Inhibition of mycobacterial growth by plumbagin derivatives

Chemical Biology and Drug Design

Volumn 76, Issue 1, 2010, Pages 34-42

  Mathew, Ritta ^a   Kruthiventi, Anil K ^a   Prasad, Jalli V ^a   Kumar, Sadula P ^a   Srinu, Garlapati ^a   Chatterji, Dipankar ^a,b  

^a INSTITUTE OF LIFE SCIENCES   (India)

^b INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

FIC; Inhibition; M. smegmatis; Menaquinone; MIC; Plumbagin

Indexed keywords

ACETYLPLUMBAGIN; ANTIMYCOBACTERIAL AGENT; BENZOATE PLUMBAGIN; BUTYRATE PLUMBAGIN; CINNAMATE PLUMBAGIN; CROTONATE PLUMBAGIN; IODOBENZOATE PLUMBAGIN; LEVULINOATE PLUMBAGIN; PLUMBAGIN; PLUMBAGIN DERIVATIVE; PROPIONATE PLUMBAGIN; RIFAMPICIN; UNCLASSIFIED DRUG; NAPHTHOQUINONE; TUBERCULOSTATIC AGENT;

ANTIBACTERIAL ACTIVITY; ARTICLE; BIOFILM; CELL RESPIRATION; CONTROLLED STUDY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON TRANSPORT; ESTERIFICATION; IC 50; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; OXYGEN CONSUMPTION; PRIORITY JOURNAL; CHEMISTRY; DRUG EFFECTS; GROWTH, DEVELOPMENT AND AGING; MICROBIAL SENSITIVITY TEST; MYCOBACTERIUM; MYCOBACTERIUM INFECTIONS;

ANTITUBERCULAR AGENTS; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM; MYCOBACTERIUM INFECTIONS; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NAPHTHOQUINONES;

CORYNEBACTERINEAE; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS;

EID: 77953013923     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2010.00987.x     Document Type: Article

References (45)

1. Cole S.T., Brosch R., Parkhill J., Garnier T., Churcher C., Harris D., Gordon S.V. et al. (1998) Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence. Nature 393 : 537 544.
2. Sassetti C.M., Boyd D.H., Rubin E.J. (2003) Genes required for mycobacterial growth defined by high density mutagenesis. Mol Microbiol 48 : 77 84.
3. Boshoff H.I., Barry C.E. III. (2005) Tuberculosis - metabolism and respiration in the absence of growth. Nat Rev Microbiol 3 : 70 80.
4. Mdluli K., Spigelman M. (2006) Novel targets for tuberculosis drug discovery. Curr Opin Pharmacol 6 : 459 467.
5. Teh J.S., Yano T., Rubin H. (2007) Type II NADH: menaquinone oxidoreductase of Mycobacterium tuberculosis. Infect Disord Drug Targets 7 : 169 181.
6. Zhang Y. (2005) The magic bullets and tuberculosis drug targets. Annu Rev Pharmacol Toxicol 45 : 529 564.
7. Anishetty S., Pulimi M., Pennathur G. (2005) Potential drug targets in Mycobacterium tuberculosis through metabolic pathway analysis. Comput Biol Chem 29 : 368 378.
8. Raman K., Yeturu K., Chandra N. (2008) Target TB: a target identification pipeline for Mycobacterium tuberculosis through an interactome, reactome and genome-scale structural analysis. BMC Syst Biol 2 : 109 130.
9. Sherman M.M., Petersen L.A., Poulter C.D. (1989) Isolation and characterization of isoprene mutants of Escherichia coli. J Bacteriol 171 : 3619 3628.
10. Lester R.L., Crane F.L. (1959) The natural occurrence of coenzyme Q and related compounds. J Biol Chem 234 : 2169 2175.
11. Noll H. (1958) The chemistry of the native constituents of the acetone-soluble fat of Mycobacterium tuberculosis (Brevannes). II. Isolation and properties of a new crystalline naphthoquinone derivative related to vitamin K2. J Biol Chem 232 : 919 929.
12. Segel W.P., Goldman D.S. (1963) The requirement for a naphthoquinone in the reduced nicotinamide-adenine dinucleotide oxidase system of Mycobacterium tuberculosis. Biochim Biophys Acta 73 : 380 390.
13. Kusunose E., Goldman D.S. (1963) The enzymic reduction of naphthoquinones by reduced nicotinamide-adenine dinucleotide. Biochim Biophys Acta 73 : 391 398.
14. Dowd P., Ham S.W., Naganathan S., Hershline R. (1995) The mechanism of action of vitamin K. Annu Rev Nutr 15 : 419 440.
15. Suttie J.W. (1995) The importance of menaquinones in human nutrition. Annu Rev Nutr 15 : 399 417.
16. Weinstein E.A., Yano T., Li L.S., Avarbock D., Avarbock A., Helm D., McColm A.A., Duncan K., Lonsdale J.T., Rubin H. (2005) Inhibitors of type II NADH: menaquinone oxidoreductase represent a class of antitubercular drugs. Proc Natl Acad Sci USA 102 : 4548 4553.
17. Kurosu M., Narayanasamy P., Biswas K., Dhiman R., Crick D.C. (2007) Discovery of 1,4-dihydroxy-2-naphthoate prenyltransferase inhibitors: new drug leads for multidrug-resistant gram-positive pathogens. J Med Chem 50 : 3973 3975.
18. Lu X., Zhang H., Tonge P.J., Tan D.S. (2008) Mechanism-based inhibitors of MenE, an acyl-CoA synthetase involved in bacterial menaquinone biosynthesis. Bioorg Med Chem Lett 18 : 5963 5966.
19. Kurosu M., Crick D.C. (2009) MenA is a promising drug target for developing novel lead molecules to combat Mycobacterium tuberculosis. Med Chem 5 : 197 207.
20. Dhiman R.K., Mahapatra S., Slayden R.A., Boyne M.E., Lenaerts A., Hinshaw J.C., Angala S.K., Chatterjee D., Biswas K., Narayanasamy P., Kurosu M., Crick D.C. (2009) Menaquinone synthesis is critical for maintaining mycobacterial viability during exponential growth and recovery from non-replicating persistence. Mol Microbiol 72 : 85 97.
21. 2) and ubiquinone (coenzyme Q). In : Neidhardt F.C., Curtiss R. III., Ingraham J.L., Lin E.C.C., Low K.B., Magasanik B., Reznikoff W.S., Riley M., Schaechter M., Umbarger H.E., editors. Escherichia coli and Salmonella: Cellular and Molecular Biology, 2nd edn.
22. Meganathan R. (2001) Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms. Vitam Horm 61 : 173 218.
23. Meganathan R., Bentley R. (1981) Biosynthesis of o-succinylbenzoic acid in a men -Escherichia coli mutant requires decarboxylation of L-glutamate at the C-1 position. Biochemistry 20 : 5336 5340.
24. Bentley R., Meganathan R. (1982) Biosynthesis of vitamin K (menaquinone) in bacteria. Microbiol Rev 46 : 241 280.
25. Truglio J.J., Theis K., Feng Y., Gajda R., Machutta C., Tonge P.J., Kisker C.J. (2003) Crystal structure of Mycobacterium tuberculosis MenB, a key enzyme in vitamin K2 biosynthesis. J Biol Chem 278 : 42352 42360.
26. Gutierrez J.A., Crowder T., Rinaldo-Matthis A., Ho M.-C., Almo S.C., Schramm V.L. (2009) Transition state analogs of 5′-methylthioadenosine nucleosidase disrupt quorum sensing. Nat Chem Biol 5 : 251 257.
27. Van der Vijver L.M. (1972) Distribution of plumbagin in the Plumbaginaceae. Phytochemistry 11 : 3247 3248.
28. de Paiva S.R., Figueiredo M.R., Aragão T.V., Kaplan M.A.C. (2003) Antimicrobial activity in vitro of plumbagin isolated from Plumbago species. Mem Inst Oswaldo Cruz, Rio de Janeiro 98 : 959 961.
29. de Lima O.G., d'Albuquerque I.L., Maciel G.M., Maciel M.C. (1968) Antimicrobial substances of superior plants. XXVII. Isolation of plumbagin from Plumbago scandens L. Rev Inst Antibiot (Recife) 8 : 95 97.
30. Borges-Argáez R., Canche-Chay C.I., Peña-Rodríguez L.M., Said-Fernández S., Molina-Salinas G.M. (2007) Antimicrobial activity of Diospyros anisandra. Fitoterapia 78 : 370 372.
31. Tran T., Saheba E., Arcerio A.V., Chavez V., Li Q.Y., Martinez L.E., Primm T.P. (2004) Quinones as antimycobacterial agents. Bioorg Med Chem 12 : 4809 4813.
32. Copp B.R., Pearce A.N. (2007) Natural product growth inhibitors of Mycobacterium tuberculosis. Nat Prod Rep 24 : 278 297.
33. Reyrat J.-M., Kahn D. (2001) Mycobacterium smegmatis: an absurd model for tuberculosis? Trends Microbiol 9 : 472 473.
34. Ojha A.K., Mukherjee T.K., Chatterji D. (2000) High intracellular level of guanosine tetraphosphate in Mycobacterium smegmatis changes the morphology of the bacterium. Infect Immun 68 : 4084 4091.
35. Naresh K., Bharati B.K., Jayaraman N., Chatterji D. (2008) Synthesis and mycobacterial growth inhibition activities of bivalent and monovalent arabinofuranoside containing alkyl glycosides. Org Biomol Chem 6 : 2388 2393.
36. Taneja N.K., Tyagi J.S. (2007) Resazurin reduction assays for screening of anti-tubercular compounds against dormant and actively growing Mycobacterium tuberculosis, Mycobacterium bovis BCG and Mycobacterium smegmatis. J Antimicrob Chemother 60 : 288 293.
37. Mathew R., Mukherjee R., Balachandar R., Chatterji D. (2006) Deletion of the rpoZ gene, encoding the omega subunit of RNA polymerase, results in pleiotropic surface-related phenotypes in Mycobacterium smegmatis. Microbiology 152 : 1741 1750.
38. O'Toole G.A., Pratt L.A., Watnick P.I., Newman D.K., Weaver V.B., Kolter R. (1999) Genetic approaches to study of biofilms. Methods Enzymol 310 : 91 109.
39. Kumar M., Chatterji D. (2008) Cyclic di-GMP: a second messenger required for long-term survival, but not for biofilm formation, in Mycobacterium smegmatis. Microbiology 154 : 2942 2955.
40. Odds F.C. (2003) Synergy, antagonism, and what the chequerboard puts between them. J Antimicrob Chemother 52 : 1.
41. Vall-Spinosa A., Lester W., Moulding T., Davidson P.T., McClatchy J.K. (1970) Rifampin in the treatment of drug-resistant Mycobacterium tuberculosis infections. N Engl J Med 283 : 616 621.
42. Boshoff H.I., Myers T.G., Copp B.R., McNeil M.R., Wilson M.A., Barry C.E. III. (2004) The transcriptional responses of Mycobacterium tuberculosis to inhibitors of metabolism: novel insights into drug mechanisms of action. J Biol Chem 279 : 40174 40184.
43. Lall N., Das Sarma M., Hazra B., Meyer J.J. (2003) Antimycobacterial activity of diospyrin derivatives and a structural analogue of diospyrin against Mycobacterium tuberculosis in vitro. J Antimicrob Chemother 51 : 435 438.
44. Tyagi J.S., Sharma D. (2002) Mycobacterium smegmatis and tuberculosis. Trends Microbiol 10 : 68 69.
45. Barry C.E. III. (2001) Mycobacterium smegmatis: an absurd model for tuberculosis? Trends Microbiol 9 : 473 474.