The macrolide-ketolide antibiotic binding site is formed by structures in domains II and V of 23S ribosomal RNA

Molecular Microbiology

Volumn 31, Issue 2, 1999, Pages 623-631

  Hansen, Lykke Haastrup ^a   Mauvais, Pascale ^b   Douthwaite, Stephen ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^b Lab for Bacterial Biochemistry   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ERYTHROMYCIN; KETOLIDE; MACROLIDE; PEPTIDYLTRANSFERASE; RIBOSOME RNA;

ARTICLE; BINDING AFFINITY; CHEMICAL MODIFICATION; CONTROLLED STUDY; DERIVATIZATION; DRUG BINDING SITE; ESCHERICHIA COLI; NONHUMAN; PRIORITY JOURNAL; RNA STRUCTURE; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; BASE SEQUENCE; BINDING SITES; CELL DIVISION; ERYTHROMYCIN; ESCHERICHIA COLI; KETOLIDES; MACROLIDES; MOLECULAR SEQUENCE DATA; NUCLEIC ACID CONFORMATION; RNA, RIBOSOMAL, 23S;

EID: 0032950956     PISSN: 0950382X     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1365-2958.1999.01202.x     Document Type: Article

References (34)

1. Agouridas, C., Bonnefoy, A., and Chantot, J.F. (1997a) Antibacterial activity of RU 64004 (HMR 3004), a novel ketolide derivative active against respiratory pathogens. Antimicrob Agents Chemother 41: 2149-2158.
2. Agouridas, C., Benedetti, Y., Bonnefoy, A., Collette, P., Denis, A., Mauvais, P., Labbe, G., and Chantot, J.F. (1997b) Ketolides: a new class of macrolide antibacterials, structural characteristics and biological properties of RU 004. Clin Infect Dis Ther 21: 279-285.
3. Baranov, P.V., Sergiev, P.V., Dontsova, O.A., Bogdanov, A.A., and Brimacombe, R. (1998) The database of ribosomal cross links. Nucleic Acids Res 26: 187-189.
4. Cooperman, B.S., Weitzmann, C.J., and Fernández, C.L. (1990) Antibiotic probes of Escherichia coli peptidyltransferase. In The Structure, Function, and Evolution of Ribosomes. Hill, W., Dahlberg, A., Garrett, R.A., Moore, P.B., Schlessinger, D., and Warner, J. (eds). pp. 491-501. Washington, DC: American Society for Microbiology Press.
5. Cundliffe, E. (1986) Involvement of specific portions of ribosomal RNA in defined ribosomal functions: a study utilising antibiotics. In Structure, Function and Genetics of Ribosomes. Hardesty, B., and Kramer, G. (eds). pp. 586-604. New York: Springer-Verlag.
6. Cundliffe, E. (1990) Recognition sites for antibiotics in rRNA. In The Structure, Function, and Evolution of Ribosomes. Hill, W., Dahlberg, A., Garrett, R.A., Moore, P.B., Schlessinger, D., and Warner, J. (eds). pp. 479-490. Washington, DC: American Society for Microbiology Press.
7. Douthwaite, S. (1992a) Functional interactions within 23S rRNA involving the peptidyltransferase center. J Bacteriol 174: 1333-1338.
8. Douthwaite, S. (1992b) Interaction of the antibiotics clindamycin and lincomycin with Escherichia coli 23S ribosomal RNA. Nucleic Acids Res 20: 4717-4720.
9. Douthwaite, S., and Aagaard, C. (1993) Erythromycin binding is reduced in ribosomes with conformational alterations in the 23S rRNA peptidyl transferase loop. J Mol Biol 232: 725-731.
10. Douthwaite, S., Powers, T., Lee, J.Y., and Noller, H.F. (1989) Defining the structural requirements for a helix in 23S ribosomal RNA that confers erythromycin resistance. J Mol Biol 209: 655-665.
11. Ednie, L.M., Spangler, S.K., Jacobs, M.R., and Appelbaum, P.C. (1997) Susceptibilities of 228 penicillin- and erythromycin-susceptible and -resistant pneumococci to RU 64004 (HMR 3004), a new ketolide, compared with susceptibilities to 16 other agents. Antimicrob Agents Chemother 41: 1033-1036.
12. Egebjerg, J., and Garrett, R.A. (1991) The binding sites of the antibiotics pactamycin and celesticetin on ribosomal RNAs. Biochimie 73: 1145-1149.
13. Elliott, R.L., Pireh, D., Nilius, A.M., Johnson, P.M., Flamm, R.K., Chu, D.T.W., et al. (1997) Novel 3-deoxy-3-descladinosyl-6-o-methyl erythromycin A analogues. Synthesis and in vitro activity. Bioorg Med Chem Lett 7: 641-646.
14. Gale, E.F., Cundliffe, E., Reynolds, P.E., Richmond, M.H., and Waring, M.J. (1981) The Molecular Basis of Antibiotic Action. London: John Wiley and Sons.
15. Griesgraber, G., Or, Y.S., Chu, D.T.W., Nilius, A.M., Johnson, P.M., Flamm, R.K., et al. (1996) 3-keto-11,12-carbazate derivatives of 6-O-methylerythromycin A. Synthesis and in vitro activity. J Antibiot 49: 465-477.
16. Gutell, R.R., Larsen, N., and Woese, C.R. (1994) Lessons from an evolving rRNA: 16S and 23S rRNA structures from a comparative perspective. Microbiol Rev 58: 10-26.
17. Jamjian, C., Biedenback, D.J., and Jones, R. (1997) In vitro evaluation of a novel ketolide antimicrobial agent, RU 64004. Antimicrob Agents Chemother 41: 454-459.
18. Lázaro, E., Rodrigrez-Fonseca, C., Porse, B., Urena, D., Garrett, R.A., and Ballesta, J.P.G. (1996) A sparsomycin-resistant mutant of Halobacterium salinarium lacks a modification at nucleotide U2603 in the peptidyl transferase centre of 23S rRNA. J Mol Biol 261: 231-238.
19. Leviev, I.G., Rodrigez-Fonseca, C., Phan, H., Garrett, R.A., Geilek, G., Noller, H.F., et al. (1994) A conserved secondary structural motif in 23S rRNA defines the site of interaction of amicetin, a universal inhibitor of peptide bond formation. EMBO J 13: 1682-1686.
20. Moazed, D., and Noller, H.F. (1987) Chloramphenicol, erythromycin, carbomycin and vernamycin B protect overlapping sites in the peptidyl transferase region of 23S ribosomal RNA. Biochimie 69: 879-884.
21. Noller, H.F. (1984) Structure of ribosomal RNA. Annu Rev Biochem 53: 119-162.
22. Noller, H.F. (1991) Ribosomal RNA and translation. Annu Rev Biochem 60: 191-227.
23. 14C-erythromycin to E. coli ribosomes. Antimicrob Agents Chemother 6: 479-486.
24. Rodriguez-Fonseca, C., Amils, R., and Garrett, R.A. (1995) Fine structure of the peptidyl transferase centre on 23S- like rRNAs deduced from chemical probing of antibiotic-ribosome complexes. J Mol Biol 247: 224-235.
25. Sambrook, J., Fritsch, E.F., and Maniatis, T. (1989) Molecular Cloning: A Laboratory Manual, 2nd edn. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press.
26. Schülin, T., Wennersten, C.B., Moellering, R.C., and Eliopoulos, G.M. (1997) In vitro activity of RU 64004 (HMR 3004), a new ketolide antibiotic, against Gram-positive bacteria. Antimicrob Agents Chemother 41: 1192-1202.
27. Sigmund, C.D., Ettayebi, M., Borden, A., and Morgan, E.A. (1988) Antibiotic resistance mutations in ribosomal RNA genes of Escherichia coli. Methods Enzymol 164: 673-690.
28. Skinner, R.H., Cundliffe, E., and Schmidt, F.J. (1983) Site of action of a ribosomal RNA methylase responsible for resistance to erythromycin and other antibiotics. J Biol Chem 258: 12702-12706.
29. Stern, S., Moazed, D., and Noller, H.F. (1988) Structural analysis of RNA using chemical and enzymatic probing monitored by primer extension. Methods Enzymol 164: 481-489.
30. Tenson, T., DeBlasio, A., and Mankin, A.S. (1996) A functional peptide encoded in the Escherichia coli 23S rRNA. Proc Natl Acad Sci USA 93: 5641-5646.
31. Vázquez, D. (1979) Inhibitors of Protein Synthesis. New York: Springer-Verlag.
32. Vester, B., and Garrett, R.A. (1987) A plasmid-coded and site-directed mutation in Escherichia coli 23S RNA that confers resistance to erythromycin: implications for the mechanism of action of erythromycin. Biochimie 69: 891-900.
33. Weisblum, B. (1995) Erythromycin resistance by ribosome modification. Antimicrob Agents Chemother 39: 577-585.
34. Xiong, L., Shah, S., Mauvais, P., and Mankin, A.S. (1999) A ketolide resistance mutation in domain II of 23S rRNA reveals the proximity of hairpin 35 to the peptidyl transferase centre. Mol Microbiol 31: 633-639.