The streptogramin antibiotics: Update on their mechanism of action

Expert Opinion on Investigational Drugs

Volumn 7, Issue 4, 1998, Pages 591-599

  Beyer, Dieter ^a   Pepper, Karen ^a  

^a SANOFI   (France)

Author keywords

antibiotics; methicillin resistant Staphylococcus aureus; peptidyl transferase; quinupristin dalfopristin (RP 59500); ribosome; streptogramins; translation; virginiamycin

Indexed keywords

EID: 0001689294     PISSN: 13543784     EISSN: 17447658     Source Type: Journal    
DOI: 10.1517/13543784.7.4.591     Document Type: Article

References (69)

1. HIRAMATSU K, HANAKI H, INO T et al.: Methicillin- resistant Staphylococcus aureus clinical strain with reduced vancomycin susceptibility. J. Antimicrob. Che-mother. (1997) 40: 135–136.
2. HIRAMATSU K, ARITAKA N, HANAKI H et al.: Dissemina-tion in Japanese hospitals of strains of Staphylococcus aureus heterogeneously resistant to vancomycin. Lan-cet (1997) 350: 1670–1673.
3. J. Antibact. Chemother. (1992):30: (Supplement A). (Entire volume)
4. VAZQUEZ D: The streptogramin family of antibiotics. In: Antibiotics Vol. III. Corcoran JN, Hahn FE (Eds.), Sprin-ger, Berlin, Heidelberg, New York (1975): 521–534.
5. MARTINELLI E, ZERILLI LF, VOLPE G, PAGANI HE, CAR-ELLI B: New antibiotics from Actinoplanes strains. Structure of A 17002 C. J. Antibiol (1979) 30: 108–114.
6. WEN-CHIH L, SEINER V, DEAN LD et al.: Production ofvernamycin by a Micromonospora. J. Antibiol (1981) 34: 1515–1516.
7. PARIS JM, BARRIERE JC, SMITH C, BOST PE: The chemis-try of pristinamycins. In: Recent Progress in the Chemical Synthesis of Antibiotics. Lukacs G, Ohno M (Eds.), Springer Verlag, Berlin, Germany (1990): 183–248.
8. BARRIERE JC, BOUANCHAUD DH, DESNOTTES JF, PARIS JM: Streptogramin analogues. Exp. Opin. Invest. Drugs (1994) 3: 115–131.
9. NEU HC, CHIN NX, GU JW: The in vitro activity of new streptogramins, RP 59500, RP 57669 and RP54476, alone and in combination. J. Antimicrob. Chemother. (1992) 30 (Suppl. 483–94.
10. BARRIERE JC, PARIS JM: RP 59500 and related semisyn-thetic streptogramins. Drugs Future (1993) 18: 833–845.
11. AMILS R, REIMIREZ L, SANZ JL et al.: Phylogeny of antibi-otic action. In: The Ribosome, Structure, Function & Evolution. Hill WE et al. (Eds.), American Society for Microbiology, Washington DC, USA (1990 645–654.
12. YAMAGUCHI H, YOSHIDA Y, TANAKA N: Inhibition by mikamycins of polypeptide synthesis directed by na-tive messengers and synthetic polynucleotides. J. Bio-chem. (1966) 60: 246–255.
13. DI GIAMBATTISTA M, COCITO C: Action of ions and pHon the binding of virginiamycin S to ribosomes. Bio-chim. Biophys. Acta (1983) 757: 92–100.
14. CLAYS K, DI GIAMBATTISTA M, PERSOONS A, ENGEL-BORGHS Y: A fluorescence lifetime study of virginia-mycin S using multifrequency phase fluorometry. Biochemistry (1991) 30: 7271–7276.
15. CONTRERAS A, VAZQUEZ, D: Synergistic interaction of the streptogramins with the ribosome. Eur. J. Biochem. (1977) 74: 549–551.
16. MOUREAU P, ENGELBORGHS Y, DI GIAMBATTISTA M,COCITO C: Fluorescence stopped flow analysis of the interaction of virginiamycin components and eryth-romycin with bacterial ribosomes. J. Biol. Chem. (1983) 258: 14233–14238.
17. VANNUFFEL P, DI GIAMBATTISTA M, MORGAN EA, COCITO C: Identification of a single base change in ri-bosomal RNA leading to erythromycin resistance. Biol. Chem. (1992) 267: 8377–8382.
18. BEYER D, VANNUFFEL P, PEPPER K: Quinupristin (RP57669): a new tool to investigate ribosome-group B streptogramin interactions. (In Press.)
19. DI GIAMBATTISTA M, CHINALI G, COCITO C: The mo-lecular bases of the inhibitory activities of type A and type B synergimycins and related antibiotics on ribo-somes. j Antimicrob. Chemother. (1989) 24: 485–507.
20. DI GIAMBATTISTA M, ENGELBORGHS Y, NYSSEN E, CLAYS K, COCITO C: Interaction between virginiamy-cin S and ribosomes is partly provided by a salt bridge with a Mg2+ ion. Biochemistry (1991) 30: 7277–7282.
21. DI GIAMBATTISTA M, THIELEN APGM, MAASSEN JA, MOLLER W, COCITO C: Localization of virginiamycin S binding site on bacterial ribosomes by fluorescence energy transfer. Biochemistry (1986) 25: 3540–3547.
22. DE BETHUNE MP, NIERHAUS KH: Characterisation of the binding of virginiamycin S to Escherichia coli ri-bosomes. Eur.J. Biochem. (1978) 86: 187–191.
23. FRANCESCHI FJ, NIERHAUS KH: Ribosomal proteins L15 and L16 are mere late assembly proteins of the large ri-bosomal subunit. Analysis of an Escherichia coli mu-tant lacking L15. J. Biol. Chem. (1990) 265: 16676–16682.
24. DI GIAMBATTISTA M, NYSSEN E, PECHER A, COCITO C: Affinity labeling of the virginiamycin S binding site on bacterial ribosome. Biochemistry (1990) 29: 9203–9211.
25. BISCHOF O, KRUFT V, WITTMANN-LIEBOLD B: Analysis of the puromycin binding site in the 70S ribosome of Escherichia coli at the peptide level. J. Biol. Chem. (1994) 269: 18315–18319.
26. BISCHOF O, URLAUB H, KRUFT V, WITTMANN-LIEBOLDB: Peptide environment of the peptidyl transferase center from Escherichia coli 70S ribosomes as deter-mined by thermoaffinity labeling with dihydrospira-mycin. J. Biol. Chem. (1995) 270: 23060–23064.
27. DI GIAMBATTISTA M, ENGELBORGHS Y, NYSSEN E, COCITO C: Kinetics of binding of macrolides, linco-samides, and synergimycins to ribosomes. J. Biol. Chem. (1987) 262: 8591–8597.
28. TERAOKA H, NIERHAUS KH: Proteins from Escherichiacoliribosomes involved in binding of erythromycin. J. Mol Biol. (1978) 126: 185–193.
29. LOTTI M, DABBS ER, HASENBANK R, STOFFLER-MEILIKE M, STOFFLER G: Characterisation of a mutant from Escherichia coli lacking protein L15 and localisation of protein L15 by immuno-electron microscopy. Mol. Gen. Gent. (1983) 192: 295–300.
30. PARDO D, ROSSET R: Properties of ribosomes from erythromycin resistant mutants from Escherichia coli. Mol. Gen. Gent. (1977) 156: 267–271.
31. ARE VALO MA, TEJEDOR F, POLO F, BALETS JPG: Protein components of the erythromycin binding site in bacte-rial protein synthesis. J. Biol. Chem. (1988) 263: 58–63.
32. WEISBLUM, B: Erythromycin resistance by ribosome modification. Antimicrob. Agents Chemother. (1995) 39: 577–585.
33. LACROIX P, AUMERCIER M, CAPMAU ML, LE GOFFIC F:Studies on pristinamycin synergism in Staphylococ-cus aureus. J. Antibiot. (1986) 39: 1314–1321.
34. FOURNET MP, DEFORGES L, ZINI R, BARRE J, TILLEMENTJP: Binding studies of macrolides, lincosamides and streptogramins to Streptococcus G group using [311]-e rythro my c in. Biochem. Pharmacol. (1987) 36: 3495–3500.
35. SIGMUND CD, MORGAN EA: Erythromycin resistancedue to a mutation in a ribosomal RNA operon of Escherichia coli. Proc. Natl. Acad. Sci. USA (1982) 79: 5602–5606.
36. VESTER B, GARRETT A: Plasmid-coded and site-directedmutation in Escherichia coli 23S RNA that confers re-sistance to erythromycin: implications for the mechanism of action of erythromycin. Biochimie (1987) 8: 891–900.
37. PERNODET JL, FISH S, BLONDELET-ROUAULT MH, CUNDLIFFE E: The macrolide-lincosamide-streptogramin B resistance phenotypes characterized by using a specifically deleted, antibiotic-sensitive strain of Streptomyces lividans. Antimicrob. Agents Che-mother. (1996) 40: 581–585.
38. VANNUFFEL P, DI GIAMBATTISTA M, COCITO C: The role of rRNA bases in the interaction of peptidyltransferase inhibitors with bacterial ribosomes. J. Biol. Chem. (1992) 267: 16114–16120.
39. DOUTHWAITE S, AAGAARD C: Erythromycin binding is reduced in ribosomes with conformational alterations in the 23S rRNA peptidyl transferase. j Mol. Biol. (1993) 232: 725–731.
40. MOAZED D, NOLLER HF: Chloramphenicol, erythromy-cin, carbomycin and vernamycin B protect overlap-ping sites in the peptidyltransferase region of 23S ribosomal RNA. Biochimie (1987) 69: 879–884.
41. VANNUFFEL P, DI GIAMBATTISTA M, COCITO C: Chemi-cal probing of a virginiamycin M-promoted conforma-tional change of the peptidyltransferase domain. Nucl. Acids Res. (1994) 22: 4449–4453.
42. RODRIGUEZ-FONSECA C, AMILS R, GARRETT RA: Fine structure of the peptidyl transferase center on 23S-like rRNAs deduced from chemical probing of antibiotic-ribosome complexes. J. Mol. Biol. (1995) 247: 224–235.
43. CHINALI G, NYSSEN E, DI GIAMBATTISTA M, COCITO C:Inhibition of polypeptide synthesis in cell-free sys-tems by virginiamycin S and erythromycin. Evidence for a common mode of action of type B synergimycins and 14-membered macrolides. Biochim. Biophys. Acta (1988) 949: 71–78.
44. CHINALI G, NYSSEN E, DI GIAMBATTISTA M, COCITO C: Action of erythromycin and virginiamycin S on polypeptide synthesis in cell-free systems. Biochim. Biophys. Acta (1988) 951: 42–52.
45. MENNINGER JR, COLEMAN RA, TSAI LN: Erythromycin, lincosamides, peptidyl-tRNA dissociation, and ribo-somal editing. Mol. Genet. (1994) 243: 225–233.
46. MENNINGER JR: The accumulation of peptidyl-transfer RNA of isoaccepting transfer RNA families in Escheri-chia co/iwith temperature-sensitive peptidyl-transfer RNA hydrolase. J. Biol. Chem. (1978) 253: 6808–6813.
47. AUMERCIER M, BOUHALLAB S, CAPMAU ML, LE GOFFIC F: RP 59500: a proposed mechanism for its bactericidal activity. J. Antimicrob. Chemother. (1992) 30 (Suppl A): 9–14.
48. CHITTUM HS, CHAMPNEY W: Erythromycin inhibits the assembly of the large ribosomal subunit in growing Escherichia colicells. Curr. Microbiol (1995) 30: 273–279.
49. CHAMPNEY WS, BURDINE R: Macrolide antibiotics in-hibit 50S ribosomal subunit assembly in Bacillus sub-tilis and Staphylococcus aureus. Antimicrob. Agents Chemother. (1995) 39:2141-2144.
50. OBERBACJMER I: Streptogramine als modellsysteme fur den kationentransport durch membranen. Disserta-tion. Georg-August-Universitat, Goettingen (1979).
51. MINH HOA DT, DINH KINH C, DANG TRIEU Q: Spectro-photometric titration method for the determination of thermodynamic parameters of metal complexing. Z. Chem. (1990) 30: 224–225.
52. AUMERCIER M, BOUHALLAB S, CAPMAU ML, LE GOFFIC F: Irreversible binding of pristinamycin IIA (strepto-gramin A) to ribosomes explains its “lasting damage” effect. J. Antibiot. (1986) 39: 1322–1328.
53. CHINALI G, VANLINDEN F, COCITO C: Action of virginia-mycin M on the stability of different ribosomal com-plexes to ultracentrifugation. Biochim. Biophys. Acta (1988) 950: 67–74.
54. COCITO C, VOORMA HO, BOSCH L: Interference of vir-giniamycin M with the initiation and the elongation of peptide chains in cell-free systems. Biochim. Biophys. Acta (1974) 340: 285–298.
55. CHINALI G, DI GIAMBATTISTA M, COCITO C: Ribosome protection by tRNA derivatives against inactivation by virginiamycin M: evidence for two types of interaction of tRNA with the donor site of peptidyl transferase. Biochemistry (1987) 26: 1592–1597.
56. CHINALI G, MOUREAU P, COCITO C: The mechanism of action of virginiamycin M on the binding of aminoacyl-tRNA to ribosomes directed by elongation factor Tu. Eur. j Biochem. (1981) 118: 577–583.
57. CHINALI G, MOUREAU P, COCITO C: The action of vir-giniamycin M on the acceptor, donor, and catalytic sites of peptidyltransferase. J. Biol. Chem. (1984) 259: 9563–9568.
58. ODOM OW, HARDESTY B: Use of 50 S-binding antibiot-ics to characterize the ribosomal site to which peptidyl-tRNA is bound. J. Biol. Chem. (1992) 267: 19117–19122.
59. NIERHAUS KH: The allosteric three-site model for the ribosomal elongation cycle: features and future. Bio-chemistry (1990) 29: 4997–5008.
60. NIERHAUS KH, BEYER D, DABROWSKI M et al: The elon-gating ribosome: structural and functional aspects. Biochem. Cell Biol. (1995) 73, 1011–1021.
61. NOLLER HF, MOAZED D, STERN S et al.: Structure of rRNA and its functional interaction in translation. In: The Ribosome, Structure, Function & Evolution. Hill WE et al. (Eds.), American Society for Microbiology, Washington DC, USA (1990 645–654.
62. STEINER G, KUECHLER E, BARTA A: Photoaffinity label-ing at the peptidyl transferase center reveals two dif-ferent positions for the A- and P-sites in domain V of 23S rRNA. EMBO J (1988) 7: 3949–3955.
63. BOUANCHAUD D: In vitro and in vivo synergic activity and fractional inhibitory concentration (FIC) of the components of a semisynthetic streptogramin, RP 59500. J. Antimicrob. Chemother. (1992) 30 (Suppl A): 95–99.
64. ELIOPOULOS GM, MOELLERING RC: Antimicrobial com-binations. In: Antibiotics in Laboratory Medicine, 4th Lorian V (Ed.), Wiliams & Wilkins, Baltimore, Maryland, USA (YEAR): 330–396.
65. SIEGRIST S, VELITCHKOVITCH S, LE GOFFIC F, MOREAU N: Mechanism of action of a 16-membered macrolide. Characteristics of dihydrosaramicin binding to Escherichia coli ribosome and the effects of some competitors. J. Antibiol (1982) 35: 866–874.
66. PARFAIT R, DE BETHUNE MP, COCITO C: A spectrofluo-rimetric study of the interaction between virginiamy-cin S and bacterial ribosomes. Mol Gen. Genet. (1978) 166: 45–51.
67. MOUREAU P, ENGELBORGHS Y, DI GIAMBATTISTA M,COCITO C: Fluorescence stopped flow analysis of the interaction of virginiamycin components and eryth-romycin with bacterial ribosomes. J. Biol. Chem. (1983) 258: 14233–14238.
68. PARFAIT R, COCITO C: Lasting damage to bacterial ribo-somes by reversibly bound virginiamycin M. Proc. Natl. Acad. ScL USA (1980) 77: 5492–5496.
69. NYSSEN E, DI GIAMBATTISTA M, COCITO C: Analysis of the reversible binding of virginiamycin M to ribosome and particle functions after removal of the antibiotic. Biochim. Biophys. Acta (1989) 1009: 39–46.