Development of aminoglycoside antibiotics effective against resistant bacterial strains

Current Topics in Medicinal Chemistry

Volumn 10, Issue 18, 2010, Pages 1898-1926

  Yang, Lin ^a   Ye, Xin Shan ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

Aminoglycoside antibiotics; Antimicrobial activity; Bacterial resistance; Drug modifying enzymes; Inhibitor

Indexed keywords

1 N (4 AMINO 2 HYDROXYBUTYRYL) 3',4' DIDEOXYNEAMINE DERIVATIVE; 2'' AMINO 2'' DEOXYARBEKACIN; 2'' AMINO 5,2'' DIDEOXY 5 EPIAMINOARBEKACIN; 5 DEOXY 5 EPIAMINO ARBEKACIN; 5 EPI ARBEKACIN; 5,4'' DIEPI ABERKACIN; ACYLTRANSFERASE; AMIKACIN; AMINOGLYCOSIDE ANTIBIOTIC AGENT; DIBEKACIN; GENTAMICIN; HABEKACIN; ISEPAMICIN; KANAMYCIN; NEAMINE; NEOMYCIN; NETILMICIN; PAROMOMYCIN; PYRANMYCIN DERIVATIVE; SISOMICIN; SPECTINOMYCIN; STREPTOMYCIN; TOBRAMYCIN; UNCLASSIFIED DRUG;

ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL STRAIN; CHEMICAL MODIFICATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN;

EID: 78649909618     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802610793176684     Document Type: Article

References (73)

1. Magnet, S.; Blanchard, J. S. Molecular insights into aminoglycoside action and resistance. Chem. Rev., 2005, 105, 477-498.
2. Jana, S.; Deb, J.K. Molecular targets for design of novel inhibitors to circumvent aminoglycoside resistance. Curr. Drug Targets, 2005, 6, 353-361.
3. Durante-Mangoni, E.; Grammatikos, A.; Utili, R.; Falagas, M. E. Do we still need the aminoglycosides. Int. J. Antimicrob. Agents, 2009, 33, 201-205.
4. Silva, J. G.; Carvalho, I. New insights into aminoglycoside antibiotics and derivatives. Curr. Med. Chem., 2007, 14, 1101-1119.
5. Zhou, J.; Wang, G. N.; Zhang, L. H.; Ye, X. S. Modifications of aminoglycoside antibiotics targeting RNA. Med. Res. Rev., 2007, 27, 279-316.
6. Ritter, T.K.; Wong, C. H. Carbohydrate-based antibiotics: a new approach to tackling the problem of resistance. Angew. Chem. Int. Ed., 2001, 40, 3508-3533.
7. Waksman, S. My Life With the Microbes, Simon and Schuster: New York, 1954.
8. Waksman S. The Conquest of Tuberculosis, University of California Press Berkeley, 1964.
9. Beaucaire, G. The role of aminoglycosides in modern therapy. J. Chemother., 1995, 7 (suppl. 2), 111-123.
10. Moazed, D.; Noller, H. F. Interaction of antibiotics with functional sites in 16S ribosomal RNA. Nature, 1987, 327, 389-394.
11. Purohit, P.; Stem, S. Interactions of a small RNA with antibiotic and RNA ligands of the 30S subunit. Nature, 1994, 370, 659-662.
12. Fourmy, D.; Recht, M. I.; Blanchard, S.C.; Puglisi, J. D. Structure of the A site of Escherichia coli 16S ribosomal RNA complexed with an aminoglycoside antibiotic. Science, 1996, 274, 1367-1371.
13. Mingeot-Leclercq, M-P.; Glupczynski, Y.; Tulkens, P.M. Aminoglycosides: activity and resistance. Antimicrob. Agents Chemother., 1999, 43, 727-737.
14. Noller, H. F. RNA structure: reading the ribosome. Science, 2005, 309, 1508-1514.
15. Tor, Y. The ribosomal A-site as an inspiration for the design of RNA binders. Biochimie., 2006, 88, 1045-1051.
16. Zapp, M.; Stern, S.; Green, M. R. Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. Cell, 1993, 74, 969-978.
17. Stage, T. K.; Hertel, K. J.; Uhlenbeck, O. C. Inhibition of the hammerhead ribozyme by neomycin. RNA 1995, 1, 95-101
18. Frankei, A.D.; Young, J. A.T. HIV-1: fifteen proteins and an RNA. Ann. Rev. Biochem., 1998, 67, 1-25.
19. Tam, V. K.; Kwong, D.; Tor, Y. Fluorescent HIV-1 dimerization initiation site: design, properties, and use for ligand discovery. J. Am. Chem. Soc., 2007, 129, 3257-3266.
20. Ennifar, E.; Paillart, J.-C.; Bodlenner, A.; Walter, P.; Weibel, J.-M.; Aubertin, A.-M.; Pale, P.; Dumas, P.; Marquet, R. Targeting the dimerization initiation site of HIV-1 RNA with aminoglycosides: from crystal to cell. Nucleic Acid Res., 2006, 34, 2328-2339.
21. Ennifar, E.; Paillart, J. C.; Bernacchi, S.; Walter, P.; Pale, P.; Decout, J. L.; Marquet, R.; Dumas, P. A structure-based approach for targeting the HIV-1 genomic RNA dimerization initiation site. Biochimie, 2007, 89, 1195-1203.
22. Watanabe, A.; Nagai, J.; Adachi, Y.; Katsube, T.; Kitahara, Y.; Murakami, T.; Takano, M. Targeted prevention of renal accumulation and toxicity of gentamicin by aminoglycoside binding receptor antagonists. J. Control. Release, 2004, 95, 423-433.
23. Corrado, A.P.; Morais, I.P.; Prado, W. A. Aminoglycoside antibiotics as a tool for the study of the biological role of calcium ions. Historical overview. Acta. Physiol. Pharmacol. Latinoam, 1989, 39, 419-430.
24. Rougier, F.; Claude, D.; Maurin, M.; Sedoglavic, A.; Ducher, M.; Corvaisier, S.; Jelliffe, R.; Maire, P. Aminoglycoside nephrotoxicity: modeling, simulation, and control. Antimicrob. Agents Chemother., 2003, 47, 1010-1016.
25. Nakashima, T.; Teranishi, M.; Hibi, T.; Kobayashi, M.; Umemura, M. Vestibular and cochlear toxicity of aminoglycosides-a review. Acta Oto-Laryngol. 2000, 120, 904-911.
26. Lima, A. L. C. M.; Marseillan, R. F.; Corrado, A. P. Aminoglycoside antibiotics: structure-toxicity relationship. Symposia of the Giovanni Lorenzini Foundation. 1981, 10(New Trends Antibiot.: Res. Ther.), pp. 274-276.
27. Davies, J. Inactivation of antibiotics and the dissemination of resistance genes. Science, 1994, 264(5157), 375-382.
28. Roestamadji, J.; Grapsas, I.; Mobashery, S. Loss of individual electrostatic interactions between aminoglycoside antibiotics and resistance enzymes as an effective means to overcoming bacterial drug resistance. J. Am. Chem. Soc., 1995, 117, 11060-11069.
29. Kim, C.; Haddad, J.; Vakulenko, S. B.; Meroueh, S. O.; Wu, Y.; Yan, H.; Mobashery, S. Fluorinated aminoglycosides and their mechanistic implication for aminoglycoside 3'-phosphotransferases from Gram-negative bacteria. Biochemistry, 2004, 43, 2373-2383.
30. Fridman, M.; Belakhov, V.; Yaron, S.; Baasov, T. A new class of branched aminoglycosides: pseudo-pentasaccharide derivatives of neomycin B. Org. Lett., 2003, 5, 3575-3578.
31. Hainrichson, M.; Pokrovskaya, V.; Shallom-Shezifi, D.; Fridman, M.; Belakhov, V.; Shachar, D.; Yaronb, S.; Baasov, T. Branched aminoglycosides: Biochemical studies and antibacterial activity of neomycin B derivatives. Bioorg. Med. Chem., 2005, 13, 5797-5807.
32. Fridman, M.; Belakhov, V.; Lee, L. V.; Liang, F. S.; Wong, C. H.; Baasov, T. Dual effect of synthetic aminoglycosides: Antibacterial activity against Bacillus anthracis and inhibition of anthrax lethal factor. Angew. Chem., Int. Ed., 2005, 44, 447-452.
33. Kondo S.; Shibahara, S.; Usui, T.; Kudo, T.; Tamura A, Gomi S, et al. New 2-amino derivatives of arbekacin, potent aminoglycoside antibiotics against methicillin-resistant Staphylococcus aureus. J. Antibiot., 1993, 46, 531-534.
34. Inouye, S.; Tamura, A.; Niizato, T.; Takeuchi, T.; Hamada, M.; Kondo, S. Antibacterial activity and nephrotoxicity of two novel 2-amino derivatives of arbekacin. J. Infect. Chemother., 1996, 2, 84-89.
35. Kondo, S.; Hotta, K. Semisynthetic aminoglycoside antibiotics: Development and enzymatic modifications. J. Infect. Chemother, 1999, 5, 1-9.
36. Minowa, N.; Akiyama, Y.; Hiraiwa, Y.; Maebashi, K.; Usui, T.; Ikeda, D. Synthesis and antibacterial activity of novel neamine derivatives. Bioorg. Med. Chem. Lett., 2006, 16, 6351-6354.
37. Hiraiwa, Y.; Usui, T.; Akiyama, Y.; Maebashi, K.; Minowa, N.; Ikeda, D. Synthesis and antibacterial activity of 5-deoxy-5-episubstituted arbekacin derivatives. Bioorg. Med. Chem. Lett., 2007, 17, 3540-3543.
38. Hiraiwa, Y.; Minowa, N.; Usui, T.; Akiyama, Y.; Maebashi, K.; Ikeda, D. Effect of varying the 4''-position of arbekacin derivatives on antibacterial activity against MRSA and Pseudomonas aeruginosa. Bioorg. Med. Chem. Lett., 2007, 17, 6369-6372.
39. Li, J.; Chen, H. N.; Chang, H. W.; Wang, J. H.; Chang, C-W. T. Tuning the regioselectivity of the Staudinger reaction for the facile synthesis of kanamycin and neomycin class antibiotics with N-1 modification. Org. Lett., 2005, 7, 3061-3064.
40. Cohen, M. L. Epidemiology of drug resistance: implications for a post-antimicrobial era. Science, 2002, 257, 1050-1055.
41. Neu, H. C. The crisis in antibiotic resistance. Science, 2002, 257, 1064-1072.
42. Chang, C-W. T.; Hui, Y.; Elchert, B.; Wang, J. H.; Li, J.; Rai, R. Pyranmycins, a novel class of aminoglycosides with improved acid stability: The SAR of D-pyranoses on ring III of pyranmycin. Org. Lett., 2002, 4, 6403-6406.
43. Wong, C.-H.; Hendrix, M.; Manning, D. D.; Rosenbohm, C.; Greenberg, W. A. A library approach to the discovery of small molecules that recognize RNA: Use of a 1,3-hydroxyamine motif as core. J. Am. Chem. Soc., 1998, 120, 8319-8327.
44. Hendrix, M.; Alper, P. B.; Priestley, S.; Wong, C.-H. Hydroxyamines as a new motif for the molecular recognition of phosphodiesters: Implications for aminogloycoside-RNA interactions. Angew. Chem., Int. Ed. Engl., 1997, 36, 95-98.
45. Elchert, B.; Li, J.; Wang, J. H.; Hui, Y.; Rai, R.; Ptak, R.; Ward, P.; Takemoto, J. Y.; Bensaci, M.; Chang, C-W. T. Application of the synthetic aminosugars for glycodiversification: Synthesis and antimicrobial studies of pyranmycin. J. Org. Chem., 2004, 69, 1513-1523.
46. Li, J.; Chiang, F. I.; Chen H. N.; Chang, C-W. T. Synthesis and antibacterial activity of pyranmycin derivatives with N-1 and O-6 modifications. Bioorg. Med. Chem., 2007, 15, 7711-7719.
47. Wright, G. D.; Ladak, P.; Overexpression and characterization of the chromosomal aminoglycoside 6'-N-acetyltransferase from Enterococcus faecium. Antimicrob. Agents Chemother., 1997, 41, 956-960.
48. Draker, K. A.; Wright, G. D.; Molecular mechanism of the Enterococcal aminoglycoside 6'-N-acetyltransferase': Role of GNATconserved residues in the chemistry of antibiotic inactivation. Biochem., 2004, 43, 446-454.
49. Draker, K. A.; Northrop, D. B.; Wright, G. D. Kinetic mechanism of the GCN5-related chromosomal aminoglycoside acetyltransferase AAC(6')-Ii from enterococcus faecium: Evidence of dimmer subunit cooperativity. Biochem., 2003, 42, 6565-6574.
50. Gao, F.; Yan, X.; Baettig, O. M.; Berghuis, A. M.; Auclair, K. Regio- and chemoselective 6'-N-derivatization of aminoglycosides: Bisubstrate inhibitors as probes to study aminoglycoside 6'-Nacetyltransferases. Angew. Chem., Int. Ed, 2005, 44, 6859-6862.
51. Gao, F.; Yan, X.; Shakya, T.; Baettig, O. M.; Ait-Mohand-Brunet, S.; Berghuis, A. M.; Wright, G. D.; Auclair, K. Synthesis and structure-activity relationships of truncated bisubstrate inhibitors of aminoglycoside 6'-N-Acetyltransferases. J. Med. Chem., 2006, 49, 5273-5281.
52. Yan, X.; Gao, F.; Yotphan, S.; Bakirtzian, P.; Auclair, K. The use of aminoglycoside derivatives to study the mechanism of aminoglycoside 6'-N-acetyltransferase and the role of 6'-NH2 in antibacterial activity. Bioorg. Med. Chem., 2007, 15, 2944-2951.
53. Gao, F.; Yan, X.; Zahr, O.; Larsen, A.; Vong, K.; Auclair, K. Synthesis and use of sulfonamide-, sulfoxide-, or sulfone-containing aminoglycoside-CoA bisubstrates as mechanistic probes for aminoglycoside N-6'-acetyltransferase. Bioorg. Med. Chem., 2008, 18, 5518-5522.
54. Gao, F.; Yan, X.; Auclair, K. Synthesis of a phosphonate-linked aminoglycoside-coenzyme a bisubstrate and use in mechanistic studies of an enzyme involved in aminoglycoside resistance. Chem. Eur. J., 2009, 15, 2064-2070.
55. Allen, N. E.; Alborn, W. E.; Hobbs, J. N.; Kirst, H. A. 7-Hydroxytropolone: An inhibitor of aminoglycoside-2-O-adenylyltransferase. Antmicrob. Agents Chemother., 1982, 22, 824-831.
56. Roestamadji, J.; Grapsas, I.; Mobashery, S. Mechanism-based inactivation of bacterial aminoglycoside 3'-phosphotransferases. J. Am. Chem. Soc., 1995, 117, 80-84.
57. Haddad, J.; Vakulenko, S.; Mobashery, S. An antibiotic cloaked by its own resistance enzyme. J. Am. Chem. Soc., 1999, 121, 11922-11923.
58. Roestamadji, J.; Mobashery, S. Inactivation of bacterial antibiotic resistance enzyme aminolgycoside 3'-phosphotransferase type IIa. Bioorg. Med. Chem. Lett., 1998, 8, 3483-3488.
59. Liu, M.; Haddad, J.; Azucena, E.; Kotra, L. P.; Kirzhner, M.; Mobashery, S. Tethered bisubstrate derivatives as probes for mechanism and as inhibitors of aminoglycoside 3'-phosphotransferases. J. Org. Chem., 2000, 65, 7422-7431.
60. Asensio, J. L.; Hidalgo, A.; Bastida, A.; Torrado, M.; Corzana, F.; Chiara, J. L.; Garcia-Junceda, E.; Canada, J.; Jimenez-Barbero, J. A simple structural-based approach to prevent aminoglycoside inactivation by bacterial defense proteins. Conformational restriction provides effective protection against neomycin-B nucleotidylation by ANT4. J. Am. Chem. Soc., 2005, 127, 8278-8279.
61. Bastida, A.; Hidalgo, A.; Chiara, J. L.; Torrado, M.; Corzana, F.; Perez-Canadillas, J. M.; Groves, P.; Garcia-Junceda, E.; Gonzalez, C.; Jimenez-Barbero, J.; Asensio, J. L. Exploring the use of conformationally locked aminoglycosides as a new strategy to overcome bacterial resistance. J. Am. Chem. Soc., 2006, 128, 100-116.
62. Hanessian, S.; Szychowski, J.; Campos-Reales Pineda, N. B.; Furtos, A.; Keillor J.W. 6-Hydroxy to 6'''-amino tethered ring-to-ring macrocyclic aminoglycosides as probes for APH(3')-IIIa kinase. Bioorg. Med. Chem. Lett., 2007, 17, 3221-3225.
63. Sucheck, S. J.; Wong, A. L.; Koeller, K. M.; Boehr, D. D.; Draker, K.A.; Sears, P.; Wright, G. D.; Wong, C. H. Design of bifunctional antibiotics that target bacterial rRNA and inhibit resistance-causing enzymes. J. Am. Chem. Soc., 2000, 122, 5230-5231.
64. Agnelli, F.; Sucheck, S. J.; Marby, K. A.; Rabuka, D.; Yao, S. L.; Sears, P. S.; Liang, F. S.; Wong, C. H. Dimeric aminoglycosides as antibiotics. Angew. Chem. Int. Ed, 2004, 43, 1562-1566.
65. Zhang, J. J.; Chiang, F. I.; Wu, L.; Czyryca, P. G.; Li, D.; Chang, C-W. T. Surprising alteration of antibacterial activity of 5''- modified neomycin against resistant bacteria. J. Med. Chem., 2008, 51, 7563-7573.
66. Pokrovskaya, V.; Belakhov, V.; Hainrichson, M.; Yaron, S.; Baasov, T. Design, Synthesis, and evaluation of novel fluoroquinoloneaminoglycoside hybrid antibiotics. J. Med. Chem., 2009, 52, 2243-2254.
67. Bera, S.; Zhanel, G. G.; Schweizer, F. Design, Synthesis, and antibacterial activities of neomycin-lipid conjugates: Polycationic lipids with potent Gram-positive activity. J. Med. Chem., 2008, 51, 6160-6164.
68. Zhou, Y. F.; Gregor, V. E.; Sun, Z. X.; Ayida, B. K.; Winters, G. C.; Murphy, D. E.; Simonsen, K. B.; Vourloumis, D.; Fish, S.; Froelich, J. M.; Wall, D.; Hermann, T. Structure-guided discovery of novel aminoglycoside mimetics as antibacterial translation inhibitors. Antmicrob. Agents Chemother., 2005, 49, 4942-4949.
69. Zhou, Y. F.; Chow, C.; Murphy, D. E.; Sun, Z. X.; Bertolini, T.; Froelich, J. M.; Webber, S. E.; Hermann, T.; Wall, D. Antibacterial activity in serum of the 3,5-diamino-piperidine translation inhibitors. Bioorg. Med. Chem. Lett., 2008, 18, 3369-3375.
70. Pang, L. J.; Wang, D.; Zhou, J.; Zhang, L. H.; Ye, X. S. Synthesis of neamine-derived pseudodisaccharides by stereo- and regioselective functional group transformations. Org. Biomol. Chem., 2009, 7, 4252-4266.
71. Yamauchi, N.; Kakinuma, K. Enzymatic carbocycle formation in microbial secondary metabolism. The mechanism of the 2-deoxyscyllo-inosose synthase reaction as a crucial step in the 2-deoxystreptamine biosynthesis in Streptomyces fiadiae. J. Org. Chem., 1995, 60, 5614-5619.
72. Boehr, D. D.; Draker, K. A.; Koteva, K.; Bains, M.; Hancock, R. E.; Wright, G. D. Broad-spectrum peptide inhibitors of aminoglycoside antibiotic resistance enzymes. Chem. Biol., 2003, 10, 189-196.
73. Welch, K. T.; Virga, K. G.; Whittemore, N. A.; Ó́zen, C.; Wright, E.; Brown, C. L.; Leeb, R. E.; Serpersu, E. H. Discovery of noncarbohydrate inhibitors of aminoglycoside-modifying enzymes. Bioorg. Med. Chem. Lett., 2005, 13, 6252-6263.