A rhodanine derivative CCR-11 inhibits bacterial proliferation by inhibiting the assembly and GTPase activity of FtsZ

Biochemistry

Volumn 51, Issue 27, 2012, Pages 5434-5442

  Singh, Parminder ^a   Jindal, Bhavya ^a   Surolia, Avadhesha ^b   Panda, Dulal ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-BACTERIAL ACTIVITY; ANTIBACTERIAL AGENT; ASSEMBLY DYNAMICS; BACILLUS SUBTILIS CELLS; BACTERIAL CELLS; BACTERIAL CYTOKINESIS; DISSOCIATION CONSTANT; GTPASE ACTIVITY; H-BONDING; HYDROPHOBIC INTERACTIONS; IN-VITRO; INHIBITORY CONCENTRATION; MEMBRANE INTEGRITY; MINIMAL INHIBITORY CONCENTRATION; MYCOBACTERIUM SMEGMATIS; NUCLEOIDS; RHODANINE; SUBTILIS; THIAZOLIDIN-4-ONES; TRIFLUOROMETHYL;

BACTERIA; CELL PROLIFERATION; DISSOCIATION;

CYTOLOGY;

2 THIOXO 5 [[[3 (TRIFLUOROMETHYL)PHENYL]FURAN 2 YL]METHYLENE]THIAZOLIDIN 4 ONE; 5 [[5 (2 METHOXY 4 NITROPHENYL)FURAN 2 YL]METHYLENE] 2 THIOXOTHIAZOLIDIN 4 ONE; 5 [[5 (4 BROMOPHENYL)FURAN 2 YL]METHYLENE] 2 THIOXOTHIAZOLIDIN 4 ONE; ANTIINFECTIVE AGENT; CCR 11; CCR 4; CCR 85; FTSZ PROTEIN; GUANOSINE TRIPHOSPHATASE; HYDROGEN; OXYGEN; RHODANINE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BACTERIAL CELL; BACTERIAL GROWTH; CELL ELONGATION; CELL MEMBRANE; CELL PROLIFERATION; CONTROLLED STUDY; CYTOKINESIS; DISSOCIATION CONSTANT; DRUG EFFECT; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENZYME ACTIVITY; GROWTH INHIBITION; HELA CELL; HYDROGEN BOND; HYDROPHOBICITY; IC 50; MYCOBACTERIUM SMEGMATIS; NONHUMAN; PRIORITY JOURNAL; PROTEIN ASSEMBLY;

ANTI-BACTERIAL AGENTS; BACILLUS SUBTILIS; BACTERIAL PROTEINS; CELL PROLIFERATION; CYTOKINESIS; CYTOSKELETAL PROTEINS; GTP PHOSPHOHYDROLASES; GUANOSINE TRIPHOSPHATE; HELA CELLS; HUMANS; MOLECULAR DOCKING SIMULATION; MYCOBACTERIUM SMEGMATIS; PROTEIN MULTIMERIZATION; PROTEIN STRUCTURE, QUATERNARY; RHODAMINES; RHODANINE; THIAZOLIDINES;

BACILLUS SUBTILIS; BACTERIA (MICROORGANISMS); MYCOBACTERIUM SMEGMATIS;

EID: 84863731219     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi201813u     Document Type: Article

References (36)

1. Lutkenhaus, J. F., Wolf-Watz, H., and Donachie, W. D. (1980) Organization of genes in the ftsA-envA region of the Escherichia coli genetic map and identification of a new fts locus (ftsZ) J. Bacteriol. 142, 615-620 (Pubitemid 10044950)
2. Bi, E. and Lutkenhaus, J. (1992) Isolation and characterization of ftsZ alleles that affect septal morphology J. Bacteriol. 174, 5414-5423
3. Adams, D. W. and Errington, J. (2009) Bacterial cell division: Assembly, maintenance and disassembly of the Z ring Nat. Rev. Microbiol. 7, 642-653
4. Anderson, D. E., Gueiros-Filho, F. J., and Erickson, H. P. (2004) Assembly dynamics of FtsZ rings in Bacillus subtilis and Escherichia coli and effects of FtsZ-regulating proteins J. Bacteriol. 186, 5775-5781 (Pubitemid 39128650)
5. Stricker, J., Maddox, P., Salmon, E. D., and Erickson, H. P. (2002) Rapid assembly dynamics of the Escherichia coli FtsZ-ring demonstrated by fluorescence recovery after photobleaching Proc. Natl. Acad. Sci. U.S.A. 99, 3171-3175 (Pubitemid 34240604)
6. Addinall, S. G. and Lutkenhaus, J. (1996) FtsA is localized to the septum in an FtsZ-dependent manner J. Bacteriol. 178, 7167-7172 (Pubitemid 26424630)
7. Dai, K., Mukherjee, A., Xu, Y., and Lutkenhaus, J. (1994) Mutations in ftsZ that confer resistance to SulA affect the interaction of FtsZ with GTP J. Bacteriol. 176, 130-136 (Pubitemid 24014931)
8. Kapoor, S. and Panda, D. (2009) Targeting FtsZ for antibacterial therapy: A promising avenue Expert Opin. Ther. Targets 13, 1037-1051
9. Jaiswal, R., Patel, R. Y., Asthana, J., Jindal, B., Balaji, P. V., and Panda, D. (2010) E93R substitution of Escherichia coli FtsZ induces bundling of protofilaments, reduces GTPase activity, and impairs bacterial cytokinesis J. Biol. Chem. 285, 31796-31805
10. Lu, C., Stricker, J., and Erickson, H. P. (2001) Site-specific mutations of FtsZ: Effects on GTPase and in vitro assembly BMC Microbiol. 1, 1-7
11. Singh, P. and Panda, D. (2010) FtsZ inhibition: A promising approach for antistaphylococcal therapy Drug News Perspect. 23, 295-304
12. Vollmer, W. (2006) The prokaryotic cytoskeleton: A putative target for inhibitors and antibiotics? Appl. Microbiol. Biotechnol. 73, 37-47 (Pubitemid 44627722)
13. Schaffner-Barbero, C., MartíÂn-Fontecha, M., ChacóÂn, P., and Andreu, J. M. (2012) Targeting the Assembly of Bacterial Cell Division Protein FtsZ with Small Molecules ACS Chem. Biol. 7, 267-277
14. Beuria, T. K., Santra, M. K., and Panda, D. (2005) Sanguinarine blocks cytokinesis in bacteria by inhibiting FtsZ assembly and bundling Biochemistry 44, 16584-16593 (Pubitemid 41832040)
15. Beuria, T. K., Singh, P., Surolia, A., and Panda, D. (2009) Promoting assembly and bundling of FtsZ as a strategy to inhibit bacterial cell division: A new approach for developing novel antibacterial drugs Biochem. J. 423, 61-69
16. Jaiswal, R., Beuria, T. K., Mohan, R., Mahajan, S. K., and Panda, D. (2007) Totarol inhibits bacterial cytokinesis by perturbing the assembly dynamics of FtsZ Biochemistry 46, 4211-4220 (Pubitemid 46559388)
17. Margalit, D. N., Romberg, L., Mets, R. B., Hebert, A. M., Mitchison, T. J., Kirschner, M. W., and Raychaudhuri, D. (2004) Targeting cell division: Small-molecule inhibitors of FtsZ GTPase perturb cytokinetic ring assembly and induce bacterial lethality Proc. Natl. Acad. Sci. U.S.A. 101, 11821-11826 (Pubitemid 39095378)
18. Haydon, D. J., Stokes, N. R., Ure, R., Galbraith, G., Bennett, J. M., Brown, D. R., Baker, P. J., Barynin, V. V., Rice, D. W., Sedelnikova, S. E., Heal, J. R., Sheridan, J. M., Aiwale, S. T., Chauhan, P. K., Srivastava, A., Taneja, A., Collins, I., Errington, J., and Czaplewski, L. G. (2008) An inhibitor of FtsZ with potent and selective anti-staphylococcal activity Science 321, 1673-1675
19. Ito, H., Ura, A., Oyamada, Y., Tanitame, A., Yoshida, H., Yamada, S., Wachi, M., and Yamagishi, J. (2006) A 4-aminofurazan derivative-A189-inhibits assembly of bacterial cell division protein FtsZ in vitro and in vivo Microbiol. Immunol. 50, 759-764 (Pubitemid 44624706)
20. Reynolds, R. C., Srivastava, S., Ross, L. J., Suling, W. J., and White, E. L. (2004) A new 2-carbamoyl pteridine that inhibits mycobacterial FtsZ Bioorg. Med. Chem. Lett. 14, 3161-3164 (Pubitemid 38624584)
21. Adams, D. W., Wu, L. J., Czaplewski, L. G., and Errington, J. (2011) Multiple effects of benzamide antibiotics on FtsZ function Mol. Microbiol. 80, 68-84
22. Tomasić, T. and Masic, L. P. (2009) Rhodanine as a privileged scaffold in drug discovery Curr. Med. Chem. 16, 1596-1629
23. Bradford, M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 72, 248-254
24. Lu, C., Stricker, J., and Erickson, H. P. (1998) FtsZ from Escherichia coli, Azotobacter vinelandii, and Thermotoga maritima: Quantitation, GTP hydrolysis, and assembly Cell Motil. Cytoskeleton 40, 71-86 (Pubitemid 28225543)
25. Geladopoulos, T. P., Sotiroudis, T. G., and Evangelopoulos, A. E. (1991) A malachite green colorimetric assay for protein phosphatase activity Anal. Biochem. 192, 112-116
26. Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K., and Olson, A. J. (1998) Automated Docking Using a Lamarckian Genetic Algorithm and Empirical Binding Free Energy Function J. Comput. Chem. 19, 1639-1662 (Pubitemid 128590223)
27. Berman, H. M., Westbrook, J., Feng, Z., Gilliland, G., Bhat, T. N., Weissig, H., Shindyalov, I. N., and Bourne, P. E. (2000) The Protein Data Bank Nucleic Acids Res. 28, 235-242 (Pubitemid 30047768)
28. SchüÂ̂Âttelkopf, A. W. and van Aalten, D. M. (2004) PRODRG: A tool for high-throughput crystallography of protein-ligand complexes Acta Crystallogr. D60, 1355-1363 (Pubitemid 41079731)
29. Wiegand, I., Hilpert, K., and Hancock, R. E. (2008) Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances Nat. Protoc. 3, 163-175 (Pubitemid 351266501)
30. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, M. R. (1990) New colorimetric cytotoxicity assay for anticancer-drug screening J. Natl. Cancer Inst. 82, 1107-1112 (Pubitemid 20213250)
31. Auffinger, P., Hays, F. A., Westhof, E., and Ho, P. S. (2004) Halogen bonds in biological molecules Proc. Natl. Acad. Sci. U.S.A. 101, 16789-16794 (Pubitemid 39601317)
32. Mukherjee, A., Santra, M. K., Beuria, T. K., and Panda, D. (2005) A natural osmolyte trimethylamine N-oxide promotes assembly and bundling of the bacterial cell division protein, FtsZ and counteracts the denaturing effects of urea FEBS J. 272, 2760-2772 (Pubitemid 40825423)
33. Jordan, M. A. and Wilson, L. (2004) Microtubules as a target for anticancer drugs Nat. Rev. Cancer 4, 253-265 (Pubitemid 38525281)
34. Dumontet, C. and Jordan, M. A. (2010) Microtubule-binding agents: A dynamic field of cancer therapeutics Nat. Rev. Drug Discovery 9, 790-803
35. Scheffers, D. J., de Wit, J. G., den Blaauwen, T., and Driessen, A. J. (2002) GTP hydrolysis of cell division protein FtsZ: Evidence that the active site is formed by the association of monomers Biochemistry 41, 521-529 (Pubitemid 34062021)
36. DeLano, W. L. (2002) The PyMOL Molecular Genetics Graphics System, DeLano Scientific LLC, San Carlos, CA.