Egfr tyrosine kinase targeted compounds: In vitro antitumor activity and molecular modeling studies of new benzothiazole and pyrimido[2,1-b]benzothiazole derivatives

EXCLI Journal

Volumn 13, Issue , 2014, Pages 573-585

  Gabr, Moustafa T ^a   El Gohary, Nadia S ^a   El Bendary, Eman R ^a   El Kerdawy, Mohamed M ^a  

^a MANSOURA UNIVERSITY   (Egypt)

Author keywords

Antitumor activity; Benzothiazoles; EGFR tyrosine kinase inhibitory activity; Molecular modeling; Pyrimidobenzothiazoles

Indexed keywords

2 (5 AMINO 4 CYANO 1H PYRAZOL 1 YL) N (6 CHLOROBENZOTHIAZOL 2 YL)ACETAMIDE; 4 (5 AMINO 3 OXO 2,3 DIHYDRO 1H PYRAZOLE 1 CARBONYL) 8 CHLORO 2H PYRIMIDOL (2,1 B)BENZOTHIAZOL 2 ONE; 8 CHLORO 4 (3,5 DIOXOPYRAZOLIDINE 1 CARBONYL) 2H PYRIMIDO[2,1 B]BENZOTHIAZOL 2 ONE; 8 CHLORO 4 [5 THIOXO 4,5 DIHYDRO (1,3,4)OXADIAZOL 2 YL] 2H PYRIMIDIOL (2,1 B)BENZOTHIAZOL 2 ONE; ADENOSINE TRIPHOSPHATE; ANTINEOPLASTIC AGENT; BENZOTHIAZOLE DERIVATIVE; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; ERLOTINIB; N (6 CHLOROBENZOTHIAZOL 2 YL) 2 (3 METHYL 5 PHENYL 1H PYRAZOL 1 YL)ACETAMIDE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING KINETICS; BINDING SITE; BREAST CANCER; CANCER CELL LINE; COLON CANCER; COMPUTER AIDED DESIGN; CONTROLLED STUDY; DRUG BINDING; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; ENZYME INHIBITION; HCT 116 CELL LINE; HCT 15 CELL LINE; HT 29 CELL LINE; HUMAN; HUMAN CELL; IN VITRO STUDY; LUNG NON SMALL CELL CANCER; MDA MB 23 CELL LINE; MDA MB 468 CELL LINE; MOLECULAR MODEL; NCI H522 CELL LINE; PROTEIN EXPRESSION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 84901477593     PISSN: None     EISSN: 16112156     Source Type: Journal    
DOI: None     Document Type: Article

References (48)

1. Al-Soud YA, Al-Sa'doni HH, Saeed B, Jaber IH, Beni-Khalid MO, Al-Masoudi NA et al. Synthesis and in vitro antiproliferative activity of new benzothiazole derivatives. ARKIVOC 2008;XV:225-38.
2. Ballard P, Bradbury RH, Harris CS, Hennequin LF, Hickinson M, Kettle JG et al. Inhibitors of epidermal growth factor receptor tyrosine kinase: optimization of potency and in vivo pharmacokinetics. Bioorg Med Chem Lett 2006;16:4908-12.
3. Boyd MR, Paull KD. Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug Rev Res 1995;34:91-109.
4. Brantley E, Antony S, Kohlhagen G, Meng LH, Agama K, Stinson SF et al. Anti-tumor drug candidate 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole induces single-strand breaks and DNAprotein cross-links in sensitive MCF-7 breast cancer cells. Cancer Chemother Pharmacol 2006;58:62-72.
5. Bridges A. Chemical inhibitors of protein kinases. J Chem Rev 2001;101:2541-72.
6. Cheng Y, Cui W, Chen Q, Tung CH, Ji M, Zhang F. The molecular mechanism studies of chirality effect of PHA-739358 on Aurora kinase A by molecular dynamics simulation and free energy calculations. J Comput Aided Mol Des 2011;25:171-80.
7. Cherry M, Williams DH. Recent kinase inhibitor Xray structures: Mechanisms of inhibition and selectivity insights. Curr Med Chem 2004;11:663-73.
8. Cohen P. Protein kinases: the major drug targets of the twenty-first century?. Nat Rev Drug Discov 2002; 1:309-15.
9. Cressier D, Prouillac C, Hernandez P, Amourette C, Diserbo M, Lion C et al. Synthesis, antioxidant properties and radioprotective effects of new benzothiazoles and thiadiazoles. Bioorg Med Chem 2009;17: 5275-84.
10. El-Sherbeny MA. Synthesis of certain pyrimido[2,1-b]benzothiazole and benzothiazolo[2,3-b]quinazoline derivatives for in vitro antitumor and antiviral activities. Arzneim Forsch 2000;50:848-53.
11. Elzahabi HAS. Synthesis, characterization of some benzazoles bearing pyridine moiety: Search for novel anticancer agents. Eur J Med Chem 2011;46:4025-36.
12. Fabbro D, Ruetz S, Buchdunger E, Cowan-Jacob SW, Fendrich G, Liebetanz J et al. Protein kinases as targets for anticancer agents: from inhibitors to useful drugs. Pharmacol Ther 2002;93:79-98.
13. Gabr MT, El-Gohary NS, El-Bendary ER, El-Kerdawy MM. Synthesis and in vitro antitumor activity of new series of benzothiazole and pyrimido[2,1-b]benzothiazole derivatives. Manuscript submitted for publication, 2014.
14. Grever MR, Schepartz SA, Chabner BA. The National Cancer Institute: cancer drug discovery and development program. Semin Oncol 1992;19:622-38.
15. Grosdidier A, Zoete V, Michielin O. SwissDock, a protein-small molecule docking web service based on EADock DSS. J Comput Chem Nucleic Acids Res 2011;9:270-7.
16. Grünwald V, Hidalgo M. Developing inhibitors of the epidermal growth factor receptor for cancer treatment. J Natl Cancer Inst 2003;95:851-67.
17. Hu WP, Chen YK, Liao CC, Yu HS, Tsai YM, Huang SM et al. Synthesis and biological evaluation of 2-(4-aminophenyl)benzothiazole derivatives as photosensitizing agents. Bioorg Med Chem 2010;46:6197-207.
18. Kinnings SL, Jackson RM. ReverseScreen3D: A structure-based ligand matching method to identify protein targets. J Chem Inf Model 2011;51:624-34.
19. Kristi GB, Thomas S, Herald S. Defective down regulation of receptor tyrosine kinases in cancer. Eur Mol Biol Org 2004;23:2707-12.
20. Levitzki A. Tyrosine kinase inhibitors: Views of selectivity, sensitivity, and clinical performance. Annu Rev Pharmacol Toxicol 2012;53:161-85.
21. Ma H, Deacon S, Horiuchi K. The challenge of selecting protein kinase assays for lead discovery optimization. Expert Opin Drug Discov 2008;3:607-21.
22. Malumbres M, Barbacid M. Cell cycle kinases in cancer. Curr Opin Genet Dev 2007;17:60-5.
23. Mason JS, Good AC, Martin EJ. 3-D pharmacophores in drug discovery. Curr Pharm Design 2001;7:567-97.
24. Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D et al. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer Inst 1991;83:757-66.
25. Mortimer CG, Wells G, Crochard JP, Stone EL, Bradshaw TD, Stevens MF et al. Antitumor benzothiazoles. 26.(1) 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (GW 610, NSC 721648), a simple fluorinated 2-arylbenzothiazole, shows potent and selective inhibitory activity against lung, colon, and breast cancer cell lines. J Med Chem 2006; 49:179-85.
26. Noolvi MN, Patel HM, Kaur M. Benzothiazoles: search for anticancer agents. Eur J Med Chem 2012; 54:447-62.
27. Peng-Cheng LV, Zhou CF, Chen J, Liu PG, Wang KR, Mao WJ et al. Design, synthesis and biological evaluation of thiazolidinone derivatives as potential EGFR and HER-2 inhibitors. Bioorg Med Chem Lett 2010;18:314-9.
28. Prasad PR, Bhuvaneswari K, Kumar KP, Rajani K, Kuberkar SV. Synthesis and biological activity evaluation of some fused pyrimido-benzothiazole derivatives. J Chem Pharm Res 2012;4:1606-11.
29. Ranson M. Epidermal growth factor receptor tyrosine kinase inhibitors. Br J Cancer 2004;90:2250-5.
30. Reck M, Zandwijk NV, Gridelli C, Baliko Z, Rischin D, Allan S et al. Erlotinib in advanced non-small cell lung cancer: efficacy and safety findings of the global phase IV Tarceva Lung Cancer Survival Treatment study. J Thorac Oncol 2010;5:1616-22.
31. Roymans D, Slegers H. Phosphatidylinositol 3-kinases in tumor progression. Eur J Biochem 2001; 268:487-98.
32. Saeed S, Rashid N, Jones PG, Ali M, Hussain R. Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents. Eur J Med Chem 2010;45:1323-31.
33. Sahu PK, Sahu PK, Gupta SK, Thavaselvam D, Agarwal DD. Synthesis and evaluation of antimicrobial activity of 4H-pyrimido[2,1-b]benzothiazole, pyrazole and benzylidene derivatives of curcumin. Eur J Med Chem 2012;54:366-78.
34. Sharma FA, Sharma R, Tyagi T. Receptor tyrosine kinase inhibitors as potent weapons in war against cancers. Curr Pharm Design 2009;15:758-76.
35. Shendarkar GR, Labhsetwar LB, Butle SR, Karki SS, Sharma RH, Kuberkar SV. Synthesis and antimicrobial evaluation of some fused iminopyrimidobenzothiazole derivatives. Int J Res Pharm Biomed Sci 2011;2:1350-6.
36. Shi XH, Wang Z, Xia Y, Ye T-H, Deng M, Xu Y-Z et al. Synthesis and biological evaluation of novel benzothiazole-2-thiol derivatives as potential anticancer agents. Molecules 2012;17:3933-44.
37. Smith J. Erlotinib: small-molecule targeted therapy in the treatment of non-small cell lung cancer. Clin Ther 2005;27:1513-34.
38. Sridhar S, Seymour L, Shepherd FA. Inhibitors of epidermal growth factor receptors: a review of clinical research with a focus on non small-cell lung cancer. Lancet Oncology 2003;4:397-406.
39. Tamura K, Fukuoka M. Gefitinib in non-small cell lung cancer. Expert Opin Pharmacother 2005;6:985-93.
40. Ullrich A, Schlessinger J. Signal transduction by receptors with tyrosine kinase activity. J Cell 1990;61: 203-12.
41. Wainberg ZA, Anghel A, Desai AJ, Ayala R, Luo T, Safran B et al. Lapatinib, a dual EGFR and HER2 kinase inhibitor, selectively inhibits HER2-amplified human gastric cancer cells and is synergistic with trastuzumab in vitro and in vivo. Clin Cancer Res 2010;16:1509-19.
42. Weisberg E, Manley PW, Cowan-Jacob SW, Hochhaus A, Griffin JD. Second generation inhibitors of BCR-ABL for the treatment of imatinib resistant chronic myeloid leukemia. Nat Rev Cancer 2007;7: 345-56.
43. Whittaker S, Kirk R, Hayward R, Zambon A, Viros A, Cantarino N et al. Gatakeeper mutations medicate resistance to BRAF targeted therapies. Sci Transl Med 2010;2:35-41.
44. Wolber G, Langer T. LigandScout: 3D Pharmacophores derived from protein-bound ligands and their use as virtual screening filters. J Chem Inf Comp Sci 2005;45:160-9.
45. Wu KW, Chen PC, Wang J, Sun YC. Computation of relative binding free energy for an inhibitor and its analogs binding with Erk kinase using thermodynamic integration MD simulation. J Comput Aided Mol Des 2012; 26:1159-69.
46. Yun C, Boggon TJ, Li Y, Woo MS, Greulich MS, Meyerson M et al. Structures of lung cancer-derived EGFR mutants and inhibitor complexes: mechanism of activation and insights into differential inhibitor sensitivity. Cancer Cell 2007;11:217-27.
47. Zhang J, Yang PL, Gray NS. Targeting cancer with small molecule kinase inhibitors. Nat Rev Cancer 2009;9:28-39.
48. Zuccotto F, Ardini E, Casale E, Angiolini M. Through the "Gatekeeper Door": Exploiting the active kinase conformation. J Med Chem 2010;53:2681-94.