Binding Performance of Human Intravenous Immunoglobulin and 20(S)-7-Ethylcamptothecin
Abstract
:1. Introduction
2. Results and Discussion
2.1. Fluorescence Quenching Study
2.2. Binding Mode Study
2.3. FT-IR Spectroscopy Study
2.4. UV-Vis Spectroscopy Study
2.5. Molecular Docking Study
3. Materials and Methods
3.1. Materials
3.2. Methods
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors. |
Temperature K | Ko × 104/M−1 | α | Ko × 104/M−1 | α | KSV × 104/M−1 | Kq × 1012/M−1·s−1 |
---|---|---|---|---|---|---|
n = 2 | n = 4 | n = 2, n = 4 | ||||
CPT | ||||||
289 | 0.2636 | 0.4529 | 0.04152 | 0.4391 | 4.988 | 4.988 |
296 | 0.8933 | 0.5784 | 0.1968 | 0.5544 | 6.737 | 6.737 |
303 | 4.135 | 0.9097 | 1.645 | 0.8830 | 11.74 | 11.74 |
310 | 9.683 | 1.373 | 5.341 | 1.343 | 14.67 | 14.67 |
Topotecan chloride | ||||||
289 | 1.452 | 1.158 | 0.6501 | 1.099 | 4.743 | 4.743 |
296 | 1.528 | 1.101 | 0.6324 | 1.032 | 3.930 | 3.930 |
303 | 0.9268 | 0.8889 | 0.3119 | 0.8311 | 3.499 | 3.499 |
310 | 0.8570 | 0.7064 | 0.2028 | 0.6483 | 3.479 | 3.479 |
Irinotecan chloride | ||||||
289 | 1.500 | 1.061 | 1.790 | 0.2290 | 4.514 | 4.514 |
296 | 1.122 | 0.8402 | 1.371 | 0.1779 | 4.497 | 4.497 |
303 | 1.052 | 0.8245 | 1.306 | 0.1752 | 3.623 | 3.623 |
310 | 0.9247 | 0.8708 | 1.167 | 0.1873 | 3.376 | 3.376 |
10-Hydroxycamptothecin | ||||||
289 | 0.9805 | 0.9365 | 0.4065 | 1.118 | 3.155 | 3.155 |
296 | 0.8630 | 1.157 | 0.3477 | 0.8823 | 2.410 | 2.410 |
303 | 0.8587 | 0.9614 | 0.3347 | 0.9164 | 2.134 | 2.134 |
310 | 0.6337 | 0.8893 | 0.2304 | 0.8485 | 1.979 | 1.979 |
7-Ethylcamptothecin | ||||||
289 | 1.301 | 1.351 | 0.6763 | 1.300 | 2.744 | 2.744 |
296 | 0.6293 | 1.010 | 0.2702 | 0.9769 | 1.888 | 1.888 |
303 | 0.8375 | 1.087 | 0.3764 | 1.048 | 1.768 | 1.768 |
310 | 0.8472 | 1.161 | 0.4072 | 1.125 | 1.552 | 1.552 |
SN-38 | ||||||
289 | 1.183 | 1.185 | 0.7992 | 1.284 | 1.923 | 1.923 |
296 | 1.088 | 1.308 | 0.5671 | 1.269 | 1.907 | 1.907 |
303 | 0.4756 | 0.8135 | 0.1633 | 0.7832 | 1.308 | 1.308 |
310 | 0.2731 | 0.8007 | 0.0973 | 0.7793 | 0.8997 | 0.8997 |
Temperature K | ΔGo/KJ·mol−1 | ΔHo/KJ·mol−1 | ΔSo/J·mol−1·K−1 | ΔGo/KJ·mol−1 | ΔHo/KJ·mol−1 | ΔSo/J·mol−1·K−1 |
---|---|---|---|---|---|---|
n = 2 | n = 4 | |||||
CPT, binding mode: hydrophobic interaction | ||||||
289 | −13.39 | 131.5 | 501.4 | −8.953 | 177.8 | 645.9 |
296 | −16.72 | −13.00 | ||||
303 | −20.98 | −18.66 | ||||
310 | −23.66 | −22.12 | ||||
Topotecan, binding mode: Van der Waals force, hydrogen bonding | ||||||
289 | −23.03 | −31.68 | −27.49 | −21.10 | −44.49 | −79.66 |
296 | −23.71 | −21.54 | ||||
303 | −23.01 | −20.27 | ||||
310 | −23.34 | −19.63 | ||||
Irinotecan, binding mode: electrostatic interaction | ||||||
289 | −23.12 | −16.21 | 23.43 | −23.54 | −14.26 | 31.70 |
296 | −22.96 | −23.45 | ||||
303 | −23.34 | −23.89 | ||||
310 | −23.55 | −24.15 | ||||
10-hydroxycamptothecin, binding mode: electrostatic interaction | ||||||
289 | −22.08 | −13.90 | 28.53 | −19.97 | −18.42 | 5.646 |
296 | −22.30 | −20.07 | ||||
303 | −22.82 | −20.44 | ||||
310 | −22.56 | −19.95 | ||||
7-ethylcamptothecin, binding mode: hydrophobic interaction | ||||||
289 | −22.76 | 16.31 | 128.2 | −21.19 | 22.45 | 141.9 |
296 | −21.53 | −19.45 | ||||
303 | −22.76 | −20.74 | ||||
310 | −23.31 | −21.42 | ||||
SN-38, binding mode: Van der Waals force, hydrogen bonding | ||||||
289 | −22.53 | −55.35 | −112.1 | −21.59 | −80.35 | −202.1 |
296 | −22.87 | −21.27 | ||||
303 | −21.33 | −18.64 | ||||
310 | −20.39 | −17.73 |
Amide I components (%) | pH 4.0 | pH 7.4 | ||||
---|---|---|---|---|---|---|
IVIG | +4.0 µM Analogues | +8.0 µM Analogues | IVIG | +4.0 µM Analogues | +8.0 µM Analogues | |
CPT | ||||||
β-anti | 5.10 | 2.79 | 10.24 | 3.61 | 6.16 | 4.85 |
Turn | 8.28 | 13.72 | 3.46 | 24.88 | 3.68 | 10.46 |
β-sheet | 40.04 | 11.09 | little | 39.49 | 23.73 | little |
Remainders | 46.58 | 72.40 | ~86.30 | 32.04 | 66.43 | ~84.69 |
Topotecan | ||||||
β-anti | 5.10 | little | 8.93 | 3.61 | 4.45 | little |
Turn | 8.28 | ~32.55 | 32.66 | 24.88 | 31.03 | ~18.28 |
β-sheet | 40.04 | 15.72 | 3.22 | 39.49 | 24.26 | 27.73 |
Remainders | 46.58 | 51.73 | 55.19 | 32.04 | 40.26 | 53.99 |
Irinotecan | ||||||
β-anti | 5.10 | little | little | 3.61 | 6.16 | little |
Turn | 8.28 | ~4.97 | ~6.78 | 24.88 | 29.19 | ~14.81 |
β-sheet | 40.04 | little | little | 39.49 | 30.50 | little |
Remainders | 46.58 | ~95.03 | ~93.22 | 32.04 | 40.31 | ~85.19 |
10-Hydroxycamptothecin | ||||||
β-anti | 5.10 | 10.24 | 6.17 | 3.61 | little | little |
Turn | 8.28 | 3.46 | little | 24.88 | ~16.00 | ~33.71 |
β-sheet | 40.04 | little | 33.36 | 39.49 | little | little |
Remainders | 46.58 | ~86.31 | ~60.47 | 32.04 | ~84.00 | ~66.29 |
7-Ethylcamptothecin | ||||||
β-anti | 5.10 | little | little | 3.61 | 7.68 | 2.76 |
Turn | 8.28 | 1.36 | ~16.93 | 24.88 | 21.28 | 16.64 |
β-sheet | 40.04 | 29.98 | 26.30 | 39.49 | 15.82 | 7.57 |
Remainders | 46.58 | ~68.66 | 56.77 | 32.04 | 55.22 | 73.03 |
SN-38 | ||||||
β-anti | 5.10 | 6.84 | little | 3.61 | 11.79 | little |
Turn | 8.28 | 35.40 | ~30.23 | 24.88 | 5.19 | ~24.50 |
β-sheet | 40.04 | 1.51 | little | 39.49 | 15.37 | 32.25 |
Remainders | 46.58 | 56.25 | ~69.77 | 32.04 | 67.64 | 43.25 |
Compounds | Ratios of Lactone to Total for Three CPTs at pH 7.40 and 310 K | |
---|---|---|
SN-38 | 90.40% | 86.47~87.35% |
10-Hydroxycamptothecin | 86.68% | 56.56~68.58% |
Topotecan | 34.47% | 29.76~32.71% |
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Liu, Y.-C.; Li, Y.-Y.; Yao, X.-J.; Qi, H.-L.; Wei, X.-X.; Liu, J.-N. Binding Performance of Human Intravenous Immunoglobulin and 20(S)-7-Ethylcamptothecin. Molecules 2018, 23, 2389. https://doi.org/10.3390/molecules23092389
Liu Y-C, Li Y-Y, Yao X-J, Qi H-L, Wei X-X, Liu J-N. Binding Performance of Human Intravenous Immunoglobulin and 20(S)-7-Ethylcamptothecin. Molecules. 2018; 23(9):2389. https://doi.org/10.3390/molecules23092389
Chicago/Turabian StyleLiu, Yong-Chun, Ying-Ying Li, Xiao-Jun Yao, Hui-Li Qi, Xiao-Xia Wei, and Jian-Ning Liu. 2018. "Binding Performance of Human Intravenous Immunoglobulin and 20(S)-7-Ethylcamptothecin" Molecules 23, no. 9: 2389. https://doi.org/10.3390/molecules23092389