Several novel imatinib structure analogues were synthesized. Antiproliferative activity testing on various leukemic cell lines showed 1-2 fold less activity against K562 cells compared to imatinib. Autodock Vina’s docking studies predicted no differences in binding affinity of the titled compounds while positive relationship between activity and calculated lipophilicity was found. Further imatinib structure optimization pathways were evaluated.
| Published in | Journal of Drug Design and Medicinal Chemistry (Volume 3, Issue 2) |
| DOI | 10.11648/j.jddmc.20170302.12 |
| Page(s) | 27-31 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2024. Published by Science Publishing Group |
Imatinib, Structural Analogues, Protein Kinase Inhibitor, Molecule Design, Anticancer
| [1] | M. A. Lichtman, J. L Lieveld. “Chronic myelogenous leukemia and related disorders”, in Williams hematology, 6th ed., New York: McGraw-Hill, 2001, pp. 1125–36. |
| [2] | T. G. Lugo, A. M. Pendergast, A. J. Muller, O. N. Witte, “Tyrosine kinase activity and transformation potency of bcr-abl oncogene products”, Science, vol. 247, pp. 1079-1082, 1990. |
| [3] | M. Baccarani, F. Castagnetti, G. Gugliotta, G. Rosti, “A review of the European LeukemiaNet recommendations for the management of CML”, Ann. Hematol., vol. 94, suppl. 2, pp. 141-147, 2015. |
| [4] | M. J. Eck, P. W. Manley. “The Interplay of Structural Information and Functional Studies in Kinase Drug Design: Insights from BCR-Abl.” Current Opinion in Cell Biology, vol. 21.2, pp. 288–295, 2009. |
| [5] | F. Lee, A. Fandi, M. Voi, “Overcoming kinase resistance in chronic myeloid leukemia”, Int. J. Biochem. Cell Biol, vol. 40(3), pp: 334-343, 2008. |
| [6] | V. E. Agabekov, et al. “Preparation of 4-[(4-methyl-1-pyperazinil)-methyl]-N-[4-methyl-3-{[4-(3-pyridyl)-2-pyrimidinyl]-amino}phenyl]benzamide sulfonate”, pat. 17047, Rep. of Belarus, 30.04.2013. |
| [7] | H. G. Jørgensen, E. K. Allan, N. E. Jordanides, J. C. Mountford, T. L. Holyoake, Allan “Nilotinib exerts equipotent antiproliferative effects to imatinib and does not induce apoptosis in CD34+ CML cells”, Blood, vol. 109(9), pp 4016-4019, 2007. |
| [8] | O. Trott, A. J. Olson, “AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading”, J. Comp. Chem., vol. 31, pp. 455-461, 2010. |
| [9] | https://cactus.nci.nih.gov/translate/ |
| [10] | http://molview.org/ |
| [11] | N. M. O'Boyle, M. Banck, C. A. James, C. Morley, T. Vandermeersch, G. R. Hutchison, Open Babel: An open chemical toolbox", J. Cheminf., 3: 33, 2011. |
| [12] | http://www.molinspiration.com/cgi-bin/properties. |
| [13] | E. F. Pettersen, T. D. Goddard, C. C. Huang, G. S. Couch, D. M. Greenblatt, E. C. Meng, T. E. Ferrin, “UCSF Chimera - a visualization system for exploratory research and analysis”, J. Comp. Chem., vol. 25(13), pp. 1605-1612, 2004. |
APA Style
Aliaksandr Faryna, Elena Kalinichenko, Olga Avdoshko, Alla Belko. (2017). Design, Synthesis and Cytotoxicity Evaluation of Structural Analogues of Imatinib. Journal of Drug Design and Medicinal Chemistry, 3(2), 27-31. https://doi.org/10.11648/j.jddmc.20170302.12
ACS Style
Aliaksandr Faryna; Elena Kalinichenko; Olga Avdoshko; Alla Belko. Design, Synthesis and Cytotoxicity Evaluation of Structural Analogues of Imatinib. J. Drug Des. Med. Chem. 2017, 3(2), 27-31. doi: 10.11648/j.jddmc.20170302.12
AMA Style
Aliaksandr Faryna, Elena Kalinichenko, Olga Avdoshko, Alla Belko. Design, Synthesis and Cytotoxicity Evaluation of Structural Analogues of Imatinib. J Drug Des Med Chem. 2017;3(2):27-31. doi: 10.11648/j.jddmc.20170302.12
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Download@article{10.11648/j.jddmc.20170302.12,
author = {Aliaksandr Faryna and Elena Kalinichenko and Olga Avdoshko and Alla Belko},
title = {Design, Synthesis and Cytotoxicity Evaluation of Structural Analogues of Imatinib},
journal = {Journal of Drug Design and Medicinal Chemistry},
volume = {3},
number = {2},
pages = {27-31},
doi = {10.11648/j.jddmc.20170302.12},
url = {https://doi.org/10.11648/j.jddmc.20170302.12},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.jddmc.20170302.12},
abstract = {Several novel imatinib structure analogues were synthesized. Antiproliferative activity testing on various leukemic cell lines showed 1-2 fold less activity against K562 cells compared to imatinib. Autodock Vina’s docking studies predicted no differences in binding affinity of the titled compounds while positive relationship between activity and calculated lipophilicity was found. Further imatinib structure optimization pathways were evaluated.},
year = {2017}
}
TY - JOUR T1 - Design, Synthesis and Cytotoxicity Evaluation of Structural Analogues of Imatinib AU - Aliaksandr Faryna AU - Elena Kalinichenko AU - Olga Avdoshko AU - Alla Belko Y1 - 2017/05/19 PY - 2017 N1 - https://doi.org/10.11648/j.jddmc.20170302.12 DO - 10.11648/j.jddmc.20170302.12 T2 - Journal of Drug Design and Medicinal Chemistry JF - Journal of Drug Design and Medicinal Chemistry JO - Journal of Drug Design and Medicinal Chemistry SP - 27 EP - 31 PB - Science Publishing Group SN - 2472-3576 UR - https://doi.org/10.11648/j.jddmc.20170302.12 AB - Several novel imatinib structure analogues were synthesized. Antiproliferative activity testing on various leukemic cell lines showed 1-2 fold less activity against K562 cells compared to imatinib. Autodock Vina’s docking studies predicted no differences in binding affinity of the titled compounds while positive relationship between activity and calculated lipophilicity was found. Further imatinib structure optimization pathways were evaluated. VL - 3 IS - 2 ER -
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