Evaluation of substituted triazol-1-yl-pyrimidines as inhibitors of Bacillus anthracis acetohydroxyacid synthase

Biochimica et Biophysica Acta - Proteins and Proteomics

Volumn 1804, Issue 6, 2010, Pages 1369-1375

  Gedi, Vinayakumar ^a   Jayaraman, Kumaresan ^b   Kalme, Satish ^a   Park, Hye Yeon ^a   Park, Hae Chul ^a   La, Im Joung ^a   Hahn, Hoh Gyu ^c   Yoon, Moon Young ^a  

^a Hanyang University   (South Korea)

^b ANNA UNIVERSITY   (India)

^c Korea Institute of Science and Technology   (South Korea)

Author keywords

Acetohydroxyacid synthase; Bacillus anthracis; Docking; Reconstitution; Triazol 1 yl pyrimidines

Indexed keywords

1 (4 CHLORO 6 DIMETHOXYPYRIMIDIN 2 YL) 5 METHOXY N (2 METHYL 6 NITROPHENYL) 1H 1,2,4 TRIAZOLE 3 SULFONAMIDE; 1 (4,6 DIMETHOXYPYRIMIDIN 2 YL) 5 METHYLSULFANYL 1H [1,2,4]TRIAZOLE 3 SULFONICACID (6 CHLORO 3 FLUORO 2 NITRO PHENYL) AMIDE; 1 (4,6 DIMETHOXYPYRIMIDIN 2 YL) N (2 ISOPROPYL 6 NITROPHENYL) 5 (METHOXYMETHYL) 1H 1,2,4 TRIAZOLE 3 SULFONAMIDE; 2 (2 CHLORO PHENOXY) 3 FLUORO [1,4] NAPHTHOQUINONE; ACETOLACTATE SYNTHASE; ANTIBIOTIC AGENT; AVS 2087; AVS 2093; AVS 2236; AVS 2387; KSW 30191; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTHRAX; ANTIBIOTIC RESISTANCE; ARTICLE; BACILLUS ANTHRACIS; CATALYSIS; DRUG BINDING; DRUG SCREENING; ENZYME ACTIVE SITE; ENZYME INHIBITION; HYDROGEN BOND; IC 50; NONHUMAN; PRIORITY JOURNAL;

ALDEHYDE-KETONE TRANSFERASES; ANTHRAX; ANTI-BACTERIAL AGENTS; BACILLUS ANTHRACIS; BACTERIAL PROTEINS; CATALYTIC DOMAIN; ENZYME INHIBITORS; HYDROGEN BONDING; PROTEIN BINDING; PYRIMIDINES; RECOMBINANT PROTEINS;

BACILLUS ANTHRACIS; BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 77949914910     PISSN: 15709639     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbapap.2010.02.002     Document Type: Article

References (24)

1. Umbarger H.E., and Brown B. Isoleucine and valine metabolism in Escherichia coli: VIII. The formation of acetolactate. J. Biol. Chem. 233 (1958) 1156-1160
2. Duggleby R.G., and Pang S.S. Acetohydroxyacid synthase. J. Biochem. Mol. Biol. 33 (2000) 1-36
3. Vinogradov V., Vyazmensky M., Engel S., Belenky I., Kaplun A., Kryukov O., Barak Z., and Chipman D.M. Acetohydroxyacid synthase isozyme I from Escherichia coli has unique catalytic and regulatory properties. Biochim. Biophys. Acta 1760 (2006) 356-363
4. Vyazmensky M., Sella C., Barak Z., and Chipman D.M. Isolation and characterization of subunits of acetohydroxy acid synthase isozyme III and reconstitution of the holoenzyme. Biochemistry 35 (1996) 10339-10346
5. Hill C.M., Pang S.S., and Duggleby R.G. Purification of Escherichia coli acetohydroxyacid synthase isoenzyme II and reconstitution of active enzyme from its individual pure subunits. Biochem. J. 327 (1997) 891-898
6. Atlas R.M. Bioterrorism: from threat to reality. Annu. Rev. Microbiol. 56 (2002) 167-185
7. Guleria I., Teitelbaum R., McAdam R.A., Kalpana G., Jacobs Jr. W.R., and Bloom B.R. Auxotropic vaccines for tuberculosis. Nat. Med. 2 (1996) 334-337
8. Bange F.C., Brown A.M., and Jacobs Jr. W.R. Leucine auxotrophy restricts growth of Mycobacterium bovis BCG in macrophages. Infect. Immun. 64 (1996) 1794-1799
9. Atkins T., Prior R.G., Mack K., Russell P., Nelson M., Oyston P.C.F., Dougan G., and Titball R.W. A mutant of Burkholderia pseudomallei, auxotrophic in the branched chain amino acid biosynthetic pathway, is attenuated and protective in a murine model of melioidosis. Infect. Immun. 70 (2002) 5290-5294
10. McCourt J.A., Pang S.S., Guddat L.W., and Duggleby R.G. Elucidating the specificity of binding of sulfonylurea herbicides to acetohydroxyacid synthase. Biochemistry 44 (2005) 2330-2338
11. Kalme S., Pham C.N., Gedi V., Le D.T., Choi J.D., Kim S.K., and Yoon M.Y. Inhibitors of Bacillus anthracis acetohydroxyacid synthase. Enzym. Microb. Tech. 43 (2008) 270-275
12. McCourt J.A., and Duggleby R.G. Acetohydroxyacid synthase and its role in the biosynthetic pathway for branched-chain amino acids. Amino Acids 31 (2006) 173-210
13. Choi K.J., Yu Y.G., Hahn H.G., Choi J.D., and Yoon M.Y. Characterization of acetohydroxyacid synthase from Mycobacterium tuberculosis and the identification of its new inhibitor from the screening of a chemical library. FEBS Lett. 579 (2005) 4903-4910
14. Choi K.J., Pham C.N., Jung H., Han S.H., Choi J.D., Kim J., and Yoon M.Y. Expression of acetohydroxyacid synthase from Bacillus anthracis and its potent inhibitors. Bull. Kor. Chem. Soc. 28 (2007) 1109-1113
15. Williams A., and Kolovanov E. A rebuttal regarding recent comparisons of SciLogP ultra (Scivision Inc.) with ACD/log P prediction software. Procedings of the log P 2000 symposium (2000) 1-23
16. Buono F., Testa R., and Lundgren D.G. Physiology of growth and sporulation in Bacillus cereus: I. Effect of glutamic and other amino acids. J. Bacteriol. 91 (1966) 2291-2299
17. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. Automated docking using a Lamarckian Genetic Algorithm and an empirical binding free energy function. J. Comput. Chem. 19 (1998) 1639-1662
18. Zohar Y., Einav M., Chipman D.M., and Barak Z. Acetohydroxyacid synthase from Mycobacterium avium and its inhibition by sulfonylureas and imidazolinones. Biochim. Biophys. Acta 1649 (2003) 97-105
19. Porat I., Vinogradov M., Vyazmensky M., Lu C.D., Chipman D.M., Abdelal A.T., and Barak Z. Cloning and characterization of acetohydroxyacid synthase from Bacillus stearothermophilus. J. Bacteriol. 186 (2004) 570-574
20. Vyazmensky M., Engel S., Kryukov O., Berkovich-Berger D., and Kaplun L. Construction of an active acetohydroxyacid synthase I with a flexible linker connecting the catalytic and the regulatory subunits. Biochim. Biophys. Acta 1764 (2006) 955-960
21. Namgoong S.K., Lee H.J., Kim Y.S., Shin J.H., Che J.K., Jang D.Y., Kim G.S., Yoo J.W., Kang M.K., Kil M.W., Choi J.D., and Chang S.I. Synthesis of the quinoline-linked triazolopyrimidine analogues and their interactions with the recombinant tobacco acetolactate synthase. Biochem. Biophys. Res. Commun. 258 (1999) 797-801
22. Chen C.N., Lv L.L., Ji F.Q., Chen Q., Xu H., Niu C.W., Xi Z., and Yang G.F. Design and synthesis of N-2, 6-difluorophenyl-5-methoxyl-1, 2, 4-triazolo[1, 5-a]- pyrimidine-2-sulfonamide as acetohydroxyacid synthase inhibitor. Bioorg. Med. Chem. 17 (2009) 3011-3017
23. Choi K.J., Noh K.M., Kim D.E., Ha B.H., Kim E.E., and Yoon M.Y. Identification of the catalytic subunit of acetohydroxyacid synthase in Haemophilus influenzae and its potent inhibitors. Arch. Biochem. Biophys. 466 (2007) 24-30
24. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug. Deliv. Rev. 46 (2001) 3-26