Irreversible protein kinase inhibitors

Current Medicinal Chemistry

Volumn 18, Issue 20, 2011, Pages 2981-2994

  Garuti, L ^a   Roberti, M ^a   Bottegoni, G ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b ISTITUTO ITALIANO DI TECNOLOGIA   (Italy)

Author keywords

Antitumor activity; Covalent; Cysteine; Inhibition; Irreversible; Kinase; Michael addition; Quinazoline; Quinoline; SAR

Indexed keywords

3 QUINOLINECARBONITRILE DERIVATIVE; 4 ANILINOQUINAZOLINE DERIVATIVE; ADENOSINE TRIPHOSPHATE; AFATINIB; ANGIOGENESIS INHIBITOR; ANILINOQUINOLINE DERIVATIVE; ANTINEOPLASTIC AGENT; BRUTON TYROSINE KINASE INHIBITOR; CANERTINIB; CYSTEINE; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR 2; EPIDERMAL GROWTH FACTOR RECEPTOR 3; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; FIBROBLAST GROWTH FACTOR RECEPTOR INHIBITOR; N [4 (3 BROMOANILINO)QUINAZOLIN 6 YL] 3 (PIPERIDIN 1 YLMETHYL)OXIRANE 2 CARBOXAMIDE; N [4 [(3 BROMOPHENYL)AMINO] 6 QUINAZOLINYL] 4 (DIMETHYLAMINO) 2 BUTENAMIDE; NERATINIB; NUCLEOPHILE; PELITINIB; PROTEIN KINASE; PROTEIN KINASE B INHIBITOR; PROTEIN KINASE INHIBITOR; PYRIMIDINE DERIVATIVE; QUINAZOLINE DERIVATIVE; QUINOLINE 3 CARBONITRILE DERIVATIVE; QUINOLINE DERIVATIVE; THIENOPYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VASCULOTROPIN RECEPTOR 2 INHIBITOR; WZ 4002;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ANTINEOPLASTIC ACTIVITY; BREAST CANCER; CLINICAL TRIAL (TOPIC); COVALENT BOND; DRUG FORMULATION; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG TARGETING; ENZYME INACTIVATION; ENZYME INHIBITION; GENE MUTATION; HUMAN; IC 50; LUNG NON SMALL CELL CANCER; METASTASIS; MICHAEL ADDITION; MOLECULAR DOCKING; MOLECULARLY TARGETED THERAPY; NONHUMAN; REVIEW; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANIMALS; ANTINEOPLASTIC AGENTS; DRUG DISCOVERY; HUMANS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; NEOPLASMS; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; SEQUENCE ALIGNMENT;

EID: 79959954030     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986711796391705     Document Type: Review

References (55)

1. Fisher, P. M. The design of drug candidate molecules as selective inhibitors of therapeutically relevant protein kinases. Curr. Med. Chem., 2004, 11, 1563-83.
2. Zhang, J.; Yang, P. L.; Gray, N. S. Targeting cancer with small molecule kinase inhibitors. Nat. Rev. Cancer, 2009, 9, 28-39.
3. Bikker, J. A.; Brooijmans, N.; Wissner, A.; Mansour, T. S. Kinase domain mutations in cancer: implications for small molecule drug design strategies. J. Med. Chem., 2009, 52, 1493-509.
4. Singh, J.; Petter, R. C.; Kluge, A. F. Targeted covalent drugs of the kinase family. Curr. Opin. Chem. Biol, 2010, 14, 475-80.
5. Potashman, M. H.; Duggan, M. E. Covalent modifiers: an orthogonal approach to drug design. J. Med. Chem., 2009, 52, 1231-46.
6. Klüter, S.; Simard, J. R.; Rode, H. B.; Grütter, C.; Pawar, V.; Raaijmakers, H. C., A.; Barf, T. A.; Rabiller, M.; van Otterlo, W. A. L.; Rauh, D. Characterization of irreversible kinase inhibitors by directly detecting covalent bond formation: a tool for dissecting kinase drug resistance. ChemBioChem., 2010, 11, 2557-66.
7. Del Rio, A.; Sgobba, M.; Parenti, M. D.; Degliesposti, G.; Forestiero, R.; Percivalle, C.; Conte, P. F.; Freccero, M.; Rastelli, G. A computational workflow for the design of irreversible inhibitors of protein kinases. J. Comput. Aided Mol. Des., 2010, 24, 183-94.
8. Wissner, A.; Fraser, H. L.; Ingalls, C. L.; Dushin, R. G.; Floyd, M. B.; Cheung, K.; Nittoli, T.; Ravi, M. R.; Tan, X.; Loganzo, F. Dual irreversible kinase inhibitors: quinazoline-based inhibitors incorporating two independent reactive centers with each targeting different cysteine residues in the kinase domains of EGFR and VEGFR-2. Bioorg. Med. Chem. 2007, 15, 3635-48. (Pubitemid 46635150)
9. Carmi, C.; Cavazzoni, A.; Vezzosi, S.; Bordi, F.; Vacondio, F.; Silva, C:, Rivara, S.; Lodola, A.; Alfieri, R. R.; La Monica, S.; Galetti, M.; Ardizzoni, A.; Petroniani, P. G.; Mor, M. Novel irreversible epidermal growth factor receptor inhibitors by chemical modulation of the cysteine-trap portion. J. Med. Chem., 2010, 53, 2038-50.
10. Wissner, A.; Mansour, T. S. The development of HKI-272 and related compounds for the treatment of cancer. Arch. Pharm. Chem. Life Sci., 2008, 341, 465-77.
11. Kamath, S.; Buolamwini, J. K. Targeting EGFR and HER-2 receptor tyrosine kinases for cancer drug discovery and development. Med. Res. Rev., 2006, 26, 569-94. (Pubitemid 44230413)
12. Ocaňa, A.; Amir, E. Irreversible pan-ErbB tyrosine inhibitors and breast cancer: current status and future directions. Cancer Treat. Rev. 2009, 35, 685-91.
13. Gazdar, A. F. Epidermal growth factor receptor inhibition in lung cancer: the evolving role of individualized therapy. Cancer Metastasis Rev., 2010, 29, 37-48.
14. Nguyen, K. S.; Kobayashi, S.; Costa, D. B. Acquired resistance to epidermal growth factor receptor tyrosine kinase inhibitors in non-small-cell lung cancers dependent on the epiderrmal growth factor receptor pathway. Clin. Lung. Cancer, 2009, 10, 281-9.
15. Yun, C-H.; Mengwasser, K. E.; Toms, A. V.; Woo, M. S.; Greulich, H.; Wong, K-K.; Meyerson, M.; Eck, M. J. The T790M mutation in EGFR kinase causes drug resistance by increasing the affinity for ATP. Proc. Nat. Acad. Sci. USA, 2008, 105, 2070-5. (Pubitemid 351439466)
16. Michalczyk, A.; Klüter, S.; Rode, H. B.; Simard, J. R.; Grütter, C; Rabiller, M.; Rauh, D. Structural insights into how irreversible inhibitors can overcome drug resistance in EGFR. Bioorg. Med. Chem., 2008, 16, 3482-88. (Pubitemid 351484056)
17. Smaill, J. B.; Showalter, H. D. H.; Zhou, H.; Bridges, A. J.; McNamara, D. J.; Fry, D. W.; Nelson, J. M.; Sherwood, V.; Vincent, P. W.; Roberts, B. J.; Elliott, W. L.; Denny, W. A. Tyrosine kinase inhibitors. 18.6-substituted 4-anilinoquinazolines and 4-anilinopyrido[3, 4-d]pyrimidines as soluble, irreversible inhibitors of the epidermal growth factor receptor. J. Med. Chem., 2001, 44, 429-40. (Pubitemid 32113588)
18. Wissner, A.; Floyd, M. B.; Rabindran, S. K.; Nilakantan, R.; Greenberger, L. M.; Shen, R.; Wuang, Y-F.; Tsou, H-R. Synthesis and EGFR and HER-2 kinase inhibitory activities of 4-anilinoquinoline-3-carbonitriles: analogues of three important 4-anilinoquinazolines currently undergoing clinical evaluation as therapeutic antitumor agents. Bioorg. Med. Chem. Lett., 2002, 12, 2893-97. (Pubitemid 35266757)
19. Nemunaltis, J.; Eiserman, I.; Cunningham, C.; Serzer, N.; Williams, A.; Lenehan, P. F.; Olson, S. C.; Bycott, P.; Schilcht, M.; Zenigraft, R.; Shin, O. M.; Zinner, R. G. Phase I clinical and pharmacokinetics evaluation of oral Cl-1033 in patients with refractory cancer. Clin. Cancer Res., 2005, 15, 3845-63.
20. Zinner, R. G.; Nemunaltis, J.; Eiserman, I.; Shin, H. J.; Olson, S. C.; Christensen, J.; Huang, X.; Lenehan, P. F.; Donato, N. J.; Shin, O. M.; Anderson, M. D. Phase I clinical and pharmacodynamic evaluation of oral Cl-1033 in patients with refractory cancer. Clin. Cancer Res. 2007, 13, 3005-14.
21. Minkowsky, N.; Berezov, A. BIBW-2992, a dual receptor tyrosine kinase inhibitor for the treatment of solid tumors. Curr. Opin. Invest. Drugs. 2008, 9, 1336-46.
22. Li, D.; Ambrogio, L.; Shimamura, T.; Kubo, S.; Takahashi, M.; Chirieac, L. R.; Padera, R. F.; Shapiro, G. I.; Baum, A.; Himmelsbach, F.; Rettig, W. J.; Meyerson, M.; Solca, F.; Greulich, H.; Wong, K-K. BIBW2992, an irreversible EGFR/HER2 inhibitor highly effective in preclinical lung cancer models. Oncogene, 2008, 27, 4702-11.
23. Yap, T. A.; Vidal, L.; Adam, J.; Stephens, P.; Spicer, J.; Shaw, H.; Ang, J.; Temple, G.; Bell, S.; Shahidi, M.; Uttenreuther-Fisher, M.; Stopfer, P.; Futreal, A.; Calvert, H.; S. de Bono, J, Plummer, R. Phase I trial of the irreversible EGFR and HER2 kinase inhibitor BIBW 2992 in patients with advanced solid tumors. J. Clin. Onc., 2010, 28, 3965-72.
24. Takezawa, K.; Okamoto, I.; Tanizaki, J.; Kuwata, K.; Yamaguchi, H.; Fukuoka, M.; Nishio, K.; Nakagawa, K. Enhanced anticancer effect of the combination of BIBW2992 and thymidylate synthase-targeted agents in nonsmall cell lung cancer with the T790M mutation of epidermal growth factor receptor. Mol. Cancer Ther., 2010, 9, 1647-55.
25. Doebele, R. C.; Oton, A. B.; Peled, N.; Camidge, D. R. Bunn Jr. P. A. New strategies to overcome limitations of reversible EGFR tyrosine kinase inhibitor therapy in non-small cell lung cancer. Lung Cancer., 2010, 69, 1-12.
26. Erlichman, C.; Hidalgo, M.; Boni, J. P.; Martins, P.; Quinn, S. E.; Zacharchuk, C.; Amorusi, P.; Adjei, A. A.; Rowinsky, E. K. Phase I study of EKB-569, an irreversible inhibitor of the epidermal growth factor receptor, in patients with advanced solid tumors. J. Clin. Oncol., 2006, 24, 2252-60. (Pubitemid 46630654)
27. Folprecht, G.; Tabernero, J.; Köhne, C. H.; Zacharchuk, C.; Paz-Ares, L.; Rojo, F.; Quinn, S.; Casado, E.; Salazar, R.; Abbas, R.; Lejeune, C.; Marimón, I.; Andreu, J.; Ubbelohde, U.; Cortes-Funes, H.; Baselga, J. Phase I pharmacokinetic/pharmacodynamic study of EKB-569, an irreversible inhibitor of the epidermal growth factor receptor tyrosine kinase, in combination with irinotecan, 5-fluorouracil, and leucovorin (FOLFIRI) in first-line treatment of patients with metastasic colorectal cancer. Clin. Cancer Res., 2008, 14, 215-23. (Pubitemid 351377998)
28. Laheru, D.; Croghan, G.; Bukowski, R.; Rudek, M.; Messersmith, W.; Erlichman, C.; Pelley, R.; Jimeno, A.; Donehower, R.; Boni, J.; Abbas, R.; Martins, P.; Zacharchuk, C.; Hidalgo, M. A phase I study of EKB-569 in combination with capecitabine in patients with advanced colorectal cancer. Clin. Cancer Res., 2008, 14, 5602-9.
29. Tsou, H-R.; Mamuya, N.; Johnson, B. D.; Reich, M. F.; Gruber, B. C.; Ye. F.; Nilakantan, R.; Shen. R.; Discafani, C.; DeBlanc, R.; Davis, R.; Koehn, F. E.; Greenberger, L. M.; Wang, Y-F.; Wissner, A. 6-Substituted-4-(3- bromophenylamino) quinazolines as putative irreversible inhibitors of the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases with enhanced antitumor activity. J. Med. Chem., 2001, 44, 2719-34. (Pubitemid 32879714)
30. Cha, M. Y.; Lee, K-O.; Kim, J. W.; Lee, C. G.; Song, J. Y.; Kim, Y. H.; Lee, G. S. Park, S. M.; Kim, M. S. Discovery of a novel Her-2 dual tyrosine kinase inhibitor for the treatment of Her-1 selective inhibitor-resistant nonsmall cell lung cancer. J. Med. Chem., 2009, 52, 6880-88.
31. Wissner, A.; Overbeek, E.; Reich, M. F.; Floyd, M. B.; Johnson, B. D.; Mamuya, N.; Rosfjord, E. C.; Discafani, C.; Davis, R.; Shi, X.; Rabindran, S. K.; Gruber, B. C.; Ye, F.; Hallett, W. A.; Nilakantan, R.; Shen, R.; Wang, Y.-F.; Greenberger, L. M.; Tsou, H-R. Synthesis and structure-activity relationships of 6, 7-disubstituted 4-anilinoquinoline-3-carbonitriles. The design of an orally active, irreversible inhibitor of the tyrosine kinase activity of the epidermal growth factor receptor (EGFR) and the human epidermal growth factor receptor-2 (HER-2). J. Med. Chem., 2003, 46, 49-63. (Pubitemid 36043786)
32. Akula, N.; Bhalla, J.; Sridhar, J.; Pattabiraman, N. Binding modes of 6, 7 disubstituted 4-anilinoquinoline-3-carbonitriles to EGFR. Bioorg. Med. Chem. Lett. 2004, 14, 3397-400. (Pubitemid 38737134)
33. Tsou, H-R.; Overbeek-Klumpers, E. G.; Hallett, W. A.; Reich, M. F.; Floyd, M. B.; Johnson, B. D.; Michalak, R. S.; Nilakantan, R.; Discafani, C.; Golas, J.; Rabindran, S. K.; Shen, R.; Shi, X.; Wang, Y-F.; Upeslacis, J.; Wissner, A. Optimization of 6, 7-disubstituted-4-(arylamino) quinoline-3-carbonitriles as orally active, irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity. J. Med. Chem., 2005, 48, 1107-31. (Pubitemid 40270454)
34. Rabindran, S. K.; Discafani, C. M.; Rosfjord, E. C.; Baxter, M.; Floyd, M. B.; Golas, J.; Hallett, W. A.; Johnson, B. D.; Nilakantan, R.; Overbeek, E.; Reich, M. F.; Shen, R.; Shi, X.; Tsou, H-R.; Wang, Y-F.; Wissner, A. Antitumor activity of HKI-272, an orally active, irreversible inhibitor of the Her-2 tyrosine kinase. Cancer Res., 2004, 64, 3958-65. (Pubitemid 38697310)
35. Wong, K-K., Fracasso, P. M.; Bukowski, R. M.; Lynch, T. J.; Munster, P. N.; Shapiro, G. I.; Janne, P. A.; Eder, J. P.; Naughton, M. J.; Ellis, M. J.; Jones, S. F.; Mekhall, T.; Zacharchuk, C.; Vernette, J.; Abbas, R.; Quinn, S.; Powell, C.; Burns, H. phase I study with Neratinib (HKI-272), an irreversible Pan ErbB receptor tyrosine kinase inhibitor, in patients with solid tumors. Clin. Cancer Res., 2009, 15, 2552-8.
36. Bose, P.; Ozer, H. Neratinib: an oral, irreversible dual EGFR/Her-2 inhibitorfor breast and non-small cell lung cancer. Expert. Opin. Invest. Drugs., 2009, 18, 1735-51.
37. Burstein, H. J.; Sun, Y.; Dirix, L. Y.; Jiang, Z.; Paridaens, R.; Tan, A. R.; Awada, A.; Ranade, A.; Jiao, S.; Schwartz, G.; Abbas, R.; Powell, C.; Tumbull, K.; Vermett, J.; Zacharchuk, C.; Badwe, R. Neratinib: an irreversible ErbBreceptor tyrosine kinase inhibitor, in patients with advanced ErbB2-positive breast cancer. J. Clin. Oncol. 2010, 28, 1301-7.
38. Sequist, L. V.; Besse, B.; Lynch, T. J.; Miller, V. A.; Wong, K. K.; Gitlitz, B.; Eaton, K.; Zacharchuk, C.; Freyman, A.; Powell, C.; Ananthakrishnan, R.; Quinn, S.; Soria, J. C. Neratinib, an irreversible pan-ErbB receptor tyrosine kinase inhibitor: results of a phase Iitrial in patients with advanced non-small-cell lung cancer. J. Clin. Oncol., 2010, 28, 3076-83.
39. Pawar, V. G.; Sos, M. L.; Rode, H. B.; Rabiller, M.; Heynck, S.; van Otterlo, W. A. L.; Thomas, R. K.; Rault, D. Synthesis and biological evaluation of 4-anilinoquinolines as potent inhibitors epidermal growth factor receptor. J. Med. Chem., 2010, 53, 2892-901.
40. Klutchko, S. R.; Zhou, H.; Winters, R. T.; Tran, T. P.; Bridges, A. J.; Althaus, I. W.; Amato, D. M.; Elliott, W. L.; Ellis, P. A.; Meade, M. A.; Roberts, B. J.; Fry, D. W.; Gonzales, A. J.; Harvey, P. J.; Nelson, J. M.; Sherwood, V.; Han, H-K.; Pace, G.; Smaill, J. B.; Denny, W. A.; Showalter, H. D. H. Tyrisine kinase inhibitors. 19. 6-alkynamides of 4-anilinoquinazolines and 4-anilinopyrido[3, 4-d]pyrimidines as irreversible inhibitors of the erbB family of tyrosine kinase receptors. J. Med. Chem., 2006, 49, 1475-85. (Pubitemid 43271900)
41. Zhou, W.; Ercan, D.; Chen, L.; Yun, C-H.; Li, D.; Cappelletti, M.; Cortot, A. B.; Chirieac, L.; Iacob, R. E.; Padera, R.; Engen, J. R.; Wong, K-K.; Eck, M. J.; Gray, N. S.; Janne, P. A. Novel mutant-selective EGFR kinase inhibitors against EGFR T790M. Nature, 2009, 462, 1070-74.
42. Wood, E. R.; Shewchuk, L. M.; Ellis, B.; Brignola, P.; Brashear, R. L., Caferro, T. R.; Dickerson, S. H.; Dickinson, H. D.; Donaldson, K. H.; Gaul, M.; Griffin, R. J.; Hassell, A. M.; Keith, B.; Mullin, R.; Petrov, K. G.; Reno, M. J.; Rusnak, D. W.; Tadepalli, S. M.; Ulrich, J. C.; Wagner, C. D.; Vanderwall, D. E.; Waterson, A. G.; Williams, J. D.; White, W. L.; Uehling, D. E. 6-Ethynylthieno[3, 2-d]-and 6-ethynylthieno[2, 3-d]pyrimidin-4-anilines as tunable covalent modifiers of erbB kinases. Proc. Nat. Acad. Sci., 2008, 105, 2773-8. (Pubitemid 351723619)
43. Hubbard, R. D.; Dickerson, S. H.; Emerson, H. K.; Griffin, R. J.; Reno, M. J.; Hornberger, K. R.; Rurnak, D. W.; Wood, E. R.; Uehling, D. E.; Waterson, A. G. Dual EGFR/ErbB-2 inhibitors from novel pyrrolidinyl-acetylenic thieno[3, 2-d]pyrimidines. Bioorg. Med. Chem. Lett., 2008, 18, 5738-46.
44. Stevens, K. L.; Alligood, K. J.; Badiang Alberti, J. G.; Caferro, T. R.; Chamberlain, S. D.; Dickerson, S. H.; Dickson, H. D.; Emerson, H. K.; Griffin, R. J.; Hubbard, R. D.; Keith, B. R.; Mullin, R. J.; Petrov, K. G.; Gerding, R. M.; Reno, M. J.; Rheault, T. R.; Rusnak, D. W.; Sammond, D. M.; Smith, S. C.; Uehling, D. E.; Waterson, A. G.; Wood, E. R. Synthesis and stereochemical effects of pyrrolidinyl-acetylenic thieno[3, 2-d]pyrimidines as EGFR and ErbB-2 inhibitors. Bioorg. Med. Chem. Lett., 2009, 19, 21-26.
45. Waterson, A. G.; Petrov, K. G.; Hornberger, K. R.; Hubbard, R. D.; Sammond, D. M.; Smith, S. C.; Dickson, H. D.; Caferro, T. R.; Hinkle, K. W.; Stevens, K. L.; Dickerson, S. H.; Rusnak, D. W.; Spehar, G. M.; Wood, E. G.; Griggin, R. J.; Uehling, D. E. Synthesis and evaluation of aniline headgroups for alkynyl thienopyrimidine dual EGFR/ErbB-2 kinase inhibitors. Bioorg. Med. Chem. Lett., 2009, 19, 1332-36.
46. Wu, C.-H.; Coumar, M. S.; Chu, C.-Y.; Lin, W.-H.; Chen, Y.-R.; Che, C.-T.; Shiao, H.-Y.; Rafi, S.; Wang, S-Y.; Hsu, H.; Chen, C.-H.; Chang, C.-Y.; Chang, T.-Y.; Lien, T.-W.; Fang, M.-Y.; Yeh, K.-C.; Chen, C.-P.; Yeh, T.-K.; Hsieh, S.-H.; Hsu, J. T.-A.; Liao, C.-C.; Chao, Y.-S.; Hsieh, H.-P. Design and synthesis of tetrahydropyridothieno[2, 3-d]pyrimidine scaffold based epidermal growth factor receptor (EGFR) kinase inhibitors: the role of side chain chirality and Michael acceptor group for maximal potency. J. Med. Chem., 2010, 53, 7316-26.
47. Wissner, A.; Floyd, M. B.; Johnson, B. D.; Fraser, H.; Ingalls, C.; Nittoli, T.; Dushin, R. G.; Discafani, C.; Nilakantan, R.; Marini, J.; Ravi, M.; Cheung, K.; Tan, X.; Musto, S.; Annable, T.; Siegel, M. M.; Loganzo, F. 2-(Quinazolin-4-ylamino)-[1, 4]benzoquinones as covalent-binding, irreversible inhibitors of the kinase of vascular endothelial growth factor receptor-2. J. Med. Chem., 2005, 48, 7560-81. (Pubitemid 41698798)
48. Zhou, W.; Hur, W.; McDermott, U.; Dutt, A.; Xian, W.; Ficarro, S. B.; Zhang, J.; Sharma, S. V.; Brugge, J.; Meyerson, M.; Settleman, J.; Gray, N. S. A structure-guided approach to creating covalent FGFR inhibitors. Chem. Biol., 2010, 17, 285-95.
49. Oral-Barza, L.; Zhang, W-G.; Huang, X.; McDonald, L. A.; Salaski, E. J.; Barbieri, L. R.; Ding, W-D.; Krishnamurthy, G.; Hu, Y. B.; Lucas, J.; Bernan, V. S.; Cai, P.; Levin, J. I.; Mansour, T. S.; Gibbons, J. J.; Abraham, R. T.; Yu, K. Discovery of lactoquinomycin and related pyranonaphthoquinones as potent and allosteric inhibitors of AKT/PKB: mechanistic involvement of AKT catalytic loop cysteines. Mol. Cancer. Ther. 2007, 6, 3028-38. (Pubitemid 350206781)
50. Salaski, E. J.; Krishnamurthy, G.; Ding, W-D.; Yu, K.; Insaf, S. S.; Eid, C.; Shim, J.; Levin, J. I.; Tabei, K.; Toral-Barza, L.; Zhang, W-G.; McDonald, L. A.; Honores, E.; Hanna, C.; Yamashita, A.; Johnson, B.; Li, Z.; Laakso, L.; Powell, D.; Mansour, T. S. Pyranonaphthoquinone lactones: a new class of AKT selective kinase inhibitors alkylate a regulatory loop cysteine. J. Med. Chem., 2009, 52, 2181-84.
51. Pan, Z.; Scheerens, H.; Li, S.; Schultz, B. E.; Sprengeler, P. A.; Burrill, L. C.; Mendonca, R. V.; Sweeney, M. D.; Scott, K. C. K.; Grothaus, P. G.; Jeffery, D. A.; Spoerke, J. M.; Honigberg, L. A.; Young, P. R.; Dalrymple, S. A.; Palmer, J. T. Discovery of selective irreversible inhibitors for Bruton's tyrosine kinase. ChemMedChem., 2007, 2, 58-61.
52. Honigberg, L. A.; Smith, A. M.; Sirisawad, M.; Verner, E.; Loury, D.; Chang, B.; Li, S.; Pan, Z.; Thamm, D. H.; Miller, R. A.; Buggy, J. J. The Bruton tyrosine kinase inhibitor PCI-32765 blocks B-cell activation and is efficacious in models of autoimmune disease and B-cell malignancy. Proc. Nat. Acad. Sci. USA, 2010, 107, 13075-80.
53. Davis, R. E.; Ngo, V. N.; Lenz, G.; Tolar, P.; Young, R. M.; Romesser, P. B.; Kohlhammer, H.; Lamy, L.; Zhao, H.; Yang, Y.; Xu, W.; Shaffer, A. L.; Wright, G.; Xiao, W.; Powell, J.; Jiang, J. K.; Thomas, C. J.; Rosenwald, A.; Ott, G.; Muller-Hermelink, H. K.; Gascoyne, R. D.; Connors, J. M.; Johnson, N. A.; Rimsza, L. M.; Campo, E.; Jaffe, E. S.; Wilson, W. H.; Delabie, J.; Smeland, E. B.; Fisher, R. I.; Braziel, R. M.; Tubbs, R. R.; Cook, J.-R.; Weiserenburger, D. D.; Chan, W. C.; Pierce, S. K.; Staudt, L. M., Chronic active B-cell-receptor signalling in diffuse large B-cell lymphoma. Nature, 2010, 463, 88-92.
54. Trent, J.; Molimard, M. Pharmacokinetics and pharmacodynamics of nilotinib in gastrointestinal stromal tumors. Semin. Oncol. 2011, 38, Suppl 1, 528-33.
55. Blay, J. Y.; von Mehren, M. Nilotinib: a novel, selective tyrosine kinase inhibitor. Semin. Oncol. 2011, 38, Suppl 1, 53-9.