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Volumn 56, Issue 11, 2013, Pages 4224-4235

Structural optimization, biological evaluation, and application of peptidomimetic prostate specific antigen inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

CHYMOTRYPSIN; IODINE 125; PEPTIDOMIMETIC AGENT; PHENYLALANINE DERIVATIVE; PROSTATE SPECIFIC ANTIGEN; SERINE PROTEINASE;

EID: 84879063764     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301718c     Document Type: Article
Times cited : (19)

References (48)
  • 2
    • 0022357088 scopus 로고
    • A kallikrein-like serine protease in prostatic fluid cleaves the predominant seminal vesicle protein
    • Lilja, H. A kallikrein-like serine protease in prostatic fluid cleaves the predominant seminal vesicle protein J. Clin. Invest. 1985, 76, 1899-1903 (Pubitemid 16196061)
    • (1985) Journal of Clinical Investigation , vol.76 , Issue.5 , pp. 1899-1903
    • Lilja, H.1
  • 3
    • 0043264142 scopus 로고    scopus 로고
    • An overview of the kallikrein gene families in humans and other species: Emerging candidate tumour markers
    • DOI 10.1016/S0009-9120(03)00055-9
    • Yousef, G. M.; Diamandis, E. P. An overview of the kallikrein gene families in humans and other species: emerging candidate tumor markers Clin. Biochem. 2003, 36, 443-452 (Pubitemid 37083557)
    • (2003) Clinical Biochemistry , vol.36 , Issue.6 , pp. 443-452
    • Yousef, G.M.1    Diamandis, E.P.2
  • 4
    • 33846973970 scopus 로고    scopus 로고
    • Does PSA play a role as a promoting agent during the initiation and/or progression of prostate cancer?
    • Williams, S. A.; Singh, P.; Isaacs, J. T.; Denmeade, S. R. Does PSA play a role as a promoting agent during the initiation and/or progression of prostate cancer? Prostate 2007, 67, 312-329
    • (2007) Prostate , vol.67 , pp. 312-329
    • Williams, S.A.1    Singh, P.2    Isaacs, J.T.3    Denmeade, S.R.4
  • 5
    • 0035876331 scopus 로고    scopus 로고
    • Rapid communication: Concentration of enzymatically active prostate-specific antigen (PSA) in the extracellular fluid of primary human prostate cancers and human prostate cancer xenograft models
    • DOI 10.1002/pros.1075
    • Denmeade, S. R.; Sokoll, L. J.; Chan, D. W.; Khan, S. R.; Isaacs, J. T. Concentration of enzymatically active prostate-specific antigen (PSA) in the extracellular fluid of primary human prostate cancers and human prostatic cancer xenograft models Prostate 2001, 48, 1-6 (Pubitemid 32545071)
    • (2001) Prostate , vol.48 , Issue.1 , pp. 1-6
    • Denmeade, S.R.1    Sokoll, L.J.2    Chan, D.W.3    Khan, S.R.4    Isaacs, J.T.5
  • 7
    • 0026027671 scopus 로고
    • A complex between prostate specific antigen and a1-antichymotrypsin is the major form of prostate-specific antigen in serum of patients with prostatic cancer: Assay of the complex improves clinical sensitivity for cancer
    • Stenman, U. H.; Leinonen, J.; Alfthan, H.; Rannikko, S.; Tuhkanen, K.; Alfthan, O. A complex between prostate specific antigen and a1-antichymotrypsin is the major form of prostate-specific antigen in serum of patients with prostatic cancer: assay of the complex improves clinical sensitivity for cancer Cancer Res. 1991, 51, 222-226
    • (1991) Cancer Res. , vol.51 , pp. 222-226
    • Stenman, U.H.1    Leinonen, J.2    Alfthan, H.3    Rannikko, S.4    Tuhkanen, K.5    Alfthan, O.6
  • 11
    • 65249109808 scopus 로고    scopus 로고
    • Prostate-specific antigen is a 'chymotrypsin-like' serine protease with unique P1 substrate specificity
    • LeBeau, A. M.; Singh, P.; Isaacs, J. T.; Denmeade, S. R. Prostate-specific antigen is a 'chymotrypsin-like' serine protease with unique P1 substrate specificity Biochemistry 2009, 48, 3490-3496
    • (2009) Biochemistry , vol.48 , pp. 3490-3496
    • Lebeau, A.M.1    Singh, P.2    Isaacs, J.T.3    Denmeade, S.R.4
  • 12
    • 0030728733 scopus 로고    scopus 로고
    • Specific and efficient peptide substrates for assaying the proteolytic activity of prostate-specific antigen
    • Denmeade, S. R.; Lou, W.; Malm, J.; Lovgren, J.; Lilja, H.; Isaacs, J. T. Specific and efficient peptide substrates for assaying the proteolytic activity of prostate specific antigen Cancer Res. 1997, 57, 4924-4930 (Pubitemid 27469004)
    • (1997) Cancer Research , vol.57 , Issue.21 , pp. 4924-4930
    • Denmeade, S.R.1    Lou, W.2    Lovgren, J.3    Malm, J.4    Lilja, H.5    Isaacs, J.T.6
  • 13
    • 70450046333 scopus 로고    scopus 로고
    • Molecular insights into substrate specificity of prostate specific antigen through structural modeling
    • Singh, P.; LeBeau, A. M.; Lilja, H.; Denmeade, S. R.; Isaacs, J. I. Molecular insights into substrate specificity of prostate specific antigen through structural modeling Proteins 2009, 77, 984-993
    • (2009) Proteins , vol.77 , pp. 984-993
    • Singh, P.1    Lebeau, A.M.2    Lilja, H.3    Denmeade, S.R.4    Isaacs, J.I.5
  • 14
    • 46849112416 scopus 로고    scopus 로고
    • Potent and Selective Peptidyl Boronic Acid Inhibitors of the Serine Protease Prostate-Specific Antigen
    • DOI 10.1016/j.chembiol.2008.05.020, PII S1074552108002366
    • LeBeau, A. M.; Singh, P.; Isaacs, J. T.; Denmeade, S. R. Potent and selective peptidyl boronic acid inhibitors of the serine protease prostate-specific antigen Chem. Biol. 2008, 15, 665-674 (Pubitemid 351957911)
    • (2008) Chemistry and Biology , vol.15 , Issue.7 , pp. 665-674
    • LeBeau, A.M.1    Singh, P.2    Isaacs, J.T.3    Denmeade, S.R.4
  • 15
    • 0001168681 scopus 로고
    • [(1 R)-1-Acetamido-3-(methylthuio)propyl]boronic acid and the X-ray structure of its ethylene glycol ester
    • Matteson, D. S.; Michnick, T. J.; Willett, R. D.; Patterson, C. D. [(1 R)-1-Acetamido-3-(methylthuio)propyl]boronic acid and the X-ray structure of its ethylene glycol ester Organometallics 1989, 8, 726-729
    • (1989) Organometallics , vol.8 , pp. 726-729
    • Matteson, D.S.1    Michnick, T.J.2    Willett, R.D.3    Patterson, C.D.4
  • 16
    • 34249296349 scopus 로고    scopus 로고
    • Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases
    • DOI 10.1016/j.tet.2007.03.033, PII S004040200700395X, Tetrahedron 50th Anniversary Symposium-in-Print (Part 3)
    • Debaene, F.; Da Silva, J. A.; Pianowski, Z.; Duran, F. J.; Winssinger, N. Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metalloproteases as well as tyrosine phosphatases Tetrahedron 2007, 63, 6577-6586 (Pubitemid 46817614)
    • (2007) Tetrahedron , vol.63 , Issue.28 , pp. 6577-6586
    • Debaene, F.1    Da Silva, J.A.2    Pianowski, Z.3    Duran, F.J.4    Winssinger, N.5
  • 17
    • 0030953892 scopus 로고    scopus 로고
    • Design of a novel class of bifunctional thrombin inhibitors, synthesised by the first application of peptide boronates in solid phase chemistry
    • DOI 10.1016/S0040-4039(97)00592-3, PII S0040403997005923
    • Elgendy, S.; Patel.; Green, D.; Goodwin, C. A.; Scully, M. F.; Husman, W.; Skordalakes, E.; Kakkar, V. V.; Deadman, J. J. Design of a novel class of bifunctional thrombin inhibitors, synthesised by the first application of peptide boronates of solid phase chemistry Tetrahedron Lett. 1997, 38, 3305-3308 (Pubitemid 27193195)
    • (1997) Tetrahedron Letters , vol.38 , Issue.18 , pp. 3305-3308
    • Elgendy, S.1    Patel, G.2    Green, D.3    Goodwin, C.A.4    Scully, M.F.5    Husman, W.6    Skordalakes, E.7    Kakkar, V.V.8    Deadman, J.J.9
  • 18
    • 67650754085 scopus 로고    scopus 로고
    • Design, synthesis, biological evaluation, and structure-activity relationship (SAR) discussion of dipeptidyl boronate proteasome inhibitors, part I: Comprehensive understanding of the SAR of alpha-amino acid boronates
    • Zhu, Y.; Zhao, X.; Zhu, X.; Wu, G.; Li, Y.; Ma, Y.; Yuan, Y.; Yang, J.; Hu, Y.; Ai, L.; Gao, Q. Design, synthesis, biological evaluation, and structure-activity relationship (SAR) discussion of dipeptidyl boronate proteasome inhibitors, part I: comprehensive understanding of the SAR of alpha-amino acid boronates J. Med. Chem. 2009, 52, 4192-4199
    • (2009) J. Med. Chem. , vol.52 , pp. 4192-4199
    • Zhu, Y.1    Zhao, X.2    Zhu, X.3    Wu, G.4    Li, Y.5    Ma, Y.6    Yuan, Y.7    Yang, J.8    Hu, Y.9    Ai, L.10    Gao, Q.11
  • 19
    • 69949163678 scopus 로고    scopus 로고
    • Design, synthesis and biological evaluation of tripeptide boronic acid proteasome inhibitors
    • Zhu, Y.; Yao, S.; Xu, B.; Ge, Z.; Cui, J.; Cheng, T.; Li, R. Design, synthesis and biological evaluation of tripeptide boronic acid proteasome inhibitors Bioorg. Med. Chem. 2009, 17, 6851-6861
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 6851-6861
    • Zhu, Y.1    Yao, S.2    Xu, B.3    Ge, Z.4    Cui, J.5    Cheng, T.6    Li, R.7
  • 20
    • 77957557116 scopus 로고    scopus 로고
    • Structure-activity relationship of boronic acid derivatives of tyropeptin: Proteasome inhibitors
    • Watanabe, T.; Abe, H.; Momose, I.; Takahashi, Y.; Ikeda, D.; Akamatsu, Y. Structure-activity relationship of boronic acid derivatives of tyropeptin: proteasome inhibitors Bioorg. Med. Chem. Lett. 2010, 20, 5839-5842
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 5839-5842
    • Watanabe, T.1    Abe, H.2    Momose, I.3    Takahashi, Y.4    Ikeda, D.5    Akamatsu, Y.6
  • 26
    • 0038315416 scopus 로고    scopus 로고
    • Radiolabeled monoclonal antibodies specific to the extracellular domain of prostate-specific membrane antigen: Preclinical studies in nude mice bearing LNCaP human prostate tumor
    • Smith-Jones, P. M.; Vallabahajosula, S.; Navarro, V.; Bastidas, D.; Goldsmith, S. J.; Bander, N. H. Radiolabeled monoclonal antibodies specific to the extracellular domain of prostate-specific membrane antigen: preclinical studies in nude mice bearing LNCaP human prostate tumor J. Nucl. Med. 2003, 44, 610-617 (Pubitemid 40003748)
    • (2003) Journal of Nuclear Medicine , vol.44 , Issue.4 , pp. 610-617
    • Smith-Jones, P.M.1    Vallabhajosula, S.2    Navarro, V.3    Bastidas, D.4    Goldsmith, S.J.5    Bander, N.H.6
  • 27
    • 0026753517 scopus 로고
    • Prostate-specific antigen (PSA) is an insulin-like growth factor binding protein-3 protease found in seminal plasma
    • Cohen, P.; Graves, H. C.; Peehl, D. M.; Kamarei, M.; Giudice, L. C.; Rosenfeld, R. G. Prostate-specific antigen (PSA) is an insulin-like growth factor binding protein-3 protease found in seminal plasma J. Clin. Endocrinol. Metab. 1992, 75, 1046-1053
    • (1992) J. Clin. Endocrinol. Metab. , vol.75 , pp. 1046-1053
    • Cohen, P.1    Graves, H.C.2    Peehl, D.M.3    Kamarei, M.4    Giudice, L.C.5    Rosenfeld, R.G.6
  • 28
    • 0000057945 scopus 로고    scopus 로고
    • Alteration of the hormonal bioactivity of parathyroid hormone-related protein (PTHrP) as a result of limited proteolysis by prostate-specific antigen
    • DOI 10.1016/S0090-4295(96)00182-3
    • Iwamura, M.; Hellman, J.; Cockett, A. T.; Lilja, H.; Gershagen, S. Alteration of the hormonal bioactivity of parathyroid hormone-related protein (PTHrP) as a result of limited proteolysis by prostate-specific antigen Urology 1996, 48, 317-325 (Pubitemid 26279633)
    • (1996) Urology , vol.48 , Issue.2 , pp. 317-325
    • Iwamura, M.1    Hellman, J.2    Cockett, A.T.K.3    Lilja, H.4    Gershagen, S.5
  • 29
    • 0030211390 scopus 로고    scopus 로고
    • Prostate specific antigen cleaves parathyroid hormone-related protein in the PTH-like domain: Inactivation of PTHrP-stimulated cAMP accumulation in mouse osteoblasts
    • Cramer, S. D.; Chen, Z.; Peehl, D, M. Prostate specific antigen cleaves parathyroid hormone-related protein in the PTH-like domain: inactivation of PTHrP-stimulated cAMP accumulation in mouse osteoblasts J. Urol. 1996, 156, 526-531 (Pubitemid 126445373)
    • (1996) Journal of Urology , vol.156 , Issue.2 , pp. 526-531
    • Cramer, S.D.1    Chen, Z.2    Peehl, D.M.3
  • 30
    • 11144319971 scopus 로고    scopus 로고
    • Preferential production of latent transforming growth factor β-2 by primary prostatic epithelial cells and its activation by prostate-specific antigen
    • DOI 10.1002/jcp.20147
    • Dallas, S. L.; Zhao, S.; Cramer, S. D.; Chen, Z.; Peehl, D. M; Bonewald, L. F. Preferential production of latent transforming growth factor-2 by primary prostatic epithelial cells and its activation by prostate-specific antigen J. Cell. Physiol. 2005, 202, 361-370 (Pubitemid 40041306)
    • (2005) Journal of Cellular Physiology , vol.202 , Issue.2 , pp. 361-370
    • Dallas, S.L.1    Zhao, S.2    Cramer, S.D.3    Chen, Z.4    Peehl, D.M.5    Bonewald, L.F.6
  • 32
    • 80053208464 scopus 로고    scopus 로고
    • Enzymatically active prostate-specific antigen promotes growth of human prostate cancers
    • Williams, S. A.; Jelinek, C. A.; Litvinov, I.; Cotter, R. J.; Isaacs, J. T.; Denmeade, S. R. Enzymatically active prostate-specific antigen promotes growth of human prostate cancers Prostate 2011, 71, 1595-1607
    • (2011) Prostate , vol.71 , pp. 1595-1607
    • Williams, S.A.1    Jelinek, C.A.2    Litvinov, I.3    Cotter, R.J.4    Isaacs, J.T.5    Denmeade, S.R.6
  • 33
    • 0142157084 scopus 로고    scopus 로고
    • Molecular mechanisms of bone metastasis and therapeutic implications
    • O'Keefe, R. J.; Guise, T. A. Molecular mechanisms of bone metastasis and therapeutic implications Clin. Orthoped. Relat. Res. 2003, 415, S100-S104
    • (2003) Clin. Orthoped. Relat. Res. , vol.415
    • O'Keefe, R.J.1    Guise, T.A.2
  • 34
    • 4644261592 scopus 로고    scopus 로고
    • Mechanisms of bone metastasis
    • Roodman, G. D. Mechanisms of bone metastasis N. Engl. J. Med. 2004, 350, 1655-1664
    • (2004) N. Engl. J. Med. , vol.350 , pp. 1655-1664
    • Roodman, G.D.1
  • 40
    • 0035797899 scopus 로고    scopus 로고
    • Modulation of recombinant human prostate-specific antigen: Activation by Hofmeister salts and inhibition by azapeptides
    • DOI 10.1021/bi010364j
    • Huang, A.; Knoell, C.; Fey, G.; Hazegh-Azam, M.; Tashjian, A.; Hedstrom, L.; Abeles, R. H. Modulation of recombinant human prostate-specific antigen: activation by hofmeister salts and inhibition by azapeptides Biochemistry 2001, 40, 11734-11741 (Pubitemid 32906035)
    • (2001) Biochemistry , vol.40 , Issue.39 , pp. 11734-11741
    • Huang, X.1    Knoell, C.T.2    Frey, G.3    Hazegh-Azam, M.4    Tashjian Jr., A.H.5    Hedstrom, L.6    Abeles, R.H.7
  • 42
    • 0036093686 scopus 로고    scopus 로고
    • Free prostate-specific antigen in serum is becoming more complex
    • DOI 10.1016/S0090-4295(01)01605-3, PII S0090429501016053
    • Mikolajczyk, A. D.; Marks, L. S.; Partin, A. W.; Rittenhouse, H. G. Free prostate-specific antigen is becoming more complex Urology 2002, 59, 797-802 (Pubitemid 34522163)
    • (2002) Urology , vol.59 , Issue.6 , pp. 797-802
    • Mikolajczyk, S.D.1    Marks, L.S.2    Partin, A.W.3    Rittenhouse, H.G.4
  • 43
    • 33845556998 scopus 로고
    • R -1-Acetamido-2-phenylethaneboronic acid. A specific transition-state analog for chymotrypsin
    • Matteson, D. S.; Sadhu, K. M.; Lienhard, G. E. R -1-Acetamido-2- phenylethaneboronic acid. A specific transition-state analog for chymotrypsin J. Am. Chem. Soc. 1981, 103, 5241-5242
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 5241-5242
    • Matteson, D.S.1    Sadhu, K.M.2    Lienhard, G.E.3
  • 44
    • 0000322228 scopus 로고
    • Synthesis of 1-amino-2-phenylethane-1-boronic acid derivatives
    • Matteson, D. S.; Sadhu, K. M. Synthesis of 1-amino-2-phenylethane-1- boronic acid derivatives Organometallics 1984, 3, 614-618
    • (1984) Organometallics , vol.3 , pp. 614-618
    • Matteson, D.S.1    Sadhu, K.M.2
  • 45
    • 0000793111 scopus 로고
    • Synthesis and properties of pinanediol α-amido boronic esters
    • Matteson, D. S.; Jesthi, P. K.; Sadhu, K. M. Synthesis and properties of pinanediol α-amido boronic esters Organometallics 1984, 3, 1284-1288
    • (1984) Organometallics , vol.3 , pp. 1284-1288
    • Matteson, D.S.1    Jesthi, P.K.2    Sadhu, K.M.3
  • 46
    • 0142196876 scopus 로고    scopus 로고
    • Synthesis and Evaluation of Macrocyclic Transition State Analogue Inhibitors for α-Chymotrypsin
    • DOI 10.1021/jo034837z
    • Hansen, K. K.; Grosch, B.; Greiveldinger-Poenaru, S.; Bartlett, P. A. Synthesis and evaluation of macrocyclic transition state analog inhibitors for α-chymotrypsin J. Org. Chem. 2003, 68, 8465-8470 (Pubitemid 37329106)
    • (2003) Journal of Organic Chemistry , vol.68 , Issue.22 , pp. 8465-8470
    • Hansen, K.K.1    Grosch, B.2    Greiveldinger-Poenaru, S.3    Bartlett, P.A.4


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