Targeting multiple chorismate-utilizing enzymes with a single inhibitor: Validation of a three-stage design

Journal of Medicinal Chemistry

Volumn 53, Issue 9, 2010, Pages 3718-3729

  Ziebart, Kristin T ^a   Dixon, Seth M ^a   Avila, Belem ^a   El Badri, Mohamed H ^a   Guggenheim, Kathryn G ^a   Kurth, Mark J ^a   Toney, Michael D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO 4 DEOXYCHORISMATE SYNTHASE; ANTHRANILATE SYNTHASE; CHORISMATE MUTASE; CHORISMATE UTILIZING ENZYME; CHORISMIC ACID; ENZYME; ENZYME INHIBITOR; FLUORESCENT DYE; ISOCHORISMATE SYNTHASE; LYSINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; COMBINATORIAL LIBRARY; CONTROLLED STUDY; CROSS LINKING; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG INHIBITION; DRUG TARGETING; ENZYME ACTIVE SITE; ENZYME KINETICS; ESCHERICHIA COLI; FLUORESCENCE; NONHUMAN; STRUCTURE ACTIVITY RELATION; VALIDATION PROCESS;

ANTHRANILATE SYNTHASE; ANTI-BACTERIAL AGENTS; CARBON-NITROGEN LIGASES; CATALYTIC DOMAIN; CHORISMIC ACID; DRUG DELIVERY SYSTEMS; ENZYME INHIBITORS; HUMANS; INTRAMOLECULAR TRANSFERASES;

EID: 77952044139     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100158v     Document Type: Article

References (33)

1. Coates, A.; Hu, Y.; Bax, R.; Page, C. The future challenges facing the development of new antimicrobial drugs Nat. Rev. Drug Discovery 2002, 1, 895-910
2. Klevens, R. M.; Morrison, M. A.; Nadle, J.; Petit, S.; Gershman, K.; Ray, S.; Harrison, L. H.; Lynfield, R.; Dumyati, G.; Townes, J. M.; Craig, A. S.; Zell, E. R.; Fosheim, G. E.; McDougal, L. K.; Carey, R. B.; FridkS. K. Invasive methicillin-resistant Staphylococcus aureus infections in the United States JAMA, J. Am. Med. Assoc. 2007, 298, 1763-1771
3. Jarvis, L. M. An Uphill Battle Chem. Eng. News 2008, 86, 15-20
4. Fischbach, M. A.; Walsh, C. T. Antibiotics for Emerging Pathogens Science 2009, 325, 1089-1093
5. Dixon, S.; Ziebart, K. T.; He, Z.; Jeddeloh, M.; Yoo, C. L.; Wang, X.; Lehman, A.; Lam, K. S.; Toney, M. D.; Kurth, M. J. Aminodeoxychorismate synthase inhibitors from one-bead one-compound combinatorial libraries: "staged"inhibitor design J. Med. Chem. 2006, 49, 7413-7426
6. Roberts, F.; Roberts, C. W.; Johnson, J. J.; Kyle, D. E.; Krell, T.; Coggins, J. R.; Coombs, G. H.; Milhous, W. K.; Tzipori, S.; Ferguson, D. J.; Chakrabarti, D.; McLeod, R. Evidence for the shikimate pathway in apicomplexan parasites Nature 1998, 393, 801-805
7. Morphy, R.; Rankovic, Z. Designed multiple ligands. An emerging drug discovery paradigm J. Med. Chem. 2005, 48, 6523-6543
8. Morphy, R.; Kay, C.; Rankovic, Z. From magic bullets to designed multiple ligands Drug Discovery Today 2004, 9, 641-651
9. Weber, G.; Prajda, N.; Lui, M. S.; Denton, J. E.; Aoki, T.; Sebolt, J.; Zhen, Y. S.; Burt, M. E.; Faderan, M. A.; Reardon, M. A. Multi-enzyme-targeted chemotherapy by acivicin and actinomycin Adv. Enzyme Regul. 1982, 20, 75-96
10. Hibasami, H.; Maekawa, S.; Murata, T.; Nakashima, K. Antitumor effect of a new multienzyme inhibitor of polyamine synthetic pathway, methylglyoxal- bis(cyclopentylamidinohydrazone), against human and mouse leukemia cells Cancer Res. 1989, 49, 2065-2068
11. Zhan, P.; Liu, X. Y. Designed Multiple Ligands: An Emerging Anti-HIV Drug Discovery Paradigm Curr. Pharm. Des. 2009, 15, 1893-1917
12. Arora, P.; Goyal, A.; Natarajan, V. T.; Rajakumara, E.; Verma, P.; Gupta, R.; Yousuf, M.; Trivedi, O. A.; Mohanty, D.; Tyagi, A.; Sankaranarayanan, R.; Gokhale, R. S. Mechanistic and functional insights into fatty acid activation in Mycobacterium tuberculosis Nat. Chem. Biol. 2009, 5, 166-173
13. Barkan, D.; Liu, Z.; Sacchettini, J. C.; Glickman, M. S. Mycolic Acid Cyclopropanation is Essential for Viability, Drug Resistance, and Cell Wall Integrity of Mycobacterium tuberculosis Chem. Biol. 2009, 16, 499-509
14. Chen, J. K.; Lane, W. S.; Brauer, A. W.; Tanaka, A.; Schreiber, S. L. Biased combinatorial libraries: Novel ligands for the SH3 domain of phosphatidylinositol 3-kinase J. Am. Chem. Soc. 1993, 115, 12591-12592
15. Sternson, S. M.; Wong, J. C.; Grozinger, C. M.; Schreiber, S. L. Synthesis of 7200 small molecules based on a substructural analysis of the histone deacetylase inhibitors trichostatin and trapoxin Org. Lett. 2001, 3, 4239-4242
16. Erlanson, D. A. Fragment-based lead discovery: a chemical update Curr. Opin. Biotechnol. 2006, 17, 643-652
17. Parsons, J. F.; Jensen, P. Y.; Pachikara, A. S.; Howard, A. J.; EisensteE.; Ladner, J. E. Structure of Escherichia coli aminodeoxychorismate synthase: architectural conservation and diversity in chorismate-utilizing enzymes Biochemistry 2002, 41, 2198-2208
18. Spraggon, G.; Kim, C.; Nguyen-Huu, X.; Yee, M. C.; Yanofsky, C.; Mills, S. E. The structures of anthranilate synthase of Serratia marcescens crystallized in the presence of (i) its substrates, chorismate and glutamine, and a product, glutamate, and (ii) its end-product inhibitor, l -tryptophan Proc. Natl. Acad. Sci. U.S.A 2001, 98, 6021-6026
19. Morollo, A. A.; Eck, M. J. Structure of the cooperative allosteric anthranilate synthase from Salmonella typhimurium Nat. Struct. Biol. 2001, 8, 243-247
20. Parsons, J. F.; Shi, K. M.; Ladner, J. E. Structure of isochorismate synthase in complex with magnesium Acta Crystallogr., Sect. D: Biol. Crystallogr. 2008, 64, 607-610
21. Kolappan, S.; Zwahlen, J.; Zhou, R.; Truglio, J. J.; Tonge, P. J.; Kisker, C. Lysine 190 is the catalytic base in MenF, the menaquinone-specific isochorismate synthase from Escherichia coli: implications for an enzyme family Biochemistry 2007, 46, 946-953
22. Segel, I. H. Enzyme Kinetics: Behavior and Analysis of Rapid Equilibrium and Steady State Enzyme Systems. Wiley: New York, 1975; pp xxii, 957.
23. Payne, R. J.; Bulloch, E. M.; Abell, A. D.; Abell, C. Design and synthesis of aromatic inhibitors of anthranilate synthase Org. Biomol. Chem. 2005, 3, 3629-3635 (Pubitemid 41603761)
24. Payne, R. J.; Kerbarh, O.; Miguel, R. N.; Abell, A. D.; Abell, C. Inhibition studies on salicylate synthase Org. Biomol. Chem. 2005, 3, 1825-1827
25. Grisostomi, C.; Kast, P.; Pulido, R.; Huynh, J.; Hilvert, D. Efficient in Vivo Synthesis and Rapid Purification of Chorismic Acid Using an Engineered Escherichia coli Strain Bioorg. Chem. 1997, 25, 297-305
26. Ensch, C.; Hesse, M. Total syntheses of the spermine alkaloids (-)-(R, R)-hopromine and (±)-homaline Helv. Chim. Acta 2002, 85, 1659-1673
27. Bolognese, A.; Fierro, O.; Guarino, D.; Longobardo, L.; Caputo, R. Chiral aminoalkyl cation equivalents. 1. One-pot synthesis of orthogonally protected enantiopure S -(aminoalkyl)cysteine derivatives Eur. J. Org. Chem. 2005, 169-173
28. Lopez, P. E.; Isidro-Llobet, A.; Gracia, C.; Cruz, L. J.; Garcia-Granados, A.; Parra, A.; Alvarez, M.; Albericio, F. Use of p -nitrobenzyloxycarbonyl (pNZ) as a permanent protecting group in the synthesis of Kahalalide F analogs Tetrahedron Lett. 2005, 46, 7737-7741
29. Tietze, L. F.; PanknO.; Major, F.; Krewer, B. Synthesis of a novel pentagastrin-drug conjugate for a targeted tumor therapy Chem. - Eur. J. 2008, 14, 2811-2818
30. Bauerle, R.; Hess, J.; French, S. Anthranilate synthase-anthranilate phosphoribosyltransferase complex and subunits of Salmonella typhimurium Methods Enzymol. 1987, 142, 366-386
31. He, Z.; Toney, M. D. Direct detection and kinetic analysis of covalent intermediate formation in the 4-amino-4-deoxychorismate synthase catalyzed reaction Biochemistry 2006, 45, 5019-5028
32. He, Z.; Stigers Lavoie, K. D.; Bartlett, P. A.; Toney, M. D. Conservation of mechanism in three chorismate-utilizing enzymes J. Am. Chem. Soc. 2004, 126, 2378-2385
33. Morollo, A. A.; Bauerle, R. Characterization of composite aminodeoxyisochorismate synthase and aminodeoxyisochorismate lyase activities of anthranilate synthase Proc. Natl. Acad. Sci. U.S.A 1993, 90, 9983-9987