Screening and biological evaluation of myricetin as a multiple target inhibitor insulin, epidermal growth factor, and androgen receptor; In silico and in vitro

Investigational New Drugs

Volumn 33, Issue 3, 2015, Pages 575-593

  Singh, Pushpendra ^a   Bast, Felix ^a  

^a CENTRAL UNIVERSITY OF PUNJAB   (India)

Author keywords

Androgen receptor Estrogen receptor; Cancer; Maestro 9.6; Natural compounds; Receptor tyrosine kinases

Indexed keywords

ANDROGEN RECEPTOR; ANDROGEN RECEPTOR ANTAGONIST; EPIDERMAL GROWTH FACTOR; ESTROGEN RECEPTOR; FLAVONOID; HYPERGLYCEMIC AGENT; INSULIN; LIGAND; MESSENGER RNA; MYRICETIN; REACTIVE OXYGEN METABOLITE;

ANTAGONISTS AND INHIBITORS; CELL MOTION; CELL PROLIFERATION; CHEMICAL DATABASE; CHEMISTRY; COMPUTER SIMULATION; DRUG EFFECTS; GENE EXPRESSION REGULATION; GENETICS; HUMAN; METABOLISM; MOLECULAR DOCKING; PRECLINICAL STUDY; SOFTWARE; THERMODYNAMICS; TUMOR CELL LINE;

ANDROGEN RECEPTOR ANTAGONISTS; CELL LINE, TUMOR; CELL MOVEMENT; CELL PROLIFERATION; COMPUTER SIMULATION; DATABASES, CHEMICAL; DRUG EVALUATION, PRECLINICAL; EPIDERMAL GROWTH FACTOR; FLAVONOIDS; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; INSULIN; INSULIN ANTAGONISTS; LIGANDS; MOLECULAR DOCKING SIMULATION; REACTIVE OXYGEN SPECIES; RECEPTORS, ANDROGEN; RECEPTORS, ESTROGEN; RNA, MESSENGER; SOFTWARE; THERMODYNAMICS;

EID: 84937762854     PISSN: 01676997     EISSN: 15730646     Source Type: Journal    
DOI: 10.1007/s10637-015-0240-8     Document Type: Article

References (61)

1. Paule B, Brion N (2003)EGF receptors in urological cancer. Molecular basis and therapeutic involvements. In: Annales de médecine interne. p 448
2. Di Lorenzo G, Tortora G, D'Armiento FP, De Rosa G, Staibano S, Autorino R, D'Armiento M, De Laurentiis M, De Placido S, Catalano G (2002) Expression of epidermal growth factor receptor correlates with disease relapse and progression to androgen-independence in human prostate cancer. Clin Cancer Res 8(11):3438-3444
3. Traish A, Morgentaler A (2009) Epidermal growth factor receptor expression escapes androgen regulation in prostate cancer: a potential molecular switch for tumour growth. Br J Cancer 101(12):1949-1956. doi: 10.1038/sj.bjc.6605376
4. Sharma SV, Bell DW, Settleman J, Haber DA (2007) Epidermal growth factor receptor mutations in lung cancer. Nat Rev Cancer 7(3):169-181. doi: 10.1038/nrc2088
5. Scagliotti GV, Selvaggi G, Novello S, Hirsch FR (2004) The biology of epidermal growth factor receptor in lung cancer. Clin Cancer Res 10(12):4227s-4232s
6. Buck E, Gokhale PC, Koujak S, Brown E, Eyzaguirre A, Tao N, Lerner L, Chiu MI, Wild R, Epstein D (2010) Compensatory insulin receptor (IR) activation on inhibition of insulin-like growth factor-1 receptor (IGF-1R): rationale for cotargeting IGF-1R and IR in cancer. Mol Cancer Ther 9(10):2652-2664. doi: 10.1158/1535-7163.MCT-10-0318
7. Singh P, Alex JM, Bast F (2014) Insulin receptor (IR) and insulin-like growth factor receptor 1 (IGF-1R) signaling systems: novel treatment strategies for cancer. Med Oncol 31(1):1-14. doi: 10.1007/s12032-013-0805-3
8. Giudice J, Leskow FC, Arndt-Jovin DJ, Jovin TM, Jares-Erijman EA (2011) Differential endocytosis and signaling dynamics of insulin receptor variants IR-A and IR-B. J Cell Sci 124(5):801-811. doi: 10.1242/jcs.076869
9. Avnet S, Sciacca L, Salerno M, Gancitano G, Cassarino MF, Longhi A, Zakikhani M, Carboni JM, Gottardis M, Giunti A (2009) Insulin receptor isoform A and insulin-like growth factor II as additional treatment targets in human osteosarcoma. Cancer Res 69(6):2443-2452. doi: 10.1158/0008-5472.CAN-08-2645
10. Zhang H, Fagan DH, Zeng X, Freeman KT, Sachdev D, Yee D (2010) Inhibition of cancer cell proliferation and metastasis by insulin receptor downregulation. Oncogene 29(17):2517-2527. doi: 10.1038/onc.2010.17
11. Vincent EE, Elder DJ, Curwen J, Kilgour E, Hers I, Tavaré JM (2013) Targeting non-small cell lung cancer cells by dual inhibition of the insulin receptor and the insulin-like growth factor-1 receptor. PLoS One 8(6), e66963. doi: 10.1371/journal.pone.0066963. Print 2013
12. Frasca F, Pandini G, Scalia P, Sciacca L, Mineo R, Costantino A, Goldfine I, Belfiore A, Vigneri R (1999) Insulin receptor isoform A, a newly recognized, high-affinity insulin-like growth factor II receptor in fetal and cancer cells. Mol Cell Biol 19(5):3278-3288
13. Pandini G, Frasca F, Mineo R, Sciacca L, Vigneri R, Belfiore A (2002) Insulin/insulin-like growth factor I hybrid receptors have different biological characteristics depending on the insulin receptor isoform involved. J Biol Chem 277(42):39684-39695
14. Hendrickson AEW, Haluska P, Schneider PA, Loegering DA, Peterson KL, Attar R, Smith BD, Erlichman C, Gottardis M, Karp JE (2009) Expression of insulin receptor isoform A and insulin-like growth factor-1 receptor in human acute myelogenous leukemia: effect of the dual-receptor inhibitor BMS-536924 in vitro. Cancer Res 69(19):7635-7643. doi: 10.1158/0008-5472.CAN-09-0511
15. Bianco R, Melisi D, Ciardiello F, Tortora G (2006) Key cancer cell signal transduction pathways as therapeutic targets. Eur J Cancer 42(3):290-294. doi: 10.1016/j.ejca.2005.07.034
16. Singh P, Bast F (2014) Multitargeted molecular docking study of plant-derived natural products on phosphoinositide-3 kinase pathway components. Med Chem Res 23(4):1690-1700. doi: 10.1007/s00044-013-0774-2
17. Singh P, Bast F (2014) In silico molecular docking study of natural compounds on wild and mutated epidermal growth factor receptor. Med Chem Res 23:5074-5085. doi: 10.1007/s00044-014-1090-1
18. Phillips P, Sangwan V, Borja-Cacho D, Dudeja V, Vickers S, Saluja A (2011) Myricetin induces pancreatic cancer cell death via the induction of apoptosis and inhibition of the phosphatidylinositol 3-kinase (PI3K) signaling pathway. Cancer Lett 308(2):181-188. doi: 10.1016/j.canlet.2011.05.002
19. Sun F, Zheng XY, Ye J, Wu TT, Jl W, Chen W (2012) Potential anticancer activity of myricetin in human T24 bladder cancer cells both in vitro and in vivo. Nutr Cancer 64(4):599-606. doi: 10.1080/01635581.2012.665564
20. Zhang X, Chen S, Tang L, Shen Y, Luo L, Xu C, Liu Q, Li D (2013) Myricetin induces apoptosis in Hepg2 cells through Akt/P70s6k/Bad signaling and mitochondrial apoptotic pathway. Anticancer Agents Med Chem 13(10):1575-1581
21. Lee KW, Kang NJ, Rogozin EA, Kim H-G, Cho YY, Bode AM, Lee HJ, Surh Y-J, Bowden GT, Dong Z (2007) Myricetin is a novel natural inhibitor of neoplastic cell transformation and MEK1. Carcinogenesis 28(9):1918-1927
22. Singh P, Bast F (2015) High-throughput virtual screening, identification and in vitro biological evaluation of novel inhibitors of signal transducer and activator of transcription 3. Med Chem Res. doi: 10.1007/s00044-015-1328-6
23. da Rocha AB, Lopes RM, Schwartsmann G (2001) Natural products in anticancer therapy. Curr Opin Pharmacol 1(4):364-369
24. Sunil H (2012) Inhibition studies of naturally occurring terpene based compounds with cyclin-dependent kinase 2 enzyme. J Comput Sci Syst Biol 5:2
25. Sarkar FH, Li Y (2006) Using chemopreventive agents to enhance the efficacy of cancer therapy. Cancer Res 66(7):3347-3350
26. Hillman GG (2012) Dietary agents in cancer chemoprevention and treatment. J Oncol. doi: 10.1155/2012/749310
27. Phosrithong N, Ungwitayatorn J (2010) Molecular docking study on anticancer activity of plant-derived natural products. Med Chem Res 19(8):817-835
28. Cho JY, Park J (2008) Contribution of natural inhibitors to the understanding of the PI3K/PDK1/PKB pathway in the insulin-mediated intracellular signaling cascade. Int J Mol Sci 9(11):2217-2230
29. Friesner RA, Murphy RB, Repasky MP, Frye LL, Greenwood JR, Halgren TA, Sanschagrin PC, Mainz DT (2006) Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. J Med Chem 49(21):6177-6196
30. Halgren TA, Murphy RB, Friesner RA, Beard HS, Frye LL, Pollard WT, Banks JL (2004) Glide: a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. J Med Chem 47(7):1750-1759
31. Friesner RA, Banks JL, Murphy RB, Halgren TA, Klicic JJ, Mainz DT, Repasky MP, Knoll EH, Shelley M, Perry JK (2004) Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem 47(7):1739-1749
32. Shivakumar D, Williams J, Wu Y, Damm W, Shelley J, Sherman W (2010) Prediction of absolute solvation free energies using molecular dynamics free energy perturbation and the OPLS force field. J Chem Theory Comput 6(5):1509-1519
33. Jorgensen WL, Maxwell DS, Tirado-Rives J (1996) Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids. J Am Chem Soc 118(45):11225-11236
34. Jorgensen WL, Tirado-Rives J (1988) The OPLS [optimized potentials for liquid simulations] potential functions for proteins, energy minimizations for crystals of cyclic peptides and crambin. J Am Chem Soc 110(6):1657-1666
35. Lu JJ, Crimin K, Goodwin JT, Crivori P, Orrenius C, Xing L, Tandler PJ, Vidmar TJ, Amore BM, Wilson AG (2004) Influence of molecular flexibility and polar surface area metrics on oral bioavailability in the rat. J Med Chem 47(24):6104-6107
36. Jorgensen WL, Duffy EM (2002) Prediction of drug solubility from structure. Adv Drug Deliv Rev 54(3):355-366
37. Mechoulam H, Pierce EA (2005) Expression and activation of STAT3 in ischemia-induced retinopathy. Invest Ophthalmol Vis Sci 46(12):4409-4416
38. Shih Y-W, Wu P-F, Lee Y-C, Shi M-D, Chiang T-A (2009) Myricetin suppresses invasion and migration of human lung adenocarcinoma A549 cells: possible mediation by blocking the ERK signaling pathway. J Agric Food Chem 57(9):3490-3499
39. Tzeng T-F, Liou S-S, Liu I-M (2011) Myricetin ameliorates defective post-receptor insulin signaling via β-endorphin signaling in the skeletal muscles of fructose-fed rats. Evid Based Complement Alternat Med 2011:150752. doi: 10.1093/ecam/neq017
40. Liu I-M, Tzeng T-F, Liou S-S, Lan T-W (2007) Myricetin, a naturally occurring flavonol, ameliorates insulin resistance induced by a high-fructose diet in rats. Life Sci 81(21):1479-1488
41. Simon AR, Rai U, Fanburg BL, Cochran BH (1998) Activation of the JAK-STAT pathway by reactive oxygen species. Am J Physiol-Cell Physiol 275(6):C1640-C1652
42. Walker SR, Nelson EA, Zou L, Chaudhury M, Signoretti S, Richardson A, Frank DA (2009) Reciprocal effects of STAT5 and STAT3 in breast cancer. Mol Cancer Res 7(6):966-976
43. Kumamoto T, Fujii M, Hou D-X (2009) Myricetin directly targets JAK1 to inhibit cell transformation. Cancer Lett 275(1):17-26
44. Morales P, Haza AI (2012) Selective apoptotic effects of piceatannol and myricetin in human cancer cells. J Appl Toxicol 32(12):986-993
45. Safina A, Sotomayor P, Limoge M, Morrison C, Bakin AV (2011) TAK1-TAB2 signaling contributes to bone destruction by breast carcinoma cells. Mol Cancer Res 9(8):1042-1053
46. Gomes LR, Terra LF, Wailemann RA, Labriola L, Sogayar MC (2012) TGF-β1 modulates the homeostasis between MMPs and MMP inhibitors through p38 MAPK and ERK1/2 in highly invasive breast cancer cells. BMC Cancer 12(1):26
47. Dumont N, Arteaga CL (2003) Targeting the TGFβ signaling network in human neoplasia. Cancer Cell 3(6):531-536
48. Alonso H, Bliznyuk AA, Gready JE (2006) Combining docking and molecular dynamic simulations in drug design. Med Res Rev 26(5):531-568
49. Gupta GP, Massagué J (2006) Cancer metastasis: building a framework. Cell 127(4):679-695
50. Javelaud D, Mauviel A (2004) Mammalian transforming growth factor-βs: Smad signaling and physio-pathological roles. Int J Biochem Cell Biol 36(7):1161-1165
51. Fortunel NO, Hatzfeld A, Hatzfeld JA (2000) Transforming growth factor-β: pleiotropic role in the regulation of hematopoiesis. Blood 96(6):2022-2036
52. Chang C, Lee S, Yeh S, Chang T (2013) Androgen receptor (AR) differential roles in hormone-related tumors including prostate, bladder, kidney, lung, breast and liver. Oncogene 33(25):3225-3234
53. Lonergan PE, Tindall DJ (2011) Androgen receptor signaling in prostate cancer development and progression. J Carcinog 10(1):20
54. Maggiolini M, Recchia A, Bonofiglio D, Catalano S, Vivacqua A, Carpino A, Rago V, Rossi R, Ando S (2005) The red wine phenolics piceatannol and myricetin act as agonists for estrogen receptor α in human breast cancer cells. J Mol Endocrinol 35(2):269-281
55. Wang Y, Kreisberg JI, Ghosh PM (2007) Cross-talk between the androgen receptor and the phosphatidylinositol 3-kinase/Akt pathway in prostate cancer. Curr Cancer Drug Targets 7(6):591-604
56. Naderi A, Hughes-Davies L (2008) A functionally significant cross-talk between androgen receptor and ErbB2 pathways in estrogen receptor negative breast cancer. Neoplasia (NY) 10(6):542
57. Craft N, Shostak Y, Carey M, Sawyers CL (1999) A mechanism for hormone-independent prostate cancer through modulation of androgen receptor signaling by the HER-2/neu tyrosine kinase. Nat Med 5(3):280-285
58. Lee AV, Cui X, Oesterreich S (2001) Cross-talk among estrogen receptor, epidermal growth factor, and insulin-like growth factor signaling in breast cancer. Clin Cancer Res 7(12):4429s-4435s
59. Levin ER (2003) Bidirectional signaling between the estrogen receptor and the epidermal growth factor receptor. Mol Endocrinol 17(3):309-317
60. Sak K (2014) Cytotoxicity of dietary flavonoids on different human cancer types. Pharmacogn Rev 8(16):122
61. Labbé D, Provençal M, Lamy S, Boivin D, Gingras D, Béliveau R (2009) The flavonols quercetin, kaempferol, and myricetin inhibit hepatocyte growth factor-induced medulloblastoma cell migration. J Nutr 139(4):646-652