Recent developments in pleuromutilin derivatives: A promising class against bacterial respiratory disease

Current Respiratory Medicine Reviews

Volumn 6, Issue 2, 2010, Pages 91-101

  Gonçalves, Raoni Schroeder Borges ^a   de Souza, Marcus Vinícius Nora ^a  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

Author keywords

Drugs; Natural products; Pleuromutilin; Respiratory diseases

Indexed keywords

ANTIBIOTIC AGENT; CARBOMYCIN; CEFTRIAXONE; CEPHALOSPORIN; CHLORAMPHENICOL; CHLORTETRACYCLINE; DIACETOXYMUTILIN; ERYTHROMYCIN; FUSIDIC ACID; LEVOFLOXACIN; MINOCYCLINE; PENICILLIN G; PLEUROMUTILIN; PSEUDOMONIC ACID; PUROMYCIN; RETAPAMULIN; STREPTOMYCIN; TIAMULIN; UNCLASSIFIED DRUG; VALNEMULIN; VANCOMYCIN;

ABRASION; ANTIBIOTIC RESISTANCE; ANTIMICROBIAL ACTIVITY; ARTICLE; CROSS RESISTANCE; DRUG EFFICACY; HUMAN; IMPETIGO; IN VITRO STUDY; IN VIVO STUDY; LACERATION; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS INFECTION; MYCOBACTERIUM TUBERCULOSIS; MYCOPLASMA; NONHUMAN; PLEUROTUS; PRIORITY JOURNAL; RESPIRATORY TRACT DISEASE; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE;

EID: 77952611310     PISSN: 1573398X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157339810791171287     Document Type: Article

References (50)

1. Butler MS, Buss AD. Natural products-The future scaffolds for novel antibiotics. Biochem Pharmacol 2006; 71: 919-29.
2. Lam KS. New aspects of natural products in drug discovery. Trends Microbiol 2007; 15: 279-89.
3. Newman DJ, Cragg GM, Snader KM. Natural products as sources of new drugs over the period 1981-2002. J Nat Prod 2003; 66: 1022-37.
4. Butler MS. The role of natural product chemistry in drug discovery. J Nat Prod 2004; 67: 2141-53.
5. Wainwright M. The history of the therapeutic use of crude penicillin. Med Hist 1987; 31: 41-50.
6. Chandel AK, Rao LV, Narasu ML, Singh OM. The realm of penicillin G acylase in -lactam antibiotics. Enzym Microb Tech 2008; 421: 199-207.
7. Sakula A. Selman Waksman (1888-1973), discoverer of streptomycin: a centenary review. Br J Dis Chest 1988; 82: 23-31.
8. Levine DP. Vancomycin: a history. Clin Infect Dis 2006; 42: S5-S12.
9. Ehrlich J, Bartz QR, Smith RM, Joslyn DA, Burkholder PR. Chloromycetin, a new antibiotic from a soil actinomycete. Science 1947; 106: 417.
10. Shivastava P. Cephalosporin C production - A review. Asian J Microbiol Biotechnol Environ Sci 2007; 9: 413-26.
11. McGuire JM, Bunch RL, Anderson RC, et al. Ilotycin, a new antibiotic. Antibiot Chemother 1952; 2: 281-3.
12. McManus PS, Stockwell VO, Sundin GW, Jones AL. Antibiotic use in plant agriculture. Annu Rev Phytopathol 2002; 40: 443-65.
13. Aksoy DY, Unal S. New antimicrobial agents for the treatment of Gram-positive bacterial infections. Clin Microbiol Infect 2008; 14: 411-20.
14. Yeh PJ, Hegreness MJ, Aiden AP, Kishony R. Drug interactions and the evolution of antibiotic resistance. Nat Rev Microbiol 2009; 7: 460-6.
15. http://www.who.int/vaccine_research/diseases/ari/en/index.html [Accessed 15/10/2009].
16. http://www.who.int/vaccine_research/documents/ARI08042009.pdf [Accessed 31/07/2009].
17. Drews J, Georgopoulos G, Laber G, Schutze E, Unger J. Antimicrobial activity of 81.723 hfu, a new pleuromutilin derivative. Antimicrob Agents Chemother 1975; 7: 507-16.
18. Berner H, Schultz G, Fisher G. Chemistry of pleuromutilins, 3. synthesis of 14-O-acetyl-19,20-dihydro-A-nor-mutilins. Monatsh Chem 1981; 112: 1441-50.
19. Poulsen SM, Karlsson M, Johansson LB, Vester B. The pleuromutilin drugs tiamulin and valnemulin bind to the RNA at the peptidyl transferase centre on the ribosome. Mol Microbiol 2001; 41: 1091-99.
20. Hunt E. Pleuromutilin antibiotics. Drugs Future 2000; 25: 1163-8.
21. Kavanagh F, Hervey A, Robbins WJ. Antibiotic substances from basidiomycetes. VIII. Pleurotus multilus (Fr.) Sacc. and Pleuotus passeckerianus Pilat. Proc Natl Acad Sci USA 1951; 37: 570-4.
22. Anchel M. Chemical studies with pleuromutilin. J Biol Chem 1952; 199: 133-40.
23. Arigoni D. Structure of a new type of terpene. Gazz Chim Ital 1962; 92: 884-901.
24. Birch AJ, Cameron DW, Holzapfel CW, Richards RW. Diterpenoid nature of pleuromutilin. Chem Ind 1963; 374-5.
25. Riedl K. Studies on pleuromutilin and some of its derivatives. J Antibiot 1976; 29: 132-9.
26. Egger H, Reinshagen H. New pleuromutilin derivatives with enhanced antimicrobial activity I. Synthesis. J Antibiot 1976; 29: 915-22.
27. Egger H, Reinshagen H. New pleuromutilin derivatives with enhanced antimicrobial activity II. Structure-activity correlations. J Antibiot 1976; 29: 923-27.
28. ®), tiamulin and enrofloxacin and the in vitro development of resistance to certain antimicrobial agents in Mycoplasma hyopneumoniae. Res Vet Sci 1997; 63: 157-60.
29. Hodgin LA, Högenauer G. The mode of action of pleuromutilin derivatives. Eur J Biochem 1974; 47: 527-33.
30. Högenauer G. The mode of action of pleuromutilin derivatives. Eur J Biochem 1975; 52: 93-8.
31. Dornhelm P, Högenauer G. The effects of tiamulin, a semisynthetic pleuromutilin derivative, on bacterial polypeptide chain initiation. Eur J Biochem 1978; 91: 465-73.
32. Högenauer G, Ruf C. Ribosomal binding region for the antibiotic tiamulin: stoichiometry, subnit location, and affinity for various analogs. Antimicrob Agents Chemother 1981; 19: 260-5.
33. Högenauer G, Egger H, Ruf C, Stumper B. Affinity labeling of Escherichia coli ribosomes with a covalently binding derivative of he antibiotic pleuromutilin. Biochemistry 1981; 20: 546-52.
34. Schuwirth BS, Borovinskaya MA, Hau CW, et al. Structures of the bacterial ribosome at 3.5 Å resolution. Science 2005; 310: 827-34.
35. Selmer M, Dunham CM, Murphy FV, et al. Structure of the 70S ribosome complexed with mRNA and tRNA. Science 2006; 313: 1935-42.
36. Schlünzen F, Pyetan E, Fucini P, Yonath A, Harms JM. Inhibition of peptide bond formation by pleuromutilins: the structure of the 50S ribosomal subunit from Dinococcus radiodurans in complex with tiamulin. Mol Microbiol 2004; 54: 1287-94.
37. Scangarella-Oman NE, Shawar RM, Bouchillon S, Hoban D. Microbiological profile of a new topical antibacterial: retapamulin ointment 1%. Expert Rev Anti Infect Ther 2009; 7: 269-79.
38. Rittenhouse S, Biswas S, Broskey J, et al. Selection of retapamulin, a novel pleuromutilin for topical use. Antimicrob Agents Chemother 2006; 50: 3882-85.
39. Yang LPH, Keam SJ. Retapamulin. Drugs 2008; 68: 855-73.
40. European Medicines Agency. Summary of product characteristics: product information. Available from. http://www.emea.europa.eu [Accessed 31/07/2009].
41. Lolk L, Pohlsgaard J, Jepsen AS, et al. A click chemistry approach to pleuromutilin conjugates with nucleosides or acyclic nucleoside derivatives and their binding to the bacterial ribosome. J Med Chem 2008; 51: 4957-67.
42. Hirokawa Y, Kinoshita H, Tanaka T, et al. Water-soluble pleuromutilin derivative with excellent in vitro and in vivo antibacterial activity against Gram-positive pathogens. J Med Chem 2008; 51: 1991-4.
43. Hirokawa Y, Kinoshita H, Tanaka T, et al. Pleuromutilin derivatives having a purine ring. Part 1: new compounds with promising antibacterial activity against resistant Gram-positive pathogens. Bioorg Med Chem Lett 2008; 18: 3556-61.
44. Hirokawa Y, Kinoshita H, Tanaka T, et al. Pleuromutilin derivatives having a purine ring. Part 2: Influence of the central spacer on the antibacterial activity against Gram-positive pathogens. Bioorg Med Chem Lett 2009; 19: 170-4.
45. Hirokawa Y, Kinoshita H, Tanaka T, et al. Pleuromutilin derivatives having a purine ring. Part 3: synthesis and antibacterial activity of novel compounds possessing a piperazine ring spacer. Bioorg Med Chem Lett 2009; 19: 175-9.
46. Springer DM, Bunker A, Luh B-Y, et al. Cyclopentanone ringcleaved pleuromutilin derivatives. Eur J Med Chem 2007; 42: 109-13.
47. Xu P, Zhanf Y-Y, Sun Y-X, et al. Novel pleuromutilin derivatives with excellent antibacterial activity against Staphylococcus aureus. Chem Biol Drug Des 2009; 73: 655-60.
48. Thirring K, Ascher G, Paukner S, Heilmayer W, Novak R. Mutilin derivatives and their use as pharmaceutical. WO2007079515 July 2007.
49. Thirring K, Heilmayer W. Organic compounds. WO2009009813 January 2009.
50. Thirring K, Heilmayer W. Pleuromutilin derivatives and their use as antimicrobials. WO2009009812 January 2009.