Development of inhibitor-directed enzyme prodrug therapy (IDEPT) for prostate cancer

Bioconjugate Chemistry

Volumn 25, Issue 10, 2014, Pages 1752-1760

  Martin, Stacy E ^a   Ganguly, Tanushree ^a   Munske, Gerhard R ^a   Fulton, Melody D ^a   Hopkins, Mark R ^a   Berkman, Clifford E ^a   Black, Margaret E ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELLS; CYTOLOGY; DISEASE CONTROL; ENZYMES; SYNTHESIS (CHEMICAL); UROLOGY;

'CURRENT; CLICK CHEMISTRY; ENZYME-PRODRUG THERAPIES; LUNG CANCER; MEMBRANE-BOUND; PROSTATE CANCER CELLS; PROSTATE CANCERS; PROSTATE-SPECIFIC MEMBRANE ANTIGENS; THERAPEUTIC AGENTS; UNNATURAL AMINO ACIDS;

DISEASES;

AMINO ACID; PROSTATE SPECIFIC MEMBRANE ANTIGEN; TUMOR MARKER; 4-AZIDOPHENYLALANINE; ANTINEOPLASTIC AGENT; AZIDE; GLUTAMATE CARBOXYPEPTIDASE II; GLUTAMATE CARBOXYPEPTIDASE II, HUMAN; MEMBRANE ANTIGEN; PHENYLALANINE; PRODRUG;

ARTICLE; CANCER CELL CULTURE; CANCER THERAPY; CELL KILLING; CELL MEMBRANE; CLICK CHEMISTRY; CONTROLLED STUDY; CYTOTOXICITY ASSAY; ENZYME PRODRUG THERAPY; GENETIC COMPLEMENTATION; HUMAN; HUMAN CELL; IN VITRO STUDY; INHIBITOR DIRECTED ENZYME PRODRUG THERAPY; NONHUMAN; PROSTATE CANCER; PROTEIN EXPRESSION; PROTEIN PURIFICATION; SUICIDE GENE; ANALOGS AND DERIVATIVES; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG EFFECTS; MALE; METABOLISM; PATHOLOGY; PROSTATE; PROSTATIC NEOPLASMS; SYNTHESIS; TUMOR CELL LINE;

ANTIGENS, SURFACE; ANTINEOPLASTIC AGENTS; AZIDES; CELL LINE, TUMOR; CLICK CHEMISTRY; DRUG DELIVERY SYSTEMS; GLUTAMATE CARBOXYPEPTIDASE II; HUMANS; MALE; PHENYLALANINE; PRODRUGS; PROSTATE; PROSTATIC NEOPLASMS;

EID: 84908017254     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc500362n     Document Type: Article

References (50)

1. Wang, L., Xie, J., and Schultz, P. G. (2006) Expanding the genetic code Annu. Rev. Biophys. Biomol. Struct. 35, 225-249
2. Young, T. S., Ahmad, I., Yin, J. A., and Schultz, P. G. (2010) An enhanced system for unnatural amino acid mutagenesis in E. coli J. Mol. Biol. 395, 361-374
3. Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click chemistry: diverse chemical function from a few good reactions Angew. Chem., Int. Ed. 40, 2004-2021
4. Best, M. D. (2009) Click chemistry and bioorthogonal reactions: unprecedented selectivity in the labeling of biological molecules Biochemistry 48, 6571-6584
5. Plass, T., Milles, S., Koehler, C., Schultz, C., and Lemke, E. A. (2011) Genetically encoded copper-free click chemistry Angew. Chem., Int. Ed. 50, 3878-3881
6. Kim, C. H., Axup, J. Y., Dubrovska, A., Kazane, S. A., Hutchins, B. A., Wold, E. D., Smider, V. V., and Schultz, P. G. (2012) Synthesis of bispecific antibodies using genetically encoded unnatural amino acids J. Am. Chem. Soc. 134, 9918-9921
7. Seo, T. S., Li, Z., Ruparel, H., and Ju, J. (2002) Click chemistry to construct fluorescent oligonucleotides for DNA sequencing J. Org. Chem. 68, 609-612
8. Codelli, J. A., Baskin, J. M., Agard, N. J., and Bertozzi, C. R. (2008) Second-generation difluorinated cyclooctynes for copper-free click chemistry J. Am. Chem. Soc. 130, 11486-11493
9. von Maltzahn, G., Ren, Y., Park, J.-H., Min, D.-H., Kotamraju, V. R., Jayakumar, J., Fogal, V., Sailor, M. J., Ruoslahti, E., and Bhatia, S. N. (2008) In vivo tumor cell targeting with "click" nanoparticles Bioconjugate Chem. 19, 1570-1578
10. Agard, N. J., Prescher, J. A., and Bertozzi, C. R. (2004) A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems J. Am. Chem. Soc. 126, 15046-15047
11. Katsuragi, T., Sonoda, T., Matsumoto, K., Sakai, T., and Tonomura, K. (1989) Purification and some properties of cytosine deaminase from bakers' yeast Agric. Biol. Chem. 53, 1313-1319
12. Kievit, E., Nyati, M. K., Ng, E., Stegman, L. D., Parsels, J., Ross, B. D., Rehemtulla, A., and Lawrence, T. S. (2000) Yeast cytosine deaminase improves radiosensitization and bystander effect by 5-fluorocytosine of human colorectal cancer xenografts Cancer Res. 60, 6649-6655
13. Huber, B. E., Austin, E. A., Richards, C. A., Davis, S. T., and Good, S. S. (1994) Metabolism of 5-fluorocytosine to 5-fluorouracil in human colorectal tumor cells transduced with the cytosine deaminase gene: significant antitumor effects when only a small percentage of tumor cells express cytosine deaminase Proc. Natl. Acad. Sci. U.S.A. 91, 8302-8306
14. Greco, O. and Dachs, G. U. (2001) Gene directed enzyme/prodrug therapy of cancer: historical appraisal and future prospectives J. Cell. Physiol. 187, 22-36
15. Park, J. I., Cao, L., Platt, V. M., Huang, Z., Stull, R. A., Dy, E. E., Sperinde, J. J., Yokoyama, J. S., and Szoka, F. C. (2009) Antitumor therapy mediated by 5-fluorocytosine and a recombinant fusion protein containing TSG-6 hyaluronan binding domain and yeast cytosine deaminase Mol. Pharmaceutics 6, 801-812
16. Goblirsch, M., Zwolak, P., Ramnaraine, M. L., Pan, W., Lynch, C., Alaei, P., and Clohisy, D. R. (2006) Novel cytosine deaminase fusion gene enhances the effect of radiation on breast cancer in bone by reducing tumor burden, osteolysis, and skeletal fracture Clin. Cancer Res. 12, 3168-3176
17. Kievit, E., Bershad, E., Ng, E., Sethna, P., Dev, I., Lawrence, T. S., and Rehemtulla, A. (1999) Superiority of yeast over bacterial cytosine deaminase for enzyme/prodrug gene therapy in colon cancer xenografts Cancer Res. 59, 1417-1421
18. Wallace, P. M., MacMaster, J. F., Smith, V. F., Kerr, D. E., Senter, P. D., and Cosand, W. L. (1994) Intratumoral generation of 5-fluorouracil mediated by an antibody-cytosine deaminase conjugate in combination with 5-fluorocytosine Cancer Res. 54, 2719-2723
19. Freytag, S. O., Movsas, B., Aref, I., Stricker, H., Peabody, J., Pegg, J., Zhang, Y., Barton, K. N., Brown, S. L., Lu, M., Savera, A., and Kim, J. H. (2007) Phase I trial of replication-competent adenovirus-mediated suicide gene therapy combined with IMRT for prostate cancer Mol. Ther. 15, 1016-1023
20. Korkegian, A. M., Black, M. E., Baker, D., and Stoddard, B. L. (2005) Computational thermostabilization of an enzyme Science 308, 857-860
21. Stolworthy, T. S., Korkegian, A. M., Willmon, C. L., Ardiani, A., Cundiff, J., Stoddard, B. L., and Black, M. E. (2008) Yeast cytosine deaminase mutants with increased thermostability impart sensitivity to 5-fluorocytosine J. Mol. Biol. 377, 854-869
22. Ostertag, D., Amundson, K. K., Lopez Espinoza, F., Martin, B., Buckley, T., da Silva, A. P. G., Lin, A. H., Valenta, D. T., Perez, O. D., Ibañez, C. E., Chen, C.-I., Pettersson, P. L., Burnett, R., Daublebsky, V., Hlavaty, J., Gunzburg, W., Kasahara, N., Gruber, H. E., Jolly, D. J., and Robbins, J. M. (2012) Brain tumor eradication and prolonged survival from intratumoral conversion of 5-fluorocytosine to 5-fluorouracil using a nonlytic retroviral replicating vector Neuro-Oncology 14, 145-159
23. Erbs, P., Exinger, F., and Jund, R. (1997) Characterization of the saccharomyces cerevisiae FCY1 gene encoding cytosine deaminase and its homologue FCA1 of candida albicans Curr. Genet. 31, 1-6
24. Hayden, M. S., Linsley, P. S., Wallace, A. R., Marquardt, H., and Kerr, D. E. (1998) Cloning, overexpression, and purification of cytosine deaminase from saccharomyces cerevisiae Protein Expression Purif. 12, 173-184
25. Bostwick, D. G., Pacelli, A., Blute, M., Roche, P., and Murphy, G. P. (1998) Prostate specific membrane antigen expression in prostatic intraepithelial neoplasia and adenocarcinoma Cancer 82, 2256-2261
26. Murphy, G. P., Su, S., Jarisch, J., and Kenny, G. M. (2000) Serum levels of PSMA Prostate 42, 318-319
27. Wright, G. L., Jr., Grob, B. M., Haley, C., Grossman, K., Newhall, K., Petrylak, D., Troyer, J., Konchuba, A., Schellhammer, P. F., and Moriarty, R. (1996) Upregulation of prostate-specific membrane antigen after androgen-deprivation therapy Urology 48, 326-334
28. Chang, S. S., Reuter, V. E., Heston, W. D. W., Bander, N. H., Grauer, L. S., and Gaudin, P. B. (1999) Five different anti-prostate-specific membrane antigen (PSMA) antibodies confirm PSMA expression in tumor-associated neovasculature Cancer Res. 59, 3192-3198
29. Chang, S. S., O'Keefe, D. S., Bacich, D. J., Reuter, V. E., Heston, W. D. W., and Gaudin, P. B. (1999) Prostate-specific membrane antigen is produced in tumor-associated neovasculature Clin. Cancer Res. 5, 2674-2681
30. Banerjee, S. R., Foss, C. A., Castanares, M., Mease, R. C., Byun, Y., Fox, J. J., Hilton, J., Lupold, S. E., Kozikowski, A. P., and Pomper, M. G. (2008) Synthesis and evaluation of technetium-99m-and rhenium-labeled inhibitors of the prostate-specific membrane antigen (PSMA) J. Med. Chem. 51, 4504-4517
31. Jayaprakash, S., Wang, X., Heston, W. D., and Kozikowski, A. P. (2006) Design and synthesis of a PSMA inhibitor-doxorubicin conjugate for targeted prostate cancer therapy ChemMedChem 1, 299-302
32. Kularatne, S. A., Wang, K., Santhapuram, H.-K. R., and Low, P. S. (2009) Prostate-specific membrane antigen targeted imaging and therapy of prostate cancer using a PSMA inhibitor as a homing ligand Mol. Pharmaceutics 6, 780-789
33. Lapi, S. E., Wahnishe, H., Pham, D., Wu, L. Y., Nedrow-Byers, J. R., Liu, T., Vejdani, K., VanBrocklin, H. F., Berkman, C. E., and Jones, E. F. (2009) Assessment of an 18F-labeled phosphoramidate peptidomimetic as a new prostate-specific membrane antigen-targeted imaging agent for prostate cancer J. Nucl. Med. 50, 2042-2048
34. Kularatne, S. A., Venkatesh, C., Santhapuram, H.-K. R., Wang, K., Vaitilingam, B., Henne, W. A., and Low, P. S. (2010) Synthesis and biological analysis of prostate-specific membrane antigen-targeted anticancer prodrugs J. Med. Chem. 53, 7767-7777
35. Liu, T., Toriyabe, Y., Kazak, M., and Berkman, C. E. (2008) Pseudoirreversible inhibition of prostate-specific membrane antigen by phosphoramidate peptidomimetics Biochemistry 47, 12658-12660
36. Liu, T., Nedrow-Byers, J. R., Hopkins, M. R., Wu, L. Y., Lee, J., Reilly, P. T. A., and Berkman, C. E. (2012) Targeting prostate cancer cells with a multivalent PSMA inhibitor-guided streptavidin conjugate Bioorg. Med. Chem. Lett. 22, 3931-3934
37. Liu, T., Wu, L. Y., Kazak, M., and Berkman, C. E. (2008) Cell-surface labeling and internalization by a fluorescent inhibitor of prostate-specific membrane antigen Prostate 68, 955-964
38. Goerke, A. R. and Swartz, J. R. (2009) High-level cell-free synthesis yields of proteins containing site-specific non-natural amino acids Biotechnol. Bioeng. 102, 400-416
39. Chin, J. W., Santoro, S. W., Martin, A. B., King, D. S., Wang, L., and Schultz, P. G. (2002) Addition of p-azido-l-phenylalanine to the genetic code of escherichia coli J. Am. Chem. Soc. 124, 9026-9027
40. Ipata, P. L., Marmocchi, F., Magni, G., Felicioli, R., and Polidoro, G. (1971) Baker's yeast cytosine deaminase. Some enzymatic properties and allosteric inhibition by nucleosides and nucleotides Biochemistry 10, 4270-4276
41. Mahan, S. D., Ireton, G. C., Stoddard, B. L., and Black, M. E. (2004) Alanine-scanning mutagenesis reveals a cytosine deaminase mutant with altered substrate preference Biochemistry 43, 8957-8964
42. Austin, E. A. and Huber, B. E. (1993) A first step in the development of gene therapy for colorectal carcinoma: cloning, sequencing, and expression of Escherichia coli cytosine deaminase Mol. Pharmacol. 43, 380-387
43. Liu, T., Nedrow-Byers, J. R., Hopkins, M. R., and Berkman, C. E. (2011) Spacer length effects on in vitro imaging and surface accessibility of fluorescent inhibitors of prostate specific membrane antigen Bioorg. Med. Chem. Lett. 21, 7013-7016
44. Deiters, A., Cropp, T. A., Mukherji, M., Chin, J. W., Anderson, J. C., and Schultz, P. G. (2003) Adding amino acids with novel reactivity to the genetic code of Saccharomyces cerevisiae J. Am. Chem. Soc. 125, 11782-11783
45. Deiters, A. and Schultz, P. G. (2005) In vivo incorporation of an alkyne into proteins in Escherichia coli Bioorg. Med. Chem. Lett. 15, 1521-1524
46. Liu, T., Toriyabe, Y., and Berkman, C. E. (2006) Purification of prostate-specific membrane antigen using conformational epitope-specific antibody-affinity chromatography Protein Expression Purif. 49, 251-255
47. Goodwin, M. L. and Drew, R. H. (2008) Antifungal serum concentration monitoring: an update J. Antimicrob. Chemother. 61, 17-25
48. Andes, D., Pascual, A., and Marchetti, O. (2009) Antifungal therapeutic drug monitoring: established and emerging indications Antimicrob. Agents Chemother. 53, 24-34
49. Maung, J., Mallari, J. P., Girtsman, T. A., Wu, L. Y., Rowley, J. A., Santiago, N. M., Brunelle, A. N., and Berkman, C. E. (2004) Probing for a hydrophobic a binding register in prostate-specific membrane antigen with phenylalkylphosphonamidates Bioorg. Med. Chem. 12, 4969-4979
50. Wone, D. W. G., Rowley, J. A., Garofalo, A. W., and Berkman, C. E. (2006) Optimizing phenylethylphosphonamidates for the inhibition of prostate-specific membrane antigen Bioorg. Med. Chem. 14, 67-76