Literature DB >> 24900282

Toward Overcoming Staphylococcus aureus Aminoglycoside Resistance Mechanisms with a Functionally Designed Neomycin Analogue.

Stephen Hanessian1, Alexandre Giguère1, Justyna Grzyb1, Juan Pablo Maianti1, Oscar M Saavedra1, James B Aggen2, Martin S Linsell2, Adam A Goldblum2, Darin J Hildebrandt2, Timothy R Kane2, Paola Dozzo2, Micah J Gliedt2, Rowena D Matias2, Lee Ann Feeney2, Eliana S Armstrong2.   

Abstract

Deoxygenation of the diol groups in rings A and D of neomycin in combination with the introduction of an N1-(l)-HABA group in the 2-deoxystreptamine subunit (ring B) leads to a novel and potent antibiotic (1) with activity against strains of S. aureus carrying known aminoglycoside resistance determinants, as well as against an extended panel of Methicillin-resistant S. aureus isolates (n = 50). Antibiotic 1 displayed >64 fold improvement in MIC50 and MIC90 against this MRSA collection when compared to the clinically relevant aminoglycosides amikacin and gentamicin. The synthesis was achieved in six steps and 15% overall yield.

Entities:  

Keywords:  Aminoglycoside; MRSA; antibiotics; deoxygenation; enzymatic modification; neomycin analogues; resistance

Year:  2011        PMID： 24900282      PMCID： PMC4018147          DOI： 10.1021/ml200202y

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  21 in total

1.  Structure-based design, synthesis and A-site rRNA co-crystal complexes of novel amphiphilic aminoglycoside antibiotics with new binding modes: a synergistic hydrophobic effect against resistant bacteria.

Authors:  Stephen Hanessian; Kandasamy Pachamuthu; Janek Szychowski; Alexandre Giguère; Eric E Swayze; Michael T Migawa; Boris François; Jiro Kondo; Eric Westhof
Journal:  Bioorg Med Chem Lett       Date:  2010-09-19       Impact factor: 2.823

2.  Kinetic determinants of high-fidelity tRNA discrimination on the ribosome.

Authors:  Kirill B Gromadski; Marina V Rodnina
Journal:  Mol Cell       Date:  2004-01-30       Impact factor: 17.970

3.  Prevalence of Staphylococcus aureus nasal colonization in the United States, 2001-2002.

Authors:  Matthew J Kuehnert; Deanna Kruszon-Moran; Holly A Hill; Geraldine McQuillan; Sigrid K McAllister; Gregory Fosheim; Linda K McDougal; Jasmine Chaitram; Bette Jensen; Scott K Fridkin; George Killgore; Fred C Tenover
Journal:  J Infect Dis       Date:  2005-12-15       Impact factor: 5.226

4.  Substrate promiscuity of an aminoglycoside antibiotic resistance enzyme via target mimicry.

Authors:  Desiree H Fong; Albert M Berghuis
Journal:  EMBO J       Date:  2002-05-15       Impact factor: 11.598

5.  Semisynthetic aminoglycoside antibiotics. IV. 3',4'-Dideoxyparomomycin and analogues.

Authors:  C Battistini; G Franceschi; F Zarini; G Cassinelli; F Arcamone; A Sanfilippo
Journal:  J Antibiot (Tokyo)       Date:  1982-01       Impact factor: 2.649

6.  The prevalence of aminoglycoside resistance and corresponding resistance genes in clinical isolates of staphylococci from 19 European hospitals.

Authors:  F J Schmitz; A C Fluit; M Gondolf; R Beyrau; E Lindenlauf; J Verhoef; H P Heinz; M E Jones
Journal:  J Antimicrob Chemother       Date:  1999-02       Impact factor: 5.790

Review 7.  Molecular genetics of aminoglycoside resistance genes and familial relationships of the aminoglycoside-modifying enzymes.

Authors:  K J Shaw; P N Rather; R S Hare; G H Miller
Journal:  Microbiol Rev       Date:  1993-03

8.  Invasive methicillin-resistant Staphylococcus aureus infections in the United States.

Authors:  R Monina Klevens; Melissa A Morrison; Joelle Nadle; Susan Petit; Ken Gershman; Susan Ray; Lee H Harrison; Ruth Lynfield; Ghinwa Dumyati; John M Townes; Allen S Craig; Elizabeth R Zell; Gregory E Fosheim; Linda K McDougal; Roberta B Carey; Scott K Fridkin
Journal:  JAMA       Date:  2007-10-17       Impact factor: 56.272

9.  Epidemiological and microbiological characterization of infections caused by Staphylococcus aureus with reduced susceptibility to vancomycin, United States, 1997-2001.

Authors:  Scott K Fridkin; Jeff Hageman; Linda K McDougal; Jasmine Mohammed; William R Jarvis; Trish M Perl; Fred C Tenover
Journal:  Clin Infect Dis       Date:  2003-01-31       Impact factor: 9.079

10.  In vitro activities of 28 antimicrobial agents against Staphylococcus aureus isolates from tertiary-care hospitals in Korea: a nationwide survey.

Authors:  Hong Bin Kim; Hee-Chang Jang; Hee Jung Nam; Yeong Seon Lee; Bong Su Kim; Wan Beom Park; Ki Deok Lee; Young Joo Choi; Sang Won Park; Myoung-Don Oh; Eui-Chong Kim; Kang Won Choe
Journal:  Antimicrob Agents Chemother       Date:  2004-04       Impact factor: 5.191
View more
  6 in total

1.  Design, Multigram Synthesis, and in Vitro and in Vivo Evaluation of Propylamycin: A Semisynthetic 4,5-Deoxystreptamine Class Aminoglycoside for the Treatment of Drug-Resistant Enterobacteriaceae and Other Gram-Negative Pathogens.

Authors:  Takahiko Matsushita; Girish C Sati; Nuwan Kondasinghe; Michael G Pirrone; Takayuki Kato; Prabuddha Waduge; Harshitha Santhosh Kumar; Adrian Cortes Sanchon; Malgorzata Dobosz-Bartoszek; Dimitri Shcherbakov; Mario Juhas; Sven N Hobbie; Thomas Schrepfer; Christine S Chow; Yury S Polikanov; Jochen Schacht; Andrea Vasella; Erik C Böttger; David Crich
Journal:  J Am Chem Soc       Date:  2019-03-13       Impact factor: 15.419

2.  Catalytic site-selective thiocarbonylations and deoxygenations of vancomycin reveal hydroxyl-dependent conformational effects.

Authors:  Brandon S Fowler; Kai M Laemmerhold; Scott J Miller
Journal:  J Am Chem Soc       Date:  2012-05-23       Impact factor: 15.419

3.  N6', N6''', and O4' Modifications to Neomycin Affect Ribosomal Selectivity without Compromising Antibacterial Activity.

Authors:  Girish C Sati; Dimitri Shcherbakov; Sven N Hobbie; Andrea Vasella; Erik C Böttger; David Crich
Journal:  ACS Infect Dis       Date:  2017-04-06       Impact factor: 5.084

Review 4.  Comprehensive review of chemical strategies for the preparation of new aminoglycosides and their biological activities.

Authors:  Nishad Thamban Chandrika; Sylvie Garneau-Tsodikova
Journal:  Chem Soc Rev       Date:  2018-02-19       Impact factor: 54.564

5.  Synthesis of a Pseudodisaccharide Suitable for Synthesis of Ring I Modified 4,5-2-Deoxystreptamine Type Aminoglycoside Antibiotics.

Authors:  Amr Sonousi; Andrea Vasella; David Crich
Journal:  J Org Chem       Date:  2020-05-08       Impact factor: 4.354

6.  Identification and evaluation of improved 4'-O-(alkyl) 4,5-disubstituted 2-deoxystreptamines as next-generation aminoglycoside antibiotics.

Authors:  Stefan Duscha; Heithem Boukari; Dimitri Shcherbakov; Sumantha Salian; Sandrina Silva; Ann Kendall; Takayuki Kato; Rashid Akbergenov; Deborah Perez-Fernandez; Bruno Bernet; Swapna Vaddi; Pia Thommes; Jochen Schacht; David Crich; Andrea Vasella; Erik C Böttger
Journal:  MBio       Date:  2014-09-30       Impact factor: 7.867
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.