Aminoglycoside antibiotics

Antimicrobials: New and Old Molecules in the Fight Against Multi-Resistant Bacteria

Volumn 9783642399688, Issue , 2014, Pages 193-209

  Kirst, Herbert A ^a   Marinelli, Flavia ^b  

^a University of Insubria ^*  (United States)

^b UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84930257496     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-3-642-39968-8_10     Document Type: Chapter

References (74)

1. Aggen JB et al (2010) Synthesis and spectrum of the neoglycoside ACHN-490. Antimicrob Agents Chemother 54:4636-4642
2. Ali BH, Al Za'abi M, Blunden G, Nemmar A (2011) Experimental gentamicin nephrotoxicity and agents that modify it: A mini-review of recent research. Basic Clin Pharmacol Toxicol 109:225-232
3. Ariano RE, Zelenitsky SA, Kassum DA (2008) Aminoglycoside-induced vestibular injury: maintaining a sense of balance. Ann Pharmacother 42:1282-1289
4. Armstrong ES, Miller GH (2010) Combating evolution with intelligent design: The neoglycoside ACHN-490. Curr Opin Microbiol 13:565-573
5. Arya DP (2007) Aminoglycoside antibiotics: from chemical biology to drug discovery. John Wiley & Sons, Hoboken
6. Becker B, Cooper MA (2013) Aminoglycoside antibiotics in the 21st century. ACS Chem Biol 8:105-115
7. Borders DB (2005) Antibiotics, survey. In: Seidel A (ed) Kirk-Othmer Encyclopedia of Chemical Technology, 5th edition. John Wiley & Sons, New York
8. Bracco D et al (2008) Pharmacokinetic variability of extended interval tobramycin in burn patients. Burns 34:791-796
9. Brodersen DE, Clemons WM Jr, Carter AP, Morgan-Warren RJ, Wimberly BT, Ramakrishnan V (2000) The structural basis for the action of the antibiotics tetracycline, pactamycin, and hygromycin B on the 30S ribosomal subunit. Cell 103:1143-1154
10. Carter AP, Clemons WM, Brodersen DE, Morgan-Warren RJ, Wimberly BT, Ramakrishnan V (2000) Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics. Nature 407:340-348
11. Chaudhary M, Naidu GK, Kumar S, Payaasi A (2012) Comparative antibacterial activity of a novel semisynthetic antibiotic: etimicin sulphate and other aminoglycosides. World J Microbiol Biotechnol 28:3365-3371
12. Cochran TG, Abraham DJ, Martin LL (1972) Stereochemistry and absolute configuration of the antibiotic spectinomycin: An X-ray diffraction study. J Chem Soc, Chem Commun 1972:494-495
13. Cooper DJ (1971) Comparative chemistry of some aminoglycoside antibiotics. Pure Appl Chem 28:455-467
14. Cundliffe E, Demain AL (2010) Avoidance of suicide in antibiotic-producing microbes. J Ind Microbiol Biotechnol 37:643-672
15. Doi Y, Arakawa Y (2007) 16S ribosomal RNA methylation: emerging resistance mechanism against aminoglycosides. Clin Infect Dis 45:88-94
16. Dozzo P, Moser HE (2010) New aminoglycoside antibiotics. Expert Opin Ther Patents 20:1321-1341
17. Elanco Animal Health (2013) http://www.elanco.us./product-services
18. El'Garch F, Jeannot K, Hocquet D, Llanes-Barakat C, Plésiat P (2007) Cumulative effects of several nonenzymatic mechanisms on the resistance of Pseudomonas aeruginosa to aminoglycosides. Antimicrob Agents Chemother 51:1016-1021
19. Falagas ME, Karageorgopoulos DE, Georgantzi GG, Sun C, Wang R, Rafailidis PI (2012) Susceptibility of Gram-negative bacteria to isepamicin: A systemic review. Expert Rev Anti-Infect Ther 10:207-218
20. Gilbert DN, Leggett JE (2009) Aminoglycosides. In: Mandell GL, Bennett JE, Dolin R (eds) Mandell, Douglas and Bennett's Principles and Practice of Infectious Diseases, 7th edn, chapter 26. Churchill Livingstone, New York
21. Girolami RL, Stamm JM (1977) Fortimicins A and B, new aminoglycoside antibiotics. IV. J Antibiot 30:564-570
22. Harvey SC, Li X, Skolnick P, Kirst HA (2000) The antibacterial and NMDA receptor activating properties of aminoglycosides are dissociable. Eur J Pharmacol 387:1-7
23. Hichens M, Rinehart KL Jr (1963) Chemistry of the neomycins. XII. J Am Chem Soc 85:1547-1548
24. Karasawa T, Steyger PS (2011) Intracellular mechanisms of aminoglycoside-induced cytotoxicity. Integr Biol 3:879-886
25. Kawaguchi H, Naito T (1983) Amikacin. In: Bindra JS, Lednicer D (eds) Chronicles of drug discovery, vol 2, Chapter 10. Wiley, New York
26. Kawaguchi H, Naito T, Nakagawa S, Fujisawa K (1972) BB-K 8, a new semisynthetic aminoglycoside antibiotic. J Antibiot 25:695-708
27. Kirst HA, Allen NE (2007) Aminoglycoside antibiotics. In: Triggle DJ, Taylor JB (eds) Comprehensive medicinal chemistry II, vol 7. Elsevier, Oxford
28. Koch KF, Rhoades JA, Hagaman EW, Wenkert E (1974) Carbon-13 nuclear magnetic resonance spectral analysis of tobramycin and related antibiotics. J Am Chem Soc 96:3300-3305
29. Kondo S, Iinuma K, Yamamoto H, Maeda K, Umezawa H (1973) Syntheses of 1-n-(S)-4-amino-2-hydroxybutyryl)-kanamycin B and-30, 40-dideoxykanamycin B active against kanamycinresistant bacteria. J Antibiot 26:412-415
30. Kotretsou S, Mingeot-Leclercq MP, Constantinou-Kokotou V et al (1995) Synthesis and antimicrobial and toxicological studies of amino acid and peptide derivatives of kanamycin A and netilmicin. J Med Chem 38:4710-4719
31. Kudo F, Eguchi T (2009) Biosynthetic enzymes for the aminolgycosides butirosin and neomycin. Methods Enzymol 459:493-519
32. Li C-R, Yang X-Y, Lou R-H et al (2008) In vitro antibacterial activity of vertilmicin and its susceptibility to modifications by the recombinant AAC(60)-APH(20) enzyme. Antimicrob Agents Chemother 52:3875-3882
33. Lo JY, Ho KM, Lo AC (2012) Surveillance of gonococcal antimicrobial susceptibility resulting in early detection of emerging resistance. J Antimicrob Chemother 67:1422-1426
34. Magnet S, Blanchard JS (2005) Molecular insights into aminoglycoside action and resistance. Chem Rev 105:477-497
35. Marchand I, Damier-Piolle L, Courvalin P, Lambert T (2004) Expression of the RND-type efflux pump AdeABC in Acinetobacter baumannii is regulated by the AdeRS two-component system. Antimicrob Agents Chemother 48:3298-3304
36. Matt T, Ng CL, Lang K et al (2012) Dissociation of antibacterial activity and aminoglycoside ototoxicity in the 4-monosubstituted 2-deoxystreptamine apramycin. Proc Nat Acad Sci US 109:10984-10989
37. McCormick C et al (2008) Effectiveness of a new tobramycin (0.3%) and dexamethasone (0.05%) formulation in the treatment of experimental Pseudomonas keratitis. Curr Med Res Opin 24:1569-1575
38. Mitscher LA (2010) Tetracycline, aminoglycoside, macrolide, and miscellaneous antibiotics. In: Abraham DJ, Rotella DP (eds) Burger's medicinal chemistry, drug discovery, and development, 7th edn. Wiley, New York
39. Mortensen JE, Nanavaty J, Veenhuizen MF, Shryock TR (1996) Reviewing apramycin's properties and use in controlling colibacillosis in pigs. Vet Med 91:473-477
40. Nagabhushan TL, Cooper AB, Tsai H, Daniels PJL, Miller GH (1978) The syntheses and biological properties of 1-N-(S-4-amino-2-hydroxybutyryl)-gentamicin B and 1-N-(S-3-amino-2-hydroxypropionyl)-gentamicin B. J Antibiot 31:681-687
41. Neidle S, Rogers D, Hursthouse MB (1968) The crystal and molecular structure of streptomycin oximeselenate. Tetrahedron Lett 9:4725-4728
42. Neuss N, Koch KF, Molloy BB, Day W, Huckstep LL, Dorman DE, Roberts JD (1970) Structure of hygromycin B. Helv Chim Acta 53:2314-2319
43. O'Connor S, Lam LKT, Jones ND, Chaney MO (1976) Apramycin, a unique aminocyclitol antibiotic. J Org Chem 41:2087-2092
44. Ohnishi Y, Kameyama S, Onaka H, Horinouchi S (1999) The A-factor regulatory cascade leading to streptomycin biosynthesis in Streptomyces griseus: identification of a target gene of the Afactor receptor. Mol Microbiol 34:102-111
45. Pagkalis S, Mantadakis E, Mavros MN, Ammari C, Falagas ME (2011) Pharmacological considerations for the proper use of aminoglycosides. Drugs 71:2277-2294
46. Park JW, Park SR, Nepal KK, Han AR, Ban YH, Yoo YJ, Kim EJ, Kim EM, Kim D, Sohng JK, Yoon YJ (2011) Discovery of parallel pathways of kanamycin biosynthesis allows antibiotic manipulation. Nat Chem Biol 7:843-852
47. Park SR, Park JW, Ban YH, Sohng JK, Yoon YJ (2013) 2-Deoxystreptamine-containing aminoglycoside antibiotics: recent advances in the characterization and manipulation of their biosynthetic pathways. Nat Prod Rep 30:11-20
48. Pasquale TR, Tam JS (2005) Non antimicrobial effects of antibacterial agents. Clin Infect Dis 40:127-135
49. Penha FM, Rodrigues EB, Maia M et al (2010) Retinal and ocular toxicity in ocular application of drugs and chemicals-part II. Ophthalmic Res 44:205-224
50. Piepersberg W (1997) Molecular biology, biochemistry and fermentation of aminoglycoside antibiotics. In: Strohl WR (ed) Biotechnology of antibiotics, 2nd edn, Marcel Dekker Inc., New York
51. Poole K (2005) Aminoglycoside resistance in Pseudomonas aeruginosa. Antimicrob Agents Chemother 49:479-487
52. Prayle A, Smyth AR (2010) Aminoglycoside use in cystic fibrosis: Therapeutic strategies and toxicity. Curr Opin Pulm Med 16:604-610
53. Price KE, Godfrey JC, Kawaguchi H (1977) Effect of structural modifications on the biological properties of aminoglycoside antibiotics containing 2-deoxystreptamine and supplement. In: Perlman D (ed) Structure-activity relationships among the semisynthetic antibiotics. Academic Press, New York
54. Quiros Y et al (2011) An integrative overview on the mechanisms underlying the renal tubular cytotoxicity of gentamicin. Toxicol Sci 119:245-256
55. Reimann H, Cooper DJ, Mallams AK et al (1974) The structure of sisomicin, a novel unsaturated aminocyclitol antibiotic from Micromonospora inyoensis. J Org Chem 39:1451-1457
56. Schatz A, Bugie E, Waksman SA (1944) Streptomycin, a substance exhibiting antibiotic activity against Gram-positive and Gram-negative bacteria. Proc Soc Exp Biol Med 55:66-69
57. Selimoglu E (2007) Aminoglycoside-induced ototoxicity. Curr Pharm Design 13:119-126
58. Singh MP (2001) Tobramycin. Curr Opin Investig Drugs 2:755-765
59. Tsai A, Uemura S, Johansson M, Puglisi EV, Marshall RA, Aitken CE, Korlach J, Ehrenberg M, Puglisi JD (2013) The impact of aminoglycosides on the dynamics of translation elongation. Cell Rep. 3:497-508
60. Tenover FC, Elvrum PM (1988) Detection of two different kanamycin resistance genes in naturally occurring isolates of Campylobacter jejuni and Campylobacter coli. Antimicrob Agents Chemother 32:1170-1173
61. Tenover FC, Tickler I, Armstrong ES, Kubo A, Lopez S, Persing DH, Miller GH (2011) Activity of ACHN-490 against methicillin-resistant Staphylococcus aureus (MRSA) isolates from patients in US hospitals. Int J Antimicrob Agents 38:352-354
62. Umezawa H, Ueda M et al (1957) Production and isolation of a new antibiotic: kanamycin. J Antibiot 10:181-188
63. Umezawa H, Umezawa S, Tsuchiya T, Okazaki Y (1971) 30, 40-dideoxy-kanamycin B active against kanamycin-resistant Escherichia coli and Pseudomonas aeruginosa. J Antibiot 24:485-487
64. Waksman SA (1953) Streptomycin: background, isolation, properties, and utilization. Science 118:259-266
65. Waksman SA, Lechevalier HA (1949) Neomycin, a new antibiotic active against streptomycinresistant bacteria, including tuberculosis organisms. Science 109:305-307
66. Walsh C (2000) Antibiotics. Actions, origins, resistance. ASM Press, Washington, DC
67. Warchol ME (2010) Cellular mechanisms of aminoglycoside ototoxicity. Curr Opin Otolaryngol Head Neck Surg 18:454-458
68. Wehmeier UF, Piepersberg W (2009) Enzymology of aminoglycosides biosynthesis-deduction from gene clusters. Methods Enzymol 459:459-491
69. Woo PWK, Dion HW, Bartz QR (1971) Butirosins A and B, aminoglycoside antibiotics. III. Structures. Tetrahedron Lett 12:2625-2628
70. Wright JJ (1976) Synthesis of 1-N-ethylsisomicin: A broad-spectrum semisynthetic aminoglycoside antibiotic. J Chem Soc, Chem Commun 1976:206-208
71. Wright GD (1999) Aminoglycoside-modifying enzymes. Curr Opin Microbiol 2:499-503
72. Yonath A (2005) Antibiotics targeting ribosomes: resistance, selectivity, synergism and cellular regulation. Annu Rev Biochem 74:649-679
73. Xie J, Talaska AE, Schacht J (2011) New developments in aminoglycoside therapy and ototoxicity. Hearing Res 281:28-37
74. Zhanel GG, Lawson CD, Zelenitsky S (2012) Comparison of the next-generation aminoglycoside plazomicin to gentamicin, tobramycin and amikacin. Expert Rev Anti-Infect Ther 10:459-473