Discovery of Schaeffer's Acid Analogues as Lead Structures of Mycobacterium tuberculosis TypeII Dehydroquinase Using a Rational Drug Design Approach

ChemMedChem

Volumn 8, Issue 1, 2013, Pages 54-58

  Schmidt, Marco F ^a   Korb, Oliver ^b   Howard, Nigel I ^a   Dias, Marcio V B ^a   Blundell, Tom L ^a   Abell, Chris ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b CAMBRIDGE CRYSTALLOGRAPHIC DATA CENTRE   (United Kingdom)

Author keywords

Antibiotics; Drug design; Drug discovery; Molecular modeling; Mycobacterium tuberculosis

Indexed keywords

6 HYDROXY 2 NAPHTHALENESULFONIC ACID; BACTERIAL ENZYME; LYASE; MYCOBACTERIUM TUBERCULOSIS TYPE II DEHYDROQUINASE; SCHAEFFER ACID DERIVATIVE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; DRUG DESIGN; DRUG STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL; VIRUS VIRULENCE;

ANTITUBERCULAR AGENTS; CATALYTIC DOMAIN; DRUG DESIGN; HUMANS; HYDRO-LYASES; MODELS, MOLECULAR; MYCOBACTERIUM TUBERCULOSIS; SHIKIMIC ACID; STRUCTURE-ACTIVITY RELATIONSHIP; TUBERCULOSIS;

EID: 84871660955     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201200508     Document Type: Article

References (31)

1. R. Koch, Berl. Klin. Wochenschr. 1882, 19, 221-230;
2. A. Koul, E. Arnoult, N. Lournis, J. Guillemont, K. Andries, Nature 2011, 469, 483-490;
3. Tuberculosis, World Health Organization, Geneva, 2012; http://www.who.int/tb/en/ (Last accessed: November 13, 2012).
4. T. Parish, N. G. Stoker, Microbiology 2002, 148, 3069-3077.
5. T. Krell, M. J. Horsburgh, A. Cooper, S. M. Kelly, J. R. Coggins, J. Biol. Chem. 1996, 271, 24492-24497;
6. L. D. B. Evans, A. W. Roszak, L. J. Noble, D. A. Robinson, P. A. Chalk, J. L. Matthews, J. R. Coggins, N. C. Price, A. J. Lapthorn, FEBS Lett. 2002, 530, 24-30;
7. A. Peón, J. M. Otero, L. Tizón, V. F. V. Prazeres, A. L. Llamas-Saiz, G. C. Fox, M. J. vanRaaij, H. Lamb, A. R. Hawkins, F. Gago, L. Castedo, C. González-Bello, ChemMedChem 2010, 5, 1726-1733;
8. M. V. Diaz, W. C. Snee, K. M. Bromfield, R. J. Payne, S. K. Palaninathan, A. Ciulli, N. I. Howard, C. Abell, J. C. Sacchettini, T. L. Blundell, Biochem. J. 2011, 436, 729-739.
9. C. Sánchez-Sixto, V. F. V. Prazeres, L. Castedo, H. Lamb, A. R. Hawkins, C. González-Bello, J. Med. Chem. 2005, 48, 4871-4881;
10. R. J. Payne, F. Peyrot, O. Kerbah, A. D. Abell, C. Abell, ChemMedChem 2007, 2, 1015-1029;
11. A. T. Tran, K. M. Cergol, N. P. West, J. E. Randall, W. J. Britton, S. A. Bokhari, M. Ibrahim, A. J. Lapthorn, R. J. Payne, ChemMedChem 2011, 6, 262-265;
12. L. Tizo'n, J. M. Otero, V. F. V. Prazeres, A. L. Llamas-Saiz, G. C. Fox, M. J. vanRaaij, H. Lamb, A. R. Hawkins, J. A. Ainsa, L. Castedo, C. Gonza'lez-Bello, J. Med. Chem. 2011, 54, 6063-6084;
13. N.I. Howard, F. Peyrot, L. Chen, M.F. Schmidt, M.V.B. Diaz, W.C. Snee, T. Iorger, J.S. Freundlich, J.C. Sacchettini, T.L. Blundell, C. Abell, unpublished results.
14. D. A. Robinson, K. A. Steward, N. C. Price, P. A. Chalk, J. R. Coggins, A. J. Lapthorn, J. Med. Chem. 2006, 49, 1282-1290;
15. P. J. Ballester, M. Mangold, N. I. Howard, R. L. MarcheseRobinson, C. Abell, J. Blumberger, J. B. O. Mitchell, J. R. Soc. Interface 2012, 9, 3196-3207.
16. i)/HAC, where HAC is the heavy atom count;
17. A. L. Hopkins, C. R. Groom, A. Alex, Drug Discovery Today 2004, 9, 430-431;
18. M. M. Hann, Med. Chem. Commun. 2011, 2, 349-355.
19. B. E. Evans, K. E. Rittle, M. G. Bock, R. M. DiPardo, R. M. Freidinger, W. L. Whitter, G. F. Lundell, D. F. Veber, P. S. Anderson, R. S. L. Chang, V. J. Lotti, D. J. Cerino, T. B. Chen, P. J. Kling, K. A. Kunkel, J. P. Springer, J. Hirshfiel, J. Med. Chem. 1988, 31, 2235-2246;
20. S. Barelier, I. Krimm, Curr. Opin. Chem. Biol. 2011, 15, 469-474;
21. M. E. Welsch, S. A. Snyder, B. R. Stockwell, Curr. Opin. Chem. Biol. 2010, 14, 347-361.
22. L. Schaeffer, Justus Liebigs Ann. Chem. 1869, 152, 279-298.
23. G. Jones, P. Willett, R. C. Glen, J. Mol. Biol. 1995, 245, 43-53;
24. GOLD (version 5.1); http://www.ccdc.cam.ac.uk/products/life_sciences/gold;
25. O. Korb, T. Stützle, T. E. Exner, J. Chem. Inf. Model. 2009, 49, 84-86;
26. J. W. Liebeschuetz, J. C. Cole, O. Korb, J. Comput.-Aided Mol. Des. 2012, 26, 737-748.
27. P. Cozzini, G. E. Kellogg, F. Spyrakis, D. J. Abraham, G. Costantino, A. Emerson, F. Fanelli, H. Gohlke, L. A. Kuhn, G. M. Morris, M. Orozco, T. A. Pertinhez, M. Rizzi, C. A. Sotriffer, J. Med. Chem. 2008, 51, 6237-6255;
28. O. Korb, T. S. G. Olsson, S. J. Bowden, R. J. Hall, M. L. Verdonk, J. W. Liebeschuetz, J. C. Cole, J. Chem. Inf. Model. 2012, 52, 1262-1274.
29. M. L. Verdonk, J. C. Cole, R. Taylor, J. Mol. Biol. 1999, 289, 1093-1108.
30. P. Ehrlich, Folia Serol. 1911, 7, 697-714.
31. The PyMOL Molecular Graphics System, v.0.99rc6, W.L. DeLano, DeLano Scientific LLC, San Carlos, 2006; http://www.pymol.org/.