Efforts towards the development of new antitubercular agents: Potential for thiolactomycin based compounds

Journal of Pharmacy and Pharmaceutical Sciences

Volumn 11, Issue 2, 2008, Pages

  Kamal, Ahmed ^a   Azeeza, Shaik ^a   Shaheer Malik, M ^a   Shaik, Ahmad Ali ^a   Rao, Maddamsetty V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ETHAMBUTOL; ISONIAZID; PYRAZINAMIDE; RIFAMYCIN; STREPTOMYCIN; THIOLACTOMYCIN; THIOPHENE DERIVATIVE; TUBERCULOSTATIC AGENT;

ANIMAL; CHEMICAL STRUCTURE; DRUG DESIGN; DRUG EFFECT; LUNG TUBERCULOSIS; MICROBIOLOGICAL EXAMINATION; MYCOBACTERIUM TUBERCULOSIS; PHYSIOLOGICAL PROCESS; REVIEW; TUBERCULOSIS;

ANIMALS; ANTITUBERCULAR AGENTS; DRUG DESIGN; ETHAMBUTOL; ISONIAZID; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; PHYSIOLOGICAL PROCESSES; PYRAZINAMIDE; RIFAMYCINS; STREPTOMYCIN; THIOPHENES; TUBERCULOSIS; TUBERCULOSIS, PULMONARY;

EID: 65349107627     PISSN: None     EISSN: 14821826     Source Type: Journal    
DOI: 10.18433/J36K5K     Document Type: Article

References (154)

1. Enarson DA, Chretien J. Epidemiology of respiratory infectious diseases. Curr Opin Pulm Med 5: 128-135, 1999.
2. World Health Organisation. Tuberculosis Fact Sheet No. 104, 2000. http://www.who.int/inffs/en/fact104.html/.
3. Moran N, WHO issues another gloomy tuberculosis. report. Nat Med. 2: 377, 1996.
4. Snider DE Jr, Raviglione M, Kochi A. Global burden of tuberculosis. In B.R. Bloom (ed.), Tuberculosis: pathogenesis, protection, and control. Am. Soc. Microbiol 2: 3-11, 1994, Washington, DC.
5. Dye C, Scheele S, Dolin P, Pathania V, Raviglione MC. Global Burden of Tuberculosis. J Am Med Assoc 282: 677, 1999.
6. Farmer P, Bayona J, Beccera M, Furin J, Henry C, Hiarr H, Kim JY, Mimic C, Nardell E, Shin S. The dilemma of MDRTB in the global era. Int J Tuberc Lung Dis 2: 869-876, 1998.
7. Dony JF, Ahmad J, Khen TY. Epidemiology of tuberculosis and leprosy, Sabah, Malaysia. Tuberculosis 84: 8-18, 2004.
8. Koch R Die aetiologie der tuberkulose. Die Aetiologie der 19: 221-230, 1882.
9. Turenne CY, Tschetter L, Wolfe J, Kabani A. Necessity of quality-controlled 16S rRNAgene sequence databases: identifying nontuberculous Mycobacterium species. J Clin Microbiol 39: 3637-3648, 2001. http://www.ridomrdna.de/mycobacteria.
10. Minnikin DE. Lipids: complex lipids, their chemistry, biosynthesis and roles. In: The Biology of the Mycobacteria (Ratledge C. and Stanford J. Eds.), Vol. 1, page 95-184, 1982. Academic Press Inc. Ltd., London.
11. Walters SB, Dubnau E, Kolesnikova I, Laval F, Daffe M, Smith I. The Mycobacterium tuberculosis PhoPR two-component system regulates genes essential for virulence and complex lipid biosynthesis. Molecular Microbiol. 60: 312-330, 2006.
12. Slayden RA, and Barry CE. The role of KasA andKasB in the biosynthesis of meromycolic acids and isoniazid resistance in Mycobacterium tuberculosis. Tuberculosis 82: 149-160, 2002.
13. Chatterjee D, Khoo KH, McNeil MR, Dell A, Morris HR, Brennan PJ. Structural definition of the non-reducing termini of mannose-capped LAM from Mycobacterium tuberculosis through selective enzymatic degradation and fast atom bombardment-mass spectrometry. Glycobiology, 3: 497-500, 1993.
14. Cole ST, Brosch R, Parkhill J, Garnier T, Churcher C, Harris D, Gordon SV, Eiglmeier K, Gas S, Barry C E, Tekaia F, Badcock K, Basham D, Brown D, Chillingworth T, Connor R, Davies R, Devlin K, Feltwell T, Gentles S, Hamlin N, Holroyd S, Hornsby T, Jagels K, Krough A, McLean J, Moule S, Murphy L, Oliver K, Osborne J, Quail MA, Rajandream MA., Rogers J, Rutter S, Seeger K, Skelton J, Squares R, Squares S, Sulston JE, Taylor K Whitehead S, Barrell BG. Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence Nature 393: 537-544, 1998.
15. http://www.doe-mbi.ucla.edu/TB/
16. Clatworthy AE, Pierson E, Hung DT. Targeting virulence: a new paradigm for antimicrobial therapy. Nat Chem Biol 3: 541-548, 2007.
17. World Health Organization. Strategic framework to decrease the burden of TB/HIV documents WHO/CDS/ TB2002, 296, WHO/HIVAIDS/2002, 2. Geneva, Switzerland: World Health Organization, 2002.
18. Espinal MA. The global situation of MDR-TB. Tuberculosis 83: 44-51, 2003.
19. Amalio T, Michael I, Drug-Resistant Tuberculosis: What Do We Do Now? Drugs 59: 171-179, 2000.
20. Pablos-Mendez A, Raviglione MC, Laszlo A, Binkin N, Rieder HL, Bustreo F, Cohn DL, Lambregts-van Weezenbeek CS, Kim SJ, Chaulet P, Nunn P. Global Surveillance for Antituberculosis-Drug Resistance 1994-1997. N Engl J Med 338: 1641-1649, 1998.
21. Cohn DL, Bustreo F, Raviglione MC. Drugresistant tuberculosis: review of the worldwide situation and the WHO/IUATLD Global Surveillance Project. Clin Infect Dis, 24: S121-S130, 1997
22. Cole ST, Phillip W, Heym B. Mechanisms of drug resistance in Mycobacterium tuberculosis. Curr Top Microbiol Immunol, 215: 49-69, 1996.
23. Barry CE III. New horizons in the treatment of tuberculosis. Biochem Pharmacol 54: 1165-1172, 1997.
24. Barry CE, Slayden RA, Sampson AE, Lee RE. Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs. Biochem Pharmacol 59, 221-231, 2000.
25. Tomasz A. Multiple-antibiotic-resistant pathogenic bacteria. A report on the Rockefeller University Workshop. N Eng J Med 330: 1247-1251, 1994.
26. Global Tuberculosis Control: Surveillance, Planning, Financing WHO REPORT 2008, 51-54.
27. Davidson PT, Le HQ. Drug Treatment of Tuberculosis-1992. Drugs. 43: 651-673, 1992.
28. Tillotson GS. Quinolones: structure-activity relationships and future predictions. J Med Microbiol 44: 320-324, 1996.
29. Grange J. Antimycobacterial agents. In: O'Grady F, Lambert H P, Finch RG, Greenwood D editors. Antibiotic and chemotherapy, 7th edition. Edinburg: Churchil Livingstone 449-512, 1997.
30. Greenwood D, Historical introduction. In: O'Grady F, Lambert HP, Finch RG, Greenwood D. editors. Antibiotic and chemotherapy, 7th edition. Edinburg: Churchill Livingston 2-9, 1997.
31. Finken M, Kirschner P, Meier A, Wrede A, Bottger EC. Molecular basis of streptomycin resistance in Mycobacterium tuberculosis: alterations of the ribosomal protein S12 gene and point mutations within a functional 16S ribosomal RNA pseudoknot. Mol Microbial 9: 1239-1246, 1993.
32. Zhang Y, Heym B, Allen B, Young D, Cole S. The catalase-peroxidase gene and isoniazid resistance of Mycobacterium tuberculosis. Nature 358: 591-593, 1992.
33. Zhang Y, Garbe T, Young D. Transformation with katG restores isoniazid-sensitivity in Mycobacterium tuberculosis isolates resistant to a range of drug concentrations. Mol Microbiol 8 521-524, 1993.
34. Heym B, Alzari PM, Honore N, Cole ST. Missense mutations in the catalase-peroxidase gene, katG, are associated with isoniazid resistance in Mycobacterium tuberculosis. Mol Microbiol 15: 235-245, 1995.
35. Mdluli K, Slayden RA, Zhu Y, Ramaswamy S, Pan X, Mead D, Crane DD, Musser JM, Barry CE III. Inhibition of Mycobacterium tuberculosis beta-ketoacyl ACP synthetase by isoniazid. Science 280: 1607-1610, 1998.
36. The name rifamycin (originally rifomycin) is derived from the title of a French movie, Rififi, popular at the time of the antibiotic's discovery. Sensi, P. History of the development of rifamycin. Rev Infect Dis 5: S402-S406, 1983.
37. Rinehart KL Jr, Shields LS. Fortschr Chemistry of the ansamycin antibiotics. Chem. Org Naturs., 33: 231-307, 1976.
38. Wehrli W. Ansamycins: Chemistry, biosynthesis and biological activity. Top Curr Chem 72: 21-49, 1977.
39. Prelog V, Oppolzer W. Rifamycins. 4. Ansamycins, a novel class of microbial metabolism products. Helv Chim Acta 56: 2279-2287, 1973.
40. Parneti F, Lancini G. Rifamycins. In: O'Grady F, Lambert HP, Finch RG, Greenwood D, editors. Antibiotic and chemotherapy, 7th edition. Edinburg: Churchill Livingston 453-459, 1997.
41. Gale EF, Cundliffe E, Reynolds PE, Richmond MH, Waring MJ. The molecular basic of antibiotic action, 2nd edition. London: John Wiley and Sons 1981.
42. Rastogi N, Labrousse V. Extracellular and intracellular activities of clarithromycin used alone and in association with ethambutol and rifampin against Mycobacterium avium complex. Antimicrob Agents Chemother 35: 462-470, 1991.
43. Inderlied CB, Barbara-Burnham L, Wu M, Young LS, Bermudez LE. Activities of the benzoxazinorifamycin KRM 1648 and ethambutol against Mycobacterium avium complex in vitro and in macrophages. Antimicrob Agents Chemother 38: 1838-1843, 1994.
44. Mikusova K, Slayeden RA, Besra GS, Brennan PJ. Biogenesis of the mycobacterial cell wall and the site of action of ethambutol. Antimicrob Agents Chemother 39: 2484-2489, 1995.
45. Tripathi RP, Tewari N, Dwivedi N, Tiwari VK. Fighting tuberculosis: An old disease with new challenges. Medicinal Research Reviews 25: 93-131, 2005.
46. Scorpio A, Zhang Y. Mutations in pncA, a gene encoding pyrazinamidase/nicotinamidase, cause resistance to the antituberculous drug pyrazinamide in tubercle bacillus. Nat Med 2: 662-667, 1996.
47. McCune RM, Feldman FM, McDermat W. Microbial persistence II. Characterstics of the sterile state of tubercular bacilli. J Exp Med 123: 469-486, 1966.
48. Konno K, Feldmann FM, Mc Dermott W. Pyrazinamide susceptibility and amidase activity of tubercle bacilli. Am Rev Resp Dis 95: 461-469, 1967.
49. Mc Dermott W, Tompsett R. Pyrazinamide sterilizing activity in vitro against semi-dormant Mycobacterium tuberculosis bacterial populations. Am Rev Tuberc, 70: 748-754, 1954.
50. Center for Disease Control. "Emergence of Mycobacterium tuberculosis with Extensive Resistance to Second-Line Drugs-Worldwide, 2000-2004". MMWR Weekly 55: 301-305, 2006.
51. Edson RS, Terrell CL. The aminoglycosides. Mayo Clin Proc 74: 519-528, 1999.
52. Garrod LP, Lambert HP, O'Grady F. Antibiotic and Chemotherapy. Churchill Livingstone, Edinburgh. 131-131, 1981.
53. Kanamycin. Tuberculosis 88: 117-118, 2008.
54. Skinner RH, Cundliffe E. Resistance to the antibiotics viomycin and capreomycin in the Streptomyces species which produce them. J Gen Microbiol 120: 95-104, 1980.
55. Le Conte P, Le Gallou F, Potel G, Struillou L, Baron D, Drugeon HB. Pharmacokinetics, toxicity, and efficacy of liposomal capreomycin in disseminated Mycobacterium avium beige mouse model. Antimicrob Agents Chemother 38: 2695-2701, 1994.
56. Da Silva AD, De Almeida MV, De Souza MVN, Couri MRC. Biological activity and synthetic methodologies for the preparation of fluoroquinolones, a class of potent antibacterial agents. Curr Med Chem 10: 21-39, 2003.
57. Wolfson JS, Hooper DC. The fluoroquinolones: Structures mechanism of action and resistance and spectra of activity in vitro. Antimicrob Agents Chemother:28: 581-586, 1985.
58. Lowther J, Bryskier A. Fluoroquinolones and tuberculosis. Curr. Med Res Opin 11: 233-258, 2002.
59. Quemard A, Laneelle G, Lacave C. Mycolic acid synthesis: a target for ethionamide in mycobacteria? Antimicrob Agents Chemother 36: 1316-1321, 1992.
60. Otten H. Antituberculosis drugs. Handbook of experimental pharmacology Berlin: Springer-Verlog 44: 158-166, 1988.
61. David HL, Takayama K, Goldman DS. Susceptibility of mycobacterial D-alanyl-Dalanine synthetase to D-cycloserine. Am Rev Resp Dis 100: 579-581, 1969.
62. Otten H. Experimental evalution of efficacy VII. Cycloserine (CS) and terizidone (TZ) In: Bartman K, editor. Antituberculosis drugs. Handbook of experimental pharmacology, Vol 44, Berlin: Springer-Verlog, 158-166, 1997.
63. Lehmann J. Para-aminosalicylic acid in the treatment of tuberculosis. Lancet 247: 15-16, 1946.
64. Zuckerman JM. The newer macrolides: azithromycin and clarithromycin Infect Dis Clin of North America, 14: 449-462, 2000.
65. Rieder HL, Arnadottir T, Trebucq A, Enarson DA. Tuberculosis treatment: dangerous regimens?. Int J Tuberc Lung Dis 5: 1-3, 2001.
66. Nunn P, Porter J, Winstanley P. Thiacetazoneavoid like poison or use with care? Trans R Soc Trop Med Hyg 87: 578-582, 1993.
67. Amaral L, Viveiros M, Molnar J. Antimicrobial activity of phenothiazines. In Vivo. 18: 725-731, 2004.
68. Mitscher LA, Baker W. Tuberculosis: A search for novel therapy starting with natural products. Med Res Rev 18: 363-374, 1998.
69. Stover CK, Warrener P, VanDevanter DR, Sherman DR, Arain TM, Langhorne MH, Anderson SW, Towell JA, Yuan Y, McMurray DN, Kreiswirth BN, Barry CE, Baker WR A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis. Nature 405: 962-966, 2000.
70. Ashtekar DR, Costa-Perira R, Nagrajan K, Vishvanathan N, Bhatt AD, Rittel W. In vitro and in vivo activities of the nitroimidazole CGI 17341 against Mycobacterium tuberculosis. Antimicrob Agents Chemother 37: 183-186, 1993.
71. Tucker JA, Allwine DA, Grega KC, Barbachyn MR, Klock JL, Adamski I, Brickner SJ, Hutchinson DK, Ford CW, Zurenko GE, Conradi A, Buston PS, Jensen RM. Piperazinyl oxazolidinone antibacterial agents containing a pyridine, diazene, or triazene heteroaromatic ring. J Med Chem 41: 3727-3735, 1998.
72. Brickner SJ, Hutchinson DK, Barbachyn MR, Manninen PR, Ulanowicz DA, Garmon A, Grega KC, Hendges SK, Toops DS, Ford CW, Zurenko GE. Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections J Med Chem 39: 673-679, 1996.
73. Eustice DC, Feldman PA, Zajac I, Slee AM. Mechanism of action of DuP 721: inhibition of an early event during initiation of protein synthesis. Antimicrob Agents Chemother 32: 1218-1222, 1988.
74. Field SK, Cowie RL. Treatment of Mycobacterium avium-intracellulare complex Lung Disease With a Macrolide, Ethambutol, and Clofazimine Chest 124: 1482-1486, 2003.
75. Kamal A, Babu AH, Ramana AV, Sinha R, Yadav JS, Arora SK. Antitubercular agents. Part 1: Synthesis of phthalimido-and naphthalimidolinked phenazines as new prototypeantitubercular agents. Bioorg. Med. Chem. Lett. 15: 1923-1926, 2005.
76. Tangalapally RP, Yendapally R, Lee RE, Lenaerts AJM, Lee RE. Synthesis and Evaluation of Cyclic Secondary Amine Substituted Phenyl and Benzyl Nitrofuranyl Amides as Novel Antituberculosis Agents. J Med Chem 48: 8261-8269, 2005.
77. Bakkestuen AK, Gundersen LL, Langli G, Liu F, Nolsoe JM. 9-Benzylpurines with inhibitory activity against mycobacterium tuberculosis. Bioorg Med Chem Lett 10: 1207-1210, 2000.
78. Gundersen LL, Meyer JN, Spilsberg B. Synthesis and antimycobacterial activity of 6-arylpurines: The requirements for the N-9 substituent in active antimycobacterial purines. J Med Chem 45, 1383-1386, 2002.
79. Scozzafava A, Mastrolorenzo A, Supuran CT. Antimycobacterial activity of 9-sulfonylated sulfenylated-6-mercaptopurine derivatives. Bioorg Med Chem Lett 11: 1675-1678, 2001.
80. Shindikar AV, Viswanathan CL. Novel fluoroquinolones: Design, synthesis, and in vivo activity in mice against mycobacterium tuberculosis H37Rv. Bioorg Med Chem Lett 15: 1803-1806, 2005.
81. Andries K, Verhasselt P, Guillemont J, Gohlmann HWH, Neefs J-M, Winkler H, Gestel JV, Timmerman P, Zhu M, Lee E, Williams P, de Chaffoy D, Huitric E, Hoffner S, Cambau E, Truffot-Pernot C, Lounis N, Jarlier V. A diarylquinoline drug active on the ATP synthase of mycobacterium tuberculosis. Science 307: 223-227, 2005.
82. Girard Y, Atkinson JG, Rokach J. A new synthesis of 1,2,4-benzothiadiazines and a selective preparation of oaminobenzenesulphonamides. J Chem Soc Perkin Trans 1 1043-1047, 1979
83. Reddy AVN, Kamal A, Sattur PB. Synthesis and biological activity of 3-pyrazolyl-4-substituted-2H-1,2,4-benzothiadiazine 1,1-dioxide. Indian J Chem 24B 1295-1297, 1985.
84. NCCLS. Susceptibility Testing of Mycobacteria, Nocardia, and Other Aerobic Actinomycetes; Tentative Standard, 2nd ed.; NCCLS document M24-T2 [ISBN 1-56238-423-6]. NCCLS, 960 West Valley Road, Suite1400, Wayne, PA 19087-1898, USA, 2000.
85. Dolezal M, Jampilek J, Osicka Z, Kunes J, Buchta V, Vichova P. Substituted 5-aroylpyrazine-2-carboxylic acid derivatives: synthesis and biological activity Il Farmaco, 58: 1105-1111, 2003.
86. Cocco MT, Congiu C, Onnis V, Pusceddu MC, Schivo ML, Logu A. Synthesis and antimycobacterial activity of some isonicotinoylhydrazones. Eur J Med Chem 34: 1071-1076, 1999.
87. Kamal A, Reddy KS, Ahmed SK, Khan MNA, Sinha RK, Yadav JS, Arora SK. Anti-tubercular agents. Part 3: Benzothiadiazines as a novel scaffold for anti-mycobacterim activiy. Bioorg Med Chem 14: 650-658, 2006.
88. Kamal A, Ahmed SK, Reddy KS, Khan MNA, Shetty RVCRNC, Siddhardha B, Murthy USN, Khan IA, Kumar M, Sharma S, Ram AB. Antitubercular agents. Part IV: Synthesis and antimycobacterial evaluation of nitroheterocyclic-based 1,2,4-benzothiadiazines. Bioorg Med Chem Lett 17: 5419-5422, 2007.
89. Deidda D, Lampis G, Fioravanti R, Biava M, Porretta G, Zanetti S, Pompei R. Bactericidal activities of the pyrrole derivative BM212 against multidrug-resistant and intramacrophagic mycobacterium tuberculosis strains. Antimicrob Agents Chemother 42: 3035-3037, 1998.
90. Jaso A, Zarrana B, Aldana I, Monge A. Synthesis of new quinoxaline-2-carboxylate 1,4-dioxide derivatives as anti-mycobacterium tuberculosis agents. J Med Chem 48: 2019-2025, 2005.
91. Jones PB, Parrish NM, Houston TA, Stapon A, Bansal NP, Dick JD, Townsend C A. A new class of antituberculosis agents. J Med Chem 43: 3304-3314, 2000.
92. Koul A, Herget T, Kleb B, Ullrich A. Interplay between mycobacteria and host signalling pathways. Nat Rev Microbiol 2: 189-202, 2004.
93. Scherr N, Honnappa S, Kunz G, Mueller P, Jayachandran R, Winkler F, Pieters J, Steinmetz M.O. Structural basis for the specific inhibition of protein kinase G, a virulence factor of Mycobacterium tuberculosis. Proc Natl Acad Sci U S A 104: 12151-12156, 2007.
94. Soellner MB, Rawls KA, Grundner C, Alber T, Ellman JA. Fragment-based substrate activity screening method for the identification of potent inhibitors of the Mycobacterium tuberculosis phosphatase PtpB. J Am Chem Soc 129, 9613-9615, 2007.
95. Hilliard JJ, Goldschmidt RM, Licata L, Baum EZ, Bush K. Multiple Mechanisms of Action for Inhibitors of Histidine Protein Kinases from Bacterial Two-Component Systems. Antimicrob Agents Chemother 43: 1693-1699, 1998.
96. Stephenson K, Yamaguchi Y, Hoch JA. The Mechanism of Action of Inhibitors of Bacterial Two-component Signal Transduction Systems. J Biol Chem 275: 38900-38904, 2000.
97. Matsushita M, Janda KD. Histidine kinases as targets for new antimicrobial agents. Bioorg Med Chem 10: 855-867, 2002.
98. Stephenson K, Hoch JA. Developing Inhibitors to Selectively Target Two Component and Phosphorelay Signal Transduction Systems of Pathogenic Microorganisms. Curr Med Chem 11: 765-773, 2004.
99. Matyk J, Waisser K, Drazkova K, Kunes J, Klimesova V, Palat K Jr.; Kaustova J. Heterocyclic isosters of antimycobacterial salicylanilides. Farmaco Ed Sci 60: 399-408, 2005.
100. Waisser K, Matyk J, Divisova H, Husakova P, Kunes J, Klimesova V, Kaustova J, Mollmann U, Dahse HM, Miko M. The Oriented Development of Antituberculotics: Salicylanilides. Arch Pharm, 339: 616-620, 2006.
101. Hlasta DJ, Demers JP, Foleno BD, Fraga-Spano S, Guan J, Hilligard JJ, Macielag MJ, Ohemeng KA, Sheppard CM, Sui Z, Webb GC, Weidner-Wells MA, Werblood H, Barrett JF. Novel inhibitors of bacterial two-component systems with gram positive antibacterial activity: Pharmacophore identification based on the screening hit closantel. Bioorg Med Chem Lett 8: 1923-1928, 1998.
102. Macielag MJ, Demers JP, Fraga-Spano SA, Hlasta DJ, Johnson SG, Kanojia RM, Russell RK, Sui Z, Weidner-Wells MA, Werblood H, Foleno BD, Goldschmidt RM, Loeloff MJ, Webb GC, Barrett JF. Substituted Salicylanilides as Inhibitors of Two-Component Regulatory Systems in Bacteria. J Med Chem 41: 2939-2945, 1998.
103. Rickman L, Saldanha JW, Hunt DM, Hoar N, Colston MJ, Millar JB, Buxton RS. A twocomponent signal transduction system with a PAS domain-containing sensor is required for virulence of Mycobacterium tuberculosis in mice. Biochem Biophys Res Commun 314: 259-267, 2004.
104. Av-Gay Y, Everett M. The eukaryotic-like Ser/Thr protein kinases of Mycobacterium tuberculosis. Trends Microbiol 8: 238-244, 2000.
105. Greenstein AE, Grundner C, Echols N, Gay LM, Lombana TN, Miecskowski CA, Pullen KE, Sung P, Alber TJ. Mol Microbiol Biotechnol 9: 167-181, 2005.
106. Peirs P, De Wit L, Braibant M, Huygen K, Content JA. Serine/Threonine Protein Kinase from Mycobacterium tuberculosis. Eur J Biochem, 244: 604-612, 1997.
107. Walburger A, Koul A, Ferrari G, Nguyen L, Prescianotto-Baschong C, Huygen K, Klebl B, Thompson C, Bacher G, Pieters J. Protein Kinase G from Pathogenic Mycobacteria Promotes Survival Within Macrophages. Science, 304: 1800-1804, 2004.
108. Koul A, Klebl B, Mueller G, Missio A, Schwab W, Hafenbradl D, Neumann L, Sommer M.-N, Mueller S, Hoppe E, Freisleben A, Backes A, Hartung C, Felber B, Zech B, Engkvist O, Keri G, Oerfi L, Banhegyi P, Greff Z, Horvath Z, Varga Z, Marko P, Pato J, Szabadkai I, Szekelyhidi Z, Waczek F. Patent WO 2005 023818; see Chem. Abstr. 2005, 142, 316820.
109. Pato J, Keri G, Orfi L, Waczeck F, Horvath Z, Banhegyi P, Szabadkai I, Marosfaldi J, Hegymegi-Barkonyi B, Szekelyhidi Z, Greff Z, Choidas A, Bacher G, Missio A, Koul A, Patent U.S. 2004 171603; see Chem. Abstr. 2004, 141, 236625p.
110. Ortega MA, Montoya ME, Jaso A, Zarranz B, Tirapu I, Aldana I, Monge A. Antimycobacterial activity of new quinoxaline-2-carbonitrile and quinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives. Pharmazie 56: 205-207, 2001.
111. Zarranz B, Jaso A, Aldana I, Monge A. Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-Oxide derivatives. Bioorg Med Chem 11: 2149-2156, 2003.
112. Zanetti S, Sechi LA, Molicotti P, Cannas S, Bua A, Deriu A, Carta A, Paglietti G. In vitro activity of new quinoxalin 1,4-dioxide derivatives against strains of Mycobacterium tuberculosis and other mycobacteria. Int J Antimicrob Agents, 25: 179-181, 2005.
113. Heath RJ, Rock CO. Fatty acid biosynthesis as a target for novel antibacterials. Curr Opin InVest Drugs 5: 146-153, 2004.
114. Slayden RA, Lee RE, Armour JW, Cooper AM, Orme IM, Brennan PJ, Besra GS. Antimycobacterial action of thiolactomycin: An inhibitor of fatty acid and mycolic acid synthesis. Antimicrob Agents Chemother 40: 2813-2819, 1996.
115. Noto T, Miyakawa S, Oishi H, Endo H, Okazaki H. Thiolactomycin, a new antibiotic. III. In vitro antibacterial activity. J Antibiot (Tokyo) 35: 401-410, 1982.
116. Miyakawa S, Suzuki K, Noto T, Harada Y, Okazaki H. Thiolactomycin, a new antibiotic. IV. Biological properties and chemotherapeutic activity in mice. J Antibiot (Tokyo) 35: 411-419, 1982.
117. Hayashi T, Yamamoto O, Sasaki H, Kawaguchi A, Okazaki H. Mechanism of action of the antibiotic thiolactomycin inhibition of fatty acid synthesis of Escherichia coli. Biochem Biophys Res Commun 115: 1108-1113, 1983.
118. Heath RJ, White SW, Rock CO. Lipid biosynthesis as a target for antimicrobial agents. Prog Lipid Res 40: 467-497, 2001.
119. Tsay JT, Rock CO, Jackowski S. Overproduction of beta-ketoacyl-acyl carrier protein synthase I imparts thiolactomycin resistance to Escherichia coli K-12. J Bacteriology 174: 508-513, 1992.
120. Oishi H, Noto T, Sasaki H, Suzuki K, Hayashi T, Okazaki H, Ando K, Sawada M. Thiolactomycin, a new antibiotic. I. Taxonomy of the producing organism, fermentation and biological properties. J Antibiot (Tokyo) 35: 391-395, 1982.
121. Sasaki H, Oishi H, Hayashi T, Noto T, Ando K, Sawada M. Thiolactomycin, A new antibiotic II. Structure elucidation. J Antibiot (Tokyo) 35: 396-400, 1982.
122. Nishida I, Kawaguchi A, Yamada M. Effect of thiolactomycin on the individual enzymes of the fatty acid synthase system in Escherichia coli. J Bio Chem 99: 1447-1454, 1986.
123. Hamada S, Fujiwara T, Shimauchi H, Ogawa T, Nishihara T, Koga T, Nehashi T, Matsuno T. Antimicrobial activities of thiolactomycin against gram-negative anaerobes associated with periodontal disease. Oral Microbiol Immunol 5: 340-345, 1990.
124. Choi KH, Kremer L, Besra GS Rock CO. Identification and substrate specificity of betaketoacyl (acyl carrier protein) synthase III (mtFabH) from mycobacterim tuberculosis. J Biol Chem 275: 28201-28207, 2000.
125. Hayashi T, Yamamoto O, Sasaki H, Okazaki H, Kawaguchi A. Inhibition of fatty acid syntheis by the antibiotic thiolactomycin. J Antibiot 37: 1456-1461, 1984.
126. Jones AL, Dancer JE, Harwood JL. The effect of thiolactomycin analogues on fatty acid synthesis in peas. Biochem Soc Trans 22, 258S.
127. Jones AL, Herbert D, Rutter AJ, Dancer JE, Harwood JL. Novel inhibitors of the condensing enzymes of the type II fatty acid synthase of pea (pisum sativum). Biochem J 347: 205-209, 2000.
128. Minnikin DE, Minnikin SM, Goodfellow M, Stanford JL. The mycolic acids of mycobacterium chelonei. J Gen Microbiol 128: 817-822, 1982.
129. Jackowski S, Zhang YM, Price AC, White SW, Rock CO. A missense mutation in the fabB (β-ketoacyl-acyl carrier protein synthase I) gene confers thiolactomycin resistance to Escherichia coli. Antimicrob Agents Chemother 46: 1246-1252, 2002.
130. Jayakumar A, Tai MH, Huang WY, Al Feel W, Hsu M, Abu-Elheiga L, Chirala SS, Wakil SJ, Human fatty acid synthase: Properties and molecular cloning. Proc Natl Acad Sci USA 92: 8695-8699, 1995.
131. Chirala SS, Huang WY, Jayakumar A, Sakai K, Wakil SJ. Human fatty acid synthase: Role of interdomain in the formation of catalytically active synthase dimmer. Proc Natl Acad Sci U S A 98: 3104-3108, 2001.
132. Payne DJ, Warren PV, Holmes DJ, Ji Y, Lonsdale JT. Bacterial fatty-acid biosynthesis: A genomics-driven target for antibacterial drug discovery. Drug Discovery Today 6: 537-544, 2001.
133. Khandekar SS, Daines RA, Lonsdale JT. Bacterial-ketoacyl-Acyl Carrier Protein Synthases as Targets for Antibacterial Agents. Curr. Protein and Peptide Sci. 4: 21-29, 2003.
134. Heath RJ. Bacterial fatty-acid biosynthesis: An antibacterial drug target waiting to be exploited Drug Discovery Today 6: 715, 2001.
135. Chirala SS, Huang WY, Jayakumar A, Sakai K, Wakil SJ. Animal fatty acid synthase: Functional mapping and cloning and expression of the domain I constituent activities. Proc Natl Acad Sci USA 94: 5588-5593, 1997.
136. Cronan JE Jr, Rock CO. Biosynthesis of membrane lipids. In: FC. Neidhardt et al Editors Escherichia coli and Salmonella typhimurium: Cellular and Molecular Biology (Second Ed.) American Society for Microbiology Washington DC 612-636, 1996.
137. Clough RC, Matthis AL, Barnum SR, Jaworski JG. Purification and characterization of 3-ketoacyl-acyl carrier protein synthase III from spinach. A condensing enzyme utilizing acetylcoenzyme A to initiate fatty acid synthesis. J Biol Chem 267: 20992-20998, 1992.
138. Waller RF, Keeling PJ, Donald RG, Striepen B, Handman E, Lang-Unnasch N, Cowman AF, Besra GS, Roos DS, McFadden GI. Nuclearencoded proteins target to the plastid in Toxoplasma gondii and Plasmodium falciparum. Proc Natl Acad Sci USA 95: 12352-12357, 1998.
139. Qiu X, Janson CA, Court RI, Smyth MG, Payne DJ, Abdel-Meguid SS. Molecular basis for triclosan activity involves a flipping loop in the active site. Protein Sci 8: 2529-2532, 1999.
140. Nie Z, Perretta C, Lu J, Su Y, Margosiak S, Gajiwala KS, Cortez J, Nikulin V, Yager KM, Appelt K, Chu S. Structure-based design, synthesis, and study of potent inhibitors of β-ketoacyl-acyl carrier protein synthase III as potential antimicrobial agents. J Med Chem 48: 1596-1609, 2005.
141. Banerjee A, Dubnau E, Quemard A, Balasubramanian V, Sun Um K, Wilson T, Collins D, de Lisle G, Jacobs WR. A gene encoding a target for isoniazid and ethionamide in Mycobacterium tuberculosis. Science 263: 227-230, 1994.
142. Schaeffer ML, Agnihotri G, Volker C, Kallender H, Brennan PJ, Lonsdale JT. Purification and biochemical characterization of the mycobacterium tuberculosis β-ketoacyl-acyl carrier protein synthases KasA and KasB. J Biol Chem 276: 47029-47037, 2001.
143. Kremer L, Douglas JD, Baulard AR. and 9 other authors. Thiolactomycin and related analogues as novel anti-mycobacterial agents targeting KasA and KasB condensing enzymes in Mycobacterium tuberculosis. J Biol Chem 275: 16857-16864, 2000.
144. Morita YS, Paul KS, Englund PT. Specialized fatty acid synthesis in African trypanosomes: myristate for GPI anchors. Science 288: 140-143, 2000.
145. Douglas JD, Senior SJ, Morehouse C, Phetsukiri B, Campbell IB, Besra GS, Minnikin DE. Analogues of thiolactomycin: Potential drugs with enhanced anti-mycobacterial activity. Microbiology 148: 3101-3109, 2002.
146. Senior SJ, Illarionov PA, Gurcha SS, Campbell IB, Schaeffer ML, Minnikin DE, Besra GS. Biphenyl-based analogues of thiolactomycin, active against mycobacterium tuberculosis mtFabH fatty acid condensing enzyme. Bioorg Med Chem Lett, 13: 3685-3688, 2003.
147. Senior SJ, Illarionov, PA, Gurcha SS, Campbell IB, Schaeffer ML, Minnikina DE Besra GS. Acetylene-based analogues of thiolactomycin, active against mycobacterium tuberculosis mtFabH fatty acid condensing enzyme. Bioorg Med Chem Lett 14: 373-376, 2004.
148. Bhowruth V, Brown AK, Senior SJ,. Snaith JS, Besra GS. Synthesis and biological evalution of a C5-biphenyl thiolactomycin library. Bioorg Med Chem Lett 17: 5643-5646, 2007.
149. Kim P, Zhang Y, Shenoy G, Nguyen Q, Boschoff HI, Manjunath UH, Goodwin MB, Lonsdale J, Price AC, Miller DJ, Duncan K, White SW, Rock CO, Barry III CE, Dowd CS. Structure-Activity Relationships at the 5-Position of thiolactomycin: An intact (5R)-isoprene unit is required for activity against the condensing enzymes from mycobacterium tuberculosis and Escherichia coli. J Med Chem 49: 159-171, 2006.
150. McFadden JM, Medghalchi SM, Thupari JN, Pinn ML, Valamudi A, Miller KI, Kuhajda FP, Townsend CA. Application of a flexible synthesis of (5R)-thiolactomycin to develop new inhibitors of type I fatty acid synthase. J Med Chem 48: 946-971, 2005.
151. Kamal A, Shaik AA, Sinha R, Yadav JS, Arora SK. Antitubercular agents. Part 2: New thiolactomycin analogues active against mycobacterium tuberculosis. Bioorg Med Chem Lett 15: 1927-1929, 2005.
152. Jones SM, Urch JE, Brun R, Harwood JL, Berry C, Gilbert IH. Analogues of thiolactomycin as potential anti-malarial and anti-trypanosomal agents. Bioorg. Med. Chem., 12: 683-692, 2004.
153. Jones SM, Urch JE, Kaiser M, Brun R., Harwood JL, Berry C, Gilbert IH. Analogues of thiolactomycin as potential antimalarial agents. J Med Chem 48: 5932-5941, 2005.
154. Sakaya SM, Contreras MS, Dirlam JP, O'Connell TN, Hayashi SF, Santoro SL, Kamicker BJ, George DM, Ziegler CB. Synthesis and structure-activity relationships of thiotetronic acid analogues of thiolactomycin. Bioorg Med Chem Lett 11: 2751-2754, 2001.