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Literature DB >> 25110571

Antifungal Amphiphilic Aminoglycosides.

Abstract

The attachment of alkyl and other hydrophobic groups to traditional antibacterial kanamycins and neomycins creates amphiphilic aminoglycosides with altered antimicrobial properties. In this review, we summarize the discovery of amphiphilic kanamycins that are antifungal, but not antibacterial, and that inhibit the growth of fungi by perturbation of plasma membrane functions. With low toxicities against plant and mammalian cells, they appear to specifically target the fungal plasma membrane. These new antifungal agents offer new options for fighting fungal pathogens and are examples of reviving old drugs to confront new therapeutic challenges.

Entities: CellLine Chemical Disease Gene Species

Year: 2014 PMID： 25110571 PMCID： PMC4125127 DOI： 10.1039/C4MD00078A

Source DB: PubMed Journal: Medchemcomm ISSN： 2040-2503 Impact factor: 3.597

38 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

Review 2. Antifungal agents: mechanisms of action.

Authors: Frank C Odds; Alistair J P Brown; Neil A R Gow
Journal: Trends Microbiol Date: 2003-06 Impact factor: 17.079

3. Neomycin-phenolic conjugates: polycationic amphiphiles with broad-spectrum antibacterial activity, low hemolytic activity and weak serum protein binding.

Authors: Brandon Findlay; George G Zhanel; Frank Schweizer
Journal: Bioorg Med Chem Lett Date: 2012-01-14 Impact factor: 2.823

4. Tuning the regioselectivity of the Staudinger reaction for the facile synthesis of kanamycin and neomycin class antibiotics with N-1 modification.

Authors: Jie Li; Hsiao-Nung Chen; Huiwen Chang; Jinhua Wang; Cheng-Wei Tom Chang
Journal: Org Lett Date: 2005-07-07 Impact factor: 6.005

5. Structure-based design, synthesis, and A-site rRNA cocrystal complexes of functionally novel aminoglycoside antibiotics: C2" ether analogues of paromomycin.

Authors: Stephen Hanessian; Janek Szychowski; Susanta Sekhar Adhikari; Guillermo Vasquez; Pachamuthu Kandasamy; Eric E Swayze; Michael T Migawa; Ray Ranken; Boris François; Julia Wirmer-Bartoschek; Jiro Kondo; Eric Westhof
Journal: J Med Chem Date: 2007-04-26 Impact factor: 7.446

6. Site-selective displacement of tobramycin hydroxyls for preparation of antimicrobial cationic amphiphiles.

Authors: Yifat Berkov-Zrihen; Ido M Herzog; Mark Feldman; Micha Fridman
Journal: Org Lett Date: 2013-11-13 Impact factor: 6.005

7. Inhibition of aminoglycoside-deactivating enzymes APH(3')-IIIa and AAC(6')-Ii by amphiphilic paromomycin O2''-ether analogues.

Authors: Janek Szychowski; Jiro Kondo; Omar Zahr; Karine Auclair; Eric Westhof; Stephen Hanessian; Jeffrey W Keillor
Journal: ChemMedChem Date: 2011-09-08 Impact factor: 3.466

8. The Pseudomonas aeruginosa membranes: a target for a new amphiphilic aminoglycoside derivative?

Authors: Myriam Ouberai; Farid El Garch; Antoine Bussiere; Mickael Riou; David Alsteens; Laurence Lins; Isabelle Baussanne; Yves F Dufrêne; Robert Brasseur; Jean-Luc Decout; Marie-Paule Mingeot-Leclercq
Journal: Biochim Biophys Acta Date: 2011-02-01

9. Antibacterial activity of amphiphilic tobramycin.

Authors: Ramesh Dhondikubeer; Smritilekha Bera; George G Zhanel; Frank Schweizer
Journal: J Antibiot (Tokyo) Date: 2012-07-11 Impact factor: 2.649

10. Surprising alteration of antibacterial activity of 5"-modified neomycin against resistant bacteria.

Authors: Jianjun Zhang; Fang-I Chiang; Long Wu; Przemyslaw Greg Czyryca; Ding Li; Cheng-Wei Tom Chang
Journal: J Med Chem Date: 2008-12-11 Impact factor: 7.446

13 in total

1. Amphiphilic Tobramycin Analogues as Antibacterial and Antifungal Agents.

Authors: Sanjib K Shrestha; Marina Y Fosso; Keith D Green; Sylvie Garneau-Tsodikova
Journal: Antimicrob Agents Chemother Date: 2015-06-01 Impact factor: 5.191

2. Detection and Quantification of Ribosome Inhibition by Aminoglycoside Antibiotics in Living Bacteria Using an Orthogonal Ribosome-Controlled Fluorescent Reporter.

Authors: Shijie Huang; Xuechen Zhu; Charles E Melançon
Journal: ACS Chem Biol Date: 2015-11-04 Impact factor: 5.100

Antifungal Amphiphilic Aminoglycosides.

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.

Review 2. Antifungal agents: mechanisms of action.

3. Neomycin-phenolic conjugates: polycationic amphiphiles with broad-spectrum antibacterial activity, low hemolytic activity and weak serum protein binding.

4. Tuning the regioselectivity of the Staudinger reaction for the facile synthesis of kanamycin and neomycin class antibiotics with N-1 modification.

5. Structure-based design, synthesis, and A-site rRNA cocrystal complexes of functionally novel aminoglycoside antibiotics: C2" ether analogues of paromomycin.

6. Site-selective displacement of tobramycin hydroxyls for preparation of antimicrobial cationic amphiphiles.

7. Inhibition of aminoglycoside-deactivating enzymes APH(3')-IIIa and AAC(6')-Ii by amphiphilic paromomycin O2''-ether analogues.

8. The Pseudomonas aeruginosa membranes: a target for a new amphiphilic aminoglycoside derivative?

9. Antibacterial activity of amphiphilic tobramycin.

10. Surprising alteration of antibacterial activity of 5"-modified neomycin against resistant bacteria.

1. Amphiphilic Tobramycin Analogues as Antibacterial and Antifungal Agents.

2. Detection and Quantification of Ribosome Inhibition by Aminoglycoside Antibiotics in Living Bacteria Using an Orthogonal Ribosome-Controlled Fluorescent Reporter.

3. A review of patents (2011-2015) towards combating resistance to and toxicity of aminoglycosides.

4. A complex game of hide and seek: the search for new antifungals.

5. Synthesis and Bioactivities of Kanamycin B-Derived Cationic Amphiphiles.

6. Identification of Ebsulfur Analogues with Broad-Spectrum Antifungal Activity.

Review 7. Antifungal amphiphilic kanamycins: new life for an old drug.

8. Antifungal amphiphilic aminoglycoside K20: bioactivities and mechanism of action.

9. Differential Effects of Linkers on the Activity of Amphiphilic Tobramycin Antifungals.

10. Antifungal Activity of Gentamicin B1 Against Systemic Plant Mycoses.