Table 1.
Mean binding energies and predicted binding constants were obtained by molecular docking for 50 curcumin compounds. Dockings were independently carried out three times with every 250,000 runs (mean values ± SD).
| Compounds | EGFR (Mean Binding Energy, kcal/mol) | EGFR (Mean pKi, µM) | NF-κB (Mean Binding Energy, kcal/mol) | NF-κB (Mean pKi, µM) | |
|---|---|---|---|---|---|
| 1 | Curcumin | −9.42 ± 0.09 | 0.13 ± 0.02 | −8.38 ± 0.16 | 0.73 ± 0.21 |
| 2 | Bisdemethoxycurcumin | −8.51 ± 0.02 | 0.58 ± 0.02 | −7.96 ± 0.05 | 1.46 ± 0.11 |
| 3 | Diacetylcurcumin | −10.72 ± 0.49 | 0.02 ± 0.02 | −9.67 ± 0.26 | 0.09 ± 0.04 |
| 4 | [18FP]-curcumin | −8.70 ± 0.21 | 0.43 ± 0.14 | −9.01 ± 0.07 | 0.25 ± 0.03 |
| 5 | Monodemethoxycurcumin | −9.04 ± 0.06 | 0.24 ± 0.02 | −8.07 ± 0.10 | 1.23 ± 0.20 |
| 6 | (E,E)-Bis(2-hydroxybenzylidene)acetone | −7.95 ± 0.01 | 1.49 ± 0.04 | −7.21 ± 0.06 | 5.19 ± 0.50 |
| 7 | Curcumin monoglucoside | −9.72 ± 0.76 | 0.11 ± 0.11 | −9.57 ± 0.34 | 0.11 ± 0.06 |
| 8 | Di-O-(2-thienoyl) curcumin | −11.71 ± 0.26 | 0.003 ± 0.002 | −10.71 ± 0.17 | 0.01 ± <0.01 |
| 9 | Cis-curcumin | −9.07 ± 0.30 | 0.24 ± 0.10 | −8.81 ± 0.33 | 0.39 ± 0.21 |
| 10 | Curcumin diglucoside | −9.10 ± 0.99 | 0.39 ± 0.35 | −10.35 ± 0.35 | 0.03 ± 0.02 |
| 11 | Tetrahydrocurcumin | −9.13 ± 0.17 | 0.21 ± 0.06 | −8.28 ± 0.21 | 0.90 ± 0.34 |
| 12 | Allyl curcumin | −10.07 ± 0.07 | 0.04 ± 0.01 | −9.15 ± 0.04 | 0.20 ± 0.01 |
| 13 | Monodemethylcurcumin | −9.96 ± 0.10 | 0.05 ± 0.01 | −8.16 ± 0.56 | 0.59 ± 0.12 |
| 14 | Didemethylcurcumin | −9.90 ± 0.07 | 0.06 ± 0.01 | −8.71 ± 0.25 | 0.49 ± 0.18 |
| 15 | Curcumin-4′-O-β-d-gentiotrioside | −7.85 ± 0,59 | 3.11 ± 0.23 | −7.51 ± 0.37 | 3.47 ± 2.05 |
| 16 | 4-Benzylidene curcumin | −10.62 ± 0.72 | 0.03 ± 0.03 | −9.10 ± 0.10 | 0.21 ± 0.04 |
| 17 | Monoglycinoyl curcumin | −12.12 ± 0.21 | 0.0013 ± 0.0006 | −10.07 ± 0.08 | 0.04 ± 0.01 |
| 18 | Ethyl curcumin | −10.09 ± 0.11 | 0.04 ± 0.01 | −9.23 ± 0.05 | 0.17 ± 0.01 |
| 19 | Curcumin dimer 1 | −11.64 ± 0.56 | 0.004 ± 0.003 | −11.11 ± 0.65 | 0.01 ± 0.01 |
| 20 | N-phenylpyrazole curcumin | −8.63 ± 0.19 | 0.49 ± 0.14 | −8.81 ± 0.01 | 0.35 ± 0.01 |
| 21 | Curcumin β-d-glucuronide | −10.36 ± 0.19 | 0.04 ± 0.02 | −10.07 ± 0.36 | 0.05 ± 0.03 |
| 22 | 3,4-Difluorobenzylidene curcumin | −10.08 ± 0.13 | 0.04 ± 0.01 | −9.30 ± 0.07 | 0.15 ± 0.02 |
| 23 | Di-O-(2-hydroxyethyl) curcumin | −9.60 ± 0.27 | 0.10 ± 0.05 | −8.97 ± 0.55 | 0.35 ± 0.27 |
| 24 | 4-(4-hydroxybenzylidene) curcumin | −10.55 ± 0.12 | 0.02 ± <0.01 | −8.98 ± 0.04 | 0.26 ± 0.02 |
| 25 | N-(3-nitrophenylpyrazole) curcumin | −10.50 ± 0.02 | 0.02 ± <0.01 | −9.57 ± 0.01 | 0.097 ± <0.01 |
| 26 | N-(4-flurophenylpyrazole) curcumin | −8.46 ± 0.19 | 0.65 ± 0.19 | −8.81 ± 0.09 | 0.35 ± 0.06 |
| 27 | N-(4-methoxyphenylpyrazole) curcumin | −8.49 ± 0.04 | 0.60 ± 0.03 | −8.95 ± 0.11 | 0.28 ± 0.05 |
| 28 | Di-O-chloropropionylethyl curcumin | −10.92 ± 0.25 | 0.01 ± <0.01 | −10.36 ± 0.59 | 0.03 ± 0.02 |
| 29 | Curcumin tri-adamantylaniniethylcarbonate | −10.75 ± 0.23 | 0.01 ± 0.01 | −12.97 ± 0.47 | 0.0004 ± 0.0003 |
| 30 | Curcumin dimer 2 | −11.08 ± 0.24 | 0.01 ± <0.01 | −12.05 ± 0.46 | 0.002 ± 0.001 |
| 31 | Curcumin tri-trithiadiazolaminoethylcarbonate | −10.35 ± 0.55 | 0.03 ± 0.02 | −10.97 ± 0.53 | 0.01 ± 0.01 |
| 32 | 4-(4-hydroxy-3-methoxybenzylidene) curcumin | −11.44 ± 0.16 | 0.004 ± 0.002 | −10.97 ± 0.53 | 0.01 ± 0.01 |
| 33 | Curcumin-β-d-glucuronide triacetate methyl ester | −10.06 ± 0.79 | 0.07 ± 0.06 | −10.35 ± 0.35 | 0.03 ± 0.02 |
| 34 | Curcumin 4′-O-β-d-gentiobiosyl 4″-O-β-d-glucoside | −9.54 ± 0.25 | 0.11 ± 0.05 | −10.23 ± 0.59 | 0.04 ± 0.04 |
| 35 | Tetrahydrocurcumin isoxazole | −9.43 ± 0.20 | 0.13 ± 0.04 | −8.60 ± 0.41 | 0.57 ± 0.32 |
| 36 | Hexahydrocurcumin | −9.25 ± 0.11 | 0.17 ± 0.03 | −8.41 ± 0.27 | 0.73 ± 0.35 |
| 37 | Bisdemethoxycurcumin isoxazole | −7.45 ± 0.01 | 3.45 ± 0.10 | −7.55 ± 0.10 | 2.96 ± 0.47 |
| 38 | Curcumin dimer 3 | −10.28 ± 0.22 | 0.03 ± 0.01 | −10.50 ± 0.77 | 0.01 ± 0.01 |
| 39 | Curcumin ED | −9.59 ± 0.08 | 0.10 ± 0.02 | −8.69 ± 0.14 | 0.43 ± 0.10 |
| 40 | Curcumin PE | −9.24 ± 0.12 | 0.17 ± 0.03 | −8.22 ± 0.22 | 0.99 ± 0.33 |
| 41 | Curcumin sulfate | −9.31 ± 0.16 | 0.15 ± 0.04 | −9.84 ± 0.08 | 0.06 ± 0.01 |
| 42 | Ferrocenyl curcumin | −8.34 ± 0.22 | 0.80 ± 0.29 | −7.10 ± 0.33 | 6.87 ± 3.92 |
| 43 | Di-O-deconyl curcumin | −10.57 ± 0.17 | 0.01 ± <0.01 | −11.58 ± 0.85 | 0.02 ± 0.01 |
| 44 | GNF-pf-2695 ((2E,5E)-2,5-bis[(3,4,5-trimethoxyphenyl) methylidene]cyclopentan-1-one) | −7.34 ± 0.07 | 4.22 ± 0.51 | −7.56 ± 0.15 | 2.93 ± 0.78 |
| 45 | Perfluoro curcumin | −7.55 ± 0.19 | 3.03 ± 0.86 | −6.86 ± 0.28 | 10.05 ± 4.03 |
| 46 | Keto-curcumin | −9.89 ± 0.41 | 0.07 ± 0.04 | −8.78 ± 0.15 | 0.37 ± 0.09 |
| 47 | Disalicyloyl curcumin | −7.67 ± 0.58 | 0.02 ± 0.02 | −6.24 ± 0.06 | 26.77 ± 3.36 |
| 48 | HO-3867 (3E,5E)-3,5-bis[(4-fluorophenyl)methylidene]-1-[(1-hydroxy-2,2,5,5-tetramethylpyrrol-3-yl)methyl]piperidin-4-one) | −9.73 ± 0.03 | 0.07 ± <0.01 | −7.79 ± 0.10 | 1.96 ± 0.33 |
| 49 | 1A6 ((1E,6E)-4-chloro-1,7-bis(3,4-dimethoxyphenyl)hepta-1,6-diene-3,5-dione) | −8.94 ± 0.06 | 0.28 ± 0.03 | −8.28 ± 0.21 | 0.90 ± 0.34 |
| 50 | 1A9 ((1E,6E)-4-chloro-1,7-di(1H-indol-3-yl)hepta-1,6-diene-3,5-dione) | −9.57 ± 0.02 | 0.10 ± 0.03 | −8.51 ± 0.11 | 0.58 ± <0.01 |