Diamidinium and iminium aromatics as new aggregators of the bacterial signaling molecule, c-di-GMP

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 2, 2012, Pages 881-885

  Kelsey, Ilana ^a   Nakayama, Shizuka ^a   Sintim, Herman O ^a  

^a UNIVERSITY OF MARYLAND   (United States)

Author keywords

Bacteria; Biofilm; c di GMP; Diamidinium intercalators; G quadruplex

Indexed keywords

2 HYDROXYSTILBAMIDINE BIS(METHANE SULFONATE); 3',5' CYCLIC DIGUANYLIC ACID; 4,4' DIAMINODIPHENYLAMINE SULFATE; AMIDINE; AURAMINE; DIAMIDINIUM; DIMINAZENE ACETURATE; DINUCLEOTIDE; DIPHENYLAMINE DERIVATIVE; GUANINE QUADRUPLEX; IMINIUM; MESYLIC ACID DERIVATIVE; NUCLEIC ACID; PENTAMIDINE ISETHIONATE; UNCLASSIFIED DRUG;

ARTICLE; BIOFILM; DRUG IDENTIFICATION; DRUG STRUCTURE; MOLECULAR INTERACTION; SIGNAL TRANSDUCTION;

AMIDINES; CYCLIC GMP; G-QUADRUPLEXES; IMINES; MOLECULAR STRUCTURE; SOLUBILITY; STEREOISOMERISM; WATER;

BACTERIA (MICROORGANISMS);

EID: 84855648306     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.12.039     Document Type: Article

References (33)

1. H.O. Sintim, J.A. Smith, J. Wang, S. Nakayama, and S. Yan Future Med. Chem. 2 2010 1005
2. Vol. 2011, Centers for Disease Control and Prevention, 2011.
3. A. Camilli, and B.L. Bassler Science 311 2006 1113
4. M. Gomelsky Mol. Microbiol. 79 2011 562
5. E.R. Lee, J.L. Baker, Z. Weinberg, N. Sudarsan, and R.R. Breaker Science 329 2010 845
6. K.D. Smith, S.V. Lipchock, T.D. Ames, J.M. Wang, R.R. Breaker, and S.A. Strobel Nat. Struct. Mol. Biol. 16 2009 1218
7. A. Roth, and R.R. Breaker Annu. Rev. Biochem. 78 2009 305
8. U. Romling, M. Gomelsky, and M.Y. Galperin Mol. Microbiol. 57 2005 629
9. K.D. Smith, C.A. Shanahan, E.L. Moore, A.C. Simon, and S.A. Strobel Proc. Natl. Acad. Sci. U.S.A. 108 2011 7757
10. N. Kulshina, N.J. Baird, and A.R. Ferre-D'Amare Nat. Struct. Mol. Biol. 16 2009 1212
11. P. Ross, H. Weinhouse, Y. Aloni, D. Michaeli, P. Weinbergerohana, R. Mayer, S. Braun, E. Devroom, G.A. Vandermarel, J.H. Vanboom, and M. Benziman Nature 325 1987 279
12. M.Y. Galperin, A.N. Nikolskaya, and E.V. Koonin FFMS Microbiol. Lett. 203 2001 11
13. J.G. Malone, R. Williams, M. Christen, U. Jenal, A.J. Spiers, and P.B. Rainey Microbiology 153 2007 980
14. H.B. Yan, and W.X. Chen Chem. Soc. Rev. 39 2010 2914
15. R. Hengge Nat. Rev. Microbiol. 7 2009 263
16. M.Y. Galperin Environ. Microbiol. 6 2004 552
17. S. Nakayama, I. Kelsey, J. Wang, and H.O. Sintim Chem. Commun. 47 2011 4766
18. Z.Y. Zhang, S. Kim, B.L. Gaffney, and R.A. Jones J. Am. Chem. Soc. 128 2006 7015
19. D.G. Brown, M.R. Sanderson, J.V. Skelly, T.C. Jenkins, T. Brown, E. Garman, D.I. Stuart, and S. Neidle EMBO J. 9 1990 1329
20. M. Rahimian, A. Kumar, M. Say, S.A. Bakunov, D.W. Boykin, R.R. Tidwell, and W.D. Wilson Biochemistry 48 2009 1573
21. D.S. Pilch, M.A. Kirolos, X. Liu, G.E. Plum, and K.J. Breslauer Biochemistry 34 1995 9962
22. S. Nakayama, I. Kelsey, J. Wang, K. Roelofs, B. Stefane, Y. Luo, V.T. Lee, and H.O. Sintim J. Am. Chem. Soc. 133 2011 4856
23. P. Lan, T. Tran, J. Mergny, and P. Alberti Nucleic Acids. Res. 39 2011 3282
24. K.M. Rahman, A.P. Reszka, M. Gunaratnam, S.M. Haider, P.W. Howard, K.R. Fox, S. Neidle, and D.E. Thurston Chem. Commun. 2009 4097
25. R.D. Gray, J. Li, and J.B. Chaires J. Phys. Chem. B 113 2009 2676
26. A.N. Lane, J.B. Chaires, R.D. Gray, and J.O. Trent Nucleic Acids. Res. 36 2008 5482
27. C. Antonacci, J.B. Chaires, and R.D. Sheardy Biochemistry 46 2007 4654
28. M. Webba da Silva Chem. Eur. J. 13 2007 9738
29. A.I. Karsisiotis, N.M. Hessari, E. Novellino, G.P. Spada, A. Randazzo, and M. Webba da Silva Angew. Chem., Int. Ed. 2011 10.1002/anie.201105193
30. J. Stilling Wien. klin. Woch. 4 1891 201
31. H. Bechhold, and P.Z. Ehrlich Physiol. Chem. 47 1906 173
32. A. Nehrbass-Stuedli, D. Boykin, R.R. Tidwell, and R. Brun Antimicrob. Agents Chemother. 55 2011 3439
33. R. Wien, J. Harrison, and W.A. Freeman Br. J. Pharmacol. Chemother. 3 1948 211