Development of molecules stimulating the activity of KLK3 – an update

References

Avgeris, M. and Scorilas, A. (2016). Kallikrein-related peptidases (KLKs) as emerging therapeutic targets: focus on prostate cancer and skin pathologies. Expert Opin. Ther. Targets 20, 801–818.10.1517/14728222.2016.1147560Search in Google Scholar PubMed

Denmeade, S.R., Sokoll, L.J., Chan, D.W., Khan, S.R., and Isaacs, J.T. (2001). Concentration of enzymatically active prostate-specific antigen (PSA) in the extracellular fluid of primary human prostate cancers and human prostate cancer xenograft models. Prostate 48, 1–6.10.1002/pros.1075Search in Google Scholar PubMed

Fortier, A.H., Nelson, B.J., Grella, D.K., and Holaday, J.W. (1999). Antiangiogenic activity of prostate-specific antigen. J. Natl. Cancer Inst. 91, 1635–1640.10.1093/jnci/91.19.1635Search in Google Scholar PubMed

Fortier, A.H., Holaday, J.W., Liang, H., Dey, C., Grella, D.K., Holland-Linn, J., Vu, H., Plum, S.M., and Nelson, B.J. (2003). Recombinant prostate specific antigen inhibits angiogenesis in vitro and in vivo. Prostate 56, 212–219.10.1002/pros.10256Search in Google Scholar PubMed

Goettig, P., Magdolen, V., and Brandstetter, H. (2010). Natural and synthetic inhibitors of kallikrein-related peptidases (KLKs). Biochimie 92, 1546–1567.10.1016/j.biochi.2010.06.022Search in Google Scholar PubMed PubMed Central

Härkönen, H.H., Mattsson, J.M., Määttä, J.A., Stenman, U.H., Koistinen, H., Matero, S., Windshugel, B., Poso, A., and Lahtela-Kakkonen, M. (2011). The discovery of compounds that stimulate the activity of kallikrein-related peptidase 3 (KLK3). ChemMedChem 6, 2170–2178.10.1002/cmdc.201100349Search in Google Scholar PubMed

Koistinen, H., Närvänen, A., Pakkala, M., Hekim, C., Mattsson, J.M., Zhu, L., Laakkonen, P., and Stenman, U.H. (2008a). Development of peptides specifically modulating the activity of KLK2 and KLK3. Biol. Chem. 389, 633–642.10.1515/BC.2008.076Search in Google Scholar PubMed

Koistinen, H., Wohlfahrt, G., Mattsson, J.M., Wu, P., Lahdenperä, J., and Stenman, U.H. (2008b). Novel small molecule inhibitors for prostate-specific antigen. Prostate 68, 1143–1151.10.1002/pros.20773Search in Google Scholar PubMed

Koistinen, H. and Stenman, U.H. (2012). PSA (Prostate-Specific Antigen) and other Kallikrein-related peptidases in prostate cancer. In: Kallikrein-Related Peptidases, Vol. 2: Novel Cancer-Related Biomarkers, V. Magdolen, C.P. Sommerhoff, H. Fritz, and M. Schmitt, eds. (Berlin, Germany: De Gruyter), pp. 61–81.10.1515/9783110303667.61Search in Google Scholar

Koistinen, H., Mattsson, J., and Stenman, U.H. (2014). KLK-targeted therapies for prostate cancer. eJIFCC 25, 77–88.Search in Google Scholar

Kote-Jarai, Z., Amin Al Olama, A., Leongamornlert, D., Tymrakiewicz, M., Saunders, E., Guy, M., Giles, G.G., Severi, G., Southey, M., Hopper, J.L., et al. (2011). Identification of a novel prostate cancer susceptibility variant in the KLK3 gene transcript. Hum. Genet. 129, 687–694.10.1007/s00439-011-0981-1Search in Google Scholar PubMed PubMed Central

Lawrence, M.G., Lai, J., and Clements, J.A. (2010). Kallikreins on steroids: structure, function, and hormonal regulation of prostate-specific antigen and the extended kallikrein locus. Endocr. Rev. 31, 407–446.10.1210/er.2009-0034Search in Google Scholar PubMed

Li, D. (2015). Strategic approaches to optimizing peptide ADME properties. Am. Assoc. Pharm. Sci. J. 17, 134–143.10.1208/s12248-014-9687-3Search in Google Scholar

Lilja, H., Cronin, A.M., Dahlin, A., Manjer, J., Nilsson, P.M., Eastham, J.A., Bjartell, A.S., Scardino, P.T., Ulmert, D., and Vickers, A.J. (2011). Prediction of significant prostate cancer diagnosed 20 to 30 years later with a single measure of prostate-specific antigen at or before age 50. Cancer 117, 1210–1219.10.1002/cncr.25568Search in Google Scholar PubMed PubMed Central

Mason, S.D. and Joyce, J.A. (2011). Proteolytic networks in cancer. Trends Cell Biol. 21, 228–237.10.1016/j.tcb.2010.12.002Search in Google Scholar PubMed PubMed Central

Mattsson, J.M., Valmu, L., Laakkonen, P., Stenman, U.H., and Koistinen, H. (2008). Structural characterization and anti-angiogenic properties of prostate-specific antigen isoforms in seminal fluid. Prostate 68, 945–954.10.1002/pros.20751Search in Google Scholar PubMed

Mattsson, J.M., Närvänen, A., Stenman, U.H., and Koistinen, H. (2012). Peptides binding to prostate-specific antigen enhance its antiangiogenic activity. Prostate 72, 1588–1594.10.1002/pros.22512Search in Google Scholar PubMed

Mattsson, J.M., Ravela, S., Hekim, C., Jonsson, M., Malm, J., Närvänen, A., Stenman, U.H., and Koistinen, H. (2014). Proteolytic activity of prostate-specific antigen (PSA) towards protein substrates and effect of peptides stimulating PSA activity. PLoS One 9, e107819.10.1371/journal.pone.0107819Search in Google Scholar PubMed PubMed Central

Meinander, K., Weisell, J., Pakkala, M., Tadd, A.C., Hekim, C., Kallionpää, R., Widell, K., Stenman, U., Koistinen, H., Närvänen, A., et al. (2013). Pseudopeptides with a centrally positioned alkene-based disulphide bridge mimetic stimulate kallikrein-related peptidase 3 activity. Med. Chem. Commun. 4, 549.10.1039/C3MD20292ESearch in Google Scholar

Meinander, K., Pakkala, M., Weisell, J., Stenman, U., Koistinen, H., Närvänen, A., and Wallén, E.A.A. (2014). Replacement of the disulfide bridge in a KLK3-stimulating peptide using orthogonally protected building blocks. ACS Med. Chem. Lett. 5, 162–165.10.1021/ml400419gSearch in Google Scholar PubMed PubMed Central

Ménez, R., Michel, S., Mueller, B.H., Bossus, M. Ducancel, F., Jolivet-Reynaud, C., and Stura, E.A. (2008). Crystal Structure of a ternary complex between human prostate-specific antigen, its substrate acyl intermediate and an activating antibody. J. Mol. Biol. 376, 1021–1033.10.1016/j.jmb.2007.11.052Search in Google Scholar PubMed

Moroz, E., Matoori, S., and Leroux, J.C. (2016). Oral delivery of macromolecular drugs: where we are after almost 100 years of attempts. Adv. Drug Deliv. Rev. 101, 108–121.10.1016/j.addr.2016.01.010Search in Google Scholar PubMed

Niu, Y., Yeh, S., Miyamoto, H., Li, G., Altuwaijri, S., Yuan, J., Han, R., Ma, T., Kuo, H.C., and Chang, C. (2008). Tissue prostate-specific antigen facilitates refractory prostate tumor progression via enhancing ARA70-regulated androgen receptor transactivation. Cancer Res. 68, 7110–7119.10.1158/0008-5472.CAN-07-6507Search in Google Scholar

Pakkala, M., Jylhäsalmi, A., Wu, P., Leinonen, J., Stenman, U.H., Santa, H., Vepsäläinen, J., Peräkylä, M., and Närvänen, A. (2004). Conformational and biochemical analysis of the cyclic peptides which modulate serine protease activity. J. Pept. Sci. 10, 439–447.10.1002/psc.557Search in Google Scholar

Pakkala, M., Hekim, C., Soininen, P., Leinonen, J., Koistinen, H., Weisell, J., Stenman, U.H., Vepsäläinen, J., and Närvänen, A. (2007). Activity and stability of human kallikrein-2-specific linear and cyclic peptide inhibitors. J. Pept. Sci. 13, 348–353.10.1002/psc.849Search in Google Scholar

Pakkala, M., Weisell, J., Hekim, C., Vepsäläinen, J., Wallen, E.A., Stenman, U.H., Koistinen, H., and Närvänen, A. (2010). Mimetics of the disulfide bridge between the N- and C-terminal cysteines of the KLK3-stimulating peptide B-2. Amino Acids 39, 233–242.10.1007/s00726-009-0433-6Search in Google Scholar

Papadopoulos, I., Sivridis, E., Giatromanolaki, A., and Koukourakis, M.I. (2001). Tumor angiogenesis is associated with MUC1 overexpression and loss of prostate-specific antigen expression in prostate cancer. Clin. Cancer Res. 7, 1533–1538.Search in Google Scholar

Rozek, A., Powers, J.P., Friedrich, C.L., and Hancock, R.E. (2003). Structure-based design of an indolicidin peptide analogue with increased protease stability. Biochemistry 42, 14130–14138.10.1021/bi035643gSearch in Google Scholar

Salman, J.W., Schoots, I.G., Carlsson, S.V., Jenster, G., and Roobol, M.J. (2015). Prostate-specific antigen as a tumor marker in prostate cancer: biochemical and clinical aspects. Adv. Exp. Med. Biol. 867, 93–114.10.1007/978-94-017-7215-0_7Search in Google Scholar

Stege, R., Grande, M., Carlstrom, K., Tribukait, B., and Pousette, A. (2000). Prognostic significance of tissue prostate-specific antigen in endocrine-treated prostate carcinomas. Clin. Cancer Res. 6, 160–165.Search in Google Scholar

Stenman, U.H., Hakama, M., Knekt, P., Aromaa, A., Teppo, L., and Leinonen, J. (1994). Serum concentrations of prostate specific antigen and its complex with α1-antichymotrypsin before diagnosis of prostate cancer. Lancet 344, 1594–1598.10.1016/S0140-6736(94)90405-7Search in Google Scholar

Tadd, A.C., Meinander, K., Luthman, K., and Wallén, E.A. (2011). Synthesis of orthogonally protected disulfide bridge mimetics. J. Org. Chem. 76, 673–675.10.1021/jo1018427Search in Google Scholar PubMed

Terrett, N. (2013). Drugs in middle space. Med. Chem. Commun. 4, 474–475.10.1039/C2MD90062ASearch in Google Scholar

Thorek, D.L., Evans, M.J., Carlsson, S.V., Ulmert, D., and Lilja, H. (2013). Prostate-specific kallikrein-related peptidases and their relation to prostate cancer biology and detection. Established relevance and emerging roles. Thromb. Haemost. 110, 484–492.10.1160/TH13-04-0275Search in Google Scholar PubMed PubMed Central

Williams, S.A., Jelinek, C.A., Litvinov, I., Cotter, R.J., Isaacs, J.T., and Denmeade, S.R. (2011). Enzymatically active prostate-specific antigen promotes growth of human prostate cancers. Prostate 71, 1595–1607.10.1002/pros.21375Search in Google Scholar PubMed PubMed Central

Wu, P., Leinonen, J., Koivunen, E., Lankinen, H., and Stenman, U.H. (2000). Identification of novel prostate-specific antigen-binding peptides modulating its enzyme activity. Eur. J. Biochem. 267, 6212–6220.10.1046/j.1432-1327.2000.01696.xSearch in Google Scholar PubMed

Ylikangas, H., Mattsson, J.M., Stenman, U.H., Koistinen, H., Poso, A., and Lahtela-Kakkonen, M. (2016). Virtual screening of small drug-like compounds stimulating the enzymatic activity of kallikrein-related peptidase 3 (KLK3). ChemmedChem, in press.10.1002/cmdc.201600181Search in Google Scholar PubMed

Zhang, Z., Liu, M., Li, B., Wang, Y., Yue, J., Liang, L., and Sun, J. (2013). Exploring the mechanism of a regulatory SNP of KLK3 by molecular dynamics simulation. J. Biomol. Struct. Dyn. 31, 426–40.10.1080/07391102.2012.703067Search in Google Scholar PubMed

Zhu, L., Koistinen, H., Wu, P., Närvänen, A., Schallmeiner, E., Fredriksson, S., Landegren, U., and Stenman, U.H. (2006). A sensitive proximity ligation assay for active PSA. Biol. Chem. 387, 769–772.10.1515/BC.2006.096Search in Google Scholar PubMed