Ionic immobilization, diversification, and release: Application to the generation of a library of methionine aminopeptidase inhibitors

Journal of Combinatorial Chemistry

Volumn 10, Issue 2, 2008, Pages 185-194

  Vedantham, Punitha ^a   Guerra, Jennifer M ^a   Schoenen, Frank ^b   Huang, Min ^a   Gor, Parul J ^a   Georg, Gunda I ^a,d   Wang, Jenna L ^a   Neuenswander, Benjamin ^b   Lushington, Gerald H ^a   Mitscher, Lester A ^a   Ye, Qi Zhuang ^a,c   Hanson, Paul R ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b Center for Chemical Methodology and Library Development   (United States)

^c INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOPEPTIDASE; METHIONYL AMINOPEPTIDASE; PROTEINASE INHIBITOR;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; ENZYMOLOGY; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

AMINOPEPTIDASES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESCHERICHIA COLI; MASS SPECTROMETRY; PROTEASE INHIBITORS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 42449149182     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc700085c     Document Type: Article

References (34)

1. Bradshaw, R. A.; Brickey, W. W.; Walker, K. W. Trends Biochem. Sci. 1998, 23, 263-267.
2. Chen, S.; Vetro, J. A.; Chang, Y.-H. Arch. Biochem. Biophys. 2002, 398, 87-93.
3. (a) Griffith, E. C.; Su, Z.; Niwayama, S.; Ramsay, C. A.; Chang. Y.-H.; Liu, J. O. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 15183-15188.
4. (b) Griffith, E. C.; Su, Z.; Turk, B. E.; Chen, S.; Chang, Y.-H.; Wu, Z.; Biemann, K.; Liu, J. O. Chem. Biol. 1997, 4, 461-471.
5. Towbin, H.; Bair, K. W.; DeCaprio, J. A.; Eck, M. J.; Kim, S.; Kinder, F. R.; Morollo, A.; Mueller, D. R.; Schindler, P.; Song, H. K.; van Oostrum, J.; Versace, R. W.; Voshol, H.; Wood, J.; Zabludoff, S.; Phillips, P. E. J. Biol. Chem. 2003, 278, 52964-52971.
6. Chang, S.-Y.; McGary, E. C.; Chang, S. J. Bacteriol. 1989, 171, 4071-4072.
7. Miller, C. G.; Kukral, A. M.; Miller, J. L.; Movva, N. R. J. Bacteriol. 1989, 171, 5215-5217.
8. Vaughan, M. D.; Sampson, P. B.; Honek, J. F. Curr. Med. Chem. 2002, 9, 385-409.
9. Steinmeyer, A. ChemMedChem. 2006, 1, 31-36.
10. Ye, Q.-Z.; Xie, S.-X.; Huang, M.; Huang, W.-J.; Lu, J.-P.; Ma, Z.-Q. J. Am. Chem. Soc. 2004, 126, 13940-13941.
11. Huang, Q.-Q.; Huang, M.; Nan, F. J.; Ye, Q.-Z. Bioorg. Med. Chem. Lett. 2005, 15, 5386-5391.
12. Vedantham, P.; Zhang, M.; Gor, P. J.; Huang, M.; Georg, G. I.; Lushington, G. H.; Mitscher, L. A.; Ye, Q.-Z.; Hanson, P. R. J. Comb. Chem. 2008, 10, 195-203.
13. McComas, W.; Chen, L.; Kim, K. Tetrahedron Lett. 2000, 41, 3573-3576.
14. Vickerstaffe, E.; Warrington, B. H.; Ladlow, M.; Ley, S. L. Org. Biomol. Chem. 2003, 1, 2419-2422.
15. Jönsson, D.; Warrington, B. H.; Ladlow, M. J. Comb. Chem. 2004, 6, 584-595.
16. Dondoni, A.; Marra, A.; Massi, A. Angew. Chem., Int. Ed. 2005, 44, 1672-1676.
17. (a) Baxendale, I. R.; Ley, S. L.; Martinelli, M. Tetrahedron 2005, 61, 5323-5349.
18. (b) Adams, G. L.; Graybill, T. L.; Sanchez, R. M.; Magaard, V. W.; Burton, G.; Rivero, R. A. Tetrahedron Lett. 2003, 44, 5041-5045.
19. Different procedures to improve the yield of the catch-release sequence including capturing the free acid on the resin twice in succession before cleavage and treating the intermediate ion-pair with a higher strength of HCl (4N, 6N, 5-6N in isopropanol) were attempted.
20. It was observed that dilute HCl could not be used with MeOH as a solvent for cleavage, since esterification of the final products were observed. For further details, please see Morwick, T. M. J. Comb. Chem. 2006, 8, 649-651.
21. Despite these high purity levels, all compounds were submitted to preparative HPLC (mass-directed fractionation) to ensure the compounds contained no residual color or Pd.
22. (a) D'souza, V. M.; Holz, R. C. Biochemistry 1999, 38, 11079-11085.
23. (b) Li, J.-Y.; Chen, L.-L.; Cui, Y.-M.; Luo, Q.-L.; Li, J.; Nan, F.-J.; Ye, Q.-Z. Biochem. Biophys. Res. Commun. 2003, 307, 172-179.
24. SYBYL 7.2; The Tripos Associates, Inc.: St. Louis, MO, 2006.
25. Clark, M.; Cramer, R. D.; Van Opdenbosch, N J. Comput. Chem. 1989, 10, 982-1012.
26. Gasteiger, J.; Marsili, M. Tetrahedron Lett. 1978, 34, 3181-3184.
27. Morris, G. M.; Goodsell, D. S.; Huey, R.; Olson, A. J. Computer-Aided Mol. Design 1996, 10, 293-304.
28. (a) Wang, T.; Wade, R. C. J. Med. Chem. 2002, 45, 4828-4837.
29. (b) Guo, J.; Hurley, M. M.; Wright, J. B.; Lushington, G. H. J. Med. Chem. 2004, 47, 5492-5500.
30. SIMCA-P; Umereics AB: Umea, Sweden, 2001.
31. A Calculator Plug-In; ChemAxon, Inc.: Budapest, Hungary, 2005.
32. SYBYL 6.9.2; The Tripos Associates: St. Louis, MO, 2004.
33. Cruciani, G.; Crivori, P.; Carrupt, P.-A.; Testa, B. THEOCHEM 2000, 503, 17-30.
34. Pearlman, R. S.; Smith, K. M. Drugs Future 1998, 23, 885.