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Molecules and Cells Jan 2009Amino acid homology analysis predicted that rbmD, a putative glycosyltransferase from Streptomyces ribosidificus ATCC 21294, has the highest homology with neoD in...
Amino acid homology analysis predicted that rbmD, a putative glycosyltransferase from Streptomyces ribosidificus ATCC 21294, has the highest homology with neoD in neomycin biosynthesis. S. fradiae BS1, in which the production of neomycin was abolished, was generated by disruption of the neoD gene in the neomycin producer S. fradiae. The restoration of neomycin by self complementation suggested that there was no polar effect in the mutant. In addition, S. fradiae BS6 was created with complementation by rbmD in S. fradiae BS1, and secondary metabolite analysis by ESI/MS, LC/MS and MS/MS showed the restoration of neomycin production in S. fradiae BS6. These gene inactivation and complementation studies suggested that, like neoD, rbmD functions as a 2-N-acetlyglucosaminyltransferase and demonstrated the potential for the generation of novel aminoglycoside antibiotics using glycosyltransferases in vivo.
Topics: Anti-Bacterial Agents; Genes, Bacterial; Genetic Complementation Test; Genetic Engineering; Glycosyltransferases; Microbial Sensitivity Tests; Multigene Family; Mutation; Neomycin; Ribostamycin; Sequence Analysis, DNA; Spectrometry, Mass, Electrospray Ionization; Streptomyces
PubMed: 19214437
DOI: 10.1007/s10059-009-0008-0 -
The Journal of Antibiotics Feb 1984The three protected sisamine derivatives 2i, 2j and 3, with a free 5-hydroxyl group, have been synthesized. Glycosylation at the 5 position with various pentofuranose...
The three protected sisamine derivatives 2i, 2j and 3, with a free 5-hydroxyl group, have been synthesized. Glycosylation at the 5 position with various pentofuranose derivatives yielded after deprotection of the 6a approximately i ribostamycin related aminoglycoside. These pseudotrisaccharides showed only low antibacterial activities with respect to the parent compounds.
Topics: Anti-Bacterial Agents; Oligosaccharides; Ribostamycin; Trisaccharides
PubMed: 6706851
DOI: 10.7164/antibiotics.37.150 -
The Japanese Journal of Antibiotics Dec 1980Ribostamycin is an aminoglycoside antibiotic produced by Streptomyces ribosidificus, and extracted and isolated by NIIDA et. al. It has been used widely clinically with...
Ribostamycin is an aminoglycoside antibiotic produced by Streptomyces ribosidificus, and extracted and isolated by NIIDA et. al. It has been used widely clinically with its characteristic of low ototoxicity. UMEMURA et al. studied the pharmacokinetics of this antibiotic in animals and reported that it has a similar pharmacokinetic behavior in vivo to kanamycin. In the present studies, the pharmacokinetic behavior of ribostamycin was studied in 5 healthy adult volunteers receiving different doses (0.5 g, 1.0 g and 1.5 g) by intramuscular injection, and 0.5 g by intravenous drip infusion. In addition, a similar study was conducted with 11 patients with varying degrees of renal dysfunction in order to study the application of ribostamycin in such patients.
Topics: Adult; Aged; Anti-Bacterial Agents; Female; Humans; Infusions, Parenteral; Injections, Intramuscular; Kidney Diseases; Kinetics; Male; Middle Aged; Ribostamycin
PubMed: 7241802
DOI: No ID Found -
Colloids and Surfaces. B, Biointerfaces Apr 2018Ribostamycin is a broad-spectrum aminoglycoside antibiotic with a molecular weight of 454.5 g/mol. Under neutral pH conditions, ribostamycin is highly positive charged...
Ribostamycin is a broad-spectrum aminoglycoside antibiotic with a molecular weight of 454.5 g/mol. Under neutral pH conditions, ribostamycin is highly positive charged because it carries multiple amino groups in its structure. Negatively charged citrate ligand capped-gold nanoparticles (AuNPs) have been studied extensively for their interactions with a wide range of biomolecules including proteins, carbohydrates, and small drug compounds. These studies are aimed at developing new therapeutics and diagnostics by exploiting the unique properties of gold nanoparticles. Under this general aim, we studied the interaction between ribostamycin and AuNPs. Using a suite of analytical techniques including dynamic light scattering (DLS), UV-vis absorption spectroscopy, and dark field optical microscope imaging (DFM), we analyzed the mixture products of AuNPs with various sizes and ribostamycin under different concentrations. Our study revealed for the first time that ribostamycin has a tendency to self-assemble into linear oligomers at increased concentrations (above 250-500 μM). Such self-assembled oligomers then interact with negatively charged AuNPs to produce rod-like AuNP assemblies. Similar findings were observed from another structurally related aminoglycoside antibiotic, amikacin. It is technically challenging to detect and characterize oligomer formation of small molecules. It is especially challenging when the interactions that are holding the oligomers are not very strong. Through their interaction with gold nanoparticles that have exceptionally strong light scattering properties, we were able to observe the self-assembling of ribostamycin and amikacin in solution using various spectroscopic and microscopic techniques. This concentration-dependent self-assembling behavior of ribostamycin and amikacin may have direct relevance to the antibiotic effect of ribostamycin, amikacin and other structurally similar antibiotics.
Topics: Amikacin; Aminoglycosides; Anti-Bacterial Agents; Gold; Metal Nanoparticles; Models, Molecular; Particle Size; Ribostamycin; Spectrophotometry, Ultraviolet
PubMed: 29413595
DOI: 10.1016/j.colsurfb.2018.01.027 -
British Journal of Audiology May 1982The pharmacokinetics of ribostamycin in serum and perilymph of guinea pigs was studied after a single s.c. injection of 400 mg/kg or 14 daily injections of the same...
The pharmacokinetics of ribostamycin in serum and perilymph of guinea pigs was studied after a single s.c. injection of 400 mg/kg or 14 daily injections of the same dose. The repetitive administration of ribostamycin did not produce functional impairment of the kidney and ototoxicity was slight. The pharmacokinetic data were analysed by non-linear least mean squares regression. Ribostamycin did not accumulate in either serum or perilymph after multiple dosing. The half-life of the drug in perilymph was 15.8 h after a single injection, but 7.6 h after the last of 14 injections. The area under the ribostamycin concentration in perilymph against time curve was also reduced after multiple dosing. These changes were found to be due to a marked increase in the rate of transfer of the drug from perilymph to serum after multiple dosing.
Topics: Animals; Anti-Bacterial Agents; Dose-Response Relationship, Drug; Ear, Inner; Guinea Pigs; Half-Life; Kidney; Kinetics; Labyrinthine Fluids; Perilymph; Regression Analysis; Ribostamycin
PubMed: 7093568
DOI: 10.3109/03005368209081453 -
The Journal of Antibiotics Jan 1975A new inactivated product of ribostamycin (SF-733), 3-N-carboxymethyl ribostamycin, was obtained from the broth of Streptomyces ribosidificus which was grown on a medium...
A new inactivated product of ribostamycin (SF-733), 3-N-carboxymethyl ribostamycin, was obtained from the broth of Streptomyces ribosidificus which was grown on a medium containing D-xylose. Detection and some biochemical mechanism of N-carboxymethylation were discussed, and structure of 3-N-carboxymethyl ribostamycin was proposed based on the chemical degradation and synthesis.
Topics: Anti-Bacterial Agents; Chemical Phenomena; Chemistry; Methylation; Ribostamycin; Streptomyces; Xylose
PubMed: 1126867
DOI: 10.7164/antibiotics.28.48 -
International Journal of Tissue... 1982Ribostamycin ototoxicity was tested in a group of 28 albino guinea-pigs of both sexes, body-weight about 250-450 g with auricular Prayer's reflex present. The mounting... (Comparative Study)
Comparative Study
Ribostamycin ototoxicity was tested in a group of 28 albino guinea-pigs of both sexes, body-weight about 250-450 g with auricular Prayer's reflex present. The mounting of the cochlea on a metal support and the scanning electron microscope observations are described, The cochleacytogram of the group treated daily with 200 mg/kg ten days consecutively is comparable to that of the non-treated group.
Topics: Animals; Anti-Bacterial Agents; Cochlea; Female; Guinea Pigs; Hair Cells, Auditory; Hair Cells, Auditory, Inner; Labyrinth Supporting Cells; Male; Microscopy, Electron, Scanning; Organ of Corti; Ribostamycin
PubMed: 7084999
DOI: No ID Found -
The Journal of Antibiotics Jun 1983
Topics: Anti-Bacterial Agents; Glucosamine; Magnetic Resonance Spectroscopy; Ribostamycin; Streptomyces; Structure-Activity Relationship
PubMed: 6874597
DOI: 10.7164/antibiotics.36.749 -
Molecules (Basel, Switzerland) May 2017Phosphoramidite building blocks of ribostamycin ( and ), that may be incorporated at any position of the oligonucleotide sequence, were synthesized. The building blocks,...
Phosphoramidite building blocks of ribostamycin ( and ), that may be incorporated at any position of the oligonucleotide sequence, were synthesized. The building blocks, together with a previously described neomycin-modified solid support, were applied for the preparation of aminoglycoside-2'--methyl oligoribonucleotide fusions. The fusions were used to clamp a single strand DNA sequence (a purine-rich strand of c-Myc promoter 1) to form triple helical 2'--methyl RNA/DNA-hybrid constructs. The potential of the aminoglycoside moieties to stabilize the triple helical constructs were studied by UV-melting profile analysis.
Topics: Aminoglycosides; DNA, Single-Stranded; Humans; Oligoribonucleotides; Promoter Regions, Genetic; Proto-Oncogene Proteins c-myc
PubMed: 28481305
DOI: 10.3390/molecules22050760 -
Angewandte Chemie (International Ed. in... Jun 2023The synthetic neomycin-sensing riboswitch interacts with its cognate ligand neomycin as well as with the related antibiotics ribostamycin and paromomycin. Binding of...
The synthetic neomycin-sensing riboswitch interacts with its cognate ligand neomycin as well as with the related antibiotics ribostamycin and paromomycin. Binding of these aminoglycosides induces a very similar ground state structure in the RNA, however, only neomycin can efficiently repress translation initiation. The molecular origin of these differences has been traced back to differences in the dynamics of the ligand:riboswitch complexes. Here, we combine five complementary fluorine based NMR methods to accurately quantify seconds to microseconds dynamics in the three riboswitch complexes. Our data reveal complex exchange processes with up to four structurally different states. We interpret our findings in a model that shows an interplay between different chemical groups in the antibiotics and specific bases in the riboswitch. More generally, our data underscore the potential of F NMR methods to characterize complex exchange processes with multiple excited states.
Topics: Neomycin; Riboswitch; Ligands; Anti-Bacterial Agents; Aminoglycosides
PubMed: 36970768
DOI: 10.1002/anie.202218064