Use of methotrexate-based peptide substrates to characterize the substrate specificity of Prostate-Specific Membrane Antigen (PSMA)

Cancer Biology and Therapy

Volumn 3, Issue 6, 2004, Pages 551-558

  Mhaka, Annastasiah ^a   Gady, Alyssa M ^a   Rosen, D Marc ^a   Lo, Kin Ming ^b   Gillies, Steven D ^b   Denmeade, Samuel R ^a,c  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b EMD SERONO INC   (United States)

^c Bunting Blaustein Cancer Research Building ^*  (United States)

Author keywords

Folate hydrolase; Methotrexate; NAALADase; Peptide; Prostate cancer; Prostate specific membrane antigen; Substrate

Indexed keywords

GLUTAMIC ACID DERIVATIVE; METHOTREXATE; PEPTIDE DERIVATIVE; PROSTATE SPECIFIC MEMBRANE ANTIGEN; ASPARTIC ACID; GLUTAMATE CARBOXYPEPTIDASE II; GLUTAMATE CARBOXYPEPTIDASE II, HUMAN; GLUTAMIC ACID; HYBRID PROTEIN; IMMUNOGLOBULIN HEAVY CHAIN; IMMUNOGLOBULIN KAPPA CHAIN; MEMBRANE ANTIGEN; PEPTIDE FRAGMENT; PRODRUG;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; DRUG STABILITY; ENZYME SPECIFICITY; HUMAN; HUMAN CELL; HYDROLYSIS; IN VITRO STUDY; ANIMAL; CELL CULTURE; EXTRACELLULAR FLUID; GENETICS; MALE; METABOLISM; MOUSE; PATHOLOGY; PROSTATE TUMOR; WESTERN BLOTTING;

ANIMALS; ANTIGENS, SURFACE; ASPARTIC ACID; BLOTTING, WESTERN; EXTRACELLULAR FLUID; GLUTAMATE CARBOXYPEPTIDASE II; GLUTAMIC ACID; HUMANS; IMMUNOGLOBULIN GAMMA-CHAINS; IMMUNOGLOBULIN KAPPA-CHAINS; MALE; METHOTREXATE; MICE; PEPTIDE FRAGMENTS; PRODRUGS; PROSTATIC NEOPLASMS; RECOMBINANT FUSION PROTEINS; SUBSTRATE SPECIFICITY; TUMOR CELLS, CULTURED;

EID: 21644470680     PISSN: 15384047     EISSN: 15558576     Source Type: Journal    
DOI: 10.4161/cbt.3.6.846     Document Type: Article

References (47)

1. Horoszewicz JS, Kawinski E, Murphy JP. Monoclonal antibodies to a new antigenic marker in epithelial cells and serum of prostatic cancer patients. Anticancer Res 1987; 7:927-35.
2. Silver DA, Pellicer I, Fair WR, Heston WDW, Cordon-Cardo C. Prostate-specific membrane antigen expression in normal and malignant tissues. Clin Cancer Res 1997; 3:81-5.
3. Kawakami M, Nakayama J. Enhanced expression of prostate-specific membrane antigen gene in prostate cancer as revealed by in situ hybridization. Cancer Res 1997; 57:2321-24.
4. Fair WR, Israeli RS, Heston WDW. Prostate-specific membrane antigen. Prostate 1997; 32:140-8.
5. Heston WDW. Characterization and glutamyl preferring carboxypeptidase function of prostate specific membrane antigen: A novel folate hydrolase. Urology 1997; 49:104-12.
6. Dumas F, Gala JL, Berteau P, Brasseur F, Eschwege P, Paradis V, et al. Molecular expression of PSMA mRNA and protein in primary renal tumors. Int J Cancer 1999; 80:799-803.
7. Gala JL, Loric S, Guiot Y, Denmeade SR, Gady A, Brasseur F, et al. Expression of prostate-specific membrane antigen in transitional cell carcinoma of the bladder: Prognostic value? Clin Cancer Res 2000; 6:4049-54.
8. Liu H, Moy P, Kim S, Xia Y, Rajasekaran A, Navarro V, et al. Monoclonal antibodies to the extracellular domain of prostate-specific membrane antigen also react with tumor vascular endothelium. Cancer Res 1997; 57:3629-34.
9. Chang SS, Reuter VE, Heston WDW, Bander NH, Grauer LS, Gaudin PB. Five different anti- prostate-specific membrane antigen (PSMA) antibodies confirm PSMA expression in tumor-associated neovasculature. Cancer Res 1999; 59:3192-8.
10. Israeli RS, Powell CT, Corr JG, Fair WR, Heston WD. Expression of the prostate-specific membrane antigen. Cancer Res 1994; 54:1807-11.
11. Wright Jr GL, Grob BM, Haley C, Grossman K, Newhall K, Petrylak D, et al. Upregulation of prostate-specific membrane antigen after androgen-deprivation therapy. Urology 1996; 48:326-34.
12. Young CY, Montgomery BT, Andrews PE, Qui SD, Bilhartz DL, Tindall DJ. Hormonal regulation of prostate-specific antigen messenger RNA in human prostatic adenocarcinoma cell line LNCaP. Cancer Res 1991; 51:3748-52.
13. Riegman PH, Vlietstra RJ, van der Korput JA, Brinkmann AO, Trapman J. The promoter of the prostate-specific antigen gene contains a functional androgen responsive element. Mol Endocrinol 1991; 5:1921-30.
14. Ross JS, Sheehan CE, Fisher HA, Kaufman Jr RP, Kaur P, Gray K, et al. Correlation of primary tumor prostate-specific membrane antigen expression with disease recurrence in prostate cancer. Clin Cancer Res 2003; 9:6357-62.
15. Luthi-Carter R, Barczak AK, Speno H, Coyle JT. Molecular characterization of human N-acetylated α-linked acidic dipeptidase (NAALADase). J Pharm Exp Therap 1998; 286:1020-5.
16. Carter RF, Feldman AR, Coyle JT. Prostate-specific membrane antigen is a hydrolase with substrate and pharmacological characteristics of a neuropeptidase. Proc Natl Acad Sci USA 1996; 93:749-53.
17. Luthi-Carter R, Berger, UV, Barczak AK, Enna M, Coyle JT. Isolation and expression of a rat brain cDNA encoding glutamate carboxypeptidase II. Proc Natl Acad Sci USA 1998; 95:3215-20.
18. Robinson MB, Blakely RD, Couto R, Coyle JT. Hydrolysis of the brain dipeptide N-acetyl-aspartyl-L-glutamate. J Biol Chem 1987; 262:14498-506.
19. Slusher BS, Robinson MB, Tsai G, Simmons RL, Richards SS, Coyle JT. Rat brain N-acetylated α-linked acidic dipeptidase activity. J Biol Chem 1990; 265:21297-301.
20. Luthi-Carter R, Barczak AK, Speno H, Coyle JT. Hydrolysis of the neuropeptide N-acetylaspartylglutamate (NAAG) by cloned human glutamate carboxypeptidaseII. Brain Res 1998; 795:341-8.
21. Tiffany CW, Lapidus RG, Merion A, Calvin DC, Slusher BS. Characterization of the enzymatic activity of PSM: Comparison with brain NAALADase. Prostate 1999; 39:28-35.
22. Pinto JT, Suffoleto BP, Berzin TM, Qiao CH, Lin S, Tong W, et al. Prostate-specific membrane antigen: A novel folate hydrolase in human prostatic carcinoma cells. Clin Cancer Res 1996; 2:1445-51.
23. Lo K-M, Sudo Y, Chen J, Yue L, Yan L, Kong S-M, et al. High level expression and characterization of Fc-X fusion proteins in mammalian cells. Protein Engineering 1998; 11:495-500.
24. Horoszewicz JS, Leong SS, Kawinski E, Karr J, Rosenthal H, Chu TM, et al. LNCAP model of human prostatic carcinoma. Cancer Res 1980; 43:1809-18.
25. Iizumi T, Yazaki T, Kanoh S, Kondo I, Koiso K. Establishment of a new prostatic carcinoma cell line (TSU-Pr1). J Urol 1987; 137:1304-6.
26. van Bokhoven A, Varella-Garcia M, Korch C, Miller GJ. TSU-Pr1 and JCA-1 cells are derivatives of T24 bladder carcinoma cells and are not of prostatic origin. Cancer Res 2001; 61:6340-4.
27. Denmeade SR, Nagy A, Gao J, Lilja H, Schally A, Isaacs JT. Enzymatic activation of a doxorubicin-peptide prodrug by prostate-specific antigen. Cancer Res 1998; 58:2537-40.
28. Denmeade SR, Sokoll LJ, Dalrymple S, Rosen DM, Gady AM, Bruzek D, et al. Dissociation between androgen responsiveness for malignant growth vs. expression of prostate specific differentiation markers PSA, hK2, and PSMA in human prostate cancer models. Prostate 2003; 54:249-57.
29. Barinka C, Rinnova M, Sacha P, Rojas C, Majer P, Slusher BS, et al. Substrate specificity, inhibition and enzymological analysis of recombinant human glutamate carboxypeptidase II. J Neurochem. 2002; 80:477-87.
30. Denmeade SR, Jakobsen CM, Janssen S, Khan SR, Garrett ES, Lilja H, et al. Prostate-specific antigen-activated thapsigargin prodrug as targeted therapy for prostate cancer. J Natl Cancer Inst 2003; 95:990-1000.
31. Piper JR, Montgomery JA. Syntheses of α- and γ-substituted amides, peptides and ester of methotrexate and their evaluation as inhibitors of folate metabolism. J Med Chem 198; 225:182-7.
32. Galivan J, Ryan TJ, Chave K, Rhee M, Yao R, Yin D. Glutamyl hydrolase. pharmacological role and enzymatic characterization. Pharmacol Ther 2000; 85:207-15.
33. Samuels LL, Goutas LJ, Priest DG, Piper JR, Sirotnak FM. Hydrolytic cleavage of methotrexate γ-polyglutamates by folylpolyglutamyl hydrolase derived from various tumors and normal tissues of the mouse. Cancer Res 1986; 46:2230-5.
34. Rhee MS, Lindau-Shepard KJ, Chave J, Galivan JH, Ryan TJ. Characterization of human cellular γ-glutamyl hydrolase. Molec Pharmacol 1998; 53:1040-6.
35. Jodrell DI, Gibson W, Bisset GM, Boyle FT, Judson IR, Jackman AL. The in vivo metabolic stability of dipeptide analogues of the quinazoline antifolate, ICI 198583, in mice. Biochemical Pharmacology 1993; 46:2229-34.
36. Gingras R, Richard C, El-Alfy M, Morales CR, Potier M, Pshezhetsky AV. Purification, cDNA cloning, and expression of a new human blood plasma glutamate carboxypeptidase homologous to N-acetyl-aspartyl-α-glutamate carboxypeptidase/prostate-specific membrane antigen. J Biol Chem 1999; 274:11742-50.
37. Yagoda A, Petrylak D. Cytotoxic chemotherapy for advanced hormone-resistant prostate cancer. Cancer 1993; 71:1098-1109.
38. Allegra CJ, Grem JL. Antimetabolites. In: DeVita VT, Hellman S, Rosenberg SA, eds. Cancer Principles & Practice of Oncology. 5th Edition. Philadelphia, PA: Lippincott-Raven Publishers; 1997:432-5.
39. Sierra EE, Goldman ID. Recent advances in the understanding of the mechanism of membrane transport of folates and antifolates. Sem Oncology 1999; 26:11-23.
40. Westerhof GR, Schornagel JH, Kathmann I, Jackman AL, Rosowsky A, Forsch RA, et al. Carrier- and receptor-mediated transport of folate antagonists targeting folate-dependent enzymes: Correlates of molecular-structure and biological activity. Mol Pharmacol 1995; 48:459-41.
41. Holm J, Hansen SI, Hoier-Madsen M. High affinity folate binding in human prostate. Bioscience Rep 1993; 13:99-105.
42. Horne DW, Reed KA. Transport of methotrexate into PC-3 human prostate cancer cells. Arch Biochem Biophys 2001; 394:39-44.
43. Benns JM, Kim SW. Tailoring new gene delivery designs for specific targets. J Drug Target 2000; 8:1-12.
44. Mathias CJ, Hubers D, Low PS, Green MA. Synthesis of [(99m)Tc]DTPA-folate and its evaluation as a folate-receptor-targeted radiopharmaceutical. Bioconjug Chem 2000; 11:253-7.
45. Lu JY, Lowe DA, Kennedy MD, Low PS. Folate-targeted enzyme prodrug cancer therapy utilizing penicillin-V amidase and a doxorubicin prodrug. J Drug Target 1999; 7:43-53.
46. Li S, Deshmukh HM, Huang L. Folate-mediated targeting of antisense oligodeoxynucleotides to ovarian cancer cells. Pharm Res 1998; 15:1540-5.
47. Quintana A, Raczka E, Piehler L, Lee I, Myc A, Majoros I, et al. Design and function of a dendrimer-based therapeutic nanodevice targeted to tumor cells through the folate receptor. Pharm Res 2002; 19:1310-6.