Aminoglycosides: Activity and Resistance
Antimicrobial Agents and ChemotherapyPublished 1 April 1999Open access
Marie‐Paule Mingeot‐Leclercq, Y. Glupczynski, Paul M. Tulkens
Citations1,098
SJR quartileQ1
SJR score1.43
SNIP1.10
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TL;DR
Aminoglycosides are highly potent, broad-spectrum antibiotics with many desirable properties for the treatment of life-threatening infections and have a history marked by the successive introduction of a series of milestone compounds.
Abstract
Aminoglycosides are highly potent, broad-spectrum antibiotics with many desirable properties for the treatment of life-threatening infections ([28][1]). Their history begins in 1944 with streptomycin and was thereafter marked by the successive introduction of a series of milestone compounds (
Keywords
Immunology and MicrobiologyMedicineBiochemistry, Genetics and Molecular Biology
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33 Citations1994Matsuhisa Inoue, Masato Nonoyama +2 more
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Aminoglycoside resistance mechanisms from recent studies were compared with those found in earlier studies in the USA and Europe for three pathogen groups and different genes which produce different proteins with the same aminoglycosid-modifying activity are now known are presented.
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Results suggest that resistance to low levels of tobramycin was due to formation of a complex between the enzyme and the antibiotic.
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His residues are not required for aminoglycoside phosphorylation by APH(3')-IIIa, and the conserved His 188 is thus not a phosphate accepting residue but does seem to be important for proper enzyme folding.
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One compound, 6'-N-L-Ala-netilmicin (9a), showed a 2-fold decrease of inhibitory potency compared to its parent drug, and a conformational analysis revealed that it adopts two equally probable conformations and orientations when interacting with phosphatidylinositol.
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25 Citations1975David Loebenberg, Mae Counelis +1 more
The antibiotic appears to have promise as an anticestode agent, being more active than paromomycin against Hymenolepis nana and active as a single oral dose at low levels against Taenia spp.
BiochemistryActive-Site Labeling of an Aminoglycoside Antibiotic Phosphotransferase (APH(3')-IIIa)
23 Citations1994Geoffrey A. McKay, Renée A. Robinson +2 more
The importance of the N-terminal region of APHs in ATP binding, a region of these enzymes which has heretofore not been considered for involvement in substrate binding, is established.
The Journal of AntibioticsAMINOGLYCOSIDE ANTIBIOTICS. II.
23 Citations1973TAKAYUKI NAITÔ, Susumu Nakagawa +7 more
The present paper describes the two configurational isomers of BB-K8, which bear the DL- and D-HABA residue at the C-l amino group of kanamycin A, as well as the three positional isomers, which are acylated with L- HABA at theC-3, C-6' and C-3" amino groups of kanamicin A.
The Journal of AntibioticsAMINOGLYCOSIDE ANTIBIOTICS. III
22 Citations1973HLROSHI TSUKIURA, Kei-Ichi Fujisawa +7 more
The bioactive degradation products from butirosins and the semi-synthesis ofbutirosin analogs are reported and it is reported that these products are similar to those reported in this paper.
Antimicrobial Agents and ChemotherapyCloning and characterization of an aminoglycoside 6'-N-acetyltransferase gene from Citrobacter freundii which confers an altered resistance profile
21 Citations1997H Y Wu, George H. Miller +3 more
Hybridization studies performed with an intragenic probe specific for aac(6')-In indicate that this gene is prevalent within Venezuela but has not been observed outside of the country.
Journal of Carbohydrate ChemistrySynthesis of Amino Acid Derivatives of Neamine and 2-Deoxystreptamine to be used as Mutasynthons
21 Citations1991Minas P. Georgiadis, Violetta Constantinou‐Kokotou +1 more
Journal of Carbohydrate ChemistrySynthesis of 2′,3′-Dideoxy-2′-Fluorokanamycin A
20 Citations1985Tsutomu Tsuchiya, Yoshiaki Takahashi +3 more
Carbohydrate ResearchA synthesis of 3′,4 dideoxykanamycin B
19 Citations1976Toshiaki Miyake, Tsutomu Tsuchiya +2 more
Carbohydrate ResearchSynthesis of 5-deoxy-5-fluoro and 5-deoxy-5,5-difluoro derivatives of kanamycin B in its analogs. Study on structure-toxicity relationships
18 Citations1992Tetsuo Shitara, Yoshihiko Kobayashi +2 more
These 5-deoxy-5-fluoro and 5- deoxy- 5,5-difluoro derivatives showed markedly decreased toxicity as compared with the parent compounds.
Epidemiology and InfectionUrinary isolates of apramycin-resistant<i>Escherichia coli</i>and<i>Klebsiella pneumoniae</i>from Dublin
18 Citations1995Alan P. Johnson, M. Malde +3 more
Genetic linkage between the gene encoding AAC(3)IV and genes encoding resistance to ampicillin and either tetracycline or trimethoprim means that the relatively widespread use of these antimicrobial agents provides a selective pressure for the persistence of resistance to apramycin and gentamicin even in the absence of bacterial exposure to aminoglycosides.
Carbohydrate ResearchA synthetic study of methyl 3-deoxy-3-fluoro-α-d-glucopyranosides from methyl 2,3-anhydro-α-d-allopyranosides, and synthesis of 3′-deoxy-3′-fluorokanamycin A and 3′-chloro-3′-deoxykanamycin A
17 Citations1992Eijiro Umemura, Tsutomu Tsuchiya +2 more
Carbohydrate ResearchSynthesis of 3′-deoxy-3′-fluorokanamycin A and 3′,4′-dideoxy-3′-fluorokanamycin A
17 Citations1991Yoshiaki Takahashi, Tsutomu Tsuchiya +2 more
3',4'-Dideoxy-3'-fluorokanamycin A (22) has been prepared from 12 through selective 4'-chlorodeoxygenation, a key reaction and both 14 and 22 were more active than 3'-deoxykanamycin C against both sensitive and resistant bacteria.
Journal of Medicinal ChemistryNew derivatives of kanamycin B obtained by modifications and substitutions in position 6''. 2. In vitro and computer-aided toxicological evaluation with respect to interactions with phosphatidylinositol
16 Citations1991M. P. Mingeot-Leclercq, Ann Van Schepdael +5 more
The 6''-Deoxy-6''-chlorokanamycin B was the only derivative showing both a decrease and a decrease of inhibitory potency toward phospholipase A1 associated with the maintenance of a satisfactory microbiological activity (actually equal or slightly better than that of kanamycinB).
Journal of Medicinal ChemistryNew derivatives of kanamycin B obtained by combined modifications in positions 1 and 6". Synthesis, microbiological properties, and in vitro and computer-aided toxicological evaluation
15 Citations1991Ann Van Schepdael, Roger Busson +6 more
The structural differences between gentamicins and kanamycins play an important, still undescribed role both in their effective recognition by aminoglycoside-inactivating enzymes, and also in the interactions with phospholipids, which in turn cause nephrotoxicity.
Carbohydrate ResearchSynthesis of low-toxicity, 5-deoxy-5-fluoro and 5-deoxy-5,5-difluoro derivatives of arbekacin and its analogs, and study of structure-toxicity relationships
13 Citations1993Tsutomu Tsuchiya, Tetsuo Shitara +5 more
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