Bivalent inhibitors for disrupting protein surface-substrate interactions and for dual inhibition of protein prenyltransferases

Journal of the American Chemical Society

Volumn 133, Issue 4, 2011, Pages 958-963

  Machida, Shinnosuke ^a   Kato, Nobuo ^a   Harada, Kazuo ^b   Ohkanda, Junko ^a  

^a OSAKA UNIVERSITY   (Japan)

^b TOKYO GAKUGEI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL SPACERS; CHEMICAL PROBES; DUAL-ENZYMES; ENZYMATIC REACTION; ENZYME ACTIVE SITES; FARNESYLATION; FARNESYLTRANSFERASE; FLAT INTERFACE; GALLATE; GERANYLGERANYLATION; GGTASE I; INHIBITORY ACTIVITY; LOW-MOLECULAR-WEIGHT COMPOUNDS; POTENTIAL APPLICATIONS; PROTEIN SURFACE; PROTEIN-PROTEIN INTERACTIONS; SUBSTRATE INTERACTION; TETRAPEPTIDE;

CHEMICAL COMPOUNDS; ENZYMES; PEPTIDES;

SURFACE REACTIONS;

DIMETHYLALLYLTRANSFERASE; ENZYME INHIBITOR; GALLIC ACID; GERANYLTRANSFERASE; MEMBRANE PROTEIN; PROTEIN FARNESYLTRANSFERASE; PROTEIN FARNESYLTRANSFERASE INHIBITOR;

ARTICLE; BINDING SITE; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME SUBSTRATE; ENZYME SUBUNIT; MOLECULAR WEIGHT; PROTEIN PROTEIN INTERACTION; THERMODYNAMICS;

ALKYL AND ARYL TRANSFERASES; AMINO ACID SEQUENCE; ANIMALS; BIOMIMETIC MATERIALS; CATALYTIC DOMAIN; DIMETHYLALLYLTRANSTRANSFERASE; DRUG DESIGN; ENZYME INHIBITORS; GALLIC ACID; HUMANS; MODELS, MOLECULAR; PEPTIDE FRAGMENTS; PRENYLATION; PROTEIN BINDING; PROTO-ONCOGENE PROTEINS P21(RAS); SURFACE PROPERTIES;

EID: 79851487933     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jal086112     Document Type: Article

References (35)

1. Wells, J. A.; McClendon, C. L. Nature 2007, 450, 1001-1009.
2. Robinson, J. A.; DeMarco, S.; Gombert, F.; Moehle, K.; Obrecht, D. Dmg Discovery Today 2008. 13, 944-951.
3. Blazer, L. L.; Neubig, R. R. Neuropsychopharmacology 2009, 34, 126-141.
4. Saraogi, I.; Hebda, J. A.; Becerril, J.; Estroff, L. A.; Miranker, AD.; Hamilton, A. D. Angew. Chem. Int. Ed. 2010, 49, 736-739.
5. Bach, A.; Chi, C. N.; Pang, G. F.; Olsen, L.; Kristensen, A. S.; Jemth, P.; Strømgaard, K. Angew. Chem. Int. Ed. 2009, 48, 9685-9689.
6. Srinivas, N.; et al. Science 2010, 327, 1010-1013.
7. Heinis, C.; Rutherford, T.; Freund, S.; Winter, G. Nat. Chem. Biol. 2009, 5, 501-507.
8. Home, W. S.; Johnson, L. M.; Ketas, T. J.; Klasse, P. J.; Lu, M.; Moore, J. P.; Gellman, S. M. Proc. Natl. Acad. Sci. U. SA. 2009, 106, 14751-14756.
9. Michel, J.; Harker, E. A.; Tirado-Rives, J.; Jorgensen, W. L.; Schepartz, A. J. Am. Chem. Soc. 2009, 131, 6356-6357.
10. Rosenzweig, B. A.; Ross, N. T.; Tagore, D. M.; Jayawickramarajah, J.; Saraogi, I.; Hamilton, A D. J. Am. Chem. Sor. 2009. 131, 5020-5021.
11. Kim, Y.; Cao, Z.; Tan, W. Proc. Natl. Acad. Sci. U. S. A 2008, 105, 5664-5669.
12. Tanoue, T.; Nishida, E. Cell. Signal. 2003, 15, 455-462.
13. Rudolph, J. Nature Rev. Cancer 2007, 7, 202-211.
14. Sohn, J.; Buhrman, G.; Rudolph, J. Biochemistry 2007, 46, 807-818.
15. Kazi, A.; Carie, A.; Blaskovich, M. A.; Bucher, C.; Thai, V.; Moulder, S.; Peng, H.; Carrico, D.; Pusateri, E.; Pledger, W. J.; Berndt, N.; Hamilton, A. D.; Sebti, S. M. Mol. Cell. Biol. 2009, 29, 2254-2263.
16. Gelb, M. H.; Brunsveld, L.; Hrycyna, C. A.; Michaelis, S.; Tamanoi, F.; Boorhis, W. C. V.; Waldmann, H. Nat. Chem. Biol. 2006, 2, 518-528.
17. Liu, M.; Sjogren, A-K. M.; Karlsson, C.; Ibrahim, M. X.; Andersson, K. M. E.; Olofsson, F. J.; Wahlstrom, A M.; Dalin, M.; Yu, H.; Chem, Z.; Yang, S. H.; Young, S. G.; Bergo, M. O. Proc. Natl. Acad. Sci. U. SA. 2010, 107, 6471-6476.
18. Casey, P. J.; Seabra, M. C. J. Biol. Chem. 1996, 271, 5289-5292.
19. Long, S. B.; Casey, P. J.; Beese, L. S. Structure 2000, 8, 209-222.
20. Whyte, D. B.; Kirschmeier, P.; Hockenberry, T. N.; Nunez-Oliva, I.; James, L.; Catino, J. J.; Bishop, W. R.; Pai, J. J. Biol. Chem. 1997, 272, 14459-14464.
21. Rowell, C. A.; Kowalczyk, J. J.; Lewis, M. D.; Garcia, A. M. J. Biol. Chem. 1997, 272, 14093-14097.
22. James, G. L.; Goldstein, J. L.; Brown, M. S. J. Biol. Chem. 1995, 270, 6221-6226.
23. Zhang, F. L.; Kirschmeier, P.; Carr, D.; James, L.; Bond, R. W.; Wang, L.; Patton, R.; Windsor, W.; Syto, R.; Zhang, R.; Bishop, W. R. J. Biol. Chem. 1997, 272, 10232-10239.
24. Smalera, I.; Williamson, J. M.; Baginsky, W.; Leiting, B.; Mazur, P. Biochim. Biovhvs. Acta 2000, 1480, 132-144.
25. Fiordalisi, J. J.; Johnson, R. L., II.; Weinbaum, C. A.; Sakabe, K.; Chen, Z.; Casey, P. J.; Cox, A. D. J. Biol. Chem. 2003, 278, 41718-41727.
26. Machida, S.; Usuba, K.; Blaskovich, M. A.; Yano, A.; Harada, K.; Sebti, S. M.; Kato, N.; Ohkanda, J. Chem.-Eur. I. 2008, 14, 1392-1401.
27. Ohkanda, J.; Satoh, R.; Kato, N. Chem. Commun. 2009, 6949-6951.
28. Pompiliano, D. L.; Gomez, R P.; Anthony, J. J. JAm. Chem. Soc. 1992, 114, 7945-7946.
29. Cheng, Y.; Prusoff, W. H. Biochem. Pharmacol. 1973, 22, 3099-3108.
30. Miyashita, O.; Onuchic, J. N.; Okamura, M. Y. Biochemistry 2003, 42, 11651-11660.
31. Lane, K. T.; Beese, L. S. J. Lipid Res. 2006, 47, 681-699.
32. Lobell, R B.; et al. Cancer Res. 2001, 61, 8758-8768.
33. deSolms, S. J.; Ciccarone, T. M.; MacTough, S. C.; Shaw, A W.; Buser, C. A.; Ellis-Hutchings, M.; Fernandes, C.; Hamilton, K. A.; Huber, H. E.; Kohl, N. E.; Beese, L. S.; Taylor, J. S. J. Med. Chem. 2003, 46, 2973-2984.
34. Martin, N. E.; et al. Clin. Cancer Res. 2004, 10, 5447-5454.
35. Fu, H.; Moomaw, J. F.; Moomaw, C. R.; Casey, P. J. J. Biol. Chem. 1996, 271, 28541-28548.