Design and synthesis of a siderophore conjugate as a potent PSMA inhibitor and potential diagnostic agent for prostate cancer

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 4, 2008, Pages 1648-1657

  Ding, Pingyu ^a   Helquist, Paul ^a   Miller, Marvin J ^a,b  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b HANS KNÖLL INSTITUTE   (Germany)

Author keywords

Inhibitor; NAALADase; PSMA; Siderophore conjugate

Indexed keywords

DIAGNOSTIC AGENT; PROSTATE SPECIFIC MEMBRANE ANTIGEN; SIDEROPHORE CONJUGATE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CANCER DIAGNOSIS; DRUG SYNTHESIS; IC 50; IRON BINDING CAPACITY; NUCLEAR MAGNETIC RESONANCE IMAGING; PROSTATE CANCER;

CROSS-LINKING REAGENTS; DRUG DESIGN; ENZYME INHIBITORS; GLUTAMATE CARBOXYPEPTIDASE II; HUMANS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE IMAGING; MALE; PROSTATE-SPECIFIC ANTIGEN; PROSTATIC NEOPLASMS; SIDEROPHORES;

EID: 39049135745     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.11.030     Document Type: Article

References (49)

1. Carter R.E., and Coyle J.T. In: Barrett A.J., Rawlings N.D., and Woessner J.F. (Eds). Handbook of Proteolytic Enzymes (1998), Academic, New York 1434-1437
2. Bruno V., Battaglia G., Copani A., Giffard R.G., Raciti G., Raffaele R., Shinozaki H., and Nicoletti F. Eur. J. Pharmacol. 7 (1995) 1906
3. Choi D.W., and Rothman S.M. Annu. Rev. Neurosci. 13 (1990) 171
4. Zhou J., Neale J.H., Pomper M.G., and Kozikowski A.P. Nat. Rev. Drug Discov. 4 (2005) 1015
5. Jackson P.F., Cole D.C., Slusher B.S., Stetz S.L., Ross L.E., Donzanti B.A., and Trainor D.A. J. Med. Chem. 39 (1996) 619
6. Kozikowski A.P., Zhang J., Nan F., Petukhov P.A., Grajkowska E., Wroblewski J.T., Yamamoto T., Bzdega T., Wroblewska B., and Neale J.H. J. Med. Chem. 47 (2004) 1729-1738
7. Kozikowski A.P., Nan F., Conti P., Zhang J., Ramadan E., Bzdega T., Wroblewska B., Neale J.H., Pshenichkin S., and Wroblewski J.T. J. Med. Chem. 44 (2001) 298
8. Jackson P.F., Tays K.L., Maclin K.M., Ko Y.-S., Li W., Vitharana D., Tsukamoto T., Stoermer D., Lu X.-C.M., Wozniak K., and Slusher B.S. J. Med. Chem. 44 (2001) 4170
9. Vitharana D., France J.E., Scarpetti D., Bonneville G.W., Majer P., and Tsukamoto T. Tetrahedron: Asymmetry 13 (2002) 1609
10. Tsukamoto T., Majer P., Vitharana D., Ni C., Hin B., Lu X.-C.M., Thomas A.G., Wozniak K.M., Calvin D.C., Wu Y., Slusher B.S., Scarpetti D., and Bonneville G.W. J. Med. Chem. 48 (2005) 2319
11. Carter R.E., Feldman A.R., and Coyle J.T. Proc. Natl. Acad. Sci. 93 (1996) 749
12. Tiffany C.W., Lapidus R.G., Merion A., Calvin D.C., and Slusher B.S. Prostate 39 (1999) 28
13. Asatiani E., and Gelmann E.P. Expert Opin. Ther. Targets 9 (2005) 283
14. Elsasser-Beile U., Wolf P., Gierschner D., Buhler P., Schultze-Seemann W., and Wetterauer U. Prostate 66 (2006) 1359
15. Farokhzad O.C., Cheng J.J., Teply B.A., Sherifi I., Jon S., Kantoff P.W., Richie J.P., and Langer R. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 6315
16. Chu T.C., Shieh F., Lavery L.A., Levy M., Richards-Kortum R., Korgel B.A., and Ellington A.D. Biosens. Bioelectron. 21 (2006) 1859
17. Misra P., Humblet V., Pannier N., Maison W., and Frangioni J.V. J. Nucl. Med. 48 (2007) 1379
18. Davis M.I., Bennett M.J., Thomas L.M., and Bjorkman P.J. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 5981
19. Oliver A.J., Wiest O., Helquist P., Miller M.J., and Tenniswood M. Bioorg. Med. Chem. 11 (2003) 4455
20. Tang H., Brown M., Ye Y., Huang G., Zhang Y., Wang Y., Zhai H., Chen X., Shen T.Y., and Tenniswood M. Biochem. Biophys. Res. Commun. 307 (2003) 8 Other diagnostic methods, see:
21. Foss C.A., Mease R.C., Fan H., Wang Y., Ravert H.T., Dannals R.F., Olszewski R.T., Heston W.D., Kozikowski A.P., and Pomper M.G. Clin. Cancer Res. 11 (2005) 4022
22. Ohnishi S., Lomnes S.J., Laurence R.G., Gogbashian A., Mariani G., and Frangioni J.V. Mol. Imaging 4 (2005) 448
23. Wone D.W.G., Rowley J.A., Garofalo A.W., and Berkman C.E. Bioorg. Med. Chem. 14 (2006) 67
24. Mallari J.P., Choy C.J., Hu Y., Martinez A.R., Hosaka M., Toriyabe Y., Maung J., Blecha J.E., Pavkovic S.F., and Berkman C.E. Bioorg. Med. Chem. 12 (2004) 6011
25. Maung J., Mallari J.P., Girtsman T.A., Wu L.Y., Rowley J.A., Santiago N.M., Brunelle A.N., and Berkman C.E. Bioorg. Med. Chem. 12 (2004) 4969
26. Ding P., Helquist P., and Miller M.J. Org. Biomol. Chem. 5 (2007) 826
27. Humblet V., Misra P., and Frangioni J.V. Contrast Med. Mol. Imaging 1 (2006) 196
28. Richardson N., Davies J.A., and Raduchel B. Polyhedron 18 (1999) 2457
29. Roosenberg II J.M., Lin Y.M., Lu Y., and Miller M.J. Curr. Med. Chem. 7 (2000) 159
30. Luo M., Fadeev E.A., and Groves J.T. J. Am. Chem. Soc. 127 (2005) 1726
31. Chaubet F., van Duong K.N., Courtieu J., Gaudemer A., Gref A., Crumbliss A.L., and Caudle M.T. Can. J. Chem. 72 (1994) 2361
32. Dhungana S., Heggemann S., Heinishc L., Möllmann U., Boukhalfa H., and Crumbliss A.L. Inorg. Chem. 40 (2001) 7079
33. Benz G. Liebigs Ann. Chem. (1984) 1424
34. Benz G., and Schmidt D. Liebigs Ann. Chem. (1984) 1434
35. Lin Y.-M., and Miller M.J. J. Org. Chem. 64 (1999) 7451
36. Lee B.H., and Miller M.J. Tetrahedron Lett. 25 (1984) 927
37. Dolence E.K., Minnick A.A., and Miller M.J. J. Med. Chem. 33 (1990) 461
38. Dolence E.K., Lin C.-E., and Miller M.J. J. Med. Chem. 34 (1991) 956
39. Sonpatki V.M., Herbert M.R., Sandvoss L.M., and Seed A.J. J. Org. Chem. 66 (2001) 7283
40. Dalcanale E., and Montanari F. J. Org. Chem. 51 (1986) 567
41. Holzapfel C.W., and Pettit G.R. J. Org. Chem. 50 (1985) 2323
42. Nagarajan S., and Ganem B. J. Org. Chem. 52 (1987) 5044
43. Hendry D., Hough L., and Richardson A.C. Tetrahedron Lett. 28 (1987) 4601
44. Lim M.-I., and Marquez V.E. Tetrahedron Lett. 24 (1983) 5559
45. Sterzycki R. Synthesis (1979) 724
46. Ding P., and Ghosez L. Tetrahedron 58 (2002) 1565
47. Chen C., Layton M.E., Sheehan S.M., and Shair M.D. J. Am. Chem. Soc. 122 (2000) 7424
48. Barinka C., Rinnova M., Sacha P., Rojas C., Majer P., Slusher B.S., and Konvalinka J. J. Neurochem. 80 (2002) 477
49. Rojas C., Frazier S.T., Flanary J., and Slusher B.S. Anal. Biochem. 310 (2002) 50