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At least 19 recordsLinked to original sources
PubMed1989

[Oleandomycin and its natural and synthetic analogs. II. Structure and properties of oleandomycin B, a new compound of the oleandomycin group].

The revealed regularities of mass spectroscopic disintegration of oleandomycin and its derivatives made it possible to determine analytic criteria for identification of compounds related by their structure to oleandomycin. Analysis of the extracts from oleandomycin fermentation broth filtrates on the basis of the selected group of diagnostic ions showed that along with the main antibiotic there formed during the biosynthesis oleandomycin B, a structurally close minor component. The structure of the substance was assigned and its physico-chemical and biological properties were studied.

Chemical Phenomena↗
PubMed1989

[Oleandomycin and its natural and synthetic analogs. I. Dissociative ionization of oleandomycin and its derivatives].

Regularities of dissociative ionization of compounds belonging to the oleandomycin group were studied. Mass spectra of oleandomycin and some of its derivatives including anhydrooleandomycin, oleandomycin chlorhydrine, desoleandomycin, oleandomycin oxide, trimethylsilyl and acetyl derivatives were analyzed comparatively. Directions of disintegration with breakage of the glycoside bonds, macrolactone and carbon cycles were detected. The data are useful in structural analysis of not described oleandomycin-related compounds formed during biosynthesis and isolation of the main product.

Chemical Phenomena↗
PubMed1987

Resistance to oleandomycin in Streptomyces antibioticus, the producer organism.

Resistance to oleandomycin in Streptomyces antibioticus, the producer organism, was studied. The organism was highly resistant in vivo to the antibiotic but sensitive to other macrolides and lincosamides. Protein synthesis in vivo by mycelium of S. antibioticus was more resistant to oleandomycin than that by mycelium of Streptomyces albus G, an oleandomycin-sensitive strain, and this resistance was dependent on the age of the culture, older mycelium of S. antibioticus being more resistant to oleandomycin than young mycelium. [3H]Oleandomycin was capable of binding to the same extent to the 50S subunits of the ribosomes of both organisms. Oleandomycin also inhibited in vitro protein synthesis by ribosomes obtained from an oleandomycin-production medium at the time when maximum levels of oleandomycin were being produced. A clear difference between the ability of the two organisms to incorporate exogenous oleandomycin was observed. Thus, while S. albus G took up oleandomycin, S. antibioticus showed a decreased permeability to the antibiotic, suggesting a role for cell permeability in self-resistance.

Bacterial Proteins↗
PubMed1984

Synthesis and biological activities of 4"-deoxy-4"-sulfonamido-oleandomycin derivatives.

Chemical modification of the macrolide antibiotic oleandomycin (C-1) is described. Reductive amination of 11-acetyl-4"-deoxy-4"-oxo-oleandomycin (C-6) with ammonium acetate provides amino-oleandomycin derivative C-7 in which the 4"-amine is oriented in the axial configuration. The structure-activity relationship of a series of 4"-sulfonamide analogs prepared from amino-oleandomycin derivative C-7 is discussed. Noteworthy is the significant in vitro potency enhancement of the para-chlorobenzenesulfonamide analog C-12 over that of the parent oleandomycin. The absolute configuration of the 4"-amino-oleandomycin derivative C-7 was established through X-ray analysis of the para-iodobenzenesulfonamide analog C-14.

Animals↗
PubMed1977

[The clinical effect of antibiotics in the macrolide family on bronchial asthma. Non-antimicrobial actions of oleandomycin [author's transl)].

Non-antimicrobial actions of oleandomycin (triacetyloleandomycin and oleandomycin phosphate) were studied in patients with bronchial asthma. Twenty-one cases of the disease without associating infections entered the study, and they were given 750mg of oleandomycin or triacetryloleandomycin in three divided doses daily for two weeks. Clinical manifestations and laboratory findings were compared to assess the effectiveness of the antibiotic therapy between the three 2-week periods before, during and after the therapy. Improvements in clinical manifestations were attained in 11 of 21 cases (52.3%), and last after discontinuance of the therapy in 8(38.1%). The blood level of 11-OHCS as determined by the Demoorr's fluorescence method increased by greater than 20% at the end of thearpy in 7 of 18 cases (38.9%). In 5 of the 7 cases favorable responses were seen clinically to the oleandomycin therapy. The serum IgE level determined by the radioimmunosorbent test was compared before and after the therapy to reveal that oleandomycin caused decrease of IgE in 10 and increase in 9 of 20 cases examined. The oleandomycin therapy resulted increases by greater than 20% of the vital capacity and FEV 1.0 in 2 and 3, respectively, of 15 cases. Jaundice in association with elevations of the GOT, GPT and alkaline phosphatase developed in one patient, and generalized skin eruption in another. Both of these cases were given triacetyloleandomycin.

11-Hydroxycorticosteroids↗
PubMed1985

[Inhibition of oleandomycin biosynthesis by glucose].

The results of the study on the effect of glucose and various carbohydrates on biosynthesis of oleandomycin by Streptomyces antibioticus are presented. It was found that glucose added at the beginning or by the 48th hour of the fermentation process on the complex medium inhibited oleandomycin biosynthesis. To investigate the mechanism of the glucose effect, a fermentation medium was developed. It provided variation of the carbohydrate composition, determination of the protein content in the culture and evaluation of the mycelium productivity. With the use of this medium it was shown that monosaccharides such as galactose, fructose and glucose significantly activated the mycelium growth as compared to lactose and sucrose. At the same time glucose completely inhibited oleandomycin biosynthesis when added either as an only carbohydrate component or in combination with galactose or fructose, while the presence of the other two monosaccharides did not prevent antibiotic production, though the mycelium productivity was lowered as compared to that with the use of the disaccharide. Therefore, the inhibitory effect of glucose on biosynthesis of oleandomycin was not connected with activation of the culture growth by it. Acidification of the medium on cultivation of the streptomycete in the presence of glucose only partially explained its inhibitory effect, since inhibition was maintained on the medium with addition of CaCO3 which stabilizes pH. Addition of 2-deoxy-D-glucose, a nonmetabolized glucose analog, to the fermentation medium retarded antibiotic production. It is possible that the inhibitory effect of glucose on biosynthesis of oleandomycin is not associated with its metabolism.

Culture Media↗
PubMed1965

The international standard for oleandomycin.

At the request of the WHO Expert Committee on Biological Standardization a batch of oleandomycin was submitted to an international collaborative study in six laboratories situated in four countries. In this study the material was assayed by plate diffusion methods, which varied in details of technique and design, against the US Food and Drug Administration's reference preparation for oleandomycin. On the basis of the results obtained the material has been established as the International Standard for Oleandomycin and the International Unit of Oleandomycin is defined as the activity in 0.001176 mg of the International Standard. The US Food and Drug Administration's standard and the International Standard are each part of the same parent batch of oleandomycin and the validity of such an assay has been compared with the more usual assay situation when there is some degree of difference between the preparations under comparison.

Biological Assay↗
PubMed1976

[Study of the growth patterns of Act. antibioticus and the biosynthesis of oleandomycin].

The study of some regularities of the oleandomycin-producing organism growth during the first stage of cultivation showed that an increase in the ammount of starch in the medium from 2 to 10 per cent promoted the growth and its specific rate. When the organism was cultivated on media with 2--6 per cent of starch, addition of ammonium sulfate in a concentration of 0.25--0.5 per cent was favourable for its growth. When the amount of starch was 8--10 per cent, ammonium sulfate in a concentration of 0.25--1.5 per cent had almost no effect on the growth and its specific rate. It was found that an increase in the amount of starch in the medium without ammonium sulfate promoted the mycelium growth and oleandomycin biosynthesis by 20 per cent, the time of cultivation being prolongated. Ammonium sulfate significantly stimulated the mycelium growth and decreased biosynthesis of oleandomycin. Additional introduction of starch solution in a concentration of 1 or 2 per cent during the first hours of the culture growth (24 hours) on the medium with 2 per cent of starch stimulated the growth, its specific rate and biosynthesis of oleandomycin by 20--30 per cent and the cultivation time increased. Simulataneous addition of starch and ammonium sulfate to the culture during the first hours of the growth (24 hours) decreased the biosynthesis of oleandomycin. The maximum respiration rate of the culture in flasks was registered in 24 hours, then it was followed by a decrease. Addition of starch and ammonium sulfate during the cultivation process, i.e. in 24, 48 and 72 hours increased every time the rate of the organism respiration.

Ammonium Sulfate↗
PubMed1977

[Effect of successive cyclic administration of oleandomycin and tetracycline on the immunogenic reactivity and indices of non-specific bodily resistance in experimental staphylococcal sepsis].

The effect of subsequent cyclic administration of oleandomycin and tetracycline on the titer of the complement, the content of lysozyme, the bactericidal properties of the serum and the presence of the antibiotic specific antibodies in the blood serum found in the Hoigne reaction were studied on rabbits. It was found that the subsequent cyclic administration of the antibiotics to both the intact animals and the animals with experimental staphylococcal sepsis was accompanied by an increase in the titer of the complement only on the 7th day of administration of oleandomycin, the first antibiotic. The subsequent administration of tetracycline and especially discontinuation of the antibiotics use resulted in a significant, stable and prolonged decrease in the complement titer. The cyclic subsequent administration of oleandomycin and tetracycline for 7 days was accompanied by an increase in the lysozyme content and serum bactericidal properties. Changes in the factors of non-specific resistance under the effect of the subsequent cyclic administration of oleandomycin and tetracycline on both the intact animals and the animals with experimental staphylococcal sepsis were accompanied by an appearance, progressive increase and prolonged preservation in the serum of the antibiotic specific antibodies found in the Hoigne reaction. A possibility of producing specific antibodies simultaneously to the 2 antibiotics, i. e. oleandomycin and tetracycline in their administration in subsequent 7-day cycles was shown.

Animals↗
PubMed1990

Biosynthesis of oleandomycin by Streptomyces antibioticus: influence of nutritional conditions and development of resistance.

The influence of different nutritional compounds on oleandomycin biosynthesis by Streptomyces antibioticus was studied, resulting in the design of a chemically defined medium for production of the antibiotic. Of the variety of carbon and nitrogen compounds tested, fructose and aspartic acid (carbon and nitrogen sources, respectively) supported the highest oleandomycin titres. Addition of propionate but not acetate, both precursors of the skeleton of the macrolide lactone ring, stimulated the biosynthesis of the antibiotic. Oleandomycin biosynthesis was repressed by glucose but not by phosphate. S. antibioticus develops oleandomycin resistance shortly before the antibiotic begins to be synthesized, showing a triphasic pattern of resistance: spores and producing mycelium are resistant, while non-producing mycelium is sensitive.

Amino Acids↗
PubMed1992

Role of glycosylation and deglycosylation in biosynthesis of and resistance to oleandomycin in the producer organism, Streptomyces antibioticus.

Cell extracts of Streptomyces antibioticus, an oleandomycin producer, can inactivate oleandomycin in the presence of UDP-glucose. The inactivation can be detected through the loss of biological activity or by alteration in the chromatographic mobility of the antibiotic. This enzyme activity also inactivates other macrolides (rosaramicin, methymycin, and lankamycin) which contain a free 2'-OH group in a monosaccharide linked to the lactone ring (with the exception of erythromycin), but not those which contain a disaccharide (tylosin, spiramycin, carbomycin, josamycin, niddamycin, and relomycin). Interestingly, the culture supernatant contains another enzyme activity capable of reactivating the glycosylated oleandomycin and regenerating the biological activity through the release of a glucose molecule. It is proposed that these two enzyme activities could be an integral part of the oleandomycin biosynthetic pathway.

Anti-Bacterial Agents↗
PubMed1990

[Kinetics of thermal inactivation of oleandomycin in aqueous and native alkaline solutions].

The process of oleandomycin inactivation in aqueous alkaline solutions with their heating was studied by using the microbiological method of the antibiotic content assay. The initial specific rate of inactivation of crystalline oleandomycin in buffer solutions and oleandomycin in the fermentation broth filtrate was evaluated. It was shown that the inactivation was retarded by the reaction products and the components of the fermentation broth filtrate. The production rate of oleandomycin anhydro derivatives amounting to 3-40 per cent of the total mass of the inactivation product was estimated by UV spectrophotometry.

Alkalies↗
PubMed1978

[Distribution of oleandomycin between the native broth and butylacetate depending on the biosynthesis conditions].

Distribution of the active substance contained in the fermentation broth of Act. antibioticus between the acqueous phase and butylacetate depended on the fermentation conditions and the procedure for the fermentation broth treatment before filtration. Increase in pH values during the fermentation process resulted in lower antibiotic distribution coefficients which may be explained by the presence of oleandomycin-X, a biologically active substance in the fermentation broth filtrates. This substance differed from oleandomycin and did not pass into butylacetate from the acqueous alkaline solution. For transference of oleandomycin-X into oleandomycin exposition of the fermentation broth filtrate at pH 5.0--5.5 is required.

Acetates↗
PubMed1977

[Study of the equilibrium conditions for the extractive purification of oleandomycin].

Dependence of the oleandomycin distribution coefficient on the antibiotic concentration, duration of the filtrate storage, extraction temperature and salting-out agents was studied. The distribution coefficient of oleandomycin in the system of fermentation broth filtrate--butylacetate was much lower (about 3 times) than that in the system of oleandomycin phosphate aqueous solution--butylacetate. Addition of sodium sulfate to the aqueous phase provided a significant increase in the oleandomycin distribution coefficient.

Acetates↗
PubMed1978

Enhancement by oleandomycin of the inhibitory effect of methylprednisolone on phytohemagglutinin-stimulated lymphocytes.

Triacetyloleandomycin (TAO) and its parent compound oleandomycin have a "steroid-sparing" effect in asthmatic patients. This study was designed to determine whether oleandomycin would enhance the inhibitory action of glucocorticosteroids in suppressing the blast transformation of phytohemagglutinin-stimulated human lymphocytes. Although oleandomycin could not be shown to inhibit the phytohemagglutinin stimulation of lymphocytes, there was a significant potentiation of steroid suppression at each concentration of methylprednisolone examined. This augmentation of glucocorticosteroid suppression of lymphocyte proliferation in vitro appears to support the clinically observed "steroid-sparing" effect of TAO and therefore its usefulness may not be limited to asthma and bronchitis.

Adult↗