On the mechanism of action of 9-O-arylalkyloxime derivatives of 6-O-mycaminosyltylonolide, a new class of 16-membered macrolide antibiotics

Molecular Pharmacology

Volumn 70, Issue 4, 2006, Pages 1271-1280

  Karahalios, Panagiotis ^a   Kalpaxis, Dimitrios L ^a   Fu, Hong ^b   Katz, Leonard ^b   Wilson, Daniel N ^c   Dinos, George P ^a  

^a UNIVERSITY OF PATRAS   (Greece)

^b KOSAN BIOSCIENCES INC   (United States)

^c MAX PLANCK INSTITUTE FOR MOLECULAR GENETICS   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

6 O MYCAMINOSYLTYLONOID; AMINO ACID DERIVATIVE; ERYTHROMYCIN; LYSINE DERIVATIVE; MACROLIDE; OXIME DERIVATIVE; PHENYLALANINE DERIVATIVE; RIBOSOME RNA; TELITHROMYCIN; TRANSFER RNA; TYLOSIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CELL FREE SYSTEM; CONTROLLED STUDY; DRUG BINDING; DRUG BINDING SITE; DRUG EFFECT; DRUG EFFICACY; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ESCHERICHIA COLI; NONHUMAN; PRIORITY JOURNAL; PROTEIN SYNTHESIS; PROTEIN TRANSPORT; RIBOSOME; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; BINDING, COMPETITIVE; DRUG RESISTANCE, BACTERIAL; ERYTHROMYCIN; ESCHERICHIA COLI; LEUCOMYCINS; MACROLIDES; MODELS, MOLECULAR; PHENYLALANINE; POLYLYSINE; PROTEIN BIOSYNTHESIS; PROTEIN STRUCTURE, TERTIARY; RIBOSOMES; RNA, TRANSFER; STRUCTURE-ACTIVITY RELATIONSHIP; TYLOSIN;

EID: 33748946046     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.106.026567     Document Type: Article

References (35)

1. Ackermann G and Rodloff AC (2003) Drugs of the 21st century: telithromycin (HMR 3647)-the first ketolide. J Antimicrob Chemother 51:497-511.
2. Berisio R, Harms J, Schluenzen F, Zarivach R, Hansen HAS, Fucini P, and Yonath A (2003) Structural insight into the antibiotic action of telithromycin against resistant mutants. J Bacteriol 185:4276-4279.
3. Bertho G, Gharbi-Benarous J, Delaforge M, Lang C, Parent A, and Girault J-P (1998) Conformational analysis of ketolides: conformations of RU004 in solution and bound to bacterial ribosomes. J Med Chem 41:3373-3386.
4. Blaha G, Stelzl U, Spahn CMT, Agrawal RK, Frank J, and Nierhaus KH (2000) Preparation of functional ribosomal complexes and the effect of buffer conditions on tRNA positions observed by cryoelectron microscopy. Methods Enzymol 317: 292-309.
5. Bommer U, Burkhardt N, Junemann R, Spahn CMT, Triana-Alonso FJ, and Nierhaus KH (1996) Ribosomes and polysomes, in Subcellular Fractionation. A Practical Approach (J Graham and D Rickwoods eds) pp 271-301, IRL Press at Oxford University Press, Oxford, UK.
6. Boon K, Vijgenboom E, Madsen LV, Talens A, Kraal B, and Bosch L (1992) Isolation and functional analysis of histidine-tagged elongation factor Tu. Eur J Biochem 210:177-183.
7. Champney WS (2003) Bacterial ribosomal subunit assembly is an antibiotic target. Curr Top Med Chem 3:929-947.
8. Di Giambattista M, Engelborghs Y, Nyssen E, and Cocito C (1987) Kinetics of binding of macrolides, lincosamides and synergimycins to ribosomes. J Biol Chem 262:8591-8597.
9. Dinos G, Synetos D, and Coutsogeorgopoulos C (1993) Interaction between the antibiotic spiramycin and a ribosomal complex active in peptide bond formation. Biochemistry 32:10638-10647.
10. Dinos GP and Kalpaxis DL (2000) Kinetic studies on the interaction between a ribosomal complex active in peptide bond formation and the macrolide antibiotics tylosin and erythromycin. Biochemistry 39:11621-11628.
11. Dinos G, Wilson DN, Teraoka Y, Szaflarski W, Fucini P, Kalpaxis D, and Nierhaus KH (2004) Dissecting the ribosomal inhibition mechanisms of edeine and pactamycin: the universally conserved residues G693 and C795 regulate P-site RNA binding. Mol Cell 13:113-124.
12. Dinos GP, Connell SR, Nierhaus KH, and Kalpaxis DL (2003) Erythromycin, roxithromycin, and clarithromycin: use of slow-binding kinetics to compare their in vitro interaction with a bacterial ribosomal complex active in peptide bond formation. Mol Pharmacol 63:617-623.
13. Erion MD and Walsh CT (1987) 1-Aminocyclopropanephosphonate: time-dependent inactivation of 1-aminocyclopropanecarboxylate deaminase and Bacillus stearothermophilus alanine racemase by slow dissociation behavior. Biochemistry 26:3417-3425.
14. Fu H, Marquez S, Gu X, Katz L, and Myles DC (2006) Synthesis and in vitro antibiotic activity of 16-membered 9-O-arylalkyloxime macrolides. Bioorg Med Chem Lett 16:1259-1266.
15. Gorman M and Morin RB (1969), inventors; Eli Lilly and Co., assignee. O-Mycaminosyl tylomolide and a process for the preparation thereof. U.S. patent 3,459,853. 1969 Aug 5.
16. Hansen JL, Ippolito JA, Ban N, Nissen P, Moore PB, and Steitz TA (2002) The structures of four macrolide antibiotics bound to the large ribosomal subunit. Mol Cell 10:117-128.
17. Hermann T (2005) Drugs targeting the ribosome. Curr Opin Struct Biol 15:355-366.
18. Katz L and Ashley GW (2005) Translation and Protein synthesis: Macrolides. Chem Rev 105:499-527.
19. Kirst HA, Debono M, Toth JE, Truedell BA, Willard KE, Ott JL, Counter FT, Felty-Duckworth AM, and Pekarek RS (1986) Synthesis and antimicrobial evaluation of acyl derivatives of 16-membered macrolide antibiotics related to tylosin. J Antibiot (Tokyo) 39:1108-1122.
20. Lovmar M, Tenson T, and Ehrenberg M (2004) Kinetics of macrolide action: the josamycin and erythromycin cases. J Biol Chem 279:53506-53515.
21. Morrison JF and Walsh C (1988) The behavior and significance of slow-binding inhibitors. Adv Enzymol Relat Areas Mol Biol 61:201-301.
22. Omura S (2002) Macrolide antibiotics: chemistry, biology and practice. Academic Press, Orlando, FL.
23. 14C]erythromycin to Escherichia coli ribosomes. Antimicrob Agents Chemother 6:479-488.
24. Picking WD, Odom OW, Tsalkova T, Serdyuk I, and Hardesty B (1991) The conformation of nascent polylysine and polyphenylalanine peptides on ribosomes. J Biol Chem 266:1534-1542.
25. Rheinberger HJ, Geigenmuller U, Wedde M, and Nierhaus KH (1988) Parameters for the preparation of Escherichia coli ribosomes and ribosomal subunits active in tRNA binding. Methods Enzymol 164:658-670.
26. Seo HS, Abedin S, Kamp D, Wilson DN, Nierhaus KH, and Cooperman BS (2006) EF-G-Dependent GTPase on the ribosome. Conformational change and fusidic acid inhibition. Biochemistry 45:2504-2514.
27. Schafer MA, Tastan AO, Patzke S, Blaha G, Spahn CM, Wilson DN, and Nierhaus KH (2002) Codon-anticodon interaction at the P site is a prerequisite for tRNA interaction in the small ribosomal subunit. J Biol Chem 277:19095-19105.
28. Schloss JV (1988) Significance of slow-binding enzyme inhibition and its relationship to reaction-intermediate analogues. Acc Chem Res 21:348-353.
29. Schlunzen F, Zarivach R, Harms J, Bashan A, Tocilj A, Albrecht R, Yonath A, and Franceschi F (2001) Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature (Lond) 413:814-821.
30. Stern S, Moazed D, and Noller H (1988) Structural analysis of RNA using chemical and enzymatic probing monitored by primer extention. Methods Enzymol 164:481-489.
31. Triman K, Becker E, Dammel C, Katz J, Mori H, Douthwaite S, Yapijakis C, Yoast S, and Noller HF (1989) Isolation of temperature-sensitive mutans of 16S rRNA in Escherichia coli. J Mol Biol 209:645-653.
32. Tu D, Blaha G, Moore PB, and Steitz TA (2005) Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell 121:257-270.
33. Vester B and Douthwaite S (2001) Macrolide resistance conferred by base substitutions in 23S rRNA. Antimicrob Agents Chemother 45:1-12.
34. Wilson DN, Harms JM, Nierhaus KH, Schlunzen F, and Fucini P (2005) Species-specific antibiotic-ribosome interactions: implications for drug development. Biol Chem 386:1239-1252.
35. Xiong L, Shah S, Mauvais P, and Mankin AS (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.