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Contact Dermatitis Aug 1989A 48-year-old man became erythrodermatous after intramuscular administration of ribostamycin, an aminoglycoside antibiotic in the same family as neomycin. Patch tests...
A 48-year-old man became erythrodermatous after intramuscular administration of ribostamycin, an aminoglycoside antibiotic in the same family as neomycin. Patch tests were positive to ribostamycin and neomycin, as well as to mercurials. There was no mercurial preservative in the injection solution. A lymphocyte transformation test was positive for ribostamycin and tobramycin, but not for gentamycin. Diagnostic and structure-activity relationship aspects of the case are discussed.
Topics: Anti-Bacterial Agents; Dermatitis, Exfoliative; Drug Eruptions; Humans; Male; Middle Aged; Patch Tests; Ribostamycin
PubMed: 2530055
DOI: 10.1111/j.1600-0536.1989.tb04701.x -
Giornale Di Clinica Medica 1983
Clinical Trial
Topics: Adolescent; Adult; Aged; Anti-Bacterial Agents; Child; Child, Preschool; Clinical Trials as Topic; Drug Evaluation; Female; Humans; Male; Middle Aged; Otitis Media; Otitis Media, Suppurative; Ribostamycin
PubMed: 6357928
DOI: No ID Found -
Reproductive Toxicology (Elmsford, N.Y.) Apr 2009No information is currently available on the safety of the aminoglycoside ribostamycin in pregnancy. We aimed to study the pregnancy outcome of women inadvertently...
No information is currently available on the safety of the aminoglycoside ribostamycin in pregnancy. We aimed to study the pregnancy outcome of women inadvertently exposed to ribostamycin during the first trimester of pregnancy. In a prospective cohort study, 102 women inadvertently exposed to ribostamycin during the first trimester of pregnancy and an age- and gravidity-matched control group, were enrolled. Study outcomes were gestational age at birth, major and minor malformations, and birth weight. Fetal outcomes were evaluated in 85 women inadvertently exposed to ribostamycin during the first-trimester of pregnancy and in 170 control subjects. Newborns were clinically examined at birth by a neonatologist and by imaging studies if any suspicious abnormalities were noted. There were 4/85 (4.9%) babies born with major malformations in the exposed group and 3/170 (1.8%) in the control group (P=0.7). Gestational age at delivery, rate of minor anomalies, rate of preterm births, and birth weight were not different between groups. In conclusion, similar to what is reported for other aminoglycoside, exposure to ribostamycin during the first-trimester of pregnancy does not appear to increase the risk of adverse fetal outcomes.
Topics: Abnormalities, Drug-Induced; Adult; Anti-Bacterial Agents; Birth Weight; Case-Control Studies; Female; Gestational Age; Humans; Infant, Newborn; Maternal Exposure; Pregnancy; Pregnancy Outcome; Pregnancy Trimester, First; Prospective Studies; Ribostamycin; Risk Assessment
PubMed: 19162171
DOI: 10.1016/j.reprotox.2008.12.008 -
Talanta Jun 2024Characterization of aminoglycoside antibiotics like ribostamycin is important due to the complex composition and common toxic impurities. Aerosol detectors are often...
Characterization of aminoglycoside antibiotics like ribostamycin is important due to the complex composition and common toxic impurities. Aerosol detectors are often employed for determination of these non-absorbent analytes. In this work, a robust and cost-effective method was developed for simultaneous detection of ribostamycin and its related substances using high-performance liquid chromatography (HPLC) with a relative new aerosol detector named nano-quantity analyte detector (NQAD). With the introduction of less toxic but more compatible ion-pairs pentafluoropropionic acid (PFPA) and trifluoroacetic acid (TFA) in the eluent, an optimized separation effect was achieved. Compared with the other two aerosol detectors namely ELSD (evaporative light scattering detector) and CAD (charged aerosol detector), method verification and quantitative detection results revealed that NQAD had higher sensitivity than ELSD with a 0.8 μg/mL limit of detection, as well as wider linear range (from 2 μg/mL to 1000 μg/mL) than both CAD (from 2 μg/mL to 200 μg/mL) and ELSD (from 8 μg/mL to 200 μg/mL) detector. The performance of NQAD helped to realize detection of ribostamycin and its impurities with significant concentration differences in a single run. With a cation suppressor to eliminate the ion-suppression caused by the ion-pairs in the eluent, the structure of nine impurities in ribostamycin sample was characterized by liquid chromatography-mass spectrum (LC-MS). Both external standard and area normalization calculation were investigated, and NQAD obtained more accurate results due to its full-range linear response-to-concentration relationship, providing an alternative for routine quality control of multi analyte systems.
PubMed: 38852340
DOI: 10.1016/j.talanta.2024.126359 -
Molecules and Cells Aug 2005A cluster of genes for ribostamycin (Rbm) biosynthesis was isolated from Streptomyces ribosidificus ATCC 21294. Sequencing of 31.892 kb of the genomic DNA of S.... (Comparative Study)
Comparative Study
A cluster of genes for ribostamycin (Rbm) biosynthesis was isolated from Streptomyces ribosidificus ATCC 21294. Sequencing of 31.892 kb of the genomic DNA of S. ribosidificus revealed 26 open reading frames (ORFs) encoding putative Rbm biosynthetic genes as well as resistance and other genes. One of ten putative Rbm biosynthetic genes, rbmA, was expressed in S. lividans TK24, and shown to encode 2-deoxy-scyllo-inosose (DOI) synthase. Acetylation of various aminoglycoside-aminocyclitol (AmAcs) by RbmI confirmed it to be an aminoglycoside 3-N-acetyltransferase. Comparison of the genetic control of ribostamycin and butirosin biosynthesis pointed to a common biosynthetic route for these compounds, despite the considerable differences between them in genetic organization.
Topics: Acetylation; Aminoglycosides; Butirosin Sulfate; Chromatography, High Pressure Liquid; Drug Resistance, Bacterial; Models, Biological; Multigene Family; Ribostamycin; Streptomyces
PubMed: 16258246
DOI: No ID Found -
Protein Science : a Publication of the... Sep 2017Aminoglycoside antibiotics represent a classical group of antimicrobials first discovered in the 1940s. Due to their ototoxic and nephrotoxic side effects, they are...
Aminoglycoside antibiotics represent a classical group of antimicrobials first discovered in the 1940s. Due to their ototoxic and nephrotoxic side effects, they are typically only used against Gram negative bacteria which have become resistant to other therapeutics. One family of aminoglycosides includes such compounds as butirosin, ribostamycin, neomycin, and kanamycin, amongst others. The common theme in these antibiotics is that they are constructed around a chemically stable aminocyclitol unit referred to as 2-deoxystreptamine (2-DOS). Four enzymes are required for the in vivo production of 2-DOS. Here, we report the structure of RbmB from Streptomyces ribosidificus, which is a pyridoxal 5'-phosphate dependent enzyme that catalyzes two of the required steps in 2-DOS formation by functioning on distinct substrates. For this analysis, the structure of the external aldimine form of RbmB with 2-DOS was determined to 2.1 Å resolution. In addition, the structure of a similar enzyme, BtrR from Bacillus circulans, was also determined to 2.1 Å resolution in the same external aldimine form. These two structures represent the first detailed molecular descriptions of the active sites for those aminotransferases involved in 2-DOS production. Given the fact that the 2-DOS unit is widespread amongst aminoglycoside antibiotics, the data presented herein provide new molecular insight into the biosynthesis of these sugar-based drugs.
Topics: Bacterial Proteins; Escherichia coli; Models, Molecular; Protein Conformation; Pyridoxal Phosphate; Recombinant Proteins; Ribostamycin; Streptomyces; Transaminases
PubMed: 28685903
DOI: 10.1002/pro.3221 -
Gene Sep 1988The nucleotide sequence of an aminoglycoside phosphotransferase gene (rph) from Streptomyces ribosidificus (a ribostamycin producer) was determined. Molecular size,... (Comparative Study)
Comparative Study
The nucleotide sequence of an aminoglycoside phosphotransferase gene (rph) from Streptomyces ribosidificus (a ribostamycin producer) was determined. Molecular size, amino acid composition and N-terminal amino acid sequence of the purified rph product confirmed the position of the coding region deduced from the nucleotide sequence. The 5' region of rph has been tested for its transcriptional controls; high-resolution mung-bean nuclease mapping of in vivo transcripts revealed one major start point, rphS1, controlled by the rphP1 promoter. This transcript was also observed in vitro in run-off experiments using purified Streptomyces RNA polymerase. This transcriptional start point coincided with the translational start site, with the mRNA 5' terminus being pppATG. The results of promoter-probing tests and insertion of a transcriptional termination fragment into the rph promoter region have shown that the rphP1 transcript was sufficient and essential for rph expression.
Topics: Amino Acid Sequence; Base Sequence; Blotting, Northern; Genes; Genes, Bacterial; Molecular Sequence Data; Nucleic Acid Hybridization; Phosphotransferases; Phosphotransferases (Alcohol Group Acceptor); Plasmids; Promoter Regions, Genetic; Restriction Mapping; Sequence Homology, Nucleic Acid; Species Specificity; Streptomyces; Substrate Specificity
PubMed: 2851496
DOI: 10.1016/0378-1119(88)90031-5 -
Advances in Carbohydrate Chemistry and... 1974
Review
Topics: Aminoglycosides; Anti-Bacterial Agents; Butirosin Sulfate; Chemical Phenomena; Chemistry; Drug Resistance, Microbial; Gentamicins; Hygromycin B; Kanamycin; Neomycin; Paromomycin; Ribostamycin; Sisomicin; Streptomycin; Structure-Activity Relationship; Tobramycin
PubMed: 4143427
DOI: 10.1016/s0065-2318(08)60264-4 -
Chemical Record (New York, N.Y.) Feb 20162-Deoxystreptamine (2DOS) is the unique chemically stable aminocyclitol scaffold of clinically important aminoglycoside antibiotics such as neomycin, kanamycin, and... (Review)
Review
2-Deoxystreptamine (2DOS) is the unique chemically stable aminocyclitol scaffold of clinically important aminoglycoside antibiotics such as neomycin, kanamycin, and gentamicin, which are produced by Actinomycetes. The 2DOS core can be decorated with various deoxyaminosugars to make structurally diverse pseudo-oligosaccharides. After the discovery of biosynthetic gene clusters for 2DOS-containing aminoglycoside antibiotics, the function of each biosynthetic enzyme has been extensively elucidated. The common biosynthetic intermediates 2DOS, paromamine and ribostamycin are constructed by conserved enzymes encoded in the gene clusters. The biosynthetic intermediates are then converted to characteristic architectures by unique enzymes encoded in each biosynthetic gene cluster. In this Personal Account, we summarize both common biosynthetic pathways and the pathways used for structural diversification.
Topics: Actinobacteria; Aminoglycosides; Anti-Bacterial Agents; Hexosamines
PubMed: 26455715
DOI: 10.1002/tcr.201500210 -
Biomolecular NMR Assignments Apr 2010The neomycin-sensing riboswitch is an engineered riboswitch developed to regulate gene expression in vivo in the lower eukaryote Saccharomyces cerevisiae upon binding to...
The neomycin-sensing riboswitch is an engineered riboswitch developed to regulate gene expression in vivo in the lower eukaryote Saccharomyces cerevisiae upon binding to neomycin B. With a size of only 27nt it is the smallest functional riboswitch element identified so far. It binds not only neomycin B but also related aminoglycosides of the 2'-deoxystreptamine class with high affinity. The regulatory activity, however, strongly depends on the identity of the aminoglycoside. As a prerequisite for the structure determination of riboswitch-ligand complexes we report here the (1)H, (15)N, (13)C and partial (31)P chemical shift assignments for the minimal functional 27nt neomycin sensing riboswitch RNA in complex with the 4,5-linked neomycin analog ribostamycin and the 4,6-linked aminoglycoside tobramycin.
Topics: Carbon Isotopes; Hydrogen; Nitrogen Isotopes; Nuclear Magnetic Resonance, Biomolecular; Phosphorus Isotopes; Protein Engineering; RNA, Fungal; RNA, Messenger; Regulatory Sequences, Ribonucleic Acid; Ribostamycin; Saccharomyces cerevisiae; Tobramycin
PubMed: 20306311
DOI: 10.1007/s12104-010-9223-z