Engineered systems for detection and discovery of nuclear hormone-like compounds

Biotechnology Progress

Volumn 24, Issue 1, 2008, Pages 8-16

  Gillies, Alison R ^a   Skretas, Georgios ^c   Wood, David W ^a,b  

^a Princeton University   (United States)

^b PRINCETON UNIVERSITY   (United States)

^c The University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMOLECULES; ESCHERICHIA COLI; HORMONES; LIGANDS;

ENGINEERED SYSTEMS; LIGAND RECOGNITION; NUCLEAR HORMONE RECEPTORS (NHR);

SYSTEMS ANALYSIS;

CARRIER PROTEIN; CELL RECEPTOR; LIGAND;

BIOLOGICAL MODEL; BIOTECHNOLOGY; CHEMISTRY; CONFERENCE PAPER; GENETICS; HUMAN; METABOLISM; METHODOLOGY; PROTEIN BINDING; PROTEIN ENGINEERING; PROTEIN TERTIARY STRUCTURE;

BIOTECHNOLOGY; CARRIER PROTEINS; HUMANS; LIGANDS; MODELS, BIOLOGICAL; PROTEIN BINDING; PROTEIN ENGINEERING; PROTEIN STRUCTURE, TERTIARY; RECEPTORS, CYTOPLASMIC AND NUCLEAR;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 38949083195     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp070144i     Document Type: Conference Paper

References (82)

1. Bourguet, W.; Germain, P.; Gronemeyer, H. Nuclear receptor ligand-binding domains: three-dimensional structures, molecular interactions and pharmacological implications. Trends Pharmacol. Sci. 2000, 21 (10), 381-388.
2. Smith, C. L.; O'Malley, B. W. Coregulator function: a key to understanding tissue specificity of selective receptor modulators. Endocr. Rev. 2004, 25 (1), 45-71.
3. Shang, Y.; Brown, M. Molecular determinants for the tissue specificity of SERMs. Science 2002, 295 (5564), 2465-2468.
4. Jordan, V. C. Tamoxifen: a most unlikely pioneering medicine. Nat. Rev. Drug Discovery 2003, 2 (3), 205-213.
5. Gronemeyer, H.; Gustafsson, J. A.; Laudet, V. Principles for modulation of the nuclear receptor superfamily. Nat. Rev. Drug Discovery 2004, 3 (11), 950-964.
6. Riggs, B. L.; Hartmann, L. C. Selective estrogen-receptor modulators - mechanisms of action and application to clinical practice. N. Engl. J. Med. 2003, 348 (7), 618-629.
7. Flamant, F.; Baxter, J. D.; Forrest, D.; Refetoff, S.; Samuels, H.; Scanlan, T. S.; Vennström, B.; Samarut, J. International Union of Pharmacology. LIX. The pharmacology and classification of the nuclear receptor superfamily: thyroid hormone receptors. Pharmacol. Rev. 2006, 58 (4), 705-711.
8. Stauffer, S. R.; Coletta, C. J.; Tedesco, R.; Nishiguchi, G.; Carlson, K.; Sun, J.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Pyrazole ligands: structure-affinity/activity relationships and estrogen receptor-alpha-selective agonists. J. Med. Chem. 2000, 43 (26), 4934-4947.
9. Meyers, M. J.; Sun, J.; Carlson, K. E.; Marriner, G. A.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Estrogen receptor-beta potency-selective ligands: structure-activity relationship studies of diarylpropionitriles and their acetylene and polar analogues. J. Med. Chem. 2001, 44 (24), 4230-4251.
10. Chiellini, G.; Apriletti, J. W.; Yoshihara, H. A.; Baxter, J. D.; Ribeiro, R. C.; Scanlan, T. S. A high-affinity subtype-selective agonist ligand for the thyroid hormone receptor. Chem. Biol. 1998, 5 (6), 299-306.
11. Nettles, K. W.; Greene, G. L. Ligand control of coregulator recruitment to nuclear receptors. Annu. Rev. Physiol. 2005, 67, 309-333.
12. Kim, C. S. Gelsolin: a novel thyroid hormone receptor-beta interacting protein that modulates tumor progression in a mouse model of follicular thyroid cancer. Endocrinology 2007, 148 (3), 1306-1312.
13. Drews, J. Drug discovery: a historical perspective. Science 2000, 287 (5460), 1960-1964.
14. Glienke, W.; Dolgova, Y.; Muller, I.; Grosch, S.; Binder, J.; Geisslinger, G.; Jonas, D. Induction of apoptosis in human prostate stromal cells by 4-hydroxytamoxifen: an alternative therapy for benign prostate hyperplasia. World J. Urol. 2004, 22 (6), 452-456.
15. Murata, M.; Nakayama, M.; Irie, H.; Yakabe, K.; Fukuma, K.; Katayama, Y.; Maeda, M. Novel biosensor for the rapid measurement of estrogen based on a ligand-receptor interaction. Anal. Sci. 2001, 17 (3), 387-390.
16. Suzuki, S.; Ohno, K.; Santa, T.; Imai, K. Study on interactions of endocrine disruptors with estrogen receptor-beta using fluorescence polarization. Anal. Sci. 2003, 19 (8), 1103-1108.
17. Ohno, K.; Fukushima, T.; Santa, T.; Waizumi, N.; Tokuyama, H.; Maeda, M.; Imai, K. Estrogen receptor binding assay method for endocrine disruptors using fluorescence polarization. Anal. Chem. 2002, 74 (17), 4391-4396.
18. Arnold, L. A.; Estebanez-Perpina, E.; Togashi, M.; Shelat, A.; Ocasio, C. A.; McReynolds, A. C.; Nguyen, P.; Baxter, J. D.; Fletterick, R. J.; Webb, P.; Guy, R. K. A high-throughput screening method to identify small molecule inhibitors of thyroid hormone receptor coactivator binding. Sci. STKE 2006, 2006 (341), 13.
19. Garrett, S. D.; Lee, H. A.; Morgan, M. R. A nonisotopic estrogen receptor-based assay to detect estrogenic compounds. Nat. Biotechnol. 1999, 17 (12), 1219-1222.
20. Crowther, J. R. The ELISA Guidebook. Methods in Molecular Biology; Humana Press: Totowa, NJ, 2000.
21. Kim, S. H.; Tamrazi, A.; Carlson, K. E.; Daniels, J. R.; Lee, I. Y.; Katzenellenbogen, J. A. Estrogen receptor microarrays: subtype-selective ligand binding. J. Am. Chem. Soc. 2004, 126 (15), 4754-4655.
22. Kim, S. H.; Tamrazi, A.; Carlson, K. E.; Katzenellenbogen, J. A. A proteomic microarray approach for exploring ligand-initiated nuclear hormone receptor pharmacology, receptor selectivity, and heterodimer functionality. Mol. Cell. Proteomics 2005, 4 (3), 267-277.
23. Rich, R. L.; Hoth, L. R.; Geoghegan, K. F.; Brown, T. A.; LeMotte, P. K.; Simons, S. P.; Hensley, P.; Myszka, D. G. Kinetic analysis of estrogen receptor/ligand interactions. Proc. Natl. Acad. Sci. U.S.A. 2002, 99 (13), 8562-8567.
24. De, S.; Macara, I. G.; Lannigan, D. A. Novel biosensors for the detection of estrogen receptor ligands. J. Steroid Biochem. Mol. Biol. 2005, 96 (3-4), 235-244.
25. Folkertsma, S.; van Noort, P. I.; de Heer, A.; Carati, P.; Brandt, R.; Visser, A.; Vriend, G.; de Vlieg, J. The use of in vitro peptide binding profiles and in silico ligand-receptor interaction profiles to describe ligand-induced conformations of the retinoid X receptor alpha ligand-binding domain. Mol. Endocrinol. 2007, 21 (1), 30-48.
26. Whitby, R. J.; Dixon, S.; Maloney, P. R.; Delerive, P.; Goodwin, B. J.; Parks, D. J.; Willson, T. M. Identification of small molecule agonists of the orphan nuclear receptors liver receptor homolog-1 and steroidogenic factor-1. J. Med. Chem. 2006, 49 (23), 6652-6655.
27. Liu, J.; Knappenberger, K. S.; Kack, H.; Andersson, G.; Nilsson, E.; Dartsch, C.; Scott, C. W. A homogeneous in vitro functional assay for estrogen receptors: coactivator recruitment. Mol. Endocrinol. 2003, 17 (3), 346-355.
28. Weatherman, R. V.; Chang, C. Y.; Clegg, N. J.; Carroll, D. C.; Day, R. N.; Baxter, J. D.; McDonnell, D. P.; Scanlan, T. S.; Schaufele, F. Ligand-selective interactions of ER detected in living cells by fluorescence resonance energy transfer. Mol. Endocrinol. 2002, 16 (3), 487-496.
29. Owens, W.; Koeter, H. B. The OECD program to validate the rat uterotrophic bioassay: an overview. Environ. Health Perspect. 2003, 111 (12), 1527-1529.
30. Diel, P.; Schmidt, S.; Vollmer, G. In vivo test systems for the quantitative and qualitative analysis of the biological activity of phytoestrogens. J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2002, 777 (1-2), 191-202.
31. Zacharewski, T. In vitro bioassays for assessing estrogenic substances. Environ. Sci. Technol. 1997, 31, 613-623.
32. Willson, T. M.; Henke, B. R.; Momtahen, T. M.; Charifson, P. S.; Batchelor, K. W.; Lubahn, D. B.; Moore, L. B.; Oliver, B. B.; Sauls, H. R.; Triantafillou, J. A.; Wolfe, S. G.; Baer, P. G. 3-[4-(1,2-Diphenylbut-1-enyl) phenyl]acrylic acid: a non-steroidal estrogen with functional selectivity for bone over uterus in rats. J. Med. Chem. 1994, 37 (11), 1550-1552.
33. Jordan, V. C. Tamoxifen (ICI46,474) as a targeted therapy to treat and prevent breast cancer. Br. J. Pharmacol. 2006, 147 Suppl 1, S269-S276.
34. Sato, M.; Rippy, M. K.; Bryant, H. U. Raloxifene, tamoxifen, nafoxidine, or estrogen effects on reproductive and nonreproductive tissues in ovariectomized rats. FASEB J. 1996, 10 (8), 905-912.
35. Gray, L. E., Jr.; Kelce, W. R.; Wiese, T.; Tyl, R.; Gaido, K.; Cook, J.; Klinefelter, G.; Desaulniers, D.; Wilson, E.; Zacharewski, T.; Waller, C.; Foster, P.; Laskey, J.; Reel, J.; Giesy, J.; Laws, S.; McLachlan, J.; Breslin, W.; Cooper, R.; Di Giulio, R.; Johnson, R.; Purdy, R.; Mihaich, E.; Safe, S.; Colborn, T. et al. Endocrine Screening Methods Workshop report: detection of estrogenic and androgenic hormonal and antihormonal activity for chemicals that act via receptor or steroidogenic enzyme mechanisms. Reprod. Toxicol. 1997, 11 (5), 719-750.
36. Olea, N.; Sakabe, K.; Soto, A. M.; Sonnenschein, C. The proliferative effect of "anti-androgens" on the androgen-sensitive human prostate tumor cell line LNCaP. Endocrinology 1990, 126 (3), 1457-1463.
37. Joyeux, A.; Balaguer, P.; Germain, P.; Boussioux, A. M.; Pons, M.; Nicolas, J. C. Engineered cell lines as a tool for monitoring biological activity of hormone analogs. Anal. Biochem. 1997, 249 (2), 119-130.
38. Kim, S. B.; Ozawa, T.; Umezawa, Y. A genetically encoded indicator for assaying bioactive chemicals that induce nuclear transport of glucocorticoid receptor. Anal. Biochem. 2005, 347 (2), 213-220.
39. Kim, S. B.; Ozawa, T.; Watanabe, S.; Umezawa, Y. High-throughput sensing and noninvasive imaging of protein nuclear transport by using reconstitution of split Renilla luciferase. Proc. Natl. Acad. Sci. U.S.A. 2004, 101 (32), 11542-11547.
40. Perler, F. B. InBase: the intein database. Nucleic Acids Res. 2002, 30 (1), 383-4.
41. Saleh, L.; Perler, F. B. Protein splicing in cis and in trans. Chem. Rec. 2006, 6 (4), 183-193.
42. Kim, S. B.; Ozawa, T.; Umezawa, Y. Genetically encoded stress indicator for noninvasively imaging endogenous corticosterone in living mice. Anal. Chem. 2005, 77 (20), 6588-6593.
43. Paulmurugan, R.; Gambhir, S. S. An intramolecular folding sensor for imaging estrogen receptor-ligand interactions. Proc. Natl. Acad. Sci. U.S.A. 2006, 103 (43), 15883-15888.
44. Breinholt, V.; Larsen, J. C. Detection of weak estrogenic flavonoids using a recombinant yeast strain and a modified MCF7 cell proliferation assay. Chem. Res. Toxicol. 1998, 11 (6), 622-629.
45. Hasenbrink, G.; Sievernich, A.; Wildt, L.; Ludwig, J.; Lichtenberg-Frate, H. Estrogenic effects of natural and synthetic compounds including tibolone assessed in Saccharomyces cerevisiae expressing the human estrogen alpha and beta receptors. FASEB J. 2006, 20 (9), 1552-1554.
46. Chen, Z.; Zhao, H. A highly efficient and sensitive screening method for trans-activation activity of estrogen receptors. Gene 2003, 306, 127-134.
47. Azizi, B.; Chang, E. I.; Doyle, D. F. Chemical complementation: small-molecule-based genetic selection in yeast. Biochem. Biophys. Res. Commun. 2003, 306 (3), 774-780.
48. Chen, Z.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A.; Zhao, H. Directed evolution of human estrogen receptor variants with significantly enhanced androgen specificity and affinity. J. Biol. Chem. 2004, 279 (32), 33855-33864.
49. Chen, Z.; Zhao, H. Rapid creation of a novel protein function by in vitro coevolution. J. Mol. Biol. 2005, 348 (5), 1273-1282.
50. Schwimmer, L. J.; Rohatgi, P.; Azizi, B.; Seley, K. L.; Doyle, D. F. Creation and discovery of ligand-receptor pairs for transcriptional control with small molecules. Proc. Natl. Acad. Sci. U.S.A. 2004, 101 (41), 14707-14712.
51. Chockalingam, K.; Chen, Z.; Katzenellenbogen, J. A.; Zhao, H. Directed evolution of specific receptor-ligand pairs for use in the creation of gene switches. Proc. Natl. Acad. Sci. U.S.A. 2005, 102 (16), 5691-5696.
52. Chen, Y.; Rice, P. A. New insight into site-specific recombination from Flp recombinase-DNA structures. Annu. Rev. Biophys. Biomol. Struct. 2003, 32, 135-159.
53. Nichols, M.; Rientjes, J. M.; Logie, C.; Stewart, A. F. FLP recombinase/estrogen receptor fusion proteins require the receptor D domain for responsiveness to antagonists, but not agonists. Mol. Endocrinol. 1997, 11 (7), 950-961.
54. Logie, C.; Nichols, M.; Myles, K.; Funder, J. W.; Stewart, A. F. Positive and negative discrimination of estrogen receptor agonists and antagonists using site-specific DNA recombinase fusion proteins. Mol. Endocrinol. 1998, 12 (8), 1120-1132.
55. Tucker, C. L.; Fields, S. A yeast sensor of ligand binding. Nat. Biotechnol. 2001, 19 (11), 1042-1046.
56. Israel, D. I.; Kaufman, R. J. Dexamethasone negatively regulates the activity of a chimeric dihydrofolate reductase/glucocorticoid receptor protein. Proc. Natl. Acad. Sci. U.S.A. 1993, 90 (9), 4290-4294.
57. Scherrer, L. C.; Picard, D.; Massa, E.; Harmon, J. M.; Simons, S. S., Jr.; Yamamoto, K. R.; Pratt, W. B. Evidence that the hormone binding domain of steroid receptors confers hormonal control on chimeric proteins by determining their hormone-regulated binding to heat-shock protein 90. Biochemistry 1993, 32 (20), 5381-5386.
58. Muddana, S. S.; Peterson, B. R. Fluorescent cellular sensors of steroid receptor ligands. Chembiochem 2003, 4 (9), 848-855.
59. Waldo, G. S.; Standish, B. M.; Berendzen, J.; Terwilliger, T. C. Rapid protein-folding assay using green fluorescent protein. Nat. Biotechnol. 1999, 17 (7), 691-695.
60. Skretas, G.; Wood, D. W. A bacterial biosensor of endocrine modulators. J. Mol. Biol. 2005, 349 (3), 464-474.
61. Power, R. F.; Conneely, O. M.; McDonnell, D. P.; Clark, J. H.; Butt, T. R.; Schrader, W. T.; O'Malley, B. W. High level expression of a truncated chicken progesterone receptor in Escherichia coli. J. Biol. Chem. 1990, 265 (3), 1419-1424.
62. Srinivasan, G. Overexpression of receptors of tire steroid/thyroid family. Mol. Endocrinol. 1992, 6 (6), 857-860.
63. Wittliff, J. L.; Wenz, L. L.; Dong, J.; Nawaz, Z.; Butt, T. R. Expression and characterization of an active human estrogen receptor as a ubiquitin fusion protein from Escherichia coli. J. Biol. Chem. 1990, 265 (35), 22016-22022.
64. Wooge, C. H.; Nilsson, G. M.; Heierson, A.; McDonnell, D. P.; Katzenellenbogen, B. S. Structural requirements for high affinity ligand binding by estrogen receptors: a comparative analysis of truncated and full length estrogen receptors expressed in bacteria, yeast, and mammalian cells. Mol. Endocrinol. 1992, 6 (6), 861-869.
65. Wood, D. W.; Wu, W.; Belfort, G.; Derbyshire, V.; Belfort, M. A genetic system yields self-cleaving inteins for bioseparations. Nat. Biotechnol. 1999, 17 (9), 889-892.
66. Belfort, M.; Pedersen-Lane, J. Genetic system for analyzing Escherichia coli thymidylate synthase. J. Bacteriol. 1984, 160 (1), 371-378.
67. Skretas, G.; Meligova, A. K.; Villalonga-Barber, C.; Mitsiou, D. J.; Alexis, M. N.; Micha-Screttas, M.; Steele, B. R.; Screttas, C. G.; Wood, D. W. Engineered chimeric enzymes as tools for drug discovery: generating reliable bacterial screens for the detection, discovery, and assessment of estrogen receptor modulators. J. Am. Chem. Soc. 2007, 129 (27), 8443-8457.
68. Skretas, G.; Wood, D. W. Rapid detection of subtype-selective nuclear hormone receptor binding with bacterial genetic selection. Appl. Environ. Microbiol. 2005, 71 (12), 8995-8997.
69. Tran, D. Q.; Jin, L.; Chen, J.; McLachlan, J. A.; Arnold, S. F. Evaluation of clinical and environmental anti-estrogens with human estrogen receptor expressed in Saccharomyces cerevisiae: a novel role for ABC-cassette transporters in mediating anti-estrogenic activity. Biochem. Biophys. Res. Commun. 1997, 235, 669-674.
70. Jisa, E.; Dornstauder, E.; Ogawa, S.; Inoue, S.; Muramatsu, M.; Jungbauer, A. Transcriptional activities of estrogen receptor alpha and beta in yeast properties of raloxifene. Biochem. Pharmacol. 2001, 62 (7), 953-961.
71. Horswill, A. R.; Benkovic, S. J. Cyclic peptides, a chemical genetics tool for biologists. Cell Cycle 2005, 4 (4), 552-555.
72. Scott, C. P.; Abel-Santos, E.; Jones, A. D.; Benkovic, S. J. Structural requirements for the biosynthesis of backbone cyclic peptide libraries. Chem. Biol. 2001, 8 (8), 801-815.
73. Horswill, A. R.; Savinov, S. N.; Benkovic, S. J. A systematic method for identifying small-molecule modulators of protein-protein interactions. Proc. Natl. Acad. Sci. U.S.A. 2004, 101 (44), 15591-15596.
74. Kinsella, T. M.; Ohashi, C. T.; Harder, A. G.; Yam, G. C.; Li, W.; Peelle, B.; Pali, E. S.; Bennett, M. K.; Molineaux, S. M.; Anderson, D. A.; Masuda, E. S.; Payan, D. G. Retrovirally delivered random cyclic peptide libraries yield inhibitors of interleukin-4 signaling in human B cells. J. Biol. Chem. 2002, 277 (40), 37512-37518.
75. DeFreest, L. A.; Mesfin, F. B.; Joseph, L.; McLeod, D. J.; Stallmer, A.; Reddy, S.; Balulad, S. S.; Jacobson, H. I.; Andersen, T. T.; Bennett, J. A. Synthetic peptide derived from alpha-fetoprotein inhibits growth of human breast cancer: investigation of the pharmacophore and synthesis optimization. J. Pept. Res. 2004, 63 (5), 409-419.
76. Bennett, J. A.; Mesfin, F. B.; Andersen, T. T.; Gierthy, J. F.; Jacobson, H. I. A peptide derived from alpha-fetoprotein prevents the growth of estrogen-dependent human breast cancers sensitive and resistant to tamoxifen. Proc. Natl. Acad. Sci. U.S.A. 2002, 99 (4), 2211-2215.
77. Mesfin, F. B.; Bennett, J. A.; Jacobson, H. I.; Zhu, S.; Andersen, T. T. Alpha-fetoprotein-derived antiestrotrophic octapeptide. Biochim. Biophys. Acta 2000, 1501 (1), 33-43.
78. Kirschner, K. N.; Lexa, K. W.; Salisburg, A. M.; Alser, K. A.; Joseph, L.; Andersen, T. T.; Bennett, J. A.; Jacobson, H. I.; Shields, G. C. Computational design and experimental discovery of an antiestrogenic peptide derived from alpha-fetoprotein. J. Am. Chem. Soc. 2007, 129 (19), 6263-6268.
79. Kasher, R.; Gayer, B.; Kulik, T.; Somjen, D.; Venkatesh, N.; Fridkin, M.; Katchalski-Katzir, E.; Kohen, F. Design, synthesis, and evaluation of peptides with estrogen-like activity. Biopolymers 2004, 76 (5), 404-420.
80. Venkatesh, N.; Zaltsman, Y.; Somjen, D.; Gayer, B.; Boopathi, E.; Kasher, R.; Kulik, T.; Katchalski-Katzir, E.; Kohen, F. A synthetic peptide with estrogen-like activity derived from a phage-display peptide library. Peptides 2002, 23 (3), 573-580.
81. Breithofer, A.; Graumann, K.; Scicchitano, M. S.; Karathanasis, S. K.; Butt, T. R.; Jangbauer, A. Regulation of human estrogen receptor by phytoestrogens in yeast and human cells. J. Steroid Biochem. Mol. Biol. 1998, 67, 421-429.
82. Norris, J. D.; Paige, L. A.; Christensen, D. J.; Chang, C.-Y.; Huacani, M. R.; Fan, D.; Hamilton, P. T.; Fowlkes, D. M.; McDonnell, D. P. Peptide antagonists of the human estrogen receptor. Science 1999, 285 (5428), 744-746.