phenylthiohydantoin

Summary

Summary: Thiohydantoin benzene derivative.

Top Publications

  1. Grant G, Crankshaw M. Identification of PTH-amino acids by HPLC. Methods Mol Biol. 2003;211:247-68 pubmed
  2. Clegg N, Wongvipat J, Joseph J, Tran C, Ouk S, Dilhas A, et al. ARN-509: a novel antiandrogen for prostate cancer treatment. Cancer Res. 2012;72:1494-503 pubmed publisher
    ..Our findings offer preclinical proof of principle for ARN-509 as a promising therapeutic in both castration-sensitive and castration-resistant forms of prostate cancer. ..
  3. Schrader A, Boegemann M, Ohlmann C, Schnoeller T, Krabbe L, Hajili T, et al. Enzalutamide in castration-resistant prostate cancer patients progressing after docetaxel and abiraterone. Eur Urol. 2014;65:30-6 pubmed publisher
    ..Although cross-resistance between abiraterone and enzalutamide was a common phenomenon, it was not inevitable, and a small but significant number of patients showed significant benefit from sequential treatment. ..
  4. Noonan K, North S, Bitting R, Armstrong A, Ellard S, Chi K. Clinical activity of abiraterone acetate in patients with metastatic castration-resistant prostate cancer progressing after enzalutamide. Ann Oncol. 2013;24:1802-7 pubmed publisher
    ..Primary progression on enzalutamide may not preclude a response to abiraterone. ..
  5. Li Y, Chan S, Brand L, Hwang T, Silverstein K, Dehm S. Androgen receptor splice variants mediate enzalutamide resistance in castration-resistant prostate cancer cell lines. Cancer Res. 2013;73:483-9 pubmed publisher
  6. Tran C, Ouk S, Clegg N, Chen Y, Watson P, Arora V, et al. Development of a second-generation antiandrogen for treatment of advanced prostate cancer. Science. 2009;324:787-90 pubmed publisher
    ..These compounds thus appear to be promising candidates for treatment of advanced prostate cancer...
  7. Beer T, Armstrong A, Rathkopf D, Loriot Y, Sternberg C, Higano C, et al. Enzalutamide in metastatic prostate cancer before chemotherapy. N Engl J Med. 2014;371:424-33 pubmed publisher
    ..New treatment options are needed for patients with metastatic prostate cancer who have not received chemotherapy, in whom the disease has progressed despite androgen-deprivation therapy...
  8. Badrising S, van der Noort V, van Oort I, van den Berg H, Los M, Hamberg P, et al. Clinical activity and tolerability of enzalutamide (MDV3100) in patients with metastatic, castration-resistant prostate cancer who progress after docetaxel and abiraterone treatment. Cancer. 2014;120:968-75 pubmed publisher
    ..Enz has modest clinical activity in patients with metastatic, castrate-resistant prostate cancer who previously received Doc and AA. PSA response to Doc and AA does not predict for PSA response to ENz. ..
  9. Lin T, Lee S, Niu Y, Xu D, Liang L, Li L, et al. Differential androgen deprivation therapies with anti-androgens casodex/bicalutamide or MDV3100/Enzalutamide versus anti-androgen receptor ASC-J9(R) Lead to promotion versus suppression of prostate cancer metastasis. J Biol Chem. 2013;288:19359-69 pubmed publisher
    ..These findings suggest the potential risks of using anti-androgens and provide a potential new therapy using ASC-J9® to battle PCa metastasis at the castration-resistant stage. ..

More Information

Publications62

  1. Scher H, Beer T, Higano C, Anand A, Taplin M, Efstathiou E, et al. Antitumour activity of MDV3100 in castration-resistant prostate cancer: a phase 1-2 study. Lancet. 2010;375:1437-46 pubmed publisher
    ..Medivation, the Prostate Cancer Foundation, National Cancer Institute, the Howard Hughes Medical Institute, Doris Duke Charitable Foundation, and Department of Defense Prostate Cancer Clinical Trials Consortium. ..
  2. Loriot Y, Bianchini D, Ileana E, Sandhu S, Patrikidou A, Pezaro C, et al. Antitumour activity of abiraterone acetate against metastatic castration-resistant prostate cancer progressing after docetaxel and enzalutamide (MDV3100). Ann Oncol. 2013;24:1807-12 pubmed publisher
    ..3-4.1). Of the 12 patients assessable radiologically, only 1 (8%) attained a confirmed partial response. Abiraterone and prednisolone have modest antitumour activities in patients with mCRPC pretreated with docetaxel and enzalutamide. ..
  3. Belikov S, Oberg C, Jaaskelainen T, Rahkama V, Palvimo J, Wrange O. FoxA1 corrupts the antiandrogenic effect of bicalutamide but only weakly attenuates the effect of MDV3100 (Enzalutamide™). Mol Cell Endocrinol. 2013;365:95-107 pubmed publisher
  4. Scher H, Fizazi K, Saad F, Taplin M, Sternberg C, Miller K, et al. Increased survival with enzalutamide in prostate cancer after chemotherapy. N Engl J Med. 2012;367:1187-97 pubmed
    ..Funded by Medivation and Astellas Pharma Global Development; AFFIRM ClinicalTrials.gov number, NCT00974311.). ..
  5. Hammerer P, Madersbacher S. Landmarks in hormonal therapy for prostate cancer. BJU Int. 2012;110 Suppl 1:23-9 pubmed publisher
  6. Norris J, Ellison S, Baker J, Stagg D, Wardell S, Park S, et al. Androgen receptor antagonism drives cytochrome P450 17A1 inhibitor efficacy in prostate cancer. J Clin Invest. 2017;127:2326-2338 pubmed publisher
    ..The results of this study suggest that the ability of CYP17 inhibitors to directly antagonize the AR may contribute to their clinical efficacy in CRPC. ..
  7. Ning Y, Pierce W, Maher V, Karuri S, Tang S, Chiu H, et al. Enzalutamide for treatment of patients with metastatic castration-resistant prostate cancer who have previously received docetaxel: U.S. Food and Drug Administration drug approval summary. Clin Cancer Res. 2013;19:6067-73 pubmed publisher
    ..Enzalutamide represents the third product that the FDA has approved in the same disease setting within a period of 2 years. Clin Cancer Res; 19(22); 6067-73. ©2013 AACR. ..
  8. Schwaller B, Sigrist H. Protein modification by diazotized arsanilic acid: synthesis and characterization of the phenylthiohydantoin derivatives of azobenzene arsonate-coupled tyrosine, histidine, and lysine residues and their sequential allotment in labeled peptides. Anal Biochem. 1989;177:183-7 pubmed
    ..The amino acid derivatives phenylthiohydantoin(Pth)-azobenzene-arsonate-tyrosine, Pth-azobenzene-arsonate-histidine, and alpha-Pth-epsilon-hydroxycaproic ..
  9. Ikebe M, Reardon S. Phosphorylation of smooth myosin light chain kinase by smooth muscle Ca2+/calmodulin-dependent multifunctional protein kinase. J Biol Chem. 1990;265:8975-8 pubmed
    ..The preferred site was identified as serine 512 and the second site as serine 525. These sites are the same as the sites phosphorylated by cAMP-dependent protein kinase. ..
  10. Mueller T, Posch U, Lindner H. Separation of phenylthiohydantoin amino acids by capillary electrochromatography. Electrophoresis. 2004;25:578-85 pubmed
    ..CEC) was employed as a rapid and high-efficiency method for the isocratic separation of all 20 important phenylthiohydantoin (PTH) amino acids, the end products of Edman degradation during N-terminal protein sequencing...
  11. Yarabe H, Shamsi S, Warner I. Characterization and thermodynamic studies of the interactions of two chiral polymeric surfactants with model substances: phenylthiohydantoin amino acids. Anal Chem. 1999;71:3992-9 pubmed
    ..Five phenylthiohydantoin-DL-amino acids were separated and each enantiomeric pair was completely resolved...
  12. Evans M, Smith Jones P, Wongvipat J, Navarro V, Kim S, Bander N, et al. Noninvasive measurement of androgen receptor signaling with a positron-emitting radiopharmaceutical that targets prostate-specific membrane antigen. Proc Natl Acad Sci U S A. 2011;108:9578-82 pubmed publisher
  13. el Barbary A, Khodair A, Pedersen E, Nielsen C. S-glucosylated hydantoins as new antiviral agents. J Med Chem. 1994;37:73-7 pubmed
  14. Li H, Hassona M, Lack N, Axerio Cilies P, Leblanc E, Tavassoli P, et al. Characterization of a new class of androgen receptor antagonists with potential therapeutic application in advanced prostate cancer. Mol Cancer Ther. 2013;12:2425-35 pubmed publisher
    ..These results provide a foundation for the development of a new class of androgen receptor antagonists that can help address the problem of antiandrogen resistance in prostate cancer. ..
  15. Cai J, Myers S, Hurst H. Measurement of the hemoglobin N-(2-oxoethyl)valine adduct in ethyl carbamate-treated mice. Toxicol Appl Pharmacol. 1995;131:73-9 pubmed
    ..The adduct valine was cleaved using phenylisothiocyanate to form a substituted phenylthiohydantoin derivative of N-(2-hydroxyethyl)valine in a modified Edman degradation...
  16. Nokihara K, Kuriki T, Morita N. Two-dimensional electrophoresis as a complementary method of isolating peptide fragments of cleaved proteins for internal sequencing. J Chromatogr A. 1994;676:233-8 pubmed
    ..Electroblotted spots were easily sequenced to identify those difficult fragments which could not be obtained using HPLC. ..
  17. Lin T, Izumi K, Lee S, Lin W, Yeh S, Chang C. Anti-androgen receptor ASC-J9 versus anti-androgens MDV3100 (Enzalutamide) or Casodex (Bicalutamide) leads to opposite effects on prostate cancer metastasis via differential modulation of macrophage infiltration and STAT3-CCL2 signaling. Cell Death Dis. 2013;4:e764 pubmed publisher
  18. Rove K, Flaig T. A renaissance in the medical treatment of advanced prostate cancer. Oncology (Williston Park). 2010;24:1308-13, 1318 pubmed
    ..In recent years, however, new therapies have begun to emerge to treat this devastating form of prostate cancer. This review examines the mechanisms behind these therapeutics and the key trials seeking to validate their clinical use. ..
  19. Tempst P, Riviere L. Examination of automated polypeptide sequencing using standard phenyl isothiocyanate reagent and subpicomole high-performance liquid chromatographic analysis. Anal Biochem. 1989;183:290-300 pubmed
    ..Several modifications of the standard system were first introduced. A larger portion of the phenylthiohydantoin amino acids (70%) is analyzed...
  20. Merseburger A, Kuczyk M, Wolff J. [Pathophysiology and therapy of castration-resistant prostate cancer]. Urologe A. 2013;52:219-25 pubmed publisher
    ..To what extent the experimental findings and the recommendations in the guidelines are put into practice was the subject of a survey among urologists analyzing their treatment strategies with CRPC patients...
  21. Zhang T, Agarwal N, Sonpavde G, Dilorenzo G, Bellmunt J, Vogelzang N. Management of castrate resistant prostate cancer-recent advances and optimal sequence of treatments. Curr Urol Rep. 2013;14:174-83 pubmed publisher
    ..We will also propose a strategy for optimal sequencing of these agents in the treatment of mCRPC. ..
  22. Li J, Carr P. Evaluation of temperature effects on selectivity in RPLC separations using polybutadiene-coated zirconia. Anal Chem. 1997;69:2202-6 pubmed
    ..g., solvophobic retention-will not be helped appreciably by adjusting temperature. However, in complex mixtures with polar and ionizable solutes, optimization by varying the temperature may well be fruitful. ..
  23. Turck C, Herrmann J, Escobedo J, Williams L. Identification of phosphotyrosine residues during protein sequence analysis. Pept Res. 1991;4:36-9 pubmed
    ..peptides were subjected to protein sequence analysis using a gas-phase sequencer and on-line phenylthiohydantoin (PTH) amino acid analysis...
  24. Beer T, Tombal B. Enzalutamide in metastatic prostate cancer before chemotherapy. N Engl J Med. 2014;371:1755-6 pubmed publisher
  25. Caiazza F, Murray A, Madden S, Synnott N, Ryan E, O Donovan N, et al. Preclinical evaluation of the AR inhibitor enzalutamide in triple-negative breast cancer cells. Endocr Relat Cancer. 2016;23:323-34 pubmed publisher
    ..We conclude that targeting of the AR with drugs such as enzalutamide may provide an alternative treatment strategy for patients with AR-positive TNBC. ..
  26. Hickey T, Irvine C, Dvinge H, Tarulli G, Hanson A, Ryan N, et al. Expression of androgen receptor splice variants in clinical breast cancers. Oncotarget. 2015;6:44728-44 pubmed publisher
    ..These findings have implications for treatment response in the ongoing clinical trials of ADT in breast cancer. ..
  27. Mao Y, Carr P. Separation of barbiturates and phenylthiohydantoin amino acids using the thermally tuned tandem column concept. Anal Chem. 2001;73:1821-30 pubmed
    ..used the T3C combination of a carbon and a conventional bonded phase for the separation of barbiturates and phenylthiohydantoin amino acids (PTH-amino acids)...
  28. Munuganti R, Hassona M, Leblanc E, Frewin K, Singh K, Ma D, et al. Identification of a potent antiandrogen that targets the BF3 site of the androgen receptor and inhibits enzalutamide-resistant prostate cancer. Chem Biol. 2014;21:1476-85 pubmed publisher
    ..These findings provide evidence that targeting the AR BF3 pocket represents a viable therapeutic approach to treat patients with advanced and/or resistant prostate cancer. ..
  29. Davies R, Smith C, Lester J. Third-line Enzalutamide Following Docetaxel and Abiraterone in Metastatic Castrate-resistant Prostate Cancer. Anticancer Res. 2016;36:1799-803 pubmed
    ..lt;50%, ? or >6 months). In mCRPC, enzalutamide has modest activity after docetaxel and abiraterone. Response to previous abiraterone is not predictive of subsequent enzalutamide response. ..
  30. Kuruma H, Matsumoto H, Shiota M, Bishop J, Lamoureux F, Thomas C, et al. A novel antiandrogen, Compound 30, suppresses castration-resistant and MDV3100-resistant prostate cancer growth in vitro and in vivo. Mol Cancer Ther. 2013;12:567-76 pubmed publisher
    ..These data provide a preclinical proof-of-principle that Compound 30 could be a promising next generation anti-AR agent, especially in the context of antiandrogen-resistant tumors. ..
  31. Lim A, Attard G. Improved therapeutic targeting of the androgen receptor: rational drug design improves survival in castration-resistant prostate cancer. Curr Drug Targets. 2013;14:408-19 pubmed
    ..Rationally-designed approaches combining different strategies for targeting the AR or associated pathways also warrant clinical evaluation. ..
  32. Ha Y, Goodin S, DiPaola R, Kim I. Enzalutamide for the treatment of castration-resistant prostate cancer. Drugs Today (Barc). 2013;49:7-13 pubmed publisher
    ..Currently, a phase III trial (PREVAIL) is under way to determine the effectiveness of enzalutamide in patients who have not received prior docetaxel chemotherapy. ..
  33. van Soest R, van Royen M, de Morree E, Moll J, Teubel W, Wiemer E, et al. Cross-resistance between taxanes and new hormonal agents abiraterone and enzalutamide may affect drug sequence choices in metastatic castration-resistant prostate cancer. Eur J Cancer. 2013;49:3821-30 pubmed publisher
    ..As a potential mechanism for cross-resistance, we investigated the effects on androgen receptor (AR) nuclear translocation of these compounds...
  34. Smith M, Saad F, Rathkopf D, Mulders P, de Bono J, Small E, et al. Clinical Outcomes from Androgen Signaling-directed Therapy after Treatment with Abiraterone Acetate and Prednisone in Patients with Metastatic Castration-resistant Prostate Cancer: Post Hoc Analysis of COU-AA-302. Eur Urol. 2017;72:10-13 pubmed publisher
    ..This analysis does not support prioritization of subsequent abiraterone acetate plus prednisone or enzalutamide following initial therapy with abiraterone acetate plus prednisone. ..
  35. Bishr M, Saad F. Overview of the latest treatments for castration-resistant prostate cancer. Nat Rev Urol. 2013;10:522-8 pubmed publisher
  36. Steiner W, Clowers B, Hill H. Rapid separation of phenylthiohydantoin amino acids: ambient pressure ion-mobility mass spectrometry (IMMS). Anal Bioanal Chem. 2003;375:99-102 pubmed
    ..mass spectrometer (TOFMS) was evaluated for the first time as a detector for the identification of phenylthiohydantoin (PTH)-derivatized amino acids, the final products in the Edman sequencing process of peptides and proteins...
  37. Brune D, Denslow N, Kobayashi R, Lane W, Leone J, Madden B, et al. ABRF ESRG 2005 study: identification of seven modified amino acids by Edman sequencing. J Biomol Tech. 2006;17:308-26 pubmed
    ..The ABRF ESRG 2005 sample is the seventeenth in a series of studies designed to aid laboratories in evaluating their abilities to obtain and interpret amino acid sequence data. ..
  38. Shen H, Balk S. Development of androgen receptor antagonists with promising activity in castration-resistant prostate cancer. Cancer Cell. 2009;15:461-3 pubmed publisher
    ..In a recent issue of Science, Tran et al. describe an antagonist that prevents AR recruitment to chromatin and shows efficacy in relapsed prostate cancer. ..
  39. Mukherji D, Pezaro C, de Bono J. MDV3100 for the treatment of prostate cancer. Expert Opin Investig Drugs. 2012;21:227-33 pubmed publisher
    ..Full analysis of safety and efficacy data is awaited; however, MDV3100 appears to be a well-tolerated addition to the expanding portfolio of effective drugs for the treatment of advanced prostate cancer. ..
  40. Beuzeboc P, Ropert S, Goldwasser F, Zerbib M. [Management of metastatic castration-resistant prostate cancer following docetaxel]. Bull Cancer. 2012;99 Suppl 1:S66-72 pubmed publisher
    ..Other hormone therapies as MDV3100 or TAK700 are very promising. In undifferentiated cancers with neuroendocrine features, etoposide and platinum salts combinations have shown low efficiency. ..
  41. Ouzaid I, Ravery V, Pouessel D, Culine S. [Novel agents for the therapy of castration-resistant prostate cancer: overview of pivotal studies and new strategies to come]. Prog Urol. 2013;23:1-7 pubmed publisher
    ..The novel agents that emerged in the treatment of prostate cancer showed an efficacy in placebo controlled trials. They added new tools in the armamentarium of therapies of castration resistant prostate cancer. ..
  42. Lallous N, Volik S, Awrey S, Leblanc E, Tse R, Murillo J, et al. Functional analysis of androgen receptor mutations that confer anti-androgen resistance identified in circulating cell-free DNA from prostate cancer patients. Genome Biol. 2016;17:10 pubmed publisher
  43. Akaza H. Influences of the Results from STRIVE Trial on the Combination Androgen Depletion Therapy for Advanced Prostate Cancer. Curr Urol Rep. 2016;17:84 pubmed
    ..In addition, it can be deduced that CAB is a strong tool for hormone naïve advanced prostate cancer. Cost-effective evaluation for CAB with bicultamide or enzalutamide is warranted, especially for the resource-limited cohort. ..
  44. Turpin A, Pasquier D, Massard C, Berdah J, Culine S, Penel N. First-line management of metastatic castrate-resistant prostate cancer patients: Audit of real-life practices. Bull Cancer. 2017;104:552-558 pubmed publisher
    ..8%, 61.5%, and 63.3% of cases, respectively. This is the first study assessing real-life practices among physicians who treat patients with mCRPC. These practices were found to be homogeneous. ..
  45. Fujiki H, Zurek G. The subunits of DNA-dependent RNA polymerase from E. coli: I. Amino acid analysis and primary structure of the N-terminal regions. FEBS Lett. 1975;55:242-4 pubmed
  46. Liu C, Lou W, Zhu Y, Nadiminty N, Schwartz C, Evans C, et al. Niclosamide inhibits androgen receptor variants expression and overcomes enzalutamide resistance in castration-resistant prostate cancer. Clin Cancer Res. 2014;20:3198-3210 pubmed publisher
    ..This study was designed to identify inhibitors of AR variants and test its ability to overcome resistance to enzalutamide...
  47. Ong C, Ng C, Lee H, Li S. The use of mixed surfactants in micellar electrokinetic chromatography. Electrophoresis. 1994;15:1273-5 pubmed
    The use of mixed surfactants for the separation of nine phenylthiohydantoin amino acids (PTH amino acids) by micellar electrokinetic chromatography (MEKC) was examined...
  48. Kim W, Ryan C. Androgen receptor directed therapies in castration-resistant metastatic prostate cancer. Curr Treat Options Oncol. 2012;13:189-200 pubmed publisher
    ..In this review, the rationale for and clinical results with these new therapies will be discussed as will the future directions required to fully leverage these therapeutic modalities to the maximum clinical benefit for patients. ..
  49. Rawlinson A, Mohammed A, Miller M, Kunkler R. The role of enzalutamide in the treatment of castration-resistant prostate cancer. Future Oncol. 2012;8:1073-81 pubmed publisher
    ..In this article we discuss the characteristics of enzalutamide and provide a review of its clinical development. ..
  50. Pal S, Twardowski P, Josephson D. Beyond castration and chemotherapy: novel approaches to targeting androgen-driven pathways. Maturitas. 2009;64:61-6 pubmed publisher
    ..On the basis of these compelling data, both abiraterone and MDV3100 will be examined in the phase III setting. ..
  51. Aebersold R, Watts J, Morrison H, Bures E. Determination of the site of tyrosine phosphorylation at the low picomole level by automated solid-phase sequence analysis. Anal Biochem. 1991;199:51-60 pubmed
    ..discs and the "on-line" detection by reverse-phase high-performance liquid chromatography of the phenylthiohydantoin derivative of phosphotyrosine...
  52. Ducret A, Bures E, Aebersold R. High-sensitivity detection of 4-(3-pyridinylmethylaminocarboxypropyl) phenylthiohydantoins by capillary liquid chromatography-microelectrospray ion trap mass spectrometry. J Protein Chem. 1997;16:323-8 pubmed
    ..1 which was specific for the breakdown of 311-PTH leucine, thus allowing for the unambiguous identification of the 311-PTH derivatives of all 20 naturally occurring amino acids by their masses and fragmentation patterns. ..
  53. Kurosu Y, Murayama K, Shindo N, Shisa Y, Ishioka N. Optical resolution of phenylthiohydantoin-amino acids by capillary electrophoresis and identification of the phenylthiohydantoin-D-amino acid residue of [D-Ala2]-methionine enkephalin. J Chromatogr A. 1996;752:279-86 pubmed
    ..As a model peptide, [D-Ala2]-methionine enkephalin (L-Tyr-D-Ala-Gly-L-Phe-L-Met), was used and the sequence with DL differentiation was determined, with the exception of the fourth amino acid, L-Phe, using our proposed system. ..