | 26.98 | 18.00 ± 0.08 | 21.54 | 12.00 ± 0.05 |
25 | 33.57 | 39.44 | 36.93 | |||||
12.5 | 45.34 | 58.23 | 48.22 | |||||
6.25 | 74.69 | 75.16 | 71.36 | |||||
3.125 | 85.71 | 89.28 | 84.59 | |||||
1.56 | 93.56 | 95.34 | 92.64 | |||||
0 | 100 | 100 | 100 | |||||
4 | (H2(Zn(HNTA) (GluH)(SO4)))n | 50 | 20.43 | 10.7 ± 0.11 | 29.17 | 20.1 ± 0.10 | 23.67 | 16.1 ± 0.06 |
25 | 34.68 | 45.26 | 40.89 | |||||
12.5 | 42.97 | 57.41 | 53.72 | |||||
6.25 | 67.25 | 72.41 | 69.17 | |||||
3.125 | 80.13 | 81.04 | 86.28 | |||||
1.56 | 87.49 | 89.56 | 93.02 | |||||
0 | 100 | 100 | 100 | |||||
5 | (H(Cr(HNTA) (GluH)(SO4)))n | 50 | 77.18 | >50 | 84.62 | >50 | 76.28 | >50 |
25 | 86.27 | 93.13 | 91.36 | |||||
12.5 | 95.84 | 98.74 | 97.96 | |||||
6.25 | 99.08 | 100 | 100 | |||||
3.125 | 100 | 100 | 100 | |||||
1.56 | 100 | 100 | 100 | |||||
0 | 100 | 100 | 100 | |||||
6 | (H(Fe(HNTA) (GluH)(SO4)))n | 50 | 45.96 | 47.3 ± 0.19 | 61.84 | >50 | 42.69 | 44.1 ± 0.17 |
25 | 82.74 | 83.12 | 73.48 | |||||
12.5 | 90.36 | 91.46 | 82.97 | |||||
6.25 | 94.28 | 97.38 | 91.64 | |||||
3.125 | 98.93 | 99.17 | 98.26 | |||||
1.56 | 100 | 100 | 100 | |||||
0 | 100 | 100 | 100 |
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Okasha, R.M.; AL-Shaikh, N.E.; Aljohani, F.S.; Naqvi, A.; Ismail, E.H. Design of Novel Oligomeric Mixed Ligand Complexes: Preparation, Biological Applications and the First Example of Their Nanosized Scale. Int. J. Mol. Sci. 2019, 20, 743. https://doi.org/10.3390/ijms20030743
Okasha RM, AL-Shaikh NE, Aljohani FS, Naqvi A, Ismail EH. Design of Novel Oligomeric Mixed Ligand Complexes: Preparation, Biological Applications and the First Example of Their Nanosized Scale. International Journal of Molecular Sciences. 2019; 20(3):743. https://doi.org/10.3390/ijms20030743
Chicago/Turabian StyleOkasha, Rawda M., Najla E. AL-Shaikh, Faizah S. Aljohani, Arshi Naqvi, and Eman H. Ismail. 2019. "Design of Novel Oligomeric Mixed Ligand Complexes: Preparation, Biological Applications and the First Example of Their Nanosized Scale" International Journal of Molecular Sciences 20, no. 3: 743. https://doi.org/10.3390/ijms20030743