Development of cell-penetrating r7 fragment-conjugated helical peptides as inhibitors of estrogen receptor-mediated transcription

Bioconjugate Chemistry

Volumn 25, Issue 11, 2014, Pages 1921-1924

  Nagakubo, Takaya ^a,b   Demizu, Yosuke ^a   Kanda, Yasunari ^a   Misawa, Takashi ^a   Shoda, Takuji ^a   Okuhira, Keiichiro ^a   Sekino, Yuko ^a   Naito, Mikihiko ^a   Kurihara, Masaaki ^a,b  

^a NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TRANSCRIPTION;

CELLULAR LEVELS; COACTIVATORS; ESTROGEN RECEPTOR; HELICAL PEPTIDE; MEDIATED TRANSCRIPTION; MRNA EXPRESSION; SYNTHESISED;

PEPTIDES;

CELL PENETRATING PEPTIDE; HEPTAARGININE; PEPTIDOMIMETIC AGENT; SELECTIVE ESTROGEN RECEPTOR MODULATOR; UNCLASSIFIED DRUG; ARGININE; ESTROGEN RECEPTOR;

ARTICLE; CELLULAR DISTRIBUTION; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; DRUG CONJUGATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MASS SPECTROMETRY; PEPTIDE SYNTHESIS; PROTEIN EXPRESSION; PROTEIN SECONDARY STRUCTURE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SIGNAL TRANSDUCTION; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DEVELOPMENT; DRUG EFFECTS; GENETIC TRANSCRIPTION; METABOLISM;

ARGININE; CELL LINE; CELL-PENETRATING PEPTIDES; DRUG DISCOVERY; HUMANS; MODELS, MOLECULAR; PROTEIN STRUCTURE, SECONDARY; RECEPTORS, ESTROGEN; TRANSCRIPTION, GENETIC;

EID: 84912522114     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc500480e     Document Type: Article

References (26)

1. Holst, F., Stahl, P. R., Ruiz, C., Hellwinkel, O., Jehan, Z., Wendland, M., Lebeau, A., Terracciano, L., Al-Kuraya, K., Jänicke, F., Sauter, G., and Simon, R. (2007) Estrogen receptor alpha (ESR1) gene amplification is frequent in breast cancer Nat. Genet. 39, 655-660
2. Doisneau-Sixou, S. F., Cergio, C. M., Carroll, J. S., Hui, R., Musgrove, E. A., and Sutherland, R. L. (2003) Estrogen and antiestrogen regulation of cell cycle progression in breast cancer cells Endocrine-Related Cancer 10, 179-186
3. Foster, J. S., Henley, D. C., Bukovsky, A., Seth, P., and Wimalasena, J. (2001) Multifaceted regulation of cell cycle progression by estrogen: regulation of Cdk inhibitors and Cdc25A independent of cyclin D1-Cdk4 function Mol. Cell. Biol. 21, 794-810
4. Howell, S. J., Johnston, S. R., and Howell, A. (2004) The use of selective estrogen receptor modulators and selective estrogen receptor down-regulators in breast cancer Best Pract. Res. Clin. Endocrinol. Metab. 18, 47-66
5. Deroo, B. J. and Korach, K. S. (2006) Estrogen receptors and human disease J. Clin. Invest. 116, 561-570
6. Baumann, C. K. and Castiglione-Gertsch, M. (2007) Estrogen receptor modulators and down regulators Drugs 67, 2335-2353
7. Demizu, Y., Okuhira, H., Motoi, H., Ohno, A., Shoda, T., Fukuhara, K., Okuda, H., Naito, M., and Kurihara, M. (2012) Design and synthesis of estrogen receptor degradation inducer based on a protein knockdown strategy Bioorg. Med. Chem. Lett. 22, 1793-1796
8. Shoda, T., Okuhira, K., Kato, M., Demizu, Y., Inoue, H., Naito, M., and Kurihara, M. (2014) Design and synthesis of tamoxifen derivatives as a selective estrogen receptor down-regulator Bioorg. Med. Chem. Lett. 24, 87-89
9. Early Breast Cancer Trialists Collaborative Group (1992) Systemic treatment of early breast cancer by hormonal, cytotoxic, or immune therapy: 133 randomised trials involving 31 000 recurrences and 24 000 deaths among 75 000 women Lancet 339, 71-85
10. Fisher, B., Costantino, J. P., Wickerham, D. L., Redmond, C. K., Kavanah, M., Cronin, W. M., Vogel, V., Robidoux, A., Dimitrov, N., Atkins, J., Daly, M., Wieand, S., Tan-Chiu, E., Ford, L., and Wolmark, N. (1998) Tamoxifen for prevention of breast cancer: Report of the national surgical adjuvant breast and bowel project P-1 study J. Natl. Cancer Inst. (Bethesda) 90, 1371-1388
11. Bernstein, L., Deapen, D., Cerhan, J. R., Schwartz, S. M., Liff, J., McGann-Maloney, E., Perlman, J. A., and Ford, L. (1999) Tamoxifen therapy for breast cancer and endometrial cancer risk J. Natl. Cancer Inst. 91, 1654-1662
12. Shang, Y. and Brown, M. (2002) Molecular determinants for the tissue specificity of SERMs Science 295, 2465-2468
13. Arpino, G., Wiechmann, L., Osborne, C. K., and Schiff, R. (2008) Crosstalk between the estrogen receptor and the HER tyrosine kinase receptor family: molecular mechanism and clinical implications for endocrine therapy resistance Endocr. Rev. 29, 217-233
14. Lin, S-L., Yan, L-Y., Zhang, X-T., Yuan, J., Li, M., Qiao, J., Wang, Z-Y., Sheng, J., and Sun, Q-Y. (2010) ER-alpha36, a variant of ER-alpha, promotes tamoxifen agonist action in endometrial cancer cells via the MAPK/ERK and PI3K/Akt pathways PLoS One 5, e9013
15. Demizu, Y., Nagoya, S., Shirakawa, M., Kawamura, M., Yamagata, N., Sato, Y., Doi, M., and Kurihara, M. (2013) Development of stapled short helical peptides capable of inhibiting vitamin D receptor (VDR)-coactivator interactions Bioorg. Med. Chem. Lett. 23, 4292-4296
16. Heery, D. M., Kalkhoven, E., Hoare, S., and Parker, M. G. (1997) A signature motif in transcriptional co-activators mediates binding to nuclear receptors Nature 387, 733-736
17. Hall, J. M. and McDonnell, D. P. (2005) Coregulators in nuclear estrogen receptor action: from concept to therapeutic targeting Mol. Interventions 5, 343-357
18. Hall, J. M., Chang, C., and McDonnell, D. P. (2000) Development of peptide antagonists that target estrogen receptorß-coactivator interactions Mol. Endocrinol. 14, 2010-2023
19. Leduc, A-M., Trent, J. O., Wittliff, J. L., Bramlett, K. S., Briggs, S. L., Chirgadze, N. Y., Wang, Y., Burris, T. P., and Spatola, A. F. (2003) Helix-stabilized cyclic peptides as selective inhibitors of steroid receptor-coactivator interactions Proc. Natl. Acad. Sci. U.S.A. 100, 11273-11278
20. Galande, A. K., Bramlett, K. S., Trent, J. O., Burris, T. P., Wittliff, J. L., and Spatola, A. F. (2005) Protein inhibitors of LXXLL-based protein-protein interactions ChemBioChem 6, 1991-1998
21. Phan, T., Nguyen, H. D., Göksel, H., Möcklinghoff, S., and Brunsveld, L. (2010) Phage display selection of miniprotein binders of the Estrogen receptor Chem. Commun. 46, 8207-8209
22. Phillips, C., Roberts, L. R., Schade, M., Bazin, R., Bent, A., Davies, N. L., Moore, R., Pannifer, A. D., Pickford, A. R., Prior, S. H., Read, C. M., Scott, A., Brown, D. G., Xu, B., and Irving, S. L. (2011) Design and structure of stapled peptides binding to estrogen receptors J. Am. Chem. Soc. 46, 8207-8209
23. Carraz, M., Zwart, W., Phan, T., Michalides, R., and Brunsveld, L. (2009) Perturbation of estrogen receptor α localization with synthetic nona-arginine LXXLL-peptide coactivator binding inhibitors Chem. Biol. 16, 702-711
24. Tints, K., Prink, M., Neuman, T., and Palm, K. (2014) LXXLL peptide converts transportan 10 to a potent inducer of apoptosis in breast cancer cells Int. J. Mol. Sci. 15, 5680-5698
25. Nakase, I., Akita, H., Kogure, K., Gráslund, A., Langel, Ü., Harashima, H., and Futaki, S. (2012) Efficient intracellular delivery of nucleic acid pharmaceuticals using cell-penetrating peptides Acc. Chem. Res. 45, 1132-1139
26. Yamashita, H., Demizu, Y., Shoda, T., Sato, Y., Oba, M., Tanaka, M., and Kurihara, M. (2014) Amphipathic short helix-stabilized peptides with cell-membrane penetrating ability Bioorg. Med. Chem. 22, 2403-2408