Aminoglycosides

Armstrong, Eliana S.; Kostrub, Corwin F.; Cass, Robert T.; Moser, Heinz; Serio, Alisa W.; Miller, George H.

doi:10.1007/978-1-4614-1400-1_7

Cited by 28 publications

(57 citation statements)

References 171 publications

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“…6–9 Advantages of the AGAs as parents for optimization include their broad spectrum of activity, their non-allergenic character, and their lack of effect on the host intestinal microbiome. 9 In addition, AGAs have physicochemical properties consistent with suggested guidelines for the development of new antibacterial compounds, 10 and following decades of use in the clinic, their PK, PD and ADME properties are well-understood and largely predictable. 9 Finally, existing AGAs are available on a large scale by fermentation, and their chemistry is well-documented, 11–12 making them good candidates for optimization by chemical modification.…”

Section: Introductionmentioning

confidence: 99%

Structure-Based Design and Synthesis of Apramycin–Paromomycin Analogues: Importance of the Configuration at the 6′-Position and Differences between the 6′-Amino and Hydroxy Series

et al. 2017

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The preparation of a series of four analogues of the aminoglycoside antibiotics neomycin and paromomycin is described in which ring I, involved in critical binding interactions with the ribosomal target, is replaced by an apramycin-like dioxabicyclo[4.4.0]octane system. The effect of this modification is to lock the hydroxymethyl side chain of the neomycin or paromomycin ring I, as part of the dioxabicyclooctane ring, into either the gauche-gauche or the gauche-trans conformation (respectively axial or equatorial to the bicyclic system). The antiribosomal activity of these compounds is investigated with cell-free translation assays using both bacterial ribosomes and recombinant hybrid ribosomes carrying eukaryotic decoding A site cassettes. Compounds substituted with an equatorial hydroxyl or amino group in the newly formed ring are considerably more active than their axial diastereomers, lending strong support to crystallographically-derived models of aminoglycoside-ribosome interactions. One such bicyclic compound carrying an equatorial hydroxyl group has activity equal to that of the parent, yet displays better ribosomal selectivity, predictive of an enhanced therapeutic index. A paromomycin analog lacking the hydroxymethyl ring I side chain is considerably less active than the parent. Antibacterial activity against model Gram negative and Gram positive bacteria is reported, for selected compounds, as is activity against ESKAPE pathogens and recombinant bacteria carrying specific resistance determinants. Analogues with a bicyclic ring I carrying equatorial amino or hydroxyl groups mimicking the bound side chains of neomycin and paromomcyin, respectively, show excellent activity and, by virtue of their novel structure, retain this activity in strains that are insensitive to the parent compounds.

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Section: Introductionmentioning

confidence: 99%

Structure-Based Design and Synthesis of Apramycin–Paromomycin Analogues: Importance of the Configuration at the 6′-Position and Differences between the 6′-Amino and Hydroxy Series

et al. 2017

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“…The bactericidal effect of this class is based on irreversibly binding to the aminoacyl site of the 16S rRNA within the bacterial 30S ribosomal subunits, resulting in mistranslation of the coding protein (Armstrong et al, 2012;Wright, 2010).…”

Section: Aminoglycosidesmentioning

confidence: 99%

“…Aminoglycoside resistance is widespread in E. coli isolates worldwide (Armstrong et al, 2012). Low levels of resistance to aminoglycosides: gentamicin (0% -3.1%); neomycin (2.1% -17.2%); spectinomycin (8.8% -27.7%); streptomycin (33.5% -34%) and apramycin ( …”

Section: Aminoglycosidesmentioning

confidence: 99%

Studies on avian pathogenic Escherichia coli in commercial broiler chicken in South East Queensland

Awawdeh¹,

Turni²,

Henning³

et al.

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Avian pathogenic Escherichia coli (APEC) is the causative agent of avian colibacillosis, a localised or systemic infection resulting in clinical diseases such as colisepticemia, chronic respiratory disease and swollen-head syndrome. Globally, avian colibacillosis is the leading cause of morbidity and mortality in poultry, and it has been associated with massive economic losses and welfare problems.This organism is of public health significance as APEC is communicable to humans. The diagnosis of avian colibacillosis relies on clinical signs, typical pathological lesions and culture of E. coli from affected tissue(s). Antimicrobial therapy is often used both for treatment and control. Previous overseas studies have characterised APEC and identified virulence genes (VGs) that can be used as molecular markers for the identification of APEC. Little is known about APEC in broiler chickens in Australia.The aim of this thesis was to gain a better understanding of the epidemiology of APEC in Australian broiler flocks and how factors including presence of VGs and phylogenetic group can improve the identification of this pathotype in Australia. Firstly, three faecal DNA extraction methods were evaluated. Faeces were collected from healthy chickens and chickens with colibacillosis from commercial broiler farms in South East Queensland (SEQ). The extracted DNA was screened by a pentaplex-PCR for five APEC-associated VGs (iroN, iutA, iss, hlyF and ompT). DNA extracted from E. coli isolates cultured from the cloaca and organs of the birds were screened using the same PCR.Repeated bead beating plus column elution was the preferred DNA extraction method, as it yielded good PCR quality and adequate quantity DNA. However, identifying APEC by direct detection of the five VGs from the faecal material was not feasible as all of these genes were also detected in all of the birds. However, the VGs were more commonly detected in E. coli isolates cultured from birds with colibacillosis.A cross-sectional study was performed to estimate APEC farm-level prevalence in healthy broiler chickens in SEQ and to identify potential risk factors associated with the carriage of APEC. At the farm-level, all of the 40 farms sampled were positive for APEC, that is at least one bird per farm carried APEC, while the within-farm prevalence was 63% (95% Confidence Interval: 55.8, 70.2).Higher APEC within-farm bird-level prevalence was significantly associated with the usage of well water as a source of drinking water, failure to disinfect the water line after each flock, farm visitors not showering before entering the shed, distances greater than 20 metres between the car park and the poultry shed and the presence of wild birds within 50 metres of the shed. Chlorinating the drinking water combined with automatic water filtration reduced within-farm bird-level APEC prevalence. Page | 3Therefore, based on the results concluded from the multivariable model, improving biosecurity and water treatments might reduce APEC prevalence, decrease the risk of co...

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“…Amikacin is a semi-synthetic aminoglycoside antibiotic synthesized by chemical modification of kanamycin A (Armstrong et al, 2012;Zawilla, Li, Hoogmartens, & Adams, 2007). Therefore, it belongs to the kanamycin subclass which includes kanamycin, tobramycin, and amikacin ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…Similar to other aminoglycosides, amikacin disrupts bacterial protein synthesis by binding to the 30S ribosome of susceptible organisms. Binding interferes with mRNA binding and tRNA acceptor sites, leading to the production of nonfunctional or toxic peptides (Armstrong et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Development of a monoclonal antibody assay and immunochromatographic test strip for the detection of amikacin residues in milk and eggs

Isanga

Mukunzi

Suryoprabowo

et al. 2017

Food and Agricultural Immunology

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An amikacin-sensitive monoclonal antibody (MAb) assay and immunochromatographic test strip were developed and applied for the detection of amikacin residues in bovine milk and chicken eggs. The immunoassay was specific to amikacin and showed no cross-reactivity with other aminoglycosides. The half maximum inhibitory concentration (IC 50 ) of the assay was 0.65 ng/mL and the results were obtained within 90 min. Recoveries from spiked food matrices were within the range of 73.55-84.61% for bovine milk and 73.70-105.75% for whole egg. The strip test results were obtained within 10 min and showed a visual detection limit of 5.0 ng/mL for both food matrices. These results show that the MAb immunoassay and strip test developed in this study are very specific to amikacin and sufficiently sensitive for detection and routine monitoring of amikacin residues in food. ARTICLE HISTORY

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Aminoglycosides

Cited by 28 publications

References 171 publications

Structure-Based Design and Synthesis of Apramycin–Paromomycin Analogues: Importance of the Configuration at the 6′-Position and Differences between the 6′-Amino and Hydroxy Series

Structure-Based Design and Synthesis of Apramycin–Paromomycin Analogues: Importance of the Configuration at the 6′-Position and Differences between the 6′-Amino and Hydroxy Series

Studies on avian pathogenic Escherichia coli in commercial broiler chicken in South East Queensland

Development of a monoclonal antibody assay and immunochromatographic test strip for the detection of amikacin residues in milk and eggs

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