Page 88 - Read Online

Pippione et al. Steroidogenic enzymes in prostate cancer

2014;20:5547-57. prostate cancer drugs abiraterone and TOK-001. Nature 2012;482:116-
15. Montgomery RB, Mostaghel EA, Vessella R, Hess DL, Kalhorn 9.
TF, Higano CS, True LD, Nelson PS. Maintenance of intratumoral 33. Petrunak EM, DeVore NM, Porubsky PR, Scott EE. Structures of
androgens in metastatic prostate cancer: a mechanism for castration- human steroidogenic cytochrome P450 17A1 with substrates. J Biol
resistant tumor growth. Cancer Res 2008;68:4447-54. Chem 2014;289:32952-64.
16. Miller WL, Auchus RJ. The molecular biology, biochemistry, and 34. Estrada DF, Skinner AL, Laurence JS, Scott EE. Human cytochrome
physiology of human steroidogenesis and its disorders. Endocr Rev P450 17A1 conformational selection: modulation by ligand and
2011;32:81-151. cytochrome b5. J Biol Chem 2014;289:14310-20.
17. Stanbrough M, Bubley GJ, Ross K, Golub TR, Rubin MA, Penning 35. Gomez L, Kovac JR, Lamb DJ. CYP17A1 inhibitors in castration-
TM, Febbo PG, Balk SP. Increased expression of genes converting resistant prostate cancer. Steroids 2015;95:80-7.
adrenal androgens to testosterone in androgen-independent prostate 36. Njar VCO, Brodie AMH. Discovery and development of galeterone
cancer. Cancer Res 2006;66:2815-25. (TOK-001 or VN/124-1) for the treatment of all stages of prostate
18. Chang KH, Li R, Papari-Zareei M, Watumull L, Zhao YD, Auchus cancer. J Med Chem 2015;58:2077-87.
RJ, Sharifi N. Dihydrotestosterone synthesis bypasses testosterone to 37. Handratta VD, Vasaitis TS, Njar VC, Gediya LK, Kataria R, Chopra
drive castration-resistant prostate cancer. Proc Natl Acad Sci U S A P, Newman D Jr, Farquhar R, Guo Z, Qiu Y, Brodie AM. Novel C-17-
2011;108:13728-33. heteroaryl steroidal CYP17 inhibitors/antiandrogens: synthesis, in
19. Campbell TJ, Tindall DJ, Figg WD. Dihydrotestosterone synthesis vitro biological activity, pharmacokinetics, and antitumor activity
from adrenal precursors does not involve testosterone in castration- in the LAPC4 human prostate cancer xenograft model. J Med Chem
resistant prostate cancer. Cancer Biol Ther 2012;13:237-8. 2005;48:2972-84.
20. Wilson JD, Auchus RJ, Leihy MW, Guryev OL, Estabrook RW, 38. Ryan CJ, Smith MR, de Bono JS, Molina A, Logothetis CJ, de Souza
Osborn SM, Shaw G, Renfree MB. 5alpha-androstane-3alpha,17beta- P, Fizazi K, Mainwaring P, Piulats JM, Ng S, Carles J, Mulders PF,
diol is formed in tammar wallaby pouch young testes by a pathway Basch E, Small EJ, Saad F, Schrijvers D, Van Poppel H, Mukherjee
involving 5alpha-pregnane-3alpha,17alpha-diol-20-one as a key SD, Suttmann H, Gerritsen WR, Flaig TW, George DJ, Yu EY,
intermediate. Endocrinology 2003;144:575-80. Efstathiou E, Pantuck A, Winquist E, Higano CS, Taplin ME, Park
21. Auchus RJ. The backdoor pathway to dihydrotestosterone. Trends Y, Kheoh T, Griffin T, Scher HI, Rathkopf DE; COU-AA-302
Endocrinol Metab 2004;15:432-8. Investigators. Abiraterone in metastatic prostate cancer without
22. Locke JA, Guns ES, Lubik AA, Adomat HH, Hendy SC, Wood CA, previous chemotherapy. N Engl J Med 2013;368:138-48.
Ettinger SL, Gleave ME, Nelson CC. Androgen levels increase by 39. Kaku T, Hitaka T, Ojida A, Matsunaga N, Adachi M, Tanaka T, Hara
intratumoral de novo steroidogenesis during progression of castration- T, Yamaoka M, Kusaka M, Okuda T, Asahi S, Furuya S, Tasaka
resistant prostate cancer. Cancer Res 2008;68:6407-15. A. Discovery of orteronel (TAK-700), a naphthylmethylimidazole
23. Locke JA, Nelson CC, Adomat HH, Hendy SC, Gleave ME, derivative, as a highly selective 17,20-lyase inhibitor with potential
Guns ES. Steroidogenesis inhibitors alter but do not eliminate utility in the treatment of prostate cancer. Bioorg Med Chem
androgen synthesis mechanisms during progression to castration- 2011;19:6383-99.
resistance in LNCaP prostate xenografts. J Steroid Biochem Mol Biol 40. Toren PJ, Kim S, Pham S, Mangalji A, Adomat H, Guns ES, Zoubeidi
2009;115:126-36. A, Moore W, Gleave ME. Anticancer activity of a novel selective
24. Stuchbery R, McCoy PJ, Hovens CM, Corcoran NM. Androgen CYP17A1 inhibitor in preclinical models of castrate-resistant prostate
synthesis in prostate cancer: do all roads lead to Rome? Nat Rev Urol cancer. Mol Cancer Ther 2015;14:59-69.
2017;14:49-58. 41. Larsen M, Hansen CH, Rasmussen TB, Islin J, Styrishave B,
25. Missaghian E, Kempna P, Dick B, Hirsch A, Alikhani-Koupaei R, Olsen L, Jorgensen FS. Structure-based optimisation of non-
Jegou B, Mullis PE, Frey BM, Fluck CE. Role of DNA methylation steroidal cytochrome P450 17A1 inhibitors. Chem Commun (Camb)
in the tissue-specific expression of the CYP17A1 gene for 2017;53:3118-21.
steroidogenesis in rodents. J Endocrinol 2009;202:99-109. 42. Bonomo S, Hansen CH, Petrunak EM, Scott EE, Styrishave B,
26. Chung BC, Picado-Leonard J, Haniu M, Bienkowski M, Hall PF, Jorgensen FS, Olsen L. Promising tools in prostate cancer research:
Shively JE, Miller WL. Cytochrome P450c17 (steroid 17 alpha- selective non-steroidal cytochrome P450 17A1 inhibitors. Sci Rep
hydroxylase/17,20 lyase): cloning of human adrenal and testis cDNAs 2016;6:29468.
indicates the same gene is expressed in both tissues. Proc Natl Acad 43. Wang M, Fang Y, Gu S, Chen F, Zhu Z, Sun X, Zhu J. Discovery of
Sci U S A 1987;84:407-11. novel 1,2,3,4-tetrahydrobenzo[4, 5]thieno[2, 3-c]pyridine derivatives
27. Martinez-Arguelles DB, Papadopoulos V. Epigenetic regulation of as potent and selective CYP17 inhibitors. Eur J Med Chem
the expression of genes involved in steroid hormone biosynthesis and 2017;132:157-72.
action. Steroids 2010;75:467-76. 44. Penning TM, Burczynski ME, Jez JM, Lin HK, Ma H, Moore M,
28. Fluck CE, Miller WL. GATA-4 and GATA-6 modulate tissue-specific Ratnam K, Palackal N. Structure-function aspects and inhibitor design
transcription of the human gene for P450c17 by direct interaction with of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3). Mol Cell
Sp1. Mol Endocrinol 2004;18:1144-57. Endocrinol 2001;171:137-49.
29. Yoshimoto FK, Auchus RJ. The diverse chemistry of cytochrome 45. Sun SQ, Gu X, Gao XS, Li Y, Yu H, Xiong W, Yu H, Wang W, Li Y,
P450 17A1 (P450c17, CYP17A1). J Steroid Biochem Mol Biol Teng Y, Zhou D. Overexpression of AKR1C3 significantly enhances
2015;151:52-65. human prostate cancer cells resistance to radiation. Oncotarget
30. Estrada DF, Laurence JS, Scott EE. Substrate-modulated cytochrome 2016;7:48050-8.
P450 17A1 and cytochrome b5 interactions revealed by NMR. J Biol 46. Endo S, Hu D, Matsunaga T, Otsuji Y, El-Kabbani O, Kandeel M,
Chem 2013;288:17008-18. Ikari A, Hara A, Kitade Y, Toyooka N. Synthesis of non-prenyl
31. Manenda MS, Hamel CJ, Masselot-Joubert L, Picard ME, Shi R. analogues of baccharin as selective and potent inhibitors for aldo-keto
Androgen-metabolizing enzymes: a structural perspective. J Steroid reductase 1C3. Bioorg Med Chem 2014;22:5220-33.
Biochem Mol Biol 2016;161:54-72. 47. Lovering AL, Ride JP, Bunce CM, Desmond JC, Cummings SM,
32. DeVore NM, Scott EE. Structures of cytochrome P450 17A1 with White SA. Crystal structures of prostaglandin D2 11-ketoreductase

356 Journal of Cancer Metastasis and Treatment ¦ Volume 3 ¦ December 12, 2017