Structure–toxicity relationship of aminoglycosides: Correlation of 2′-amine basicity with acute toxicity in pseudo-disaccharide scaffolds

Chen, Lilach; Hainrichson, Mariana; Bourdetsky, Dmitry; Mor, Amram; Yaron, Sima; Baasov, Timor

doi:10.1016/j.bmc.2008.08.053

Cited by 23 publications

(25 citation statements)

References 32 publications

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“…carbohydrates Schistosoma glycans TOF Complex type from eggs. Chemical synthesis ) Synthetic glycosides α-Amino acid esters with α-DManf side chain Synthesis and antiviral evaluation TOF (DHB) (Ali & AbdelRahman, 2008) Aminoglycosides TOF (CHCA) Synthesis of pseudodisaccharide, basicity and antibacterial activity (Chen, et al, 2008c) TOF (DHB) Arbutin glucosides Use of glucansucrase from Leuconostoc mesenteroides Aryl-β -D-galactopyranosides R-TOF (DHB) Use of phase-transfer catalyst (Kröger & Thiem, 2007) Biantennary glycan plus phospholipid TOF (THAP, DHB)…”

Section: Tetrasaccharide Phosphate Frommentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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Section: Tetrasaccharide Phosphate Frommentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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“…208 Furthermore, a decrease in basicity of the amino groups, as a result of neighbouring group effect, was shown to also influence AG toxicity. 209 …”

Section: New Ways To Alleviate Aminoglycoside Toxicitymentioning

confidence: 99%

New trends in the use of aminoglycosides

Fosso

2014

Med. Chem. Commun.

100

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Despite their inherent toxicity and the acquired bacterial resistance that continuously threaten their long-term clinical use, aminoglycosides (AGs) still remain valuable components of the antibiotic armamentarium. Recent literature shows that the AGs’ role has been further expanded as multi-tasking players in different areas of study. This review aims at presenting some of the new trends observed in the use of AGs in the past decade, along with the current understanding of their mechanisms of action in various bacterial and eukaryotic cellular processes.

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“…[16] The synthetic acyl donor 16 was synthesized as previously described. [17] The pseudo-disaccharides 1, [13] 2, 3 and 4 [15] along with the pseudo-trisaccharides 5-10 [13] and 11-14 [15] were prepared by reported strategies.…”

Section: Methodsmentioning

confidence: 99%

“…In parallel to this direction of research, we also strived towards the design of new derivatives of aminoglycosides with improved antibiotic performance. For this purpose, we designed the new pseudo-disaccharide scaffold 4 (also named NB23) [15] and its pseudo-trisaccharide derivatives 11-14 ( Figure 1). These structures contain a 3',4'-methylidene moiety as a defense against the action of various aminoglycoside phosphotransferase [APH(3')] and aminoglycoside nucleotidyltransferase [ANT(4')] resistance enzymes.…”

mentioning

confidence: 99%

Combined Chemical‐Enzymatic Assembly of Aminoglycoside Derivatives with N‐1‐AHB Side Chain

et al. 2008

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A series of unprotected pseudo-disaccharides and pseudo-trisaccharides of 2-deoxystreptamine-containing aminoglycosides have been selectively acylated at the N-1 position with the valuable (S)-4-amino-2-hydroxybutanoyl (AHB) pharmacophore by using the recombinant BtrH and BtrG enzymes from butirosin biosynthesis in combination with a synthetic acyl donor. The process was optimized by performing two enzymatic steps in a sequential manner without purification of the intermediate product.

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Structure–toxicity relationship of aminoglycosides: Correlation of 2′-amine basicity with acute toxicity in pseudo-disaccharide scaffolds

Cited by 23 publications

References 32 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

New trends in the use of aminoglycosides

Combined Chemical‐Enzymatic Assembly of Aminoglycoside Derivatives with N‐1‐AHB Side Chain

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