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PubMed1994

[A quantitative determination of inducibility by 14 membered ring macrolide antibiotics in inducible resistant Staphylococcus aureus to macrolide-lincosamide-streptogramin B antibiotics].

Using Staphylococcus aureus ISP447 strain, which shows inducible resistance to macrolide-lincosamide-streptogramin B (MLS) antibiotics, the extent of MLS-resistance induced by several macrolide antibiotics [erythromycin (EM), oleandomycin (OL), or roxithromycin (RXM)] was determined in terms of a relative ratio of a growth rate of the induced cells in the presence of a challenging drug, rokitamycin (RKM), to that of uninduced cells in the absence of RKM. The ratio was referred to as a relative inducibility (%). The inducibility was obtained at an optimum-induced condition by considering the following factors: (1) exponentially growing cells, (2) the optimum concentration of an inducer drug, i.e., 50, 150, and 150 ng/ml for EM, OL, and RXM, respectively, (3) a 3-h previous incubation at 37 degrees C in the presence of the inducer, and (4) 300 ng of RKM/ml, which is found to be optimum for induced cells to challenge, because of having no inducer activity. Using these qualification methods, inducibilities of EM, OL, and RXM as an inducer were 100.4, 27.9 and 81.1%, respectively. This method is allowed to be useful for the analysis of a structure-inducibility relationship.

Anti-Bacterial Agents↗
PubMed2000

[Study of macrolide, lincosamide, and streptogramin B antibiotics resistance in Staphylococcus aureus].

Macrolide antibiotics (Mac) consist of a 12- to 16-membered lactone ring combined with a sugar moiety, and they inhibit protein synthesis via binding to 23S ribosomal RNA in bacteria. The 14- and 16-membered Mac are used for treating infectious diseases caused by Gram-positive and other bacteria; e.g., Haemophilus influenzae, Bordetella pertussis, Legionella pneumophila, Campylobacter, Treponema pallidum and Mycoplasma. Resistance to macrolide, lincosamide, and streptogramin-B (MLS) antibiotics in staphylococci is known to have the following mechanisms: 1) alteration of the target on ribosome due to dimethylation of a specific adenine residue in the 23S ribosomal RNA by the product of the erm gene, and consequently a decrease in binding of MLS antibiotics; 2) inactivation of streptogramin-B (STG-B) and lincosamide by the products of the sbh (encoding streptogramin B hydrolase) and linA' (encoding 3-lincomycin 4-clindamycin O-nucleotidyltransferase) genes, respectively; and 3) active efflux of Mac and STG-B antibiotics determined by the msrA and msrB genes in Staphylococcus epidermidis and Staphylococcus xylosus, respectively, both of which appear to act as an ATP-dependent efflux pump. I have shown that Staphylococcus aureus 8325(pEP2104) exhibits inducible resistance to PMS (partial macrolide and streptogramin B)-antibiotics [the 14-membered macrolides, erythromycin (EM), and oleandomycin (OL), and the 16-membered macrolide mycinamicin (MCM) and STG-B]. The sequence of the N-terminal amino acid residues of a 63 kDa protein (MsrSA) that appeared in the membrane of PMS-resistant strains was identical to that of an MsrA polypeptide related to enhanced efflux of [14C]EM. Ribosomes from PMS-resistant strains showed a similar affinity for EM to those from the PMS-sensitive host strain NCTC8325, and no inactivation of EM by 8325(pEP2104) was observed. In the present study, I showed the DNA sequence of the msrSA region on the constitutive PMS-resistant plasmid pMC38, PMS-inducible resistant plasmid pEP2104 and PMS-sensitive mutant plasmid pSP6, and the region that is essential for inducible expression in PMS resistance. In addition, I investigated the relationship between PMS resistance and intracellular accumulation of EM.

ATP-Binding Cassette Transporters↗
PubMed1981

Studies on nitrosamine formation by the interaction between drugs and nitrite. II. Hepatotoxicity by the simultaneous administration of several drugs and nitrite.

The alterations of biochemical parameters, namely, glutamic oxaloacetic transaminase and glutamic pyruvic transaminase in serum, hepatic microsomal drug oxidation systems, glucose-6-phosphate dehydrogenase and lysozomal enzymes in hepatic soluble fraction were investigated for the purpose of semiquantitatively estimating the hepatotoxicity caused by the interaction of several drugs and sodium nitrite in rats. The simultaneous administration of aminopyrine and sodium nitrite induced the alterations of these parameters. However, these alterations were not induced by the administration of antipyrine and sodium nitrite. Therefore the alterations were thought to be mainly due to N-nitrosodimethylamine formed. The administration of 0.4 mmole/kg of aminopyrine and 1.0 mmole/kg of sodium nitrite was thought to induce the alterations to almost the same extent as induced by 0.15 mmole/kg of N-nitrosodimethylamine. The simultaneous administrations of sodium nitrite and several other drugs with tertiary amino groups, namely oxytetracycline, diphenhydramine, oleandomycin, erythromycin and minocycline induced small alterations of these parameters. However, these alterations were not thought to relate to the hepatic injury induced by N-nitrosodimethylamine. Therefore the amount of N-nitrosodimethylamine formed from these drugs in rats was thought to be rather small. We also investigated the effect of several antioxidants on the alterations of biochemical parameters induced by aminopyrine and sodium nitrite. Ascorbic acid, sodium erythorbate and propyl gallate inhibited these alterations. On the other hand, sorbic acid did not.

Aminopyrine↗
PubMed2005

Nucleotide deoxysugars: essential tools for the glycosylation engineering of novel bioactive compounds.

The irreversible spread of new resistance mechanisms against existing therapeutical antibiotics has led to the development of technologies and strategies for the glycosylation engineering of novel antibiotics. Amino-, C-branched and O-methylated 6-deoxyhexoses play a favourite role in the biosynthesis of clinically important antibiotics like tylosin, erythromycin or oleandomycin and are essential for the antibiotic activity. They are transferred onto the aglycon by glycosyltransferases using dTDP-activated deoxyhexoses. The in vitro biochemical characterization of the biosynthetic enzymes and the glycosyltransferases are, however, hampered due to the poor synthetic access to dTDP-activated deoxysugars and their biosynthetic intermediates. The overcoming of the poor availability of dTDP-activated sugars was the target of several researchers to fulfil their distinct aims with these sugars which were mostly involved in the synthesis of different biological active compounds. Several completely different strategies were used in the past years to improve the availability of dTDP-activated deoxysugars, varying from complete enzymatic synthesis via syntheses using reaction technology for yield optimization to full organic synthesis or shortcuts like the decomposition of commercially available antibiotics and later chemical activation of the sugar moieties. This review gives a survey of the synthesis of dTDP-activated sugars by chemical and chemoenzymatic approaches and discusses the promiscuity of glycosyltransferases to evaluate the chances for applying them for the production of new bioactive compounds. It summarizes the most important enzymes in the field of synthesis using biosynthetic pathway enzymes and describes solutions for occurring challenges during application. Finally, this review will give a survey about the availability of dTDP-activated sugars in sufficient scale and will also point at important sugars which are still bottlenecks and difficult to synthesize and therefore should become a target for enhanced research efforts.

Anti-Bacterial Agents↗
PubMed1989

Metabolism of dihydroergotamine by a cytochrome P-450 similar to that involved in the metabolism of macrolide antibiotics.

1. Previous studies have shown that the macrolide antibiotics, such as oleandomycin and erythromycin, enhance their own transformation into a stable metabolite-cytochrome P-450 complex, thus impairing monooxygenase activity. This cytochrome P-450 induced by macrolides is similar to the major form induced in rats by pregnenolone-16 alpha-carbonitrile (PCN) (III A1 isozyme). 2. The cytochrome P-450 isozyme induced in rats by PCN or macrolide antibiotics bound dihydroergotamine (DHE) with high affinity and was also capable of metabolizing the drug. However, phenobarbital administration enhanced the metabolism of DHE to a greater extent than would be expected from the levels of the PB-PCNE isoenzyme, indicating that other cytochrome P-450 proteins may also be involved in DHE metabolism. 3. DHE metabolism was inhibited by macrolide antibiotics both ex vivo and in vitro. The metabolite-cytochrome P-450 complex formed by the antibiotics impairs the metabolism of DHE, so that when the complex is dissociated the metabolic activity is restored. These findings explain the observed clinical interactions between macrolides and other drugs, and such an approach may prove useful in their prediction.

Animals↗
PubMed2004

Distribution and characterization of Campylobacter spp. from Russian poultry.

The distribution of Campylobacter spp. on 13 poultry farms (broiler chicken, quail, pheasant, peacock, and turkey) from eight regions (Vladimir, Vologda, Voronezh, Kaluga, Liptsk, Moscow, Orenburg, and Orel) in Russia was surveyed. Intestinal materials were plated onto Campylobacter-selective medium and plates were incubated microaerobically at 42 degrees C for 24 or 48 h. Identification was based on colonial morphology, microscopic examination, and biochemical tests; latex agglutination assays were used for confirmation. In total, 116 isolates were derived from 370 samples. Isolation rates were similar, regardless of whether the birds were from small or large broiler production farms. Susceptibility of 48 representative (from these production sources) strains of Campylobacter spp. to 38 antimicrobial compounds was determined by disk diffusion assays. All strains tested were sensitive to amikacin, gentamycin, sisomycin, chloramphenicol, imipenem, oleandomycin, erythromycin, azitromycin, and ampicillin. The strains were also sensitive to 100 microg/disk of carbenicillin, fluoroquinolones, and to nitrofurans. Fluoroquinolone sensitivity was most notable and may be related to its limited application in poultry production within Russia. Hippurate and ribosomal RNA gene primers were developed and used to distinguish Campylobacter jejuni and Campylobacter coli and to provide a measure of strain discrimination. The combination of PCR analysis and randomly amplified polymorphic DNA (RAPD) typing were conducted for selected isolates. The various poultry species and the different locations yielded Campylobacter isolates with discrete randomly amplified polymorphic DNA patterns. The distribution and substantial diversity of Campylobacter spp. isolates appears similar to that previously reported in other countries.

Animals↗
PubMed1975

Transduction of drug resistance to tetracycline, chloramphenicol, macrolides, lincomycin and clindamycin with phages induced from Streptococcus pyogenes.

Strains of Streptococcus pyogenes isolated from pediatric patients with acute infections which were resistant to one or more of the antibiotics, tetracycline (TC), chloramphenicol (CP), macrolide antibiotics (erythromycin, kitasamycin, oleandomycin, josamycin), lincomycin (LCM) and clindamycin (CLM), were used for transduction of drug resistance. These drug-resistant strains were treated with mitomycin C to induce phages and transduction of drug resistance was attempted by means of phages so induced. It was found that transduction of resistance to the above antibiotics was possible. The transductants obtained on TC-containing selective agar plate were resistant to TC alone while those produced on CP- or erythromycin (EM)-containing selective agar plate were resistant to CP, macrolide antibiotics (Mac), LCM and CLM. From this finding, it was inferred that transduction of resistance to TC, CP, Mac, LCM and CLM via phages occurred in two different patterns, i.e., transfer of resistance to TC alone and that of resistance to CP, Mac, LCM and CLM. All of the transductants obtained were found to belong to group A. In T-typing, they were of the same T-12 type as the donor and recipient strains in a majority of cases though some were not typable.

Anti-Bacterial Agents↗
PubMed1977

Mode of action of the protein, SP127, which enhances the activity of macrolide antibiotics against Pseudomonas aeruginosa.

Antibiotics, the activity of which enhanced against Pseudomonas aeruginosa by SP127, were restricted to the basic macrolide antibiotics such as erythromycin, maridomycin and oleandomycin, the neutral macrolide antibiotics such as lankamycin and lankacidin C, vancomycin and enramycin. Synergistic activity of SP127 with the above antibiotics was found against Pseudomonas aeruginosa and several strains of Escherichia coli, but not against Proteus vulgaris and macrolide-resistant Staphylococcus aureus. SP127 had extremely weak proteolytic but no lytic activity. From the isotopic experiments, the action of SP127 was partially attributed to the promotion of antibiotic penetration to cells of Pseudomonas aeruginosa.

Anti-Bacterial Agents↗
PubMed1979

In vitro actions of some antibiotics on phospholipases.

The effects of some antibiotics on activities of phospholipase A2, B and C were investigated in vitro. Tetracyclines, macrolides, chloramphenicol and carbenicillin inhibited the activity of Crotalus adamanteus phospholipase A2 towards phospholipids of egg-yolk emulsions. When the ability to inhibit the activity of Penicillium notatum phospholipase B towards mixed micelles of phosphatidylcholine and Triton X-100 was investigated, polymyxin B was found to be inhibitory while chloramphenicol and carbenicillin were found to stimulate the activity of the phospholipase. The activity of Bacillus cereus phospholipase C towards the mixed micelles was inhibited by bleomycin, oleandomycin and chloramphenicol.

Carbenicillin↗
PubMed1996

Microbial glycosylation of macrolide antibiotics by Streptomyces hygroscopicus ATCC 31080 and distribution of a macrolide glycosyl transferase in several Streptomyces strains.

In the course of our microbial transformation study on erythromycin derivatives, Streptomyces hygroscopicus ATCC 31080, which produces a polyether antibiotic carriomycin, was found to transform erythromycin derivatives to their inactivated derivatives. The structures of inactivated derivatives prepared by enzyme reaction using the cell extract, UDP-glucose (or UDP-galactose) and Mg2+ (or Mn2+) were elucidated on the basis of analysis of thei spectral data to be the compounds glycosylated at C-2' of a desosamine moiety, indicating that the enzyme is a macrolide glycosyl transferase (MGT). The MGT activity of cell extract from S. antibioticus ATCC 11891, a producing organism of oleandomycin, could be distinguished from that of ATCC 31080, based on the ability to glycosylate tylosin. We examined 32 actinomycete strains producing such polyketides as macrolide and polyether antibiotics, and found that 15 strains of Streptomyces have macrolide glycosyl transferase activity. It suggests that the MGTs have been distributed among at least polyketide producing Streptomyces strains.

Anti-Bacterial Agents↗
PubMed1999

[Epidemiological studies on drug-resistance patterns, coagulase types, and MRSA-phage types of MRSA isolates during 1990-1994].

We examined drug-resistance patterns, coagulase types, and MRSA-phage types of 125 MRSA strains isolated from clinical specimens during the period of January 1990 and December 1994. No vancomycin-resistant strain was isolated. Twenty one antibiotics were divided into three classes, low-intermediate- and high-isolation-frequency class, based on isolation frequencies of resistant strains. Minocycline, chloramphenicol, streptomycin, and imipenem were found to be included in low-isolation-frequency class (16.8-40%). In intermediate-isolation-frequency class (45.6-62.9%), cefmetazole, amikacin, gentamicin, and tetracycline were included. Oxacillin, ampicillin, piperacillin, ceftizoxime, cefoperazone, cefazolin, erythromycin, oleandomycin, kitasamycin, clindamycin, kanamycin, tobramycin, and ofloxacin belonged to high-isolation-frequency class (97.6-100%). MIC90s of vancomycin and minocycline (1.56 and 25 micrograms/ml) were lower than that of other 13 drugs. Comparing medical ward with dental ward, imipenem-, gentamicin-, and minocycline-resistant strains at medical ward, chloramphenicol- and streptomycin-resistant strains at dental ward were isolated dominantly on each ward, MRSA isolates were classified to 39 types by drug-resistance patterns. The isolation frequencies of coagulase type II and type IV strains were 65.6% and 29.6%, respectively. At dental ward, the isolation frequency of coagulase type IV strains was higher than that of coagulase type II strains during 1990-1992. However, coagulase type II strains were isolated considerably more than type IV strains during 1993-1994. By MRSA-phage typing, MRSA isolates were grouped into 18 MRSA-phage types. One hundred and twenty five MRSA isolates were divided into 56 types by using drug-resistance patterns, coagulase typing, and MRSA-phage typing. It was considered that such classification in combination of three methods is useful to make decision of epidemic by the same MRSA strain.

Anti-Bacterial Agents↗
PubMedDate not supplied

[Formation of erythromycin resistance in Corynebacterium diphtheriae induced by long-term effect of the antibiotic].

Erythromycin resistance induced in Corynebacterium diphtheriae strains by subinhibitory concentrations of this antibiotic has been investigated. Six strains of C. diphtheriae highly susceptible to erythromycin were grown in the broth with 0.5 minimal inhibitory concentration (MIC). After 23-25 cultivations the susceptibility to erythromycin in the strains tested began to decrease gradually. After 46-52 consequent cultivations the strains became moderately resistant, and after 60-72 ones 5 cultures became resistant. The induced resistance to erythromycin was associated with that to oleandomycin. The strains of C. diphtheriae with induced resistance had no changes in morphology of colonies, saccharolytic and adhesive properties and toxigenicity, but their growth was slower than that of the original strains.

Animals↗
PubMed2000

[Macrolides: pharmacology and clinical use].

Members of macrolides are Erythromycin, Oleandomycin, Spiramycin, Roxithromycin, Josamycin, Midecamycin, Clarithromycin, Azithromycin and Dirithromycin. This review present mechanism of action, pharmacokinetic, adverse drug reactions and main clinical uses of the macrolides.

Anti-Bacterial Agents↗
PubMed1976

[Sensitivity of Mycoplasma hominis cultures isolated from clinical material to certain antibiotics].

Sensitivity to II antibiotics of 80 strains of M. hominis isolated from patients with various inflammatory processes of the urogenital tract was studied by the method of suppressing the metabolic activity. Inhibition of the arginine metabolism of mycoplasma was used as a test for determination of the growth suppression. All the strains tested were highly sensitive to tetracycline and lincomycin. Kanamycin and neomycin were less active against M. hominis. All the strains tested were resistant to erythromycin, oleandomycin, ristomycin, novobiocin and streptomycin. The inhibitory effect of tetracycline and lincomycin on M. hominis decreased by the 5th day.

Anti-Bacterial Agents↗
PubMed1992

[Antibacterial activity of rokitamycin against fresh clinical isolates].

We obtained bacterial strains which were clinically isolated and identified from outpatients with various infections in medical institutions throughout Japan. Possible antibacterial activities of rokitamycin (RKM) were examined against these isolates. Minimum inhibitory concentrations (MICs) were determined through a comparative study with reference drugs. The results of the study are summarized as follows. 1. Resistance patterns of 400 isolates which were highly resistant to macrolides (MLs) with MIC values > 100 micrograms/ml were classified into 55 patterns. Staphylococcus spp. showed cross resistance to 14-membered ring MLs with 100% cross resistance observed between erythromycin (EM) and clarithromycin (CAM), and 85.2% between EM and oleandomycin (OL). Fewer isolates showed strong resistance to 16-membered ring MLs than to 14-membered ring MLs. Cross resistances observed among the Staphylococcus isolates were 100% between acetylmidecamycin (MDM-AC) and kitasamycin (leucomycin (LM)), 93.9% between MDM-AC and josamycin (JM), and 53.3% between MDM-AC and RKM. Streptococcus spp. and Peptococcus spp. showed very similar resistance patterns to both 14- and 16-membered ring MLs, but resistance patterns to RKM were quite different. Most of anaerobic streptococci and Bacteroides fragilis group had similar resistance patterns to 14- and 16-membered ring MLs, but in some cases a pattern similar to that of Staphylococcus spp. was observed. 2. When ML-resistant bacteria isolated during 1975 to 1980 were compared to those isolated in 1986 and 1989, it was observed that resistance of Staphylococcus aureus remained almost unchanged, that of Streptococcus pyogenes was lower in the later years than during 1975 to 1980, but that of Streptococcus pneumoniae increased. 3. Most of ML-resistances of the resistant isolates were inducible, but extents of induction varied depending on drugs tested. Strong inductions were observed when 14-membered ring MLs were used, but inductions were minimal with 16-membered ring MLs. RKM appeared to induce resistance to the least extent. From these results, it appears that the RKM is quite useful clinically even in the 1990s.

Bacterial Infections↗
PubMed1976

In vitro susceptibility and resistance of animal staphylococci to macrolide antibiotics and related compounds.

Strains of Staphylococcus aureus isolated from poultry, pigs and cases of bovine mastitis and strains of S. hyicus isolated from pigs were examined for their susceptibility of the macrolides and other related antibiotics. The susceptibility of these strains to erythromycin, oleandomycin, tylosin, spiramycin, lincomycin, clindamycin, virginiamycin, and its components virginiamycin S and M, was tested by the quantitative plate dilution method. With S. aureus, 3 p. 100 of the bovine, 12 p. 100 of the avian and 53 p. 100 of porcine isolated were found to be resistant. With S. hyicus strains 76 p. 100 were found to be resistant. Most resistant strains showed the generalized constitutive macrolide-resistance type. Twelve p. 100 of the porcine S. aureus strains were resistant to the virginiamycin component M.

Anti-Bacterial Agents↗
PubMedDate not supplied

Cytochrome P-450 3A enzymes are responsible for biotransformation of FK506 and rapamycin in man and rat.

The hepatic cytochrome P-450 responsible for metabolism of the structurally related macrolides FK506 and rapamycin in humans was identified using in vitro studies. FK506 and rapamycin metabolism was significantly correlated with nifedipine oxidation in human liver microsomes of eight different individuals. Immunoinhibition with anti-P450 3A4 abolished almost all FK506 and rapamycin metabolite formation. Inactivation of P450 3A4 by incubation of human liver microsomes with triacetyl oleandomycin (50 microM) or gestodene (10 microM) inhibited metabolism of FK506 and rapamycin. In liver microsomes from dexamethasone-treated rats FK506 and rapamycin metabolism was increased compared to liver microsomes from uninduced, phenobarbital-, or 3-methylcholanthrene-induced rats. FK506 and rapamycin were metabolized by reconstituted recombinant human liver P450 3A4. It is concluded that in human and rat liver FK506 and rapamycin are metabolized primarily by cytochrome P-450 3A4.

Animals↗
PubMed1992

Effects of macrolide antibiotics on gastrointestinal motility in fasting and digestive states.

The effect of macrolide antibiotics on gastrointestinal motility was studied in unanaesthetized dogs by using strain-gauge transducers. Midecamycin acetate, leucomycin, josamycin and acetylspiramycin, which are 16-membered macrolides, did not affect the gastrointestinal motility and no symptoms of gastrointestinal disorder were observed. On the other hand, erythromycin, roxithromycin, clarithromycin and oleandomycin, which are 14-membered macrolides, caused giant contraction and disorder symptoms. Moreover, it was found that the glycosidic linkages of the lactone ring were necessary for a structure to exert strong contractile activity.

Animals↗