Erythromycin. XII.<sup>1</sup> The Isolation, Properties and Partial Structure of Erythromycin C

Wiley, Paul F.; Gale, Richard M.; Pettinga, C. W.; Gerzon, Koert

doi:10.1021/ja01579a061

Cited by 43 publications

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“…3H-EM had been purified twice by cellulose column chromatography in accordance with the method of Pettinga et al [14] or Wiley et al [24], and applied to the following experiment. Tritium labeled EM (15 mCi/mmole) was diluted tenfold with unlabeled EM.…”

Section: Accumulation Of 3h-em or 3h-jmmentioning

confidence: 99%

Decrease in Accumulation of Macrolide Antibiotics as a Mechanism of Resistance in Staphylococcus aureus

Yamagishi

Nakajima

Inoue

et al. 1971

Japanese Journal of Microbiology

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A marked difference of levels of accumulation of macrolide antibiotics (Mac) was found between Mac-sensitive (E642-1 and 209P) and Mac-resistant (M5642, MS57, U9, and 606) strains of Staphylococcus aureus by means of qualitative and quantitative bioassay methods. Though the levels of accumulation of the antibiotics in cells of Mac-resistant strains were only one-tenth that of the Mac-sensitives, satisfactory evidence for a relationship between the accumulation of the antibiotics and the degree of sensitivity to those drugs was established in a physiological sense from a kinetic measurement of Ks and v in the accumulation reaction of the antibiotics in the cells. The experiments with tritiated erythromycin or josamycin also support these results. It is suspected, by estimation of the accumulation in heated or UV-irradiated cells, that levels of accumulation of the antibiotics in cells of S. aureus could be reflected by a binding affinity of their ribosomes for these antibiotics. There was no system for inactivating the antibiotics seen in the cells of the Mac-resistants, i.e., MS642, 606, and U9.

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Section: Accumulation Of 3h-em or 3h-jmmentioning

confidence: 99%

Decrease in Accumulation of Macrolide Antibiotics as a Mechanism of Resistance in Staphylococcus aureus

Yamagishi

Nakajima

Inoue

et al. 1971

Japanese Journal of Microbiology

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“…During the determination of the structure of erythromycin A (14), it has been found that related products like erythromycin B (15) and erythromycin C (13) were also produced by Streptomyces erythreus. Recent analytical methods, like gas-liquid chromatography (11) and especially high-pressure liquid chromatography (10), have shown that these compounds were present in commercial samples of erythromycin.…”

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confidence: 99%

Antibacterial activities of erythromycins A, B, C, and D and some of their derivatives

Kibwage¹,

Hoogmartens²,

Roets³

et al. 1985

Antimicrob Agents Chemother

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The MICs of erythromycins A, B, C, and D and some of their derivatives were determined against 21 gram-positive and 15 gram-negative microorganisms. Antibacterial activity was confined to gram-positive and very few gram-negative bacteria. Erythromycin B was somewhat less active than erythromycin A, and erythromycin C and D showed about half that activity or even less. Most other derivatives had negligible activity. Determination of potency by diffusion and turbidimetric assays were in line with MICs. The examination of the results of these assays, however, revealed that there are differences between the data of different laboratories, depending on the microorganisms and conditions used.

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“…Erythromycin was initially reported in 1952 as the fermentation product of Streptomyces erythreus, an organism now reclassified as Saccharopolyspora erythraea (27,28). It was isolated as a complex comprised of one major and two minor factors labeled, respectively, as erythromycin A, B, and C ( Figure 1) (29,30). Erythromycin A has a core lactone (erythronolide A) to which is attached the aminosugar desosamine at C-5-OH and the neutral sugar cladinose at C-3-OH (31).…”

Section: Fourteen-membered Ring Macrolide Antibioticsmentioning

confidence: 99%

Macrolide Antibiotics

Kirst

2015

Kirk-Othmer Encyclopedia of Chemical Technology

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Macrolide antibiotics are one of the larger classes of fermentation‐derived natural products. In addition, many semisynthetic derivatives have been synthesized. They treat infections caused by most Gram‐positive bacteria, some susceptible Gram‐negative bacteria, and atypical bacteria such as Mycoplasma pneumoniae and Legionella pneumophila . They are orally bioavailable and accumulate in tissues and organs. They are regarded as one of the safest groups of antibiotics. Erythromycin is a 14‐membered ring macrolide and foremost member of the class. First‐generation derivatives focused on deficiencies such as compound instability in acidic environments, bitter taste, low water solubility, low oral bioavailability, and gastrointestinal and cardiac side effects. Many of these problems were at least partly solved by first‐generation derivatives such as esters and salts that made the active entities less prone to degradation. Second‐generation derivatives chemically changed substituents on the aglycone to stabilize it from intramolecular decomposition. This group includes clarithromycin and azithromycin that have become the most important macrolides to date. The problem of bacterial resistance to antibiotics was elegantly addressed by the ketolides. Telithromycin (Ketek®) was the first ketolide (third generation of erythromycin derivatives) to be approved and marketed, but postmarketing surveillance uncovered side effects and its use has been restricted. Macrolides are also important veterinary antibiotics and three new agents have been developed. Studies have continued to search for new agents using combinatorial biosynthesis, but the generation of large numbers of novel polyketides remains unfulfilled at this time.

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Erythromycin. XII.¹ The Isolation, Properties and Partial Structure of Erythromycin C

Cited by 43 publications

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Decrease in Accumulation of Macrolide Antibiotics as a Mechanism of Resistance in Staphylococcus aureus

Decrease in Accumulation of Macrolide Antibiotics as a Mechanism of Resistance in Staphylococcus aureus

Antibacterial activities of erythromycins A, B, C, and D and some of their derivatives

Macrolide Antibiotics

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Erythromycin. XII.1 The Isolation, Properties and Partial Structure of Erythromycin C

Cited by 43 publications

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Decrease in Accumulation of Macrolide Antibiotics as a Mechanism of Resistance in Staphylococcus aureus

Decrease in Accumulation of Macrolide Antibiotics as a Mechanism of Resistance in Staphylococcus aureus

Antibacterial activities of erythromycins A, B, C, and D and some of their derivatives

Macrolide Antibiotics

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Erythromycin. XII.¹ The Isolation, Properties and Partial Structure of Erythromycin C