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PubMed1985

[Macrolide antibiotics: characteristics of their interaction with organoids, intracellular distribution and the effect of sulfalene].

Interaction of erythromycin and oleandomycin with isolated subcellular fractions of rat liver homogenates and intracellular distribution of the antibiotics were studied. It was found that the macrolides were bound by the cell organoids. The binding was partially reversible. The intracellular distribution was characterized by accumulation of erythromycin and oleandomycin in the mitochondrial fraction while erythromycin preserved higher activity in cytosol as compared to oleandomycin. Sulfalen induced redistribution of the macrolides. It decreased absorption of the macrolides by the organoids and increased the concentration of free erythromycin and especially oleandomycin in cytosol.

Animals↗
PubMed1962

Transduction of resistance to some macrolide antibiotics in Staphylococcus aureus.

Pattee, P. A. (Iowa State University, Ames) and J. N. Baldwin. Transduction of resistance to some macrolide antibiotics in Staphylococcus aureus. J. Bacteriol. 84:1049-1055. 1962.-By use of phage 80 of the International Typing Series, propagated on appropriate strains of Staphylococcus aureus, two related markers controlling resistance to certain macrolide antibiotics (erythromycin, oleandomycin, spiramycin, and carbomycin) were transduced among a variety of strains of S. aureus. Unlike the markers controlling penicillinase production and resistance to chlortetracycline and novobiocin, the determinants of resistance to the macrolide antibiotics were transduced at normal frequencies (at least 300 transductants per 10(9) phage) only to certain of the recipient strains. One of the markers studied appears to control an inducible enzyme system which is specifically induced by sub-inhibitory concentrations of erythromycin and which controls resistance to erythromycin, oleandomycin, spiramycin, and carbomycin. The other marker examined confers resistance to erythromycin, oleandomycin, spiramycin, and carbomycin, and shows no evidence of being dependent upon an inducible mechanism.

Anti-Bacterial Agents↗
PubMed1994

Characterisation of a Streptomyces antibioticus gene encoding a type I polyketide synthase which has an unusual coding sequence.

A gene (ORFB) from Streptomyces antibioticus (an oleandomycin producer) encoding a large, multifunctional polyketide synthase (PKS) was cloned and sequenced. Its product shows an internal duplication and a close similarity to the third subunit of the PKS involved in erythromycin biosynthesis by Saccharopolyspora erythraea, showing the equivalent nine active site domains in the same order along the polypeptide. An unusual feature of this ORF is the GC content of most of the sequence, which is surprisingly low, for a Streptomyces gene; the large number of codons with T in the third position is particularly striking. The last 800 bp of the gene stand out as being normal in their GC content, this region corresponding almost exactly to the thioesterase domain of the gene and suggesting that this domain was a late addition to the PKS. Based on the high degree of similarity between the ORFB product and the third subunit of the erythromycin PKS and the occurrence nearby of a gene conferring oleandomycin resistance, it is possible that this gene might be involved in the biosynthesis of the oleandomycin lactone ring.

Amino Acid Sequence↗
PubMed1992

Purification and characterization of macrolide 2'-phosphotransferase type II from a strain of Escherichia coli highly resistant to macrolide antibiotics.

The resistance mechanism of Escherichia coli BM2506 to macrolides was found to be due to inactivation. Inactivated oleandomycin was identified as oleandomycin 2'-phosphate by thin-layer chromatography. A new type of macrolide-phosphorylating enzyme, macrolide 2'-phosphotransferase type II (MPH(2')II), was detected, purified 95-fold and its enzymological properties investigated. MPH(2')II was a constitutive intracellular enzyme which showed high levels of activity with both 14-member-ring and 16-member-ring macrolides. The optimum pH for the inactivation of oleandomycin was 8.2 and the optimum temperature of the reaction was 40 degrees C. Enzyme activity was lost by heat treatment at 60 degrees C for 1 min. The isoelectric point and M(r) of the enzyme were 5.3 and 48,000, respectively. Purine nucleotides, such as ITP, GTP and ATP, were effective as cofactors in the inactivation of macrolides. An inhibitory effect of iodine, EDTA, or divalent cations on MPH(2')II activity was observed.

Anti-Bacterial Agents↗
PubMed1985

Structure-activity relation among macrolide antibiotics in initiation of interdigestive migrating contractions in the canine gastrointestinal tract.

The relation between the chemical structure of commercially available macrolide antibiotics and their activity in inducing interdigestive migrating contractions (IMC) was studied in conscious dogs. It was found that the 14-membered macrolides erythromycin and oleandomycin are active in inducing IMC in the stomach in association with the endogenous release of motilin. These erythromycin- and oleandomycin-induced contractions in the stomach migrated through the small intestine in a caudad direction. Conversely, 16-membered macrolide antibiotics such as leucomycin, acetylspiramycin, and tylosin do not induce any contractions in the stomach or stimulate endogenous release of motilin. These findings suggest that the IMC-inducing activity in macrolides seems to be closely related to their chemical configuration, i.e., the structure of 14-membered macrolides with dimethylaminosugar (desosamine) bound at C-5 and neutralsugar at C-3 in glycosidic linkage in parallel is likely to be necessary for IMC-inducing activity. The mechanisms by which erythromycin and oleandomycin stimulate endogenous motilin release are not known.

Animals↗
PubMed2000

Generation of hybrid elloramycin analogs by combinatorial biosynthesis using genes from anthracycline-type and macrolide biosynthetic pathways.

Elloramycin and oleandomycin are two polyketide compounds produced by Streptomyces olivaceus Tü2353 and Streptomyces antibioticus ATCC11891, respectively. Elloramycin is an anthracycline-like antitumor drug and oleandomycin a macrolide antibiotic. Expression in S. albus of a cosmid (cos16F4) containing part of the elloramycin biosynthetic gene cluster produced the elloramycin non-glycosylated intermediate 8-demethyl-tetracenomycin C. Several plasmid constructs harboring different gene combinations of L-oleandrose (neutral 2,6-dideoxyhexose attached to the macrolide antibiotic oleandomycin) biosynthetic genes of S. antibioticus that direct the biosynthesis of L-olivose, L-oleandrose and L-rhamnose were coexpressed with cos16F4 in S. albus. Three new hybrid elloramycin analogs were produced by these recombinant strains through combinatorial biosynthesis, containing elloramycinone or 12a-demethyl-elloramycinone (= 8-demethyl-tetracenomycin C) as aglycone moiety encoded by S. olivaceus genes and different sugar moieties, coded by the S. antibioticus genes. Among them is L-olivose, which is here described for the first time as a sugar moiety of a natural product.

Anthracyclines↗
PubMed1980

[Increase in the sensitivity and a simplification of the method for the separate determination of antibiotic activities in combined preparations (oletetrin) by using media with a varying pH value].

An agar-diffusion method for determination of oleandomycin and tetracycline low levels in solutions of the drug combination was developed. The medhod may be used for investigation of oletetrin absorption and distribution in humans and animals. It provides high accuracy in separate determination of oleandomycin and tetracycline activity in solutions of the drugs at a ratio of 1 : 2. The same test-culture, Bac. subtilis, variant L2 is used for the assay of tetracycline and oleandomycin activity. The only differences are in the values of pH and the buffer solution and the standards.

Bacillus subtilis↗
PubMed1982

Localization of genes coding for macrolide resistance on the penicillinase plasmid of isolates of an epidemic Staphylococcus aureus.

Genetic localization of gene(s) coding for erythromycin and oleandomycin resistance in five isolates of phage complex 52, 52A, 80, 81, multiple antibiotic resistant epidemic Staphylococcus aureus was studied. The 100% coelimination rate of erythromycin, oleandomycin, penicillin (penicillinase production) and certain heavy metal ion resistances from each of the clinical isolates and the 100% cotransduction rate of these resistance markers from two clinical isolates as well as changes in the partially purified extrachromosomal DNA patterns of the clinical wild types after elimination and the recipients after transduction indicated that erythromycin and oleandomycin resistance determining gene(s) resided on the penicillinase-heavy metal ion resistance plasmid in each of the isolates. The electrophoretic mobility of these macrolide-penicillinase-heavy metal ion resistance plasmids (MacPc plasmids) was the same in four strains and higher in one strain. These MacPc plasmids did not confer any resistance to spiramycin and lincomycin (even after induction) or to kanamycin, which features differentiate them from MacPc plasmids pI 258 and pTU 512 formerly identified in Staphylococcus aureus in Japan.

Erythromycin↗
PubMed1983

Formation of inactive cytochrome P-450 Fe(II)-metabolite complexes with several erythromycin derivatives but not with josamycin and midecamycin in rats.

The effects of some macrolides (4 mmoles . kg-1 p.o. daily for 4 days in vivo; 0.3 mM in vitro) on hepatic drug-metabolizing enzymes in rats were compared. One group of macrolides including previously studied compounds (oleandomycin, erythromycin and troleandomycin), as well as several other erythromycin derivatives, showed induction of microsomal enzymes and formation of inactive cytochrome P-450-metabolite complexes in vivo; this formation increased in the order: oleandomycin, erythromycin ethylsuccinate, erythromycin stearate, erythromycin itself, erythromycin propionate, erythromycin estolate and troleandomycin. Troleandomycin and, to a lesser extent, erythromycin and oleandomycin formed cytochrome P-450-metabolite complexes when incubated in vitro with 1 mM NADPH and microsomes from rats pretreated with troleandomycin or phenobarbital, but not with microsomes from control rats or rats treated with 3-methylcholanthrene. In contrast, two other macrolides, josamycin and midecamycin, showed no induction of microsomal enzymes and no detectable formation of cytochrome P-450-metabolite complexes in vivo. In vitro, these macrolides failed to form detectable complexes even with microsomes from rats pretreated with troleandomycin or phenobarbital. Hexobarbital sleeping time was unaffected by preadministration of josamycin or midecamycin (4 mmoles . kg-1 p.o.) 2 hr earlier; the in vitro activity of hexobarbital hydroxylase was not inhibited by 0.3 mM josamycin or midecamycin. We conclude that, unlike several erythromycin derivatives, josamycin and midecamycin do not form inactive cytochrome P-450-metabolite complexes in rats.

Animals↗
PubMed1999

Macrolide antibiotics, drug interactions and microsomal enzymes: implications for veterinary medicine.

The macrolide group of antibiotics includes natural members, pro-drugs and semi-synthetic derivatives, thus named because they are composed of a large aglycone ring (from 14 to 16 carbon atoms), to which are attached several sugars. Some of them are amino-sugars, containing a diethylamino, tertiary amine function. A number of antibiotics, including erythromycin, oleandomycin, triacetyl-oleandomycin (troleandomycin), carbomycin, spiramycin, tylosin, rosamicin, azithromycin, clarithromycin, dirithromycin and others, are members of this group. On a comparative basis, erythromycin and oleandomycin are similar, with the same basic 14-carbon lactone ring and side chain sugars. The remaining compounds contain a basic 15- or 16-carbon lactone ring and one or two side-chain sugars. Most of the macrolides are produced by Streptomyces spp bacteria. An exception is rosamicin, which is produced by Micromonospora. Clarithromycin and azithromycin are new semi-synthetic derivatives of erythromycin.

Animals↗
PubMed1985

In-vitro comparison of macrolides, lincosamides and synergistins on Neisseria gonorrhoeae.

The MIC of erythromycin, oleandomycin, spiramycin, josamycin, lincomycin and pristinamycin was determined for 100 strains of Neisseria gonorrhoeae isolated from cases of acute urethritis in men. The method of dilution in agar was used: blood agar with the addition of 'Polyvitex' and an innoculum of 10(3)-10(4) bacteria per spot. With respect to the break points defined by the C.F.A. all the strains of N. gonorrhoeae studied are sensitive to erythromycin, spiramycin, josamycin and pristinamycin, 12% strains are resistant to oleandomycin and 75% to lincomycin. The active antibiotics are classified as follows according to the active weight expressed by the MIC50: erythromycin, pristinamycin, 0.125 mg/l; josamycin, 0.5 mg/l; spiramycin, oleandomycin, 2 mg/l.

Anti-Bacterial Agents↗
PubMed1983

Biological conversion of erythronolide B, an intermediate of erythromycin biogenesis, into new "hybrid" macrolide antibiotics.

Transformation of erythronolide B to new antibiotics was attempted by feeding this compound during the fermentation of Streptomyces antibioticus ATCC31771, a blocked mutant of an oleandomycin producing strain. As a result, four new active compounds were obtained with hybrid structures between erythromycin and oleandomycin. They were identified as 3-O-oleandrosyl-5-O-desosaminyl-15-hydroxyerythronolide B (I), 3-O-oleandrosyl-5-O-desosaminylerythronolide B (II), 3-O-oleandrosyl-5-O-desosaminyl-(8S)-8-hydroxyerythronolide B (III) and 3-O-oleandrosyl-5-O-desosaminyl-(8R)-8,19-epoxyerythronolide B (IV). They were found to be less active, but more stable to acid, than erythromycin A. From their relative biogenetical relationship together with the structure elucidated some hypotheses about late stages of oleandomycin biosynthesis are inferred too.

Anti-Bacterial Agents↗
PubMed1989

Biological properties of ER 42859, a novel erythromycin derivative.

The antimicrobial activity of a new semi-synthetic oral erythromycin derivative, ER 42859, was evaluated in vitro and in vivo in comparison with erythromycin, spiramycin, josamycin, oleandomycin and the newer semi-synthetic derivatives flurithromycin, roxithromycin and A-56268. MIC values of ER 42859 were superior to those of roxithromycin, oleandomycin, josamycin and spiramycin but generally 2-fold poorer than those of erythromycin. The activity equalled that of erythromycin against Haemophilus influenzae and was superior to that of roxithromycin and A-56268 against this organism. MIC values of the compound were greatly influenced by pH due to the dibasic nature of the molecule. ER 42859 had markedly superior activity to erythromycin, spiramycin, josamycin, oleandomycin and flurithromycin against experimental infections in mice and similar activity to roxithromycin and A-56268. Blood and tissue levels were high and prolonged in rodents. In volunteers, blood levels were prolonged but inferior to those of erythromycin.

Animals↗
PubMed1977

[Experimental transmission of antibiotic resistance in chicks].

Multi-drug resistance of Salmonella heidelberg was transmitted to normal intestinal flora (E. coli organisms were resistant to ampicillin, streptomycin, tetracycline, erythromycin, and oleandomycin. The donor strains of Salmonella heidelberg used in the experiment was a carrier of the following nine markers of resistance: ampicillin, streptomycin, chloramphenicol, kanamycin, neomycin, novobiocin, tetracycline, erythromycin, and oleandomycin. The donor strains of Salmonella heidelberg used in the experiment was a carrier of the following nine markers of resistance: ampicillin, streptomycin, chloramphenicol, kanamycin, neomycin, novobiocin, tetracycline, erythromycin, and oeandomycin, novobiocin, tetracycline, erythromycin, and oleandomycin. The resistance to drugs was transmitted with the oral administration of the donor strain at the preliminary neutralization of the action of hydrochloric acid in the stomah secretion through sodium bicarbonate (1 cm3 of a 10 per cent sol.) an hour prior to feeding the birds with Salmonella heidelberg (1 cm3 of 10(10). In other experiments carboneum tetrachloratum was injected at rates of 0.08 to 0.15 cm3 (acocrting with the body weight of birds) one day prior to infection, followed by the administration of 0.20 to 0.40 cm3 of a 2 per cent solution of omnopon. Escherichia coli organisms acquired new markers of resistance--to chloramphenicol, kanamycin, neomycin and novobiocin. The level of resistance proved equal with that to the donor strain. A total of 1.8 to 5.4 per cent of the intestinal E. coli investigated proved to be carriers of the indicated markers of resitance. Highest level in acquiring markers of multi-drug resistance (13 per cent) showed E. coli organisms isolated from the liver of birds injected additionally with C. tetrachloratum omnopon.

Animals↗
PubMedDate not supplied

Effect of agar percentage, agar thickness, and medium constituents on antibiotics assay by disc diffusion method.

The factors affecting the sensitivity of nafcillin, vancomycin, oleandomycin, chloramphenicol, methacycline and novobiocin assay, using the paper disc diffusion method, were studied. Agar concentration and pour volume were found to influence the assay sensitivity of antibiotics. The type of assay medium was effective e.g. brain heart infusion agar was the best medium for nafcillin and methacycline; synthetic amino acid medium for oleandomycin; Muller Hinton agar for vancomycin and chloramphenicol; and G & R medium for novobiovicin. All additives, including inorganic ions, sugar, organic acids, complexing agents, surface active agents and blood, decreased the activities of the studied antibiotics. Higher activities of vancomycin, methacycline were observed at pH = 5, of nafcillin, chloramphenicol, and novobiocin at pH = 6, and of oleandomycin at pH = 7.

Agar↗
PubMed1996

Analysis of macrolide antibiotics by capillary electrophoresis.

Capillary electrophoresis was utilized in the study of the macrolide antibiotics (i.e. pharmaceutical glycoconjugates) clarithromycin, erythromycin, oleandomycin, troleandomycin, and spiramycin. In order to assist in analyte solubilization, two buffer systems using acetonitrile were developed. The first system involved 30 mM sodium cholate and 20% acetonitrile in 80 mM sodium phosphate, pH 6. This buffer permitted the baseline resolution of all five glycoconjugated antibiotics. In addition, erythromycin was separated from its derivatives estolate and ethylsuccinate. In the absence of surfactants, a higher acetonitrile quantity, 65%, was used in the second buffer system, with 35 mM sodium phosphate, pH 6. Selectivity between oleandomycin and clarithromycin was reversed in this system compared to the cholate buffer, indicating solute interaction with the cholate micelles in the previous system. Calibration linearity and detection sensitivity were improved in the high acetonitrile buffer, due to decreased background absorbance. It was demonstrated that both buffer systems can be utilized for the visualization of minor components that may be present in bulk pharmaceuticals.

Acetonitriles↗
PubMed2003

Comparative study of coulometric and amperometric detection for the determination of macrolides in human urine using high-performance liquid chromatography.

A high-performance liquid chromatography (HPLC) method using chromatographic conditions optimised in a previous work was applied for the separation of three macrolide antibiotics roxithromycin (Rox), oleandomycin (Ole) and rosamicin (Ros) and further determination of two of them, roxithromycin (Rox) and oleandomycin (Ole), in human urine samples. A comparative study of the behaviour of these macrolides under the two types of electrochemical detection (EC) widely coupled with HPLC, that is coulometric (EC-C) and amperometric (EC-A), was carried out by applying the same multiresidue method. From the assays performed using both detectors the comparison was made taking relevant criteria such as detection limits, linearity, recovery and precision values into account. As a result of this comparison, the coulometric detector appears slightly more suitable than the amperometric one for macrolide analysis.

Anti-Bacterial Agents↗
PubMed1988

Immunochemical similarity of P-450 HFLa, a form of cytochrome P-450 in human fetal livers, to a form of rat liver cytochrome P-450 inducible by macrolide antibiotics.

A protein immunochemically related to P-450 HFLa, a form of cytochrome P-450 purified from human fetal livers, was detected in rat liver microsomes. The content of the immunoreactive protein in rat liver microsomes was increased by treatments with phenobarbital, pregnenolone 16 alpha-carbonitrile (PCN), erythromycin, erythromycin estolate, and oleandomycin but not with 3-methylcholanthrene, imidazole, ethanol, isosafrole, josamycin, midecamycin, or miocamycin. The activity of erythromycin N-demethylase correlated with the content of the immunoreactive protein in rat liver microsomes (r = 0.72). In addition, anti-P-450 HFLa IgG inhibited erythromycin N-demethylase in liver microsomes from erythromycin- or oleandomycin-pretreated rats. Furthermore, the content of the immunoreactive protein highly correlated with that of P-450 PB-1, which is distinct from Waxman's terminology, and is one of the forms of PCN-inducible cytochrome P-450s (r = 0.95). From these results and the results reported so far, it seems possible that P-450 HFLa is one of the forms of cytochrome P-450 inducible by glucocorticoids.

Animals↗