Table 1.
In vitro cytotoxicity (IC50, μM)a of the title compounds 4–36 against three human cancer cell lines and the human umbilical vein endothelial cell line
| Compound | R | IC50 (μM)
|
|||
|---|---|---|---|---|---|
| MCF-7 | SW-1990 | SMMC-7721 | HUVEC | ||
| 4 | H | 77.87±10.26 | 28.58±3.77 | 35.39±4.02 | 71.92±9.04 |
| 5 | 2-F | 75.01±9.35 | 64.03±8.46 | 44.52±4.88 | 44.00±5.03 |
| 6 | 3-F | 69.88±8.73 | 62.59±7.85 | 51.49±6.03 | 44.26±4.50 |
| 7 | 4-F | 73.54±10.21 | 53.63±6.33 | 54.58±5.98 | 49.82±6.13 |
| 8 | 2-Cl | 79.70±11.43 | 40.66±4.26 | 39.97±4.07 | 33.15±3.82 |
| 9 | 3-Cl | 66.09±7.12 | 46.80±4.26 | 41.10±3.69 | 48.17±4.90 |
| 10 | 4-Cl | 45.90±4.46 | 37.93±3.52 | 43.67±4.91 | 31.45±3.22 |
| 11 | 2-Br | 25.50±3.40 | 25.21±3.12 | 24.31±3.69 | 13.91±2.46 |
| 12 | 3-Br | 66.42±7.26 | 50.45±6.84 | 33.49±5.01 | 25.84±4.73 |
| 13 | 4-Br | 47.10±6.93 | 30.39±4.89 | 20.02±2.37 | 11.16±2.60 |
| 14 | 2-CH3 | 40.76±5.92 | 23.69±3.47 | 19.95±2.33 | 67.69±8.95 |
| 15 | 4-CH3 | 37.83±4.66 | 32.03±4.23 | 39.37±4.98 | 145.71±19.01 |
| 16 | 4-C(CH3)3 | 15.80±2.14 | 8.54±1.97 | 11.87±1.83 | 25.49±3.24 |
| 17 | 3-OCH3 | 41.24±6.90 | 32.64±5.67 | 21.67±3.35 | 61.66±6.78 |
| 18 | 4-OCH3 | 46.67±5.82 | 35.64±4.21 | 17.36±2.31 | 71.18±9.03 |
| 19 | 4-OCF3 | 36.68±5.63 | 28.99±3.26 | 24.97±3.41 | 10.66±1.45 |
| 20 | 3-CF3 | 86.22±10.48 | 39.29±3.76 | 32.16±5.20 | 42.60±4.56 |
| 21 | 4-CF3 | 68.07±7.56 | 36.80±3.45 | 23.28±2.63 | 14.40±2.04 |
| 22 | 2-CN | 209.35±21.58 | 80.99±10.54 | 63.99±8.26 | 14.77±2.54 |
| 23 | 4-CN | 174.37±20.47 | 101.07±15.73 | 57.31±6.26 | 47.28±5.34 |
| 24 | 4-NO2 | 206.47±23.59 | 54.23±6.55 | 63.81±8.90 | 36.47±3.46 |
| 25 | 4-CO2CH3 | 248.55±20.13 | 165.27±18.94 | 53.49±5.84 | 48.89±5.68 |
| 26 | 4-SO2CH3 | 206.84±19.65 | 100.76±9.01 | 69.68±8.93 | 74.62±9.21 |
| 27 | 2,4-2F | 70.73±6.45 | 68.98±9.33 | 35.91±4.76 | 12.08±2.11 |
| 28 | 2,6-2F | 174.17±17.26 | 46.20±5.70 | 25.31±4.34 | 46.25±5.72 |
| 29 | 3,4-2F | 81.18±10.43 | 38.46±4.65 | 43.77±5.32 | 50.73±6.73 |
| 30 | 2-F,4-Cl | 150.48±13.26 | 38.86±4.26 | 14.32±1.93 | 54.39±6.26 |
| 31 | 2-Br,4-F | 59.58±6.83 | 44.23±5.52 | 18.88±2.36 | 18.84±2.83 |
| 32 | 2,4-2Cl | 28.20±3.46 | 28.09±2.68 | 27.94±2.53 | 65.96±7.26 |
| 33 | 2,5-2Cl | 65.50±7.22 | 38.57±4.57 | 24.21±3.48 | 7.88±1.12 |
| 34 | 2,6-2Cl | 73.63±8.94 | 22.76±2.26 | 15.67±2.33 | 20.91±2.90 |
| 35 | 3,4-2Cl | 30.78±4.32 | 20.35±2.35 | 16.15±2.92 | 15.68±2.31 |
| 36 | 2,4,6-3Cl | 12.57±1.96 | 13.32±2.36 | 18.68±2.69 | 30.47±3.47 |
| BBR | 121.91±11.26 | 27.64±3.04 | 68.06±7.76 | 18.33±2.31 | |
Note:
a
IC50 is the drug concentration effective in inhibiting 50% of the cell growth measured by the MTT assay after 48 hours of drug exposure.
Abbreviations: BBR, berberine; HUVEC, human umbilical vein endothelial cell line; IC50, half-maximal inhibitory concentration; MCF-7, human breast adenocarcinoma antidrug resistance cell line; MTT, yellow tetrazolium salt 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide; R, substituent on the benzene ring; SMMC-7721, human liver carcinoma cell line; SW-1990, human pancreatic carcinoma cell line.