Specific targeting of insulin-like growth factor 1 receptor signaling in human estrogen dependent breast cancer cell by a novel tyrosine-based benzoxazepine derivative

Molecular and Cellular Endocrinology

Volumn 338, Issue 1-2, 2011, Pages 68-78

  Chakravarti, Bandana ^a   Siddiqui, Jawed A ^a   Dwivedi, Shailendra K Dhar ^a   Deshpande, Shreekant ^a   Samanta, Krishnanda ^a   Bhatta, Rabi S ^a   Panda, Gautam ^a   Prabhakar, Yenamandra S ^a   Konwar, Rituraj ^a   Sanyal, Sabaysachi ^a   Chattopadhyay, Naibedya ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Chemotherapeutic agent; Insulin like growth factor receptor; Preclinical; Receptor tyrosine kinase

Indexed keywords

4 [4 (TOLUENE 4 SULFONYL) 2,3,4,5 TETRAHYDRO BENZO[F] [1,4] OXAPEN 3 YLMETHYL]PHENOL; ANTINEOPLASTIC AGENT; CASPASE 8; ESTROGEN; INSULIN; PROTEIN BAX; PROTEIN BCL 2; SOMATOMEDIN C; SOMATOMEDIN C RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CANCER CELL; CANCER INHIBITION; CELL CYCLE ARREST; CELL CYCLE G1 PHASE; CELL LEVEL; CELL PROLIFERATION; CELL VIABILITY; CONTROLLED STUDY; DOSE RESPONSE; DRUG BINDING SITE; DRUG CYTOTOXICITY; DRUG DOSAGE FORM COMPARISON; DRUG SELECTIVITY; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG TARGETING; ENZYME ACTIVATION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; IN VIVO STUDY; MITOCHONDRIAL MEMBRANE POTENTIAL; MOLECULAR DOCKING; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; SIGNAL TRANSDUCTION;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; BINDING SITES; BREAST NEOPLASMS; CASPASE 8; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME ACTIVATION; ESTROGENS; FEMALE; HUMANS; INSULIN; INSULIN-LIKE GROWTH FACTOR I; MEMBRANE POTENTIAL, MITOCHONDRIAL; MICE; MICE, NUDE; MODELS, MOLECULAR; NEOPLASM TRANSPLANTATION; OXAZEPINES; PHOSPHORYLATION; RECEPTOR, IGF TYPE 1; SIGNAL TRANSDUCTION; SULFONAMIDES; TRANSPLANTATION, HETEROLOGOUS; TYROSINE;

EID: 79955536242     PISSN: 03037207     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mce.2011.03.012     Document Type: Article

References (71)

1. Andrechek E.R., Muller W.J. Tyrosine kinase signalling in breast cancer: tyrosine kinase-mediated signal transduction in transgenic mouse models of human breast cancer. Breast Cancer Res. 2000, 2:211-216.
2. Asano T., Yao Y., Shin S., McCubrey J., Abbruzzese J.L., Reddy S.A. Insulin receptor substrate is a mediator of phosphoinositide 3-kinase activation in quiescent pancreatic cancer cells. Cancer Res. 2005, 65:9164-9168.
3. Blum G., Gazit A., Levitzki A. Development of new insulin-like growth factor-1 receptor kinase inhibitors using catechol mimics. J. Biol. Chem. 2003, 278:40442-40454.
4. Bodmer J.L., Holler N., Reynard S., Vinciguerra P., Schneider P., Juo P., Blenis J., Tschopp J. TRAIL receptor-2 signals apoptosis through FADD and caspase-8. Nat. Cell Biol. 2000, 2:241-243.
5. Bowe D.B., Kenney N.J., Adereth Y., Maroulakou I.G. Suppression of Neu-induced mammary tumor growth in cyclin D1 deficient mice is compensated for by cyclin E. Oncogene 2002, 21:291-298.
6. Brady H., Desai S., Gayo-Fung L.M., Khammungkhune S., McKie J.A., O'Leary E., Pascasio L., Sutherland M.K., Anderson D.W., Bhagwat S.S., Stein B. Effects of SP500263, a novel, potent antiestrogen, on breast cancer cells and in xenograft models. Cancer Res. 2002, 62:1439-1442.
7. Burtrum D., Zhu Z., Lu D., Anderson D.M., Prewett M., Pereira D.S., Bassi R., Abdullah R., Hooper A.T., Koo H., Jimenez X., Johnson D., Apblett R., Kussie P., Bohlen P., Witte L., Hicklin D.J., Ludwig D.L. A fully human monoclonal antibody to the insulin-like growth factor I receptor blocks ligand-dependent signaling and inhibits human tumor growth in vivo. Cancer Res. 2003, 63:8912-8921.
8. Chang D.W., Xing Z., Capacio V.L., Peter M.E., Yang X. Interdimer processing mechanism of procaspase-8 activation. EMBO J. 2003, 22:4132-4142.
9. Curtis M.G. Comparative tolerability of first-generation selective estrogen receptor modulators in breast cancer treatment and prevention. Drug Safety 2001, 24:1039-1053.
10. Donepudi M., Mac Sweeney A., Briand C., Grutter M.G. Insights into the regulatory mechanism for caspase-8 activation. Mol. Cell 2003, 11:543-549.
11. Ehata S., Hanyu A., Hayashi M., Aburatani H., Kato Y., Fujime M., Saitoh M., Miyazawa K., Imamura T., Miyazono K. Transforming growth factor-beta promotes survival of mammary carcinoma cells through induction of antiapoptotic transcription factor DEC1. Cancer Res. 2007, 67:9694-9703.
12. Ghavami S., Eshragi M., Ande S.R., Chazin W.J., Klonisch T., Halayko A.J., McNeill K.D., Hashemi M., Kerkhoff C., Los M. S100A8/A9 induces autophagy and apoptosis via ROS-mediated cross-talk between mitochondria and lysosomes that involves BNIP3. Cell Res. 2010, 20:314-331.
13. Girnita A., Girnita L., del Prete F., Bartolazzi A., Larsson O., Axelson M. Cyclolignans as inhibitors of the insulin-like growth factor-1 receptor and malignant cell growth. Cancer Res. 2004, 64:236-242.
14. Glait C., Tencer L., Ravid D., Sarfstein R., Liscovitch M., Werner H. Caveolin-1 up-regulates IGF-I receptor gene transcription in breast cancer cells via Sp1- and p53-dependent pathways. Exp. Cell Res. 2006, 312:3899-3908.
15. Guo X., Wang X.F. Signaling cross-talk between TGF-beta/BMP and other pathways. Cell Res. 2009, 19:71-88.
16. Heldin C.H., Miyazono K., ten Dijke P. TGF-beta signalling from cell membrane to nucleus through SMAD proteins. Nature 1997, 390:465-471.
17. Hewish M., Chau I., Cunningham D. Insulin-like growth factor 1 receptor targeted therapeutics: novel compounds and novel treatment strategies for cancer medicine. Recent Pat. Anticancer Drug Discov. 2009, 4:54-72.
18. Hilmi C., Larribere L., Giuliano S., Bille K., Ortonne J.P., Ballotti R., Bertolotto C. IGF1 promotes resistance to apoptosis in melanoma cells through an increased expression of BCL2, BCL-X(L), and survivin. J. Invest. Dermatol. 2008, 128:1499-1505.
19. Hoffmann J., Bohlmann R., Heinrich N., Hofmeister H., Kroll J., Kunzer H., Lichtner R.B., Nishino Y., Parczyk K., Sauer G., Gieschen H., Ulbrich H.F., Schneider M.R. Characterization of new estrogen receptor destabilizing compounds: effects on estrogen-sensitive and tamoxifen-resistant breast cancer. J. Natl. Cancer Inst. 2004, 96:210-218.
20. Hu-Lowe D.D., Zou H.Y., Grazzini M.L., Hallin M.E., Wickman G.R., Amundson K., Chen J.H., Rewolinski D.A., Yamazaki S., Wu E.Y., McTigue M.A., Murray B.W., Kania R.S., O'Connor P., Shalinsky D.R., Bender S.L. Nonclinical antiangiogenesis and antitumor activities of axitinib (AG-013736), an oral, potent, and selective inhibitor of vascular endothelial growth factor receptor tyrosine kinases 1, 2, 3. Clin. Cancer Res. 2008, 14:7272-7283.
21. Huff K.K., Kaufman D., Gabbay K.H., Spencer E.M., Lippman M.E., Dickson R.B. Secretion of an insulin-like growth factor-I-related protein by human breast cancer cells. Cancer Res. 1986, 46:4613-4619.
22. Hynes N.E. Tyrosine kinase signalling in breast cancer. Breast Cancer Res. 2000, 2:154-157.
23. Ji Q.S., Mulvihill M.J., Rosenfeld-Franklin M., Cooke A., Feng L., Mak G., O'Connor M., Yao Y., Pirritt C., Buck E., Eyzaguirre A., Arnold L.D., Gibson N.W., Pachter J.A. A novel, potent, and selective insulin-like growth factor-I receptor kinase inhibitor blocks insulin-like growth factor-I receptor signaling in vitro and inhibits insulin-like growth factor-I receptor dependent tumor growth in vivo. Mol. Cancer Ther. 2007, 6:2158-2167.
24. Jones H.E., Goddard L., Gee J.M., Hiscox S., Rubini M., Barrow D., Knowlden J.M., Williams S., Wakeling A.E., Nicholson R.I. Insulin-like growth factor-I receptor signalling and acquired resistance to gefitinib (ZD1839; Iressa) in human breast and prostate cancer cells. Endocr. Relat. Cancer 2004, 11:793-814.
25. Kasuya J., Paz I.B., Maddux B.A., Goldfine I.D., Hefta S.A., Fujita-Yamaguchi Y. Characterization of human placental insulin-like growth factor-I/insulin hybrid receptors by protein microsequencing and purification. Biochemistry 1993, 32:13531-13536.
26. Kavitha C.V., Nambiar M., Ananda Kumar C.S., Choudhary B., Muniyappa K., Rangappa K.S., Raghavan S.C. Novel derivatives of spirohydantoin induce growth inhibition followed by apoptosis in leukemia cells. Biochem. Pharmacol. 2009, 77:348-363.
27. Kim I., Crippen G.M., Amidon G.L. Structure and specificity of a human valacyclovir activating enzyme: a homology model of BPHL. Mol. Pharmacol. 2004, 1:434-446.
28. Klein R.D., Fischer S.M. Black tea polyphenols inhibit IGF-I-induced signaling through Akt in normal prostate epithelial cells and Du145 prostate carcinoma cells. Carcinogenesis 2002, 23:217-221.
29. Kok M., Holm-Wigerup C., Hauptmann M., Michalides R., Stal O., Linn S., Landberg G. Estrogen receptor-alpha phosphorylation at serine-118 and tamoxifen response in breast cancer. J. Natl. Cancer Inst. 2009, 101:1725-1729.
30. Korzeniewski C., Callewaert D.M. An enzyme-release assay for natural cytotoxicity. J. Immunol. Methods 1983, 64:313-320.
31. Krol J., Francis R.E., Albergaria A., Sunters A., Polychronis A., Coombes R.C., Lam E.W. The transcription factor FOXO3a is a crucial cellular target of gefitinib (Iressa) in breast cancer cells. Mol. Cancer Ther. 2007, 6:3169-3179.
32. Langenfeld E.M., Kong Y., Langenfeld J. Bone morphogenetic protein-2-induced transformation involves the activation of mammalian target of rapamycin. Mol. Cancer Res. 2005, 3:679-684.
33. Lei X., Bandyopadhyay A., Le T., Sun L. Autocrine TGFbeta supports growth and survival of human breast cancer MDA-MB-231 cells. Oncogene 2002, 21:7514-7523.
34. Li H., Zhu H., Xu C.J., Yuan J. Cleavage of BID by caspase 8 mediates the mitochondrial damage in the Fas pathway of apoptosis. Cell 1998, 94:491-501.
35. Li Z., Carrier L., Belame A., Thiyagarajah A., Salvo V.A., Burow M.E., Rowan B.G. Combination of methylselenocysteine with tamoxifen inhibits MCF-7 breast cancer xenografts in nude mice through elevated apoptosis and reduced angiogenesis. Breast Cancer Res. Treat. 2009, 118:33-43.
36. Litzenburger B.C., Kim H.J., Kuiatse I., Carboni J.M., Attar R.M., Gottardis M.M., Fairchild C.R., Lee A.V. BMS-536924 reverses IGF-IR-induced transformation of mammary epithelial cells and causes growth inhibition and polarization of MCF7 cells. Clin. Cancer Res. 2009, 15:226-237.
37. Martin D.A., Siegel R.M., Zheng L., Lenardo M.J. Membrane oligomerization and cleavage activates the caspase-8 (FLICE/MACHalpha1) death signal. J. Biol. Chem. 1998, 273:4345-4349.
38. Menu E., Jernberg-Wiklund H., Stromberg T., De Raeve H., Girnita L., Larsson O., Axelson M., Asosingh K., Nilsson K., Van Camp B., Vanderkerken K. Inhibiting the IGF-1 receptor tyrosine kinase with the cyclolignan PPP: an in vitro and in vivo study in the 5T33MM mouse model. Blood 2006, 107:655-660.
39. Mishra J.K., Panda G. Diversity-oriented synthetic approach to naturally abundant S-amino acid based benzannulated enantiomerically pure medium ring heterocyclic scaffolds employing inter- and intramolecular mitsunobu reactions. J. Comb. Chem. 2007, 9:321-338.
40. Mishra J.K., Samanta K., Jain M., Dikshit M., Panda G. Amino acid based enantiomerically pure 3-substituted benzofused heterocycles: a new class of antithrombotic agents. Bioorg. Med. Chem. Lett. 2010, 20:244-247.
41. Nemecek C., Metz W.A., Wentzler S., Ding F.X., Venot C., Souaille C., Dagallier A., Maignan S., Guilloteau J.P., Bernard F., Henry A., Grapinet S., Lesuisse D. Design of potent IGF1-R inhibitors related to bis-azaindoles. Chem. Biol. Drug Des. 2010, 76:100-106.
42. Peyrat J.P., Bonneterre J., Beuscart R., Djiane J., Demaille A. Insulin-like growth factor 1 receptors in human breast cancer and their relation to estradiol and progesterone receptors. Cancer Res. 1988, 48:6429-6433.
43. Premkumar D.R., Jane E.P., Pollack I.F. Co-administration of NVP-AEW541 and dasatinib induces mitochondrial-mediated apoptosis through Bax activation in malignant human glioma cell lines. Int. J. Oncol. 2010, 37:633-643.
44. Rajabi M., Signorelli P., Gorincioi E., Ghidoni R., Santaniello E. Antiproliferative activity of N(6)-isopentenyladenosine on MCF-7 breast cancer cells: cell cycle analysis and DNA-binding study. DNA Cell Biol. 2010.
45. Resnicoff M., Rubini M., Baserga R., Rubin R. Ethanol inhibits insulin-like growth factor-1-mediated signalling and proliferation of C6 rat glioblastoma cells. Lab. Invest. 1994, 71:657-662.
46. Resnitzky D., Gossen M., Bujard H., Reed S.I. Acceleration of the G1/S phase transition by expression of cyclins D1 and E with an inducible system. Mol. Cell. Biol. 1994, 14:1669-1679.
47. Riedemann J., Macaulay V.M. IGF1R signalling and its inhibition. Endocr. Relat. Cancer 2006, 13(1):S33-43.
48. Roberts W.G., Whalen P.M., Soderstrom E., Moraski G., Lyssikatos J.P., Wang H.F., Cooper B., Baker D.A., Savage D., Dalvie D., Atherton J.A., Ralston S., Szewc R., Kath J.C., Lin J., Soderstrom C., Tkalcevic G., Cohen B.D., Pollack V., Barth W., Hungerford W., Ung E. Antiangiogenic and antitumor activity of a selective PDGFR tyrosine kinase inhibitor CP-673,451. Cancer Res. 2005, 65:957-966.
49. Sachdev D., Yee D. The IGF system and breast cancer. Endocr. Relat. Cancer 2001, 8:197-209.
50. Saikali Z., Setya H., Singh G., Persad S. Role of IGF-1/IGF-1R in regulation of invasion in DU145 prostate cancer cells. Cancer Cell Int. 2008, 8:10.
51. Salvesen G.S. Caspase 8: igniting the death machine. Structure 1999, 7:R225-229.
52. Samanta K., Chakravarti B., Mishra J.K., Dwivedi S.K., Nayak L.V., Choudhry P., Bid H.K., Konwar R., Chattopadhyay N., Panda G. Anti-tumor activity of a new series of benzoxazepine derivatives in breast cancer. Bioorg. Med. Chem. Lett. 2010, 20:283-287.
53. Sanchez-Capelo A. Dual role for TGF-beta1 in apoptosis. Cytokine Growth Factor Rev. 2005, 16:15-34.
54. Sasaoka T., Ishiki M., Sawa T., Ishihara H., Takata Y., Imamura T., Usui I., Olefsky J.M., Kobayashi M. Comparison of the insulin and insulin-like growth factor 1 mitogenic intracellular signaling pathways. Endocrinology 1996, 137:4427-4434.
55. Schlessinger J., Ullrich A. Growth factor signaling by receptor tyrosine kinases. Neuron 1992, 9:383-391.
56. Sepp-Lorenzino L. Structure and function of the insulin-like growth factor I receptor. Breast Cancer Res. Treat. 1998, 47:235-253.
57. Shankar R., Chakravarti B., Singh U.S., Ansari M.I., Deshpande S., Dwivedi S.K., Bid H.K., Konwar R., Kharkwal G., Chandra V., Dwivedi A., Hajela K. Synthesis and biological evaluation of 3,4,6-triaryl-2-pyranones as a potential new class of anti-breast cancer agents. Bioorg. Med. Chem. 2009, 17:3847-3856.
58. Shi Y., Massague J. Mechanisms of TGF-beta signaling from cell membrane to the nucleus. Cell 2003, 113:685-700.
59. Shin I., Bakin A.V., Rodeck U., Brunet A., Arteaga C.L. Transforming growth factor beta enhances epithelial cell survival via Akt-dependent regulation of FKHRL1. Mol. Biol. Cell 2001, 12:3328-3339.
60. Sprick M.R., Weigand M.A., Rieser E., Rauch C.T., Juo P., Blenis J., Krammer P.H., Walczak H. FADD/MORT1 and caspase-8 are recruited to TRAIL receptors 1 and 2 and are essential for apoptosis mediated by TRAIL receptor 2. Immunity 2000, 12:599-609.
61. Stegh A.H., Barnhart B.C., Volkland J., Algeciras-Schimnich A., Ke N., Reed J.C., Peter M.E. Inactivation of caspase-8 on mitochondria of Bcl-xL-expressing MCF7-Fas cells: role for the bifunctional apoptosis regulator protein. J. Biol. Chem. 2002, 277:4351-4360.
62. Ulanet D.B., Ludwig D.L., Kahn C.R., Hanahan D. Insulin receptor functionally enhances multistage tumor progression and conveys intrinsic resistance to IGF-1R targeted therapy. Proc. Natl. Acad. Sci. U. S. A. 2010, 107:10791-10798.
63. Ullrich A., Schlessinger J. Signal transduction by receptors with tyrosine kinase activity. Cell 1990, 61:203-212.
64. VanWeelden K., Flanagan L., Binderup L., Tenniswood M., Welsh J. Apoptotic regression of MCF-7 xenografts in nude mice treated with the vitamin D3 analog, EB1089. Endocrinology 1998, 139:2102-2110.
65. Wen B., Deutsch E., Marangoni E., Frascona V., Maggiorella L., Abdulkarim B., Chavaudra N., Bourhis J. Tyrphostin AG 1024 modulates radiosensitivity in human breast cancer cells. Br. J. Cancer 2001, 85:2017-2021.
66. Werner H., Le Roith D. The insulin-like growth factor-I receptor signaling pathways are important for tumorigenesis and inhibition of apoptosis. Crit. Rev. Oncogen. 1997, 8:71-92.
67. Yang Q., Kiernan C.M., Tian Y., Salwen H.R., Chlenski A., Brumback B.A., London W.B., Cohn S.L. Methylation of CASP8, DCR2, and HIN-1 in neuroblastoma is associated with poor outcome. Clin. Cancer Res. 2007, 13:3191-3197.
68. Youngren J.F., Gable K., Penaranda C., Maddux B.A., Zavodovskaya M., Lobo M., Campbell M., Kerner J., Goldfine I.D. Nordihydroguaiaretic acid (NDGA) inhibits the IGF-1 and c-erbB2/HER2/neu receptors and suppresses growth in breast cancer cells. Breast Cancer Res. Treat. 2005, 94:37-46.
69. Yu H., Rohan T. Role of the insulin-like growth factor family in cancer development and progression. J. Natl. Cancer Inst. 2000, 92:1472-1489.
70. Zavodovskaya M., Campbell M.J., Maddux B.A., Shiry L., Allan G., Hodges L., Kushner P., Kerner J.A., Youngren J.F., Goldfine I.D. Nordihydroguaiaretic acid (NDGA), an inhibitor of the HER2 and IGF-1 receptor tyrosine kinases, blocks the growth of HER2-overexpressing human breast cancer cells. J. Cell. Biochem. 2008, 103:624-635.
71. Zheng W.H., Quirion R. Insulin-like growth factor-1 (IGF-1) induces the activation/phosphorylation of Akt kinase and cAMP response element-binding protein (CREB) by activating different signaling pathways in PC12 cells. BMC Neurosci. 2006, 7:51.