87
Views
1
CrossRef citations to date
0
Altmetric
Research Article

Protein kinase inhibitor-induced endothelial cell cytotoxicity and its prediction based on calculated molecular descriptors

, , , , , , , , , & show all
Pages 75-83 | Received 29 Apr 2008, Accepted 28 Feb 2009, Published online: 01 Apr 2009

References

  • Manning G, Whyte DB, Martinez R, Hunter T, Sudarsanam S. The protein kinase complement of the human genome. Science 2002, 298, 1912–1934.
  • Levitzki A. Signal-transduction therapy. A novel approach to disease management. Eur J Biochem 1994, 226, 1–13.
  • Keri Gy OL, Eros D, Hegymegi-Barakonyi B, Szantai-Kis Cs, Horvath Z, Waczek F, Marosfalvy J, Szabadkai i, Pato J, Greff Z, Hafenbradl D, Daub H, Muller G, Klebl B, Ullrich A. Signal transduction therapy with rationally designed kinase inhibitors. Curr Signal Transduct Ther 2006, 1, 67–95.
  • Deininger MW, Goldman JM, Lydon N, Melo JV. The tyrosine kinase inhibitor CGP57148B selectively inhibits the growth of BCR-ABL-positive cells. Blood 1997, 90, 3691–3698.
  • Goldman JM. Tyrosine-kinase inhibition in treatment of chronic myeloid leukaemia. Lancet 2000, 355, 1031–1032.
  • Dancey J, Sausville EA. Issues and progress with protein kinase inhibitors for cancer treatment. Nat Rev Drug Discov 2003, 2, 296–313.
  • Kolibaba KS, Druker BJ. Protein tyrosine kinases and cancer. Biochim Biophys Acta 1997, 1333, F217–248.
  • Heldin CH, Westermark B. Mechanism of action and in vivo role of platelet-derived growth factor. Physiol Rev 1999, 79, 1283–1316.
  • Lembach KJ. Induction of human fibroblast proliferation by epidermal growth factor (EGF): enhancement by an EGF-binding arginine esterase and by ascorbate. Proc Natl Acad Sci USA 1976, 73, 183–187.
  • Millauer B, Wizigmann-Voos S, Schnurch H, Martinez R, Moller NP, Risau W, Ullrich A. High affinity VEGF binding and developmental expression suggest Flk-1 as a major regulator of vasculogenesis and angiogenesis. Cell 1993, 72, 835–846.
  • Schweigerer L, Neufeld G, Friedman J, Abraham JA, Fiddes JC, Gospodarowicz D. Capillary endothelial cells express basic fibroblast growth factor, a mitogen that promotes their own growth. Nature 1987, 325, 257–259.
  • Holmgren L. Antiangiogenis restricted tumor dormancy. Cancer Metastasis Rev 1996, 15, 241–245.
  • Saaristo A, Karpanen T, Alitalo K. Mechanisms of angiogenesis and their use in the inhibition of tumor growth and metastasis. Oncogene 2000, 19, 6122–6129.
  • Yoshiji H, Gomez DE, Shibuya M, Thorgeirsson UP. Expression of vascular endothelial growth factor, its receptor, and other angiogenic factors in human breast cancer. Cancer Res 1996, 56, 2013–2016.
  • Rooprai HK, Rucklidge GJ, Panou C, Pilkington GJ. The effects of exogenous growth factors on matrix metalloproteinase secretion by human brain tumour cells. Br J Cancer 2000, 82, 52–55.
  • Hata K, Nakayama K, Fujiwaki R, Katabuchi H, Okamura H, Miyazaki K. Expression of the angopoietin-1, angopoietin-2, Tie2, and vascular endothelial growth factor gene in epithelial ovarian cancer. Gynecol Oncol 2004, 93, 215–222.
  • Cervenak L, Morbidelli L, Donati D, Donnini S, Kambayashi T, Wilson JL, Axelson H, Castanos-Velez E, Ljunggren HG, Malefyt RD, Granger HJ, Ziche M, Bejarano MT. Abolished angiogenicity and tumorigenicity of Burkitt lymphoma by interleukin-10. Blood 2000, 96, 2568–2573.
  • Dhanabal M, LaRochelle WJ, Jeffers M, Herrmann J, Rastelli L, McDonald WF, Chillakuru RA, Yang M, Boldog FL, Padigaru M, McQueeney KD, Wu F, Minskoff SA, Shimkets RA, Lichenstein HS. Angioarrestin: An antiangiogenic protein with tumor-inhibiting properties. Cancer Res 2002, 62, 3834–3841.
  • Folkman J, Merler E, Abernathy C, Williams G. Isolation of a tumor factor responsible for angiogenesis. J Exp Med 1971, 133, 275–288.
  • Kern H, Wittich R, Rohr U, Kox WJ, Spies CD. Increased endothelial injury in septic patients with coronary artery disease. Chest 2001, 119, 874–883.
  • Airaghi L, Montori D, Santambrogio L, Miadonna A, Tedeschi A. Chronic systemic capillary leak syndrome. Report of a case and review of the literature. J Intern Med 2000, 247, 731–735.
  • Sousou T, Khorana AA. New insights into cancer-associated thrombosis. Arterioscler Thromb Vasc Biol 2009, 29, 316–320.
  • Ross R. The pathogenesis of atherosclerosis: a perspective for the 1990s. Nature 1993, 362, 801–809.
  • Ghiadoni L, Mosca M, Tani C, Virdis A, Taddei S, Bombardieri S. Clinical and methodological aspects of endothelial function in patients with systemic autoimmune diseases. Clin Exp Rheumatol 2008, 26, 680–687.
  • Eberhardt RT, Raffetto JD. Chronic venous insufficiency. Circulation 2005, 111, 2398–2409.
  • Epstein SE, Kornowski R, Fuchs S, Dvorak HF. Angiogenesis therapy: amidst the hype, the neglected potential for serious side effects. Circulation 2001, 104, 115–119.
  • Hirth KP Schwartz DP, Mann E, Shawver LK, Keri G, Szekely I, Bajor T, Haimichael J, őrfi L, Levitzki A, Gazit A, Ullrich A, Lammers R, Kabbinavar FF, Slamon D, Tang PC. Treatment of platelet derived growth factor related disorders such as cancers. United States, Sugen Inc., 1999, US 599014 A.
  • Strawn LM, McMahon G, App H, Schreck R, Kuchler WR, Longhi MP, Hui TH, Tang C, Levitzki A, Gazit A, Chen I, Keri G, Orfi L, Risau W, Flamme I, Ullrich A, Hirth KP, Shawver LK. Flk-1 as a target for tumor growth inhibition. Cancer Res 1996, 56, 3540–3545.
  • Kökösi J, örfi L, Szász G, Hermecz I., Kapui Z, Szabó M. Process for producing imidazo[5,1-b]quinazolin-9-one derivatives and pharmaceutically acceptable salts thereof, as well as pharmaceutical compositions comprising such active ingredient. Hungary, Semmelweis University, 1992, HU 59411A2.
  • Barker AJ, Gibson KH, Grundy W, Godfrey AA, Barlow JJ, Healy MP, Woodburn JR, Ashton SE, Curry BJ, Scarlett L, Henthorn L, Richards L. Studies leading to the identification of ZD1839 (IRESSA): An orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer. Bioorg Med Chem Lett 2001, 11, 1911–914.
  • Sun L, Tran N, Tang F, App H, Hirth P, McMahon G, Tang C. Synthesis and biological evaluations of 3-substituted indolin-2-ones: a novel class of tyrosine kinase inhibitors that exhibit selectivity toward particular receptor tyrosine kinases. J Med Chem 1998, 41, 2588–2603.
  • Stein-Gerlach M, Salassidis K, Bacher G, Mueller S. Pyridylpyrimidine derivatives as effective compounds against prion diseases. Germany, Axxima Pharmaceuticals AG, PCT Int. Appl. 2002, WO 2002093164A2.
  • Zimmermann J, Buchdunger E, Mett H, Meyer T, Lydon NB. Potent and selective inhibitors of the ABL-kinase: phenylamino-pyrimidine (PAP) derivatives. Bioorg Med Chem Lett 1997, 7, 187.
  • Paul R, Hallett WA, Hanifin JW, Reich MF, Johnson BD, LenhardRH, Dusza JP, Kerwar SS, Lin Y, Pickett WC, et al. Preparation of substituted N-phenyl-4-aryl-2-pyrimidinamines as mediator release inhibitors. J Med Chem 1993, 36, 2716–2725.
  • Oroszlan M, Herczenik E, Rugonfalvi-Kiss S, Roos A, Nauta AJ, Daha MR, Gombos I, Karadi I, Romics L, Prohaszka Z, Fust G, Cervenak L. Proinflammatory changes in human umbilical cord vein endothelial cells can be induced neither by native nor by modified CRP. Int Immunol 2006,18, 871–878.
  • Todeschini R CV. Handbook of Molecular Descriptors. Weinheim, Wiley-WCH, 2000.
  • Tardito S, Bussolati O, Gaccioli F, Gatti R, Guizzardi S, Uggeri J, Marchio L, Lanfranchi M, Franchi-Gazzola R. Non-apoptotic programmed cell death induced by a copper(II) complex in human fibrosarcoma cells. Histochem Cell Biol 2006, 126, 473–482.
  • Clarke PG. Developmental cell death: Morphological diversity and multiple mechanisms. Anat Embryol (Berl) 1990, 181, 195–213.
  • Faivre S, Delbaldo C, Vera K, Robert C, Lozahic S, Lassau N, Bello C, Deprimo S, Brega N, Massimini G, Armand JP, Scigalla P, Raymond E. Safety, pharmacokinetic, and antitumor activity of SU11248, a novel oral multitarget tyrosine kinase inhibitor, in patients with cancer. J Clin Oncol 2006, 24, 25–35.
  • D’Amato RJ, Loughnan MS, Flynn E, Folkman J. Thalidomide is an inhibitor of angiogenesis. Proc Natl Acad Sci USA 1994, 91, 4082–4085.
  • Eros D, Kovesdi I, Orfi L, Takacs-Novak K, Acsady G, Keri G. Reliability of logP predictions based on calculated molecular descriptors: A critical review. Curr Med Chem 2002, 9, 1819–1829.
  • Eros D, Keri G, Kovesdi I, Szantai-Kis C, Meszaros G, Orfi L. Comparison of predictive ability of water solubility QSPR models generated by MLR, PLS and ANN methods. Mini Rev Med Chem 2004, 4, 167–177.
  • Szantai-Kis C, Kovesdi I, Eros D, Banhegyi P, Ullrich A, Keri G, Orfi L. Prediction oriented QSAR modelling of EGFR inhibition. Curr Med Chem 2006, 13, 277–287.
  • Traxler P, Bold G, Frei J, Lang M, Lydon N, Mett H, Buchdunger E, Meyer T, Mueller M, Furet P. Use of a pharmacophore model for the design of EGF-R tyrosine kinase inhibitors: 4-(phenylamino)pyrazolo[3,4-d]pyrimidines. J Med Chem 1997, 40, 3601–3616.
  • Carroll M, Ohno-Jones S, Tamura S, Buchdunger E, Zimmermann J, Lydon NB, Gilliland DG, Druker BJ. CGP 57148, a tyrosine kinase inhibitor, inhibits the growth of cells expressing BCR-ABL, TEL-ABL, and TEL-PDGFR fusion proteins. Blood 1997, 90, 4947–4952.
  • Kubo K, Ohyama S, Shimizu T, Takami A, Murooka H, Nishitoba T, Kato S, Yagi M, Kobayashi Y, Iinuma N, Isoe T, Nakamura K, Iijima H, Osawa T, Izawa T. Synthesis and structure-activity relationship for new series of 4-phenoxyquinoline derivatives as specific inhibitors of platelet-derived growth factor receptor tyrosine kinase. Bioorg Med Chem 2003, 11, 5117–5133.
  • Rafi-Janajreh AQ, Chen D, Schmits R, Mak TW, Grayson RL, Sponenberg DP, Nagarkatti M, Nagarkatti PS. Evidence for the involvement of CD44 in endothelial cell injury and induction of vascular leak syndrome by IL-2. J Immunol 1999, 163, 1619–1627.
  • Lopez JA, Kearon C, Lee AY. Deep venous thrombosis. Hematology (Am Soc Hematol Educ Program) 2004, 439–456.
  • Ruetz S, Fabbro D, Zimmermann J, Meyer T, Gray N. Chemical and biological profile of dual Cdk1 and Cdk2 inhibitors. Current Medicinal Chemistry-Anti-Cancer Agents 2003, 3, 1–14.
  • Traxler P, Green J, Mett H, Sequin U, Furet P. Use of a pharmacophore model for the design of EGFR tyrosine kinase inhibitors: isoflavones and 3-phenyl-4(1H)-quinolones. J Med Chem 1999, 42, 1018–1026.
  • Rachid Z, Katsoulas A, Brahimi F, Jean-Claude BJ. Synthesis of pyrimidinopyridine-triazene conjugates targeted to abl tyrosine kinase. Bioorg Med Chem Lett 2003, 13, 3297–3300.
  • Peng H, Huang N, Qi J, Xie P, Xu C, Wang J, Yang C. Identification of novel inhibitors of BCR-ABL tyrosine kinase via virtual screening. Bioorg Med Chem Lett 2003, 13, 3693–3699.
  • Golas JM, Arndt K, Etienne C, Lucas J, Nardin D, Gibbons J, Frost P, Ye F, Boschelli DH, Boschelli F. SKI-606, a 4-anilino- 3-quinolinecarbonitrile dual inhibitor of Src and Abl kinases, is a potent antiproliferative agent against chronic myelogenous leukemia cells in culture and causes regression of K562 xenografts in nude mice. Cancer Res 2003, 63, 375–381.
  • Fong TA, Shawver LK, Sun L, Tang C, App H, Powell TJ, Kim YH, Schreck R, Wang X, Risau W, Ullrich A, Hirth KP, McMahon G. SU5416 is a potent and selective inhibitor of the vascular endothelial growth factor receptor (Flk-1/KDR) that inhibits tyrosine kinase catalysis, tumor vascularization, and growth of multiple tumor types. Cancer Res 1999, 59, 99–106.
  • Suzuki R, Hasegawa Y, Baba K, Saka H, Saito H, Taniguchi H, Yamamoto M, Matsumoto S, Kato K, Oishi T, Imaizumi K, Shimokata K. A phase II study of single-agent gefitinib as first-line therapy in patients with stage IV non-small-cell lung cancer. Br J Cancer 2006, 94, 1599–1603.
  • Calvo E, Baselga J. Ethnic differences in response to epidermal growth factor receptor tyrosine kinase inhibitors. J Clin Oncol 2006, 24, 2158–2163.
  • Nagaria NC, Cogswell J, Choe JK, Kasimis B. Side effects and good effects from new chemotherapeutic agents. Case 1. Gefitinib-induced interstitial fibrosis. J Clin Oncol 2005, 23, 2423–2424.
  • Buchdunger E, Matter A, Druker BJ. Bcr-Abl inhibition as a modality of CML therapeutics. Biochim Biophys Acta 2001, 1551, M11–18.
  • van Cruijsen H, Giaccone G, Hoekman K. Epidermal growth factor receptor and angiogenesis: Opportunities for combined anticancer strategies. Int J Cancer 2005, 117, 883–888.
  • Hirata A, Ogawa S, Kometani T, Kuwano T, Naito S, Kuwano M, Ono M. ZD1839 (Iressa) induces antiangiogenic effects through inhibition of epidermal growth factor receptor tyrosine kinase. Cancer Res 2002, 62, 2554–2560.
  • Gambacorti-Passerini C, Zucchetti M, Russo D, Frapolli R, Verga M, Bungaro S, Tornaghi L, Rossi F, Pioltelli P, Pogliani E, Alberti D, Corneo G, D’Incalci M. Alpha1 acid glycoprotein binds to imatinib (STI571) and substantially alters its pharmacokinetics in chronic myeloid leukemia patients. Clin Cancer Res 2003, 9, 625–632.
  • Baselga J, Rischin D, Ranson M, Calvert H, Raymond E, Kieback DG, Kaye SB, Gianni L, Harris A, Bjork T, Averbuch SD, Feyereislova A, Swaisland H, Rojo F, Albanell J. Phase I safety, pharmacokinetic, and pharmacodynamic trial of ZD1839, a selective oral epidermal growth factor receptor tyrosine kinase inhibitor, in patients with five selected solid tumor types. J Clin Oncol 2002, 20, 4292–4302.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.