메뉴 건너뛰기




Volumn 51, Issue 23, 2008, Pages 7563-7573

Surprising alteration of antibacterial activity of 5″-modified neomycin against resistant bacteria

Author keywords

[No Author keywords available]

Indexed keywords

AMINOGLYCOSIDE; FRAMYCETIN; FRAMYCETIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 57349085030     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800997s     Document Type: Article
Times cited : (82)

References (38)
  • 1
    • 0011844322 scopus 로고
    • Umezawa, H, Hooper, I. R, Eds, Springer-Verlag: New York
    • Umezawa, S.; Tsuchiya, T. In Aminoglycoside Antibiotics; Umezawa, H., Hooper, I. R., Eds.; Springer-Verlag: New York, 1982; pp 37-110.
    • (1982) Aminoglycoside Antibiotics , pp. 37-110
    • Umezawa, S.1    Tsuchiya, T.2
  • 3
    • 84889359917 scopus 로고    scopus 로고
    • Arya, D. P, Ed, John Wiley & Sons, Inc, New York
    • Wang, J.; Chang, C.-W. T. In Aminoglycoside Antibiotics; Arya, D. P., Ed.; John Wiley & Sons, Inc.: New York, 2007; pp 141-180.
    • (2007) Aminoglycoside Antibiotics , pp. 141-180
    • Wang, J.1    Chang, C.-W.T.2
  • 5
    • 34249778990 scopus 로고    scopus 로고
    • Investigation of the regioselectivity for Staudinger reaction and its application for the synthesis of aminoglycosides with N-1 modification
    • Li, J.; Chiang, F.-I.; Chen, H.-N.; Chang, C.-W. T. Investigation of the regioselectivity for Staudinger reaction and its application for the synthesis of aminoglycosides with N-1 modification. J. Org. Chem. 2007, 72, 4055-4066.
    • (2007) J. Org. Chem , vol.72 , pp. 4055-4066
    • Li, J.1    Chiang, F.-I.2    Chen, H.-N.3    Chang, C.-W.T.4
  • 6
    • 20444433905 scopus 로고    scopus 로고
    • A simple structural-based approach to prevent aminoglycoside inactivation by bacterial defense proteins. Conformational restriction provides effective protection against neomycin-B nucleotidylation by ANT4
    • 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.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 8278-8279
    • Asensio, J.L.1    Hidalgo, A.2    Bastida, A.3    Torrado, M.4    Corzana, F.5    Chiara, J.L.6    Garcia-Junceda, E.7    Canada, J.8    Jimenez-Barbero, J.9
  • 7
    • 22144490214 scopus 로고    scopus 로고
    • Conformational constraint as a means for understanding RNA-aminoglycoside specificity
    • Blount, K. F.; Zhao, F.; Hermann, T.; Tor, Y. Conformational constraint as a means for understanding RNA-aminoglycoside specificity. J. Am. Chem. Soc. 2005, 127, 9818-9829.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 9818-9829
    • Blount, K.F.1    Zhao, F.2    Hermann, T.3    Tor, Y.4
  • 8
    • 34447324374 scopus 로고    scopus 로고
    • Design and synthesis of a structurally constrained aminoglycoside
    • Kling, D.; Hesek, D.; Shi, Q.; Mobashery, S. Design and synthesis of a structurally constrained aminoglycoside. J. Org. Chem. 2007, 72, 5450-5453.
    • (2007) J. Org. Chem , vol.72 , pp. 5450-5453
    • Kling, D.1    Hesek, D.2    Shi, Q.3    Mobashery, S.4
  • 9
    • 0141483331 scopus 로고    scopus 로고
    • RNA-ligand interactions: Affinity and specificity of aminoglycoside dimers and acridine conjugates to the HIV-1 Rev response element
    • Luedtke, N. W.; Liu, Q.; Tor, Y. RNA-ligand interactions: Affinity and specificity of aminoglycoside dimers and acridine conjugates to the HIV-1 Rev response element. Biochemistry 2003, 42, 11391-11403.
    • (2003) Biochemistry , vol.42 , pp. 11391-11403
    • Luedtke, N.W.1    Liu, Q.2    Tor, Y.3
  • 10
    • 13744261523 scopus 로고    scopus 로고
    • RNA-Selective Modification by a Platinum(II) Complex Conjugated to Amino- and Guanidinoglycosides
    • Boer, J.; Blount, K. F.; Luedtke, N. W.; Elson-Schwab, L.; Tor, Y. RNA-Selective Modification by a Platinum(II) Complex Conjugated to Amino- and Guanidinoglycosides. Angew. Chem., Int. Ed. 2005, 44, 927-932.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 927-932
    • Boer, J.1    Blount, K.F.2    Luedtke, N.W.3    Elson-Schwab, L.4    Tor, Y.5
  • 11
    • 33947254088 scopus 로고    scopus 로고
    • Multisite modification of neomycin B: Combined Mitsunobu and click chemistry approach
    • Quader, S.; Boyd, S. E.; Jenkins, I. D.; Houston, T. A. Multisite modification of neomycin B: Combined Mitsunobu and click chemistry approach. J. Org. Chem. 2007, 72, 1962-1979.
    • (2007) J. Org. Chem , vol.72 , pp. 1962-1979
    • Quader, S.1    Boyd, S.E.2    Jenkins, I.D.3    Houston, T.A.4
  • 12
    • 0016223210 scopus 로고
    • Aminoglycoside antibiotics. VII. Acute toxicity of aminoglycoside antibiotics
    • Fujisawa, K.; Hashiya, T.; Kawaguchi, H. Aminoglycoside antibiotics. VII. Acute toxicity of aminoglycoside antibiotics. J. Antibiot. 1974, 27, 677-681.
    • (1974) J. Antibiot , vol.27 , pp. 677-681
    • Fujisawa, K.1    Hashiya, T.2    Kawaguchi, H.3
  • 14
    • 0142106443 scopus 로고    scopus 로고
    • A new class of branched aminoglycosides: Pseudo-pentasaccharide derivatives of neomycin B
    • 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.
    • (2003) Org. Lett , vol.5 , pp. 3575-3578
    • Fridman, M.1    Belakhov, V.2    Yaron, S.3    Baasov, T.4
  • 17
    • 0034426097 scopus 로고    scopus 로고
    • Aminoglycosides: Perspective on mechanisms of action and resistance and strategies to counter resistance
    • Kotra, L. P.; Haddad, J.; Mobashery, S. Aminoglycosides: Perspective on mechanisms of action and resistance and strategies to counter resistance. Antimicrob. Agents Chemother. 2000, 44, 3249-3256.
    • (2000) Antimicrob. Agents Chemother , vol.44 , pp. 3249-3256
    • Kotra, L.P.1    Haddad, J.2    Mobashery, S.3
  • 18
    • 0032828903 scopus 로고    scopus 로고
    • Aminoglycoside-modifying enzymes
    • Wright, G. D. Aminoglycoside-modifying enzymes. Curr. Opin. Microbiol. 1999, 2, 499-503.
    • (1999) Curr. Opin. Microbiol , vol.2 , pp. 499-503
    • Wright, G.D.1
  • 19
    • 0037770202 scopus 로고    scopus 로고
    • Versatility of aminoglycosides and prospects for their future
    • Vakulenko, S. B.; Mobashery, S. Versatility of aminoglycosides and prospects for their future. Clin. Microbiol. Rev. 2003, 16, 430-450.
    • (2003) Clin. Microbiol. Rev , vol.16 , pp. 430-450
    • Vakulenko, S.B.1    Mobashery, S.2
  • 20
    • 0034837297 scopus 로고    scopus 로고
    • Identification of aminoglycoside-modifying enzymes by susceptibility testing: Epidemiology of methicillin-resistant Staphylococcus aureus in Japan
    • Ida, T.; Okamoto, R.; Shimauchi, C.; Okubo, T.; Kuga, A.; Inoue, M. Identification of aminoglycoside-modifying enzymes by susceptibility testing: epidemiology of methicillin-resistant Staphylococcus aureus in Japan. J. Clin. Microbiol. 2001, 39, 3115-3121.
    • (2001) J. Clin. Microbiol , vol.39 , pp. 3115-3121
    • Ida, T.1    Okamoto, R.2    Shimauchi, C.3    Okubo, T.4    Kuga, A.5    Inoue, M.6
  • 21
    • 0033043536 scopus 로고    scopus 로고
    • The prevalence of aminoglycoside resistance and corresponding resistance genes in clinical isolates of staphylococci from 19 European hospitals
    • Schmitz, F. J.; Huit, A. C.; Gondolf, M.; Beyrau, R.; Lindenlauf, E.; Verhoef, J.; Heinz, H. P.; Jones, M. E. The prevalence of aminoglycoside resistance and corresponding resistance genes in clinical isolates of staphylococci from 19 European hospitals. J. Antimicrob. Chemother. 1999, 43, 253-259.
    • (1999) J. Antimicrob. Chemother , vol.43 , pp. 253-259
    • Schmitz, F.J.1    Huit, A.C.2    Gondolf, M.3    Beyrau, R.4    Lindenlauf, E.5    Verhoef, J.6    Heinz, H.P.7    Jones, M.E.8
  • 22
    • 0033979298 scopus 로고    scopus 로고
    • Detection of genes encoding aminoglycoside-modifying enzymes in staphylococci by polymerase chain reaction and dot blot hybridization
    • Udo, E. E.; Dashti, A. A. Detection of genes encoding aminoglycoside-modifying enzymes in staphylococci by polymerase chain reaction and dot blot hybridization. Int. J. Antimicrob. Agents 2000, 13, 273-279.
    • (2000) Int. J. Antimicrob. Agents , vol.13 , pp. 273-279
    • Udo, E.E.1    Dashti, A.A.2
  • 23
    • 0034770096 scopus 로고    scopus 로고
    • Aminoglycoside-streptothricin resistance gene cluster aadE-sat4-aphA-3 disseminated among multiresistant isolates of Enterococcus faecium
    • Werner, G.; Hildebrandt, B.; Witte, W. Aminoglycoside-streptothricin resistance gene cluster aadE-sat4-aphA-3 disseminated among multiresistant isolates of Enterococcus faecium. Antimicrob. Agents Chemother. 2001, 45, 3267-3269.
    • (2001) Antimicrob. Agents Chemother , vol.45 , pp. 3267-3269
    • Werner, G.1    Hildebrandt, B.2    Witte, W.3
  • 24
    • 0028358078 scopus 로고
    • Broad spectrum aminoglycoside phosphotransferase Type III from Enterococcus: Overexpression, purification, and substrate specificity
    • McKay, G. A.; Thompson, P. R.; Wright, G. D. Broad spectrum aminoglycoside phosphotransferase Type III from Enterococcus: overexpression, purification, and substrate specificity. Biochemistry 1994, 33, 6936-6944.
    • (1994) Biochemistry , vol.33 , pp. 6936-6944
    • McKay, G.A.1    Thompson, P.R.2    Wright, G.D.3
  • 25
    • 0028882693 scopus 로고
    • Kinetic mechanism of aminoglycoside phosphotransferase type IIIa
    • McKay, G. A.; Wright, G. D. Kinetic mechanism of aminoglycoside phosphotransferase type IIIa. J. Biol. Chem. 1995, 270, 24686-24692.
    • (1995) J. Biol. Chem , vol.270 , pp. 24686-24692
    • McKay, G.A.1    Wright, G.D.2
  • 26
    • 0037467430 scopus 로고    scopus 로고
    • The complex of a designer antibiotic with a model aminoacyl site of the 30S ribosomal subunit revealed by X-ray crystallography
    • Russell, R. J. M.; Murray, J. B.; Lentzen, G.; Haddad, J.; Mobashery, S. The complex of a designer antibiotic with a model aminoacyl site of the 30S ribosomal subunit revealed by X-ray crystallography. J. Am. Chem. Soc. 2003, 125, 3410-3411.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 3410-3411
    • Russell, R.J.M.1    Murray, J.B.2    Lentzen, G.3    Haddad, J.4    Mobashery, S.5
  • 27
    • 11644261806 scopus 로고    scopus 로고
    • Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Structures of 5″-substituted neomycins were docked to APH(3′)-IIIa and 16S ribosomal RNA. Models of the molecules of derivatized neomycins were prepared using HyperChem 7.5. Atomic charges were calculated using the AM1 semiempirical method in vacuo. The conformations were based on the X-ray structures of complexes of neomycin with respective molecules. Orientations of the 5″ chains were adjusted manually and the structures were subject to geometry optimization (ligand molecules only). Then, the structures of the complexes were refined, by using AutoDock 4 as local minimum optimizer. J. Comput. Chem. 1998, 19, 1639-1662.
    • (a) Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Structures of 5″-substituted neomycins were docked to APH(3′)-IIIa and 16S ribosomal RNA. Models of the molecules of derivatized neomycins were prepared using HyperChem 7.5. Atomic charges were calculated using the AM1 semiempirical method in vacuo. The conformations were based on the X-ray structures of complexes of neomycin with respective molecules. Orientations of the 5″ chains were adjusted manually and the structures were subject to geometry optimization (ligand molecules only). Then, the structures of the complexes were refined, by using AutoDock 4 as local minimum optimizer. J. Comput. Chem. 1998, 19, 1639-1662.
  • 28
    • 57349132651 scopus 로고    scopus 로고
    • Visualizations were prepared using AutoDock Tools
    • 5761
    • (b) Sanner, M. F. Visualizations were prepared using AutoDock Tools. J. Mol. Graphics Modell. 1999, 17, 5761\.
    • (1999) J. Mol. Graphics Modell , vol.17
    • Sanner, M.F.1
  • 29
    • 27244458194 scopus 로고    scopus 로고
    • Crystal structures of complexes between aminoglycosides and decoding A site oligonucleotides: Role of the number of rings and positive charges in the specific binding leading to miscoding
    • Francois, B.; Russell, R. J.; Murray, J. B.; Aboul-ela, F.; Masquida, B.; Vicens, Q.; Westhof, E. Crystal structures of complexes between aminoglycosides and decoding A site oligonucleotides: role of the number of rings and positive charges in the specific binding leading to miscoding. Nucleic Acids Res. 2005, 33, 5677-5690.
    • (2005) Nucleic Acids Res , vol.33 , pp. 5677-5690
    • Francois, B.1    Russell, R.J.2    Murray, J.B.3    Aboul-ela, F.4    Masquida, B.5    Vicens, Q.6    Westhof, E.7
  • 30
    • 0037093442 scopus 로고    scopus 로고
    • Substrate promiscuity of an aminoglycoside antibiotic resistance enzyme via target mimicry
    • Fong, D. H.; Berghuis, A. M. Substrate promiscuity of an aminoglycoside antibiotic resistance enzyme via target mimicry. EMBO J. 2002, 21, 2323-2331.
    • (2002) EMBO J , vol.21 , pp. 2323-2331
    • Fong, D.H.1    Berghuis, A.M.2
  • 32
    • 0030008129 scopus 로고    scopus 로고
    • Hachiler, H.; Santanam, P.; Kayser, R H. Sequence and characterization of a novel chromosomal aminoglycoside phosphotransferase gene, aph (3′)-IIb, in Pseudomonas aeruginosa. Antimicrob. Agents Chemother. 1996, 40, 1254-1256.
    • Hachiler, H.; Santanam, P.; Kayser, R H. Sequence and characterization of a novel chromosomal aminoglycoside phosphotransferase gene, aph (3′)-IIb, in Pseudomonas aeruginosa. Antimicrob. Agents Chemother. 1996, 40, 1254-1256.
  • 33
    • 0036310962 scopus 로고    scopus 로고
    • Monitoring antimicrobial use and resistance: Comparison with a national benchmark on reducing vancomycin use and vancomycin-resistant enterococci
    • Fridkin, S. K.; Lawton, R.; Edwards, J. R.; Tenover, F. C.; McGowan, J. E., Jr.; Gaynes, R. P. Monitoring antimicrobial use and resistance: comparison with a national benchmark on reducing vancomycin use and vancomycin-resistant enterococci. Emerg. Infect. Dis. 2002, 8, 702-707.
    • (2002) Emerg. Infect. Dis , vol.8 , pp. 702-707
    • Fridkin, S.K.1    Lawton, R.2    Edwards, J.R.3    Tenover, F.C.4    McGowan Jr., J.E.5    Gaynes, R.P.6
  • 34
    • 0028841236 scopus 로고
    • Molecular characterization and multilaboratory evaluation of Enterococcus faecalis ATCC 51299 for quality control of screening tests for vancomycin and high-level aminoglycoside resistance in Enterococci
    • Swenson, J. M.; Clark, N. C.; Sahm, D. F.; Ferraro, M. J.; Doern, G.; Hindler, J.; Jorgensen, J. H.; Pfaller, M. A.; Reller, L. B.; Weinstein, M. P.; Zabransky, R. J.; Tenover, F. C. Molecular characterization and multilaboratory evaluation of Enterococcus faecalis ATCC 51299 for quality control of screening tests for vancomycin and high-level aminoglycoside resistance in Enterococci. J. Clin. Microbiol. 1995, 33, 3019-3021.
    • (1995) J. Clin. Microbiol , vol.33 , pp. 3019-3021
    • Swenson, J.M.1    Clark, N.C.2    Sahm, D.F.3    Ferraro, M.J.4    Doern, G.5    Hindler, J.6    Jorgensen, J.H.7    Pfaller, M.A.8    Reller, L.B.9    Weinstein, M.P.10    Zabransky, R.J.11    Tenover, F.C.12
  • 37
    • 0001345246 scopus 로고    scopus 로고
    • The formation of a novel Pd/C-ethylenediamine complex catalyst: Chemoselective hydrogenation without deprotection of the O-benzyl and N-cbz groups
    • Sajiki, H.; Hattori, K.; Hirota, K. The formation of a novel Pd/C-ethylenediamine complex catalyst: Chemoselective hydrogenation without deprotection of the O-benzyl and N-cbz groups. J. Org. Chem. 1998, 63, 7990-7992.
    • (1998) J. Org. Chem , vol.63 , pp. 7990-7992
    • Sajiki, H.1    Hattori, K.2    Hirota, K.3
  • 38
    • 22244450069 scopus 로고    scopus 로고
    • Tuning the regioselectivity of Staudinger reaction for the facile synthesis of kanamycin and neomycin class antibiotics with N-1 modification
    • Li, J.; Chen, H.-N.; Chang, H.; Wang, J.; Chang, C.-W. T. Tuning the regioselectivity of Staudinger reaction for the facile synthesis of kanamycin and neomycin class antibiotics with N-1 modification. Org. Lett. 2005, 7, 3061-3064.
    • (2005) Org. Lett , vol.7 , pp. 3061-3064
    • Li, J.1    Chen, H.-N.2    Chang, H.3    Wang, J.4    Chang, C.-W.T.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.