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Chemical Compound Review

Tylosin     2-[ (2R,3S,4E,6E,9R,11R,12S,13S,14 R)-12...

Synonyms: Macrolides, Tylan, CHEMBL42743, Tylan (TN), BSPBio_003548, ...
 
 
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Disease relevance of Tylosin

 

Psychiatry related information on Tylosin

  • Water-deprivation was thought to cause reduced rate of tylosin elimination by the liver, as was shown for antipyrine--a drug which is eliminated from the body exclusively by the liver [6].
 

High impact information on Tylosin

 

Chemical compound and disease context of Tylosin

 

Biological context of Tylosin

 

Anatomical context of Tylosin

  • Nevertheless, all three antibiotics compete for binding on the ribosome with tylosin, a 16-membered ring macrolide that behaves as a slow-binding, slowly reversible inhibitor of peptidyltransferase [18].
  • Two mutants of the tylosin-producing Streptomyces fradiae defective in the biosynthesis of the macrolide antibiotic tylosin were isolated from colonies derived from regenerated protoplasts [19].
  • A possible etiologic factor is a specific enteropathogenic organism that is a common resident in the canine gastrointestinal tract and is sensitive to tylosin but difficult to eradicate [20].
  • Danofloxacin was superior to tylosin in preventing air-sac lesions, reducing the frequency of reisolation of MG, and preventing seroconversion in surviving birds [21].
  • The antibiotic combination including gentamicin, tylosin and Linco-Spectin at 500 ug/ml, 100 ug/ml and 300/600 ug/ml, respectively, was not detrimental to seminal quality and, in the parallel studies, was most efficacious in controlling microorganisms potentially present in bovine semen [22].
 

Associations of Tylosin with other chemical compounds

  • However, they severely inhibit poly(A)-dependent poly(Lys) synthesis and compete with erythromycin or tylosin for binding to common or partially overlapping sites in the ribosome [23].
  • RESULS: We show that recombinant tylosin TE II behaves in vitro as a TE towards a variety of N-acetylcysteamine and p-nitrophenyl esters [24].
  • The post-PKS tailoring enzymes of tylosin biosynthesis acted efficiently on the hybrid intermediates with the exception of TylH-catalyzed hydroxylation of the methyl group at C14, which was efficient if C4 bore a methyl group, but inefficient if a methoxyl was present [11].
  • Spiramycin and tylosin showed only limited activity against T. gondii (IC50 of 20.16 and 20.00 micrograms/ml, respectively) [25].
  • Modification of the aldehyde group in tylosin and related macrolide antibiotics dramatically enhanced the oral efficacy of the derivatives against experimental infections caused by susceptible bacteria in laboratory animals [26].
 

Gene context of Tylosin

 

Analytical, diagnostic and therapeutic context of Tylosin

  • Therefore, a liquid chromatography/tandem mass spectrometry method was developed and employed to investigate in detail the distribution and persistence of the frequently used tetracyclines and tylosin in a field fertilized with liquid manure on April 2000 and April 2001; soil sampling was performed in May 2000, November 2000, and May 2001 [32].
  • At a lower frequency, vanA E. faecium had also displaced vanA E. hirae in both the tylosin group (one of four chickens) and the control group (two of five chickens) [33].
  • An open reading frame, designated tylN, has been identified by sequence analysis at one end of the tylosin biosynthetic gene cluster of Streptomyces fradiae, alongside a cluster of genes encoding the biosynthesis of dTDP-deoxyallose [34].
  • We cloned the MLSB resistance determinant by PCR from a clinical isolate of Enterococcus faecalis 373, which is induced more strongly by a 16-membered-ring macrolide, tylosin, than by erythromycin [35].
  • Tylosin was determined by reversed-phase HPLC with UV detection at 280 nm and the mean recovery from pig tissues fortified in the range 50-200 micrograms kg-1 was 70-85%, with intra- and inter-day RSDs in the ranges 3.4-9.1 and 3.9-10.1% respectively [36].

References

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  2. Structure of 23S rRNA hairpin 35 and its interaction with the tylosin-resistance methyltransferase RlmAII. Lebars, I., Yoshizawa, S., Stenholm, A.R., Guittet, E., Douthwaite, S., Fourmy, D. EMBO J. (2003) [Pubmed]
  3. Replication mutants of Staphylococcus aureus macrolide-lincosamide-streptogramin B resistance plasmid pT48. Catchpole, I., Dyke, K.G. Mol. Microbiol. (1991) [Pubmed]
  4. Flow cytometric determination of the effects of antibacterial agents on Mycoplasma agalactiae, Mycoplasma putrefaciens, Mycoplasma capricolum subsp. capricolum, and Mycoplasma mycoides subsp. mycoides large colony type. Assunção, P., Antunes, N.T., Rosales, R.S., Poveda, C., Poveda, J.B., Davey, H.M. Antimicrob. Agents Chemother. (2006) [Pubmed]
  5. Kinetic studies on the interaction between a ribosomal complex active in peptide bond formation and the macrolide antibiotics tylosin and erythromycin. Dinos, G.P., Kalpaxis, D.L. Biochemistry (2000) [Pubmed]
  6. Disposition kinetics of tylosin tartrate administered intravenously and intramuscularly to normal and water-deprived camels. Ziv, G., Creveld, C.V., Ben-Zvi, Z., Glickman, A., Yagil, R. J. Vet. Pharmacol. Ther. (1995) [Pubmed]
  7. Genetic engineering of aminodeoxyhexose biosynthesis in Streptomyces fradiae. Butler, A.R., Bate, N., Kiehl, D.E., Kirst, H.A., Cundliffe, E. Nat. Biotechnol. (2002) [Pubmed]
  8. Genetics of Streptomyces fradiae and tylosin biosynthesis. Baltz, R.H., Seno, E.T. Annu. Rev. Microbiol. (1988) [Pubmed]
  9. Resistance to the macrolide antibiotic tylosin is conferred by single methylations at 23S rRNA nucleotides G748 and A2058 acting in synergy. Liu, M., Douthwaite, S. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  10. Purification and properties of NADPH-dependent tylosin reductase from Streptomyces fradiae. Huang, S.L., Hassell, T.C., Yeh, W.K. J. Biol. Chem. (1993) [Pubmed]
  11. Production of hybrid 16-membered macrolides by expressing combinations of polyketide synthase genes in engineered Streptomyces fradiae hosts. Reeves, C.D., Ward, S.L., Revill, W.P., Suzuki, H., Marcus, M., Petrakovsky, O.V., Marquez, S., Fu, H., Dong, S.D., Katz, L. Chem. Biol. (2004) [Pubmed]
  12. Synergy between Efflux Pump CmeABC and Modifications in Ribosomal Proteins L4 and L22 in Conferring Macrolide Resistance in Campylobacter jejuni and Campylobacter coli. Cagliero, C., Mouline, C., Cloeckaert, A., Payot, S. Antimicrob. Agents Chemother. (2006) [Pubmed]
  13. S-Adenosyl-L-methionine: macrocin O-methyltransferase activities in a series of Streptomyces fradiae mutants that produce different levels of the macrolide antibiotic tylosin. Seno, E.T., Baltz, R.H. Antimicrob. Agents Chemother. (1982) [Pubmed]
  14. Novel Macrolide Resistance Module Carried by the IncP-1{beta} Resistance Plasmid pRSB111, Isolated from a Wastewater Treatment Plant. Szczepanowski, R., Krahn, I., Bohn, N., Pühler, A., Schlüter, A. Antimicrob. Agents Chemother. (2007) [Pubmed]
  15. Cloning genes for the biosynthesis of a macrolide antibiotic. Fishman, S.E., Cox, K., Larson, J.L., Reynolds, P.A., Seno, E.T., Yeh, W.K., Van Frank, R., Hershberger, C.L. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  16. Differential roles of two SARP-encoding regulatory genes during tylosin biosynthesis. Bate, N., Stratigopoulos, G., Cundliffe, E. Mol. Microbiol. (2002) [Pubmed]
  17. Analysis of five tylosin biosynthetic genes from the tyllBA region of the Streptomyces fradiae genome. Merson-Davies, L.A., Cundliffe, E. Mol. Microbiol. (1994) [Pubmed]
  18. 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. Dinos, G.P., Connell, S.R., Nierhaus, K.H., Kalpaxis, D.L. Mol. Pharmacol. (2003) [Pubmed]
  19. Phenotypic changes associated with loss of expression of tylosin biosynthesis and resistance genes in Streptomyces fradiae. Baltz, R.H., Stonesifer, J. J. Antibiot. (1985) [Pubmed]
  20. Tylosin-responsive chronic diarrhea in dogs. Westermarck, E., Skrzypczak, T., Harmoinen, J., Steiner, J.M., Ruaux, C.G., Williams, D.A., Eerola, E., Sundbäck, P., Rinkinen, M. J. Vet. Intern. Med. (2005) [Pubmed]
  21. A comparison of danofloxacin and tylosin in the control of induced Mycoplasma gallisepticum infection in broiler chicks. Tanner, A.C., Avakian, A.P., Barnes, H.J., Ley, D.H., Migaki, T.T., Magonigle, R.A. Avian Dis. (1993) [Pubmed]
  22. A new antibiotic combination for frozen bovine semen. 2. Evaluation of seminal quality. Lorton, S.P., Sullivan, J.J., Bean, B., Kaproth, M., Kellgren, H., Marshall, C. Theriogenology (1988) [Pubmed]
  23. On the mechanism of action of 9-o-arylalkyloxime derivatives of 6-o-mycaminosyltylonolide, a new class of 16-membered macrolide antibiotics. Karahalios, P., Kalpaxis, D.L., Fu, H., Katz, L., Wilson, D.N., Dinos, G.P. Mol. Pharmacol. (2006) [Pubmed]
  24. Role of type II thioesterases: evidence for removal of short acyl chains produced by aberrant decarboxylation of chain extender units. Heathcote, M.L., Staunton, J., Leadlay, P.F. Chem. Biol. (2001) [Pubmed]
  25. Comparative activity of macrolides against Toxoplasma gondii demonstrating utility of an in vitro microassay. Chamberland, S., Kirst, H.A., Current, W.L. Antimicrob. Agents Chemother. (1991) [Pubmed]
  26. Synthesis and evaluation of tylosin-related macrolides modified at the aldehyde function: a new series of orally effective antibiotics. Kirst, H.A., Toth, J.E., Debono, M., Willard, K.E., Truedell, B.A., Ott, J.L., Counter, F.T., Felty-Duckworth, A.M., Pekarek, R.S. J. Med. Chem. (1988) [Pubmed]
  27. Tilmicosin and tylosin have anti-inflammatory properties via modulation of COX-2 and iNOS gene expression and production of cytokines in LPS-induced macrophages and monocytes. Cao, X.Y., Dong, M., Shen, J.Z., Wu, B.B., Wu, C.M., Du, X.D., Wang, Z., Qi, Y.T., Li, B.Y. Int. J. Antimicrob. Agents (2006) [Pubmed]
  28. Sequence analyses of a broad host-range plasmid containing ermT from a tylosin-resistant Lactobacillus sp. Isolated from swine feces. Whitehead, T.R., Cotta, M.A. Curr. Microbiol. (2001) [Pubmed]
  29. Amino acid catabolism and antibiotic synthesis: valine is a source of precursors for macrolide biosynthesis in Streptomyces ambofaciens and Streptomyces fradiae. Tang, L., Zhang, Y.X., Hutchinson, C.R. J. Bacteriol. (1994) [Pubmed]
  30. Effect of the silica support of bonded reversed-phase columns on chromatography of some antibiotic compounds. Moats, W.A. J. Chromatogr. (1986) [Pubmed]
  31. Tylosin does not affect GnRH-induced LH secretion in rams. Yildiz, S., Ozturkler, Y., Uzun, M., Kaya, M., Ucar, O. Reprod. Toxicol. (2004) [Pubmed]
  32. Determination of persistent tetracycline residues in soil fertilized with liquid manure by high-performance liquid chromatography with electrospray ionization tandem mass spectrometry. Hamscher, G., Sczesny, S., Höper, H., Nau, H. Anal. Chem. (2002) [Pubmed]
  33. From vanA Enterococcus hirae to vanA Enterococcus faecium: a study of feed supplementation with avoparcin and tylosin in young chickens. Robredo, B., Singh, K.V., Baquero, F., Murray, B.E., Torres, C. Antimicrob. Agents Chemother. (1999) [Pubmed]
  34. Characterization and targeted disruption of a glycosyltransferase gene in the tylosin producer, Streptomyces fradiae. Wilson, V.T., Cundliffe, E. Gene (1998) [Pubmed]
  35. Induction of ermAMR from a clinical strain of Enterococcus faecalis by 16-membered-ring macrolide antibiotics. Oh, T.G., Kwon, A.R., Choi, E.C. J. Bacteriol. (1998) [Pubmed]
  36. Determination of tylosin residues in pig tissues using high-performance liquid chromatography. De Liguoro, M., Anfossi, P., Angeletti, R., Montesissa, C. The Analyst. (1998) [Pubmed]
 
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