Development of β-amino-carbonyl compounds as androgen receptor antagonists

Acta Pharmacologica Sinica

Volumn 35, Issue 5, 2014, Pages 664-673

  Zhang, Zhi Yun ^a   Zhu, Yan Hui ^a   Zhou, Cai Hong ^a   Liu, Qing ^a   Lu, Hui Li ^a   Ge, Yun Jun ^a   Wang, Ming Wei ^a,b  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

androgen receptor; antagonist; molecular docking; prostate cancer; structural modification; amino carbonyl compound

Indexed keywords

3 [(4 METHOXY 2 NITROPHENYL)AMINO] 1 (4 NITROPHENYL) 3 PHENYLPROPAN 1 OL; ANDROGEN RECEPTOR ANTAGONIST; ANTINEOPLASTIC AGENT; BICALUTAMIDE; CARBONYL DERIVATIVE; PROSTATE SPECIFIC ANTIGEN; UNCLASSIFIED DRUG; ANDROGEN RECEPTOR; AR PROTEIN, HUMAN;

ANIMAL CELL; ANIMAL MODEL; ANIMAL TISSUE; ANTIGEN EXPRESSION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER GROWTH; CANCER INHIBITION; CELL PROLIFERATION; CHIRAL CHROMATOGRAPHY; COMPETITIVE BINDING ASSAY; CONTROLLED STUDY; DRUG DESIGN; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; GENE EXPRESSION; GENE TRANSLOCATION; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; ISOMER; LNCAP CELL LINE; MALE; MOUSE; NONHUMAN; PROSTATE CANCER; REAL TIME POLYMERASE CHAIN REACTION; SCID MOUSE; STEREOISOMERISM; TWO HYBRID SYSTEM; ANIMAL; CELL LINE; DRUG EFFECTS; HEK293 CELL LINE; METABOLISM; NUCLEOLUS; NUDE MOUSE; TUMOR CELL LINE;

ANDROGEN RECEPTOR ANTAGONISTS; ANIMALS; CELL LINE; CELL LINE, TUMOR; CELL NUCLEOLUS; CELL PROLIFERATION; HEK293 CELLS; HUMANS; MALE; MICE, NUDE; MICE, SCID; PROSTATE-SPECIFIC ANTIGEN; RECEPTORS, ANDROGEN;

EID: 84927170772     PISSN: 16714083     EISSN: 17457254     Source Type: Journal    
DOI: 10.1038/aps.2013.201     Document Type: Article

References (17)

1. Siegel R, Naishadham D, Jemal A. Cancer statistics, 2012. CA Cancer J Clin 2012; 62: 10-29.
2. Blackledge GR, Cockshott ID, Furr BJ. Casodex (bicalutamide): overview of a new antiandrogen developed for the treatment of prostate cancer. Eur Urol 1997; 31: 30-9.
3. Kolvenbag GJ, Blackledge GR, Gotting-Smith K. Bicalutamide (Casodex) in the treatment of prostate cancer: history of clinical development. Prostate 1998; 34: 61-72.
4. Tyrrell CJ, Kaisary AV, Iversen P, Anderson JB, Baert L, Tammela T, et al. A randomised comparison of 'Casodex' (bicalutamide) 150 mg monotherapy versus castration in the treatment of metastatic and locally advanced prostate cancer. Eur Urol 1998; 33: 447-56.
5. Müderris II, Bayram F, Ozçelik B, Güven M. New alternative treatment in hirsutism: bicalutamide 25 mg/day. Gynecol Endocrinol 2002; 16: 63-6.
6. Colabufo NA, Pagliarulo V, Berardi F, Contino M, Inglese C, Niso M, et al. Bicalutamide failure in prostate cancer treatment: involvement of Multi Drug Resistance proteins. Eur J Pharmacol 2008; 601: 38-42.
7. Wang Q, Li W, Zhang Y, Yuan X, Xu K, Yu J, et al. Androgen receptor regulates a distinct transcription program in androgen-independent prostate cancer. Cell 2009; 138: 245-56.
8. Tran C, Ouk S, Clegg NJ, Chen Y, Watson PA, Arora V, et al. Development of a second-generation antiandrogen for treatment of advanced prostate cancer. Science 2009; 324: 787-90.
9. Schaufele F, Carbonell X, Guerbadot M, Borngraeber S, Chapman MS, Ma AA, et al. The structural basis of androgen receptor activation: intramolecular and intermolecular amino-carboxy interactions. Proc Natl Acad Sci U S A 2005; 102: 9802-7.
10. Zhou C, Wu G, Feng Y, Li Q, Su H, Mais DE, et al. Discovery and biological characterization of a novel series of androgen receptor modulators. Br J Pharmacol 2008; 154: 440-50.
11. Ning M, Zhou C, Weng J, Zhang S, Chen D, Yang C, et al. Biological activities of a novel selective oestrogen receptor modulator derived from raloxifene (Y134). Br J Pharmacol 2007; 150: 19-28.
12. Bohl CE, Miller DD, Chen J, Bell CE, Dalton JT. Structural basis for accommodation of nonsteroidal ligands in the androgen receptor. J Biol Chem 2005; 280: 37747-54.
13. Sun C, Shi Y, Xu LL, Nageswararao C, Davis LD, Segawa T, et al. Androgen receptor mutation (T877A) promotes prostate cancer cell growth and cell survival. Oncogene 2006; 25: 3905-13.
14. Ishiguro H, Ishiguro Y, Kubota Y, Uemura H. Regulation of prostate cancer cell growth and PSA expression by angiotensin II receptor blocker with peroxisome proliferator-activated receptor gamma ligand like action. Prostate 2007; 67: 924-32.
15. Kang Z, Pirskanen A, Jänne OA, Palvimo JJ. Involvement of proteasome in the dynamic assembly of the androgen receptor transcription complex. J Biol Chem 2002; 277: 48366-71.
16. Bai VU, Cifuentes E, Menon M, Barrack ER, Reddy GP. Androgen receptor regulates Cdc6 in synchronized LNCaP cells progressing from G1 to S phase. J Cell Physiol 2005; 204: 381-7.
17. Zhang J, Hsu B A JC, Kinseth B A MA, Bjeldanes LF, Firestone GL. Indole-3-carbinol induces a G1 cell cycle arrest and inhibits prostatespecific antigen production in human LNCaP prostate carcinoma cells. Cancer 2003; 98: 2511-20.