Subtle structural changes in tetrahydroquinolines, a new class of nonsteroidal selective androgen receptor modulators, induce different functions

Journal of Chemical Information and Modeling

Volumn 52, Issue 8, 2012, Pages 2257-2264

  Nagata, Naoya ^a   Kawai, Kentaro ^a   Nakanishi, Isao ^b  

^a KAKEN PHARMACEUTICAL CO LTD   (Japan)

^b KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUPS; HYDROGEN BONDS;

AGONISTIC ACTIVITY; ANDROGEN RECEPTORS; CYANO GROUPS; DIHYDROTESTOSTERONE; HYDROXYL GROUPS; LIGAND BINDING; MOLECULAR DYNAMICS SIMULATIONS; TETRAHYDROQUINOLINES;

MOLECULAR DYNAMICS;

1,2,3,4 TETRAHYDROQUINOLINE; 1,2,3,4-TETRAHYDROQUINOLINE; ANDROGEN; ANDROGEN RECEPTOR; ANDROGEN RECEPTOR ANTAGONIST; QUINOLINE DERIVATIVE;

ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; METABOLISM; MOLECULAR DYNAMICS; PROTEIN CONFORMATION; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS;

ANDROGEN RECEPTOR ANTAGONISTS; ANDROGENS; MOLECULAR DYNAMICS SIMULATION; PROTEIN CONFORMATION; QUINOLINES; RECEPTORS, ANDROGEN; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; THERMODYNAMICS;

EID: 84865499206     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci300219g     Document Type: Article

References (37)

1. Mohler, M. L.; Bohl, C. E.; Jones, A.; Coss, C. C.; Narayanan, R.; He, Y.; Hwang, D. J.; Dalton, J. T.; Miller, D. D. Nonsteroidal selective androgen receptor modulators (SARMs): dissociating the anabolic and androgenic activities of the androgen receptor for therapeutic benefit J. Med. Chem. 2009, 52, 3597-3617
2. Narayanan, R.; Mohler, M. L.; Bohl, C. E.; Miller, D. D.; Dalton, J. T. Selective androgen receptor modulators in preclinical and clinical development Nucl. Recept. Signaling 2008, 6, e010
3. Gao, W.; Bohl, C. E.; Dalton, J. T. Chemistry and structural biology of androgen receptor Chem. Rev. 2005, 105, 3552-3370
4. Takeda, H.; Chodak, G.; Mutchnik, S.; Nakamoto, T.; Chang, C. Immunohistochemical localization of androgen receptors with mono- and polyclonal antibodies to androgen receptor J. Endocrinol. 1990, 126, 17-25 (Pubitemid 20203860)
5. Davis, S. Androgen replacement in women: a commentary J. Clin. Endocrinol. Metab. 1999, 84, 1886-1891 (Pubitemid 30647004)
6. Davis, S. R. The therapeutic use of androgens in women J. Steroid Biochem. Mol. Biol. 1999, 69, 177-184 (Pubitemid 29305535)
7. Rosen, J.; Negro-Vilar, A. Novel, non-steroidal, selective androgen receptor modulators (SARMs) with anabolic activity in bone and muscle and improved safety profile J. Musculoskeletal Neuronal Interact. 2002, 2, 222-224 (Pubitemid 34223808)
8. Tobias, S. C.; Qiu, J.; Kelly, M. J.; Scanlan, T. S. Synthesis and biological evaluation of SERMs with potent nongenomic estrogenic activity ChemMedChem 2006, 1, 565-571 (Pubitemid 43759768)
9. Kim, J.; Wu, D.; Hwang, D. J.; Miller, D. D.; Dalton, J. T. The para substituent of S-3-(phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl- phenyl)-propionamides is a major structural determinant of in vivo disposition and activity of selective androgen receptor modulators J. Pharmacol. Exp. Ther. 2005, 315, 230-239 (Pubitemid 41380516)
10. Miner, J. N.; Chang, W.; Chapman, M. S.; Finn, P. D.; Hong, M. H.; López, F. J.; Marschke, K. B.; Rosen, J.; Schrader, W.; Turner, R.; van Oeveren, A.; Viveros, H.; Zhi, L.; Negro-Vilar, A. An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate Endocrinology 2007, 148, 363-373 (Pubitemid 46021469)
11. Ostrowski, J.; Kuhns, J. E.; Lupisella, J. A.; Manfredi, M. C.; Beehler, B. C.; Krystek, S. R., Jr.; Bi, Y.; Sun, C.; Seethala, R.; Golla, R.; Sleph, P. G.; Fura, A.; An, Y.; Kish, K. F.; Sack, J. S.; Mookhtiar, K. A.; Grover, G. J.; Hamann, L. G. Pharmacological and X-ray structural characterization of a novel selective androgen receptor modulator: potent hyperanabolic stimulation of skeletal muscle with hypostimulation of prostate in rats Endocrinology 2007, 148, 4-12 (Pubitemid 46023448)
12. Miller, C. P.; Shomali, M.; Lyttle, C. R.; O'Dea, L. S.; Herendeen, H.; Gallacher, K.; Paquin, D.; Compton, D. R.; Sahoo, B.; Kerrigan, S. A.; Burge, M. S.; Nickels, M.; Green, J. L.; Katzenellenbogen, J. A.; Tchesnokov, A.; Hattersley, G. Design, synthesis, and preclinical characterization of the selective androgen receptor modulator (SARM) RAD140 ACS Med. Chem. Lett. 2011, 2, 124-129
13. Gronemeyer, H.; Gustafsson, J. Å.; Laudet, V. Principles for modulation of the nuclear receptor superfamily Nat. Rev. Drug Discovery 2004, 3, 950-964 (Pubitemid 39534319)
14. Renaud, J. P.; Moras, D. Structural studies on nuclear receptors Cell. Mol. Life Sci. 2000, 57, 1748-1769
15. Steinmetz, A. C.; Renaud, J. P.; Moras, D. Binding of ligands and activation of transcription by nuclear receptors Annu. Rev. Biophys. Biomol. Struct. 2001, 30, 329-359 (Pubitemid 32566167)
16. Weatherman, R. V.; Fletterick, R. J.; Scanlan, T. S. Nuclear-receptor ligands and ligand-binding domains Annu. Rev. Biochem. 1999, 68, 559-581 (Pubitemid 29449203)
17. Shiau, A. K.; Barstad, D.; Radek, J. T.; Meyers, M. J.; Nettles, K. W.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A.; Agard, D. A.; Greene, G. L. Structural characterization of a subtype-selective ligand reveals a novel mode of estrogen receptor antagonism Nat. Struct. Biol. 2002, 9, 359-364 (Pubitemid 34462554)
18. Singh, S. M.; Gauthier, S.; Labrie, F. Androgen receptor antagonists (antiandrogens): structure-activity relationships Curr. Med. Chem. 2000, 7, 211-247 (Pubitemid 30396447)
19. Bisson, W. H.; Abagyan, R.; Cavasotto, C. N. Molecular basis of agonicity and antagonicity in the androgen receptor studied by molecular dynamics simulations J. Mol. Graphics Modell. 2008, 4, 452-458
20. A receptors containing the α5 subunit J. Med. Chem. 2008, 51, 3788-3803 (Pubitemid 351956510)
21. Nagata, N.; Miyakawa, M.; Amano, S.; Furuya, K.; Yamamoto, N.; Inoguchi, K. Design and synthesis of tricyclic tetrahydroquinolines as a new series of nonsteroidal selective androgen receptor modulators (SARMs) Bioorg. Med. Chem. Lett. 2011, 21, 1744-1747
22. Nagata, N.; Miyakawa, M.; Amano, S.; Furuya, K.; Yamamoto, N.; Nejishima, H.; Inoguchi, K. Tetrahydroquinolines as a novel series of nonsteroidal selective androgen receptor modulators: Structural requirement for better physicochemical and biological properties Bioorg. Med. Chem. Lett. 2011, 21, 6310-6313
23. Hanada, K.; Furuya, K.; Yamamoto, N.; Nejishima, H.; Ichikawa, K.; Nakamura, T.; Miyakawa, M.; Amano, S.; Sumita, Y.; Oguro, N. Bone anabolic effects of S-40503, a novel nonsteroidal selective androgen receptor modulator (SARM), in rat models of osteoporosis Biol. Pharm. Bull. 2003, 26, 1563-1569 (Pubitemid 41699636)
24. Berendsen, H. J. C.; van der Spoel, D.; van Drunen, R. GROMACS: a message-passing parallel molecular dynamics implementation Comput. Phys. Commun. 1995, 91, 43-57
25. Lindahl, E.; Hess, B.; van der Spoel, D. GROMACS 3.0: A package for molecular simulation and trajectory analysis J. Mol. Model. 2001, 7, 306-317 (Pubitemid 36153547)
26. Schrödinger Suite 2010; Maestro, version 9.0; Prime MM-GBSA, version 1.4.1; Schrödinger, LLC: New York, NY, 2010.
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, J. Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
28. Wang, J.; Cieplak, P.; Kollman, P. A. How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules? J. Comput. Chem. 2000, 21, 1049-1074
29. Bayly, C. I.; Cieplak, P.; Cornell, W.; Kollman, P. A. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: The RESP model J. Phys. Chem. 1993, 97, 10269-10280
30. Wang, J.; Wolf, R. M.; Caldwell, J. W.; Kollman, P. A.; Case, D. A. Development and testing of a general amber force field J. Comput. Chem. 2004, 25, 1157-1174
31. Hur, E.; Pfaff, S. J.; Payne, E. S.; Grøn, H.; Buehrer, B. M.; Fletterick, R. J. Recognition and accommodation at the androgen receptor coactivator binding interface PLoS Biol. 2004, 2, 1303-1312
32. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. Comparison of simple potential functions for simulating liquid water J. Chem. Phys. 1983, 79, 926-935
33. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; DiNola, A.; Haak, J. R. Molecular dynamics with coupling to an external bath J. Chem. Phys. 1984, 81, 3684-3690
34. Darden, T.; York, D.; Pedersen, L. Particle mesh Ewald: An N -log(N) method for Ewald sums in large system J. Chem. Phys. 1993, 98, 10089-10092
35. Essman, U.; Perera, L.; Berkowitz, M. L.; Darden, T.; Lee, H.; Pedersen, L. G. A smooth particle mesh Ewald method J. Chem. Phys. 1995, 103, 8577-8593
36. Hess, B.; Bekker, H.; Berendsen, H. J. C.; Fraajie, J. G. E. M. LINCS: A linear constraint solver molecular simulations J. Comput. Chem. 1997, 18, 1463-1472 (Pubitemid 127637344)
37. Matias, P. M.; Donner, P.; Coelho, R.; Thomaz, M.; Peixoto, C.; Macedo, S.; Otto, N.; Joschko, S.; Scholz, P.; Wegg, A.; Bäsler, S.; Schäfer, M.; Egner, U.; Carrondo, M. A. Structural evidence for ligand specificity in the binding domain of the human androgen receptor. Implications for pathogenic gene mutations J. Biol. Chem. 2000, 275, 26164-1671