Molecular Requirements for the Expression of Antiplatelet Effects by Synthetic Structural Optimized Analogues of the Anticancer Drugs Imatinib and Nilotinib

References

• Versteeg HH, Heemskerk JW, Levi M, Reitsma PH. New fundamentals in hemostasis. Physiol Rev. 2013;93:327–358. doi:10.1152/physrev.00016.201123303912
   PubMed Web of Science ®Google Scholar
• Davi G, Patrono C. Platelet activation and atherothrombosis. N Engl J Med. 2007;357:2482–2494. doi:10.1056/NEJMra07101418077812
   PubMed Web of Science ®Google Scholar
• Abdol Razak NB, Jones G, Bhandari M, et al. Cancer-associated thrombosis: an overview of mechanisms, risk factors, and treatment. Cancers. 2018;10:1–21. doi:10.3390/cancers10100380
   Web of Science ®Google Scholar
• Connolly GC, Francis CW. Cancer-associated thrombosis. Hematology Am Soc Hematol Educ Program. 2013;2013:684–691. doi:10.1182/asheducation-2013.1.68424319253
   PubMed Web of Science ®Google Scholar
• Ay C, Pabinger I, Cohen AT. Cancer-associated venous thromboembolism: burden, mechanisms, and management. Thromb Haemost. 2017;117:219–230. doi:10.1160/TH16-08-061527882374
   PubMed Web of Science ®Google Scholar
• Falanga A, Marchetti M, Russo L. The mechanisms of cancer-associated thrombosis. Thromb Res. 2015;135:S8–S11. doi:10.1016/S0049-3848(15)50432-525903541
   PubMed Web of Science ®Google Scholar
• Falanga A, Russo L, Milesi V. Mechanisms and risk factors of thrombosis in cancer. Crit Rev Oncol Hematol. 2017;118:79–83. doi:10.1016/j.critrevonc.2017.08.00328917273
   PubMed Web of Science ®Google Scholar
• Connolly GC, Phipps RP, Francis CW. Platelets and cancer-associated thrombosis. Semin Oncol. 2014;41:302–310. doi:10.1053/j.seminoncol.2014.04.00925023346
   PubMed Web of Science ®Google Scholar
• Falanga A, Marchetti M. Hemostatic biomarkers in cancer progression. Thromb Res. 2018;164:S54–S61. doi:10.1016/j.thromres.2018.01.01729703485
   PubMed Web of Science ®Google Scholar
• Olsson AK, Cedervall J. The pro-inflammatory role of platelets in cancer. Platelets. 2018;29(6):569–573. doi:10.1080/09537104.2018.145305929584534
   PubMed Web of Science ®Google Scholar
• Schlesinger M. Role of platelets and platelet receptors in cancer metastasis. J Hematol Oncol. 2018;11:125. doi:10.1186/s13045-018-0669-230305116
   PubMed Web of Science ®Google Scholar
• Wojtukiewicz MZ, Sierko E, Hempel D, Tucker SC, Honn KV. Platelets and cancer angiogenesis nexus. Cancer Metastasis Rev. 2017;36:249–262. doi:10.1007/s10555-017-9673-128681240
   PubMed Web of Science ®Google Scholar
• Gay LJ, Felding-Habermann B. Contribution of platelets to tumor metastasis. Nat Rev Cancer. 2011;11(2):123–134. doi:10.1038/nrc300421258396
   PubMed Web of Science ®Google Scholar
• Palumbo JS, Talmage KE, Massari JV, et al. Platelets and fibrin(ogen) increase metastatic potential by impeding natural killer cell-mediated elimination of tumor cells. Blood. 2005;105:178–185. doi:10.1182/blood-2004-06-227215367435
   PubMed Web of Science ®Google Scholar
• Kopp HG, Placke T, Salih HR. Platelet-derived transforming growth factor-beta down-regulates nkg2d thereby inhibiting natural killer cell antitumor reactivity. Cancer Res. 2009;69:7775–7783. doi:10.1158/0008-5472.CAN-09-212319738039
   PubMed Web of Science ®Google Scholar
• Felding-Habermann B, Habermann R, Saldivar E, Ruggeri ZM. Role of beta3 integrins in melanoma cell adhesion to activated platelets under flow. J Biol Chem. 1996;271:5892–5900. doi:10.1074/jbc.271.10.58928621462
   PubMed Web of Science ®Google Scholar
• Egan K, Cooke N, Kenny D. Living in shear: platelets protect cancer cells from shear induced damage. Clin Exp Metastasis. 2014;31:697–704. doi:10.1007/s10585-014-9660-724942131
   PubMed Web of Science ®Google Scholar
• Gong L, Cai Y, Zhou XD, Yang HP. Activated platelets interact with lung cancer cells through p-selectin glycoprotein ligand-1. Pathol Oncol Res. 2012;18:989–996. doi:10.1007/s12253-012-9531-y22535539
   PubMed Web of Science ®Google Scholar
• Labelle M, Begum S, Hynes RO. Direct signaling between platelets and cancer cells induces an epithelial-mesenchymal-like transition and promotes metastasis. Cancer Cell. 2011;20(5):576–590. doi:10.1016/j.ccr.2011.09.00922094253
   PubMed Web of Science ®Google Scholar
• Elaskalani O, Berndt MC, Falasca M, Metharom P. Targeting Platelets for the Treatment of Cancer. Cancers. 2017;9:94. doi:10.3390/cancers9070094
   PubMed Web of Science ®Google Scholar
• Gresele P, Momi S, Malvestiti M, Sebastiano M. Platelet-targeted pharmacologic treatments as anticancer therapy. Cancer Metastasis Rev. 2017;36:331–355. doi:10.1007/s10555-017-9679-828707198
   PubMed Web of Science ®Google Scholar
• Rothwell PM, Wilson M, Price JF, et al. Effect of daily aspirin on risk of cancer metastasis: a study of incident cancers during randomised controlled trials. Lancet. 2012;379:1591–1601. doi:10.1016/S0140-6736(12)60209-822440947
   PubMed Web of Science ®Google Scholar
• Cao Y, Nishihara R, Wu K, et al. Population-wide impact of long-term use of aspirin and the risk for cancer. JAMA Oncol. 2016;2:762–769. doi:10.1001/jamaoncol.2015.639626940135
   PubMed Web of Science ®Google Scholar
• Wu P, Nielsen TE, Clausen MH. FDA-approved small-molecule kinase inhibitors. Trends Pharmacol Sci. 2015;36:422–439. doi:10.1016/j.tips.2015.04.00525975227
   PubMed Web of Science ®Google Scholar
• Tullemans BME, Heemskerk JWM, Kuijpers MJE. Acquired platelet antagonism: off-target antiplatelet effects of malignancy treatment with tyrosine kinase inhibitors. J Thromb Haemost. 2018;16:1686–1699. doi:10.1111/jth.2018.16.issue-929975003
   PubMed Web of Science ®Google Scholar
• Estevez B, Du X. New Concepts and mechanisms of platelet activation signaling. Physiology (Bethesda). 2017;32:162–177. doi:10.1152/physiol.00020.201628228483
   PubMed Web of Science ®Google Scholar
• Kanikarla-Marie P, Lam M, Sorokin AV, et al. Platelet metabolism and other targeted drugs; potential impact on immunotherapy. Front Oncol. 2018;8:107. doi:10.3389/fonc.2018.0010729732316
   PubMed Web of Science ®Google Scholar
• Oda A, Ikeda Y, Ochs HD, et al. Rapid tyrosine phosphorylation and activation of Bruton’s tyrosine/Tec kinases in platelets induced by collagen binding or CD32 cross-linking. Blood. 2000;95:1663–1670.10688822
   PubMed Web of Science ®Google Scholar
• Phillips DR, Nannizzi-Alaimo L, Prasad KS. Beta3 tyrosine phosphorylation in alphaIIbbeta3 (platelet membrane GP IIb-IIIa) outside-in integrin signaling. Thromb Haemost. 2001;86:246–258. doi:10.1055/s-0037-161622211487013
   PubMed Web of Science ®Google Scholar
• Sater HA, Gandhi AS, Dainer P, et al. Receptor tyrosine kinases in human platelets: a review of expression, function and inhibition in relation to the risk of bleeding or thrombocytopenia from phase I through phase III trials. J Cancer Prev Curr Res. 2017;8:1–13.
   Google Scholar
• Wang WY, Hsieh PW, Wu YC, et al. Synthesis and pharmacological evaluation of novel beta-nitrostyrene derivatives as tyrosine kinase inhibitors with potent antiplatelet activity. Biochem Pharmacol. 2007;74:601–611. doi:10.1016/j.bcp.2007.06.00117601492
   PubMed Web of Science ®Google Scholar
• Golden A, Brugge JS. Thrombin treatment induces rapid changes in tyrosine phosphorylation in platelets. Proc Natl Acad Sci U S A. 1989;86:901–905. doi:10.1073/pnas.86.3.9012464830
   PubMed Web of Science ®Google Scholar
• Maguire PB, Wynne KJ, Harney DF, et al. Identification of the phosphotyrosine proteome from thrombin activated platelets. Proteomics. 2002;2:642–648. doi:10.1002/1615-9861(200206)2:6<642:AID-PROT642>3.0.CO;2-l12112843
   PubMed Web of Science ®Google Scholar
• Seeliger MA, Nagar B, Frank F, et al. c-Src binds to the cancer drug imatinib with an inactive Abl/c-Kit conformation and a distributed thermodynamic penalty. Structure (London, England:1993). 2007;15:299–311. doi:10.1016/j.str.2007.01.015
   PubMed Web of Science ®Google Scholar
• Jackson SP, Schoenwaelder SM, Yuan Y, et al. Non-receptor protein tyrosine kinases and phosphatases in human platelets. Thromb Haemost. 1996;76:640–650. doi:10.1055/s-0038-16506378950767
   PubMed Web of Science ®Google Scholar
• Capdeville R, Buchdunger E, Zimmermann J, Matter A. Glivec (STI571, imatinib), a rationally developed, targeted anticancer drug. Nat Rev Drug Discov. 2002;1:493–502. doi:10.1038/nrd83912120256
   PubMed Web of Science ®Google Scholar
• Skobridis K, Kinigopoulou M, Theodorou V, et al. Novel imatinib derivatives with altered specificity between Bcr-Abl and FMS, KIT, and PDGF receptors. Chem Med Chem. 2010;5:130–139. doi:10.1002/cmdc.20090039419950162
   PubMed Web of Science ®Google Scholar
• Senis YA, Mazharian A, Mori J. Src family kinases: at the forefront of platelet activation. Blood. 2014;124:2013–2024. doi:10.1182/blood-2014-01-45313425115887
   PubMed Web of Science ®Google Scholar
• Kalantzi KI, Tsoumani ME, Goudevenos IA, et al. Pharmacodynamic properties of antiplatelet agents: current knowledge and future perspectives. Expert Rev Clin Pharmacol. 2012;5:319–336. doi:10.1586/ecp.12.1922697594
   PubMed Web of Science ®Google Scholar
• Tsoumani ME, Tselepis AD. Antiplatelet agents and anticoagulants: from pharmacology to clinical practice. Curr Pharm Des. 2017;23:1279–1293. doi:10.2174/138161282366617012414180628120727
   PubMed Web of Science ®Google Scholar
• Moschonas IC, Goudevenos JA, Tselepis AD. Protease-activated receptor-1 antagonists in long-term antiplatelet therapy. Current state of evidence and future perspectives. Int J Cardiol. 2015;185:9–18. doi:10.1016/j.ijcard.2015.03.04925777282
   PubMed Web of Science ®Google Scholar
• Kinigopoulou M, Filippidou M, Gogou M, et al. An optimized approach in the synthesis of imatinib intermediates and analogues. RSC Adv. 2016;6:61458–61467. doi:10.1039/C6RA09812F
   Web of Science ®Google Scholar
• Mitsios JV, Tambaki AP, Abatzis M, et al. Effect of synthetic peptides corresponding to residues 313-332 of the alphaIIb subunit on platelet activation and fibrinogen binding to alphaIIbbeta3. Eur J Biochem. 2004;271:855–862. doi:10.1111/j.1432-1033.2004.03990.x14764102
   PubMedGoogle Scholar
• Yi X, Liu M, Luo Q, et al. Toxic effects of dimethyl sulfoxide on red blood cells, platelets, and vascular endothelial cells in vitro. FEBS Open Bio. 2017;7:485–494. doi:10.1002/2211-5463.12193
   PubMed Web of Science ®Google Scholar
• Kouki A, Mitsios JV, Sakarellos-Daitsiotis M, et al. Highly constrained cyclic (S,S) -CXaaC- peptides as inhibitors of fibrinogen binding to platelets. J Thromb Haemost. 2005;3:2324–2330. doi:10.1111/j.1538-7836.2005.01487.x16129021
   PubMed Web of Science ®Google Scholar
• Dimitriou AA, Stathopoulos P, Mitsios JV, et al. Inhibition of platelet activation by peptide analogues of the beta(3)-intracellular domain of platelet integrin alpha(IIb)beta(3) conjugated to the cell-penetrating peptide Tat(48-60). Platelets. 2009;20:539–547. doi:10.3109/0953710090332421919863457
   PubMed Web of Science ®Google Scholar
• Theodorou V, Skobridis K, Tzakos AG, et al. A simple method for the alkaline hydrolysis of esters. Tetrahedron Lett. 2007;48:8230–8233. doi:10.1016/j.tetlet.2007.09.074
   Web of Science ®Google Scholar