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Macrolide antibiotics — Spiramycin, Carbomycin, Angolamycin, Methymycin and Lancamycin

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Antibiotics

Abstract

The term macrolide has been applied to members of a group of structurally related antibiotics produced by species of streptomyces. All macrolide antibiotics (Woodward, 1957) contain a large lactone ring (aglycone of 12 to 22 atoms) which contain few double bonds and no nitrogen atoms; they have one or more sugars which can be amino sugars, non-nitrogenous sugars or both. In the widest sense however, the term macrolide has been ascribed to all the antibiotics containing a large lactone ring; in this sense the polyene antibiotic and antibiotics of streptogramin A and streptogramin B groups can be also termed macrolides. This article will be restricted to the “classical” macrolides of Woodward (1957) and related compounds discovered after 1957.

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References

  • Anliker, R., u. K. Gubler: Stoffwechselprodukte von Actinomyceten. Die Konstitution des Kromycins ein Abbauprodukt des Pikromycins. Hely. Chim. Acta 40, 1768 (1957).

    Article  CAS  Google Scholar 

  • Brock, T. D., and M. L. Brock: Similarity in mode of action of chloramphenicol and erythromycin. Biochim. et Biophys. Acta 33, 274 (1959).

    CAS  Google Scholar 

  • Brockmann, H., u. W. Henkel: Pikromycin ein neues Antibiotikum aus Actinomyceten. Naturwissenschaften 37, 138 (1950).

    Article  CAS  Google Scholar 

  • Brockmann, H., u. R. Oster: Antibiotica aus Actinomyceten. Xxxviii. Zur Konstitution des Pikromycins und Kromycins (Pikromycin, VI). Chem. Ber. 90, 605 (1957).

    Article  CAS  Google Scholar 

  • Celmer, W. D.: Macrolide stereochemistry. I. The total absolute configuration of oleandomycin. J. Am. Chem. Soc. 87, 1797 (1965a).

    Article  CAS  Google Scholar 

  • Celmer, W. D.: Macrolide stereochemistry. II. Configurational assignments at certain centers in various macrolide antibiotics. J. Am. Chem. Soc. 87, 1799 (1965b).

    Article  PubMed  CAS  Google Scholar 

  • Celmer, W. D.: A configurational model for macrolide antibiotics. J. Am. Chem. Soc. 87, 1801 (1965c).

    Article  PubMed  CAS  Google Scholar 

  • Celmer, W. D.: Basic stereochemical research topics in the macrolide antibiotics. In: Biogenesis of antibiotic substances, ed by Z. VanÉK and Z. HosTÄLÉK. New-York and London: Academic Press 1965c.

    Google Scholar 

  • Chabbert, Y.: Antagonisme in vitro entre l’erythromycine et la spiramycine. Ann. Inst. Pasteur 90, 787 (1956).

    CAS  Google Scholar 

  • Corbaz, R., L. Ettlinger, E. GÄUmann, W. Keller-Schierlein, L. Neipp, V. Prelog, P. Reusser u. H. ZÄHner: Stoffwechselprodukte von Actinomyceten. Angolamycin. Helv. Chim. Acta 38, 1202 (1955).

    Article  CAS  Google Scholar 

  • Coleman, V. R., J. B. Gunnison, and E. Jawetz: Participation of erythromycin and carbomycin in combined antibiotic action in vitro. Proc. Soc. Exptl. Biol. Med. 83, 668 (1953).

    Article  CAS  Google Scholar 

  • Djerassi, C., and O. Halpern: Macrolide antibiotics. Vii. The structure of neomethymycin. Tetrahedron 3, 255 (1958).

    Article  CAS  Google Scholar 

  • Djerassi, C., and J. A. Zderic: The structure of the antibiotic methymycin. J. Am. Chem. Soc. 78, 6390 (1956).

    Article  CAS  Google Scholar 

  • Donin, M. N., J. Pagano, J. D. Dutcher, and C. M. Mckee: Methymycin, a new crystalline antibiotic. Antibiotics Ann. 1953/54, 179.

    Google Scholar 

  • English, A. R., M. F. Field, S. R. Szendy, N. J. Tagliani, and R. A. Fitts: Magnamycin. I. In vitro studies. Antibiotics Chemotherapy 2, 678 (1952).

    CAS  Google Scholar 

  • Finland, M., C. Wilcox, and E. M. Purcell: Cross resistance to antibiotics: Effect of exposures of bacteria to carbomycin or erythromycin in vivo. Proc. Soc. Exptl. Biol. Med. 81, 725 (1952).

    Article  CAS  Google Scholar 

  • FusIllo, M. H., H. E. NoYes, E. J. Pulaski, and J. Y. S. ToM: Antimicrobial spectrum and cross resistance studies of erythromycin and carbomycin. Antibiotics Chemotherapy 3, 581 (1953).

    CAS  Google Scholar 

  • Gardocki, J. F., S. Y. P’AN, A. L. Rapuzzi, G. M. Fanelli, and E. K. Timmens: Magnamycin: toxicity in experimental animals Antibiotics Chemotherapy 3, 55 (1953).

    Google Scholar 

  • Garrod, L. P., and P. M. Waterworth: Behaviour in vitro of some new antistaphylococcal antibiotics. Brit. Med. J. 1956, II 61.

    Article  Google Scholar 

  • Gastal, R.: Action de la spiramycine sur l’infection expérimentale de la souris par H. pertussis. Ann. Inst. Pasteur 94, 636 (1958).

    CAS  Google Scholar 

  • GÄUmann, E., R. HÜTter, W. Keller-Schierlein, L. Neipp, V. Prelog u. H. ZÄHner: Stoffwechselprodukte von Actinomyceten. Rely. Chim. Acta 43, 601 (1960).

    Article  Google Scholar 

  • Hochstein, F. A., and K. Murai: Magnamycin B, a second antibiotic from Streptomyces halstedii. J. Am. Chem. Soc. 76, 5080 (1954).

    Article  CAS  Google Scholar 

  • HsIE, J.-Y., R. Kotz, and W. Nusser: Analysis of cross resistance to erythromycin and carbomycin in Micrococcus pyogenes var. aureus. Antibiotics Ann. 1955/56, 773.

    Google Scholar 

  • Hudson, D. G., G. M. Yoshihara, and W. M. M. Kirby: Spiramycin. Clinical and laboratory studies. A.M.A. Arch. Internal Med. 97, 57 (1956).

    Article  CAS  Google Scholar 

  • Jones, W. F., R. L. Nichols, and M. Finland: Development of resistance and cross-resistance in vitro to erythromycin, carbomycin, spiramycin, oleandomycin and streptogramin. Proc. Soc. Exptl. Biol. Med. 93, 388 (1956).

    Article  CAS  Google Scholar 

  • Jordan, D. C.: Effect of chalcomycin on protein synthesis by Staphylococcus aureus. Can. J. Microbiol. 9, 129 (1929).

    Article  Google Scholar 

  • Lutz, A., O. Grooten et J. Hofferer: Evolution et modifications de la résistance des staphylocoques pathogènes à six antibiotiques usuels de 1950 à 1956. L’action comparée in vitro de l’érythromycine, de la magnamycine, de la spiramycine, de la novobiocine (albamycine) et de l’oléandomycine. Ann. Inst. Pasteur 92, 778 (1957).

    CAS  Google Scholar 

  • Maniar, A. C., et L. Eidus: Un des facteurs influençant l’action des antibiotiques. Ann. Inst. Pasteur 101, 887 (1961).

    CAS  Google Scholar 

  • Mathieu, N., et M. Faguet: Activité in vitro de la spiramycine en association avcc la tétracycline, l’érythromycine, la pénicilline, la streptomycine sur la multiplication de Staphylococcus aureus étudiée au microbiophotomètre. Ann. Inst. Pasteur 94, 69 (1958).

    CAS  Google Scholar 

  • Miyake, A., H. Iwasaki, T. Takewata, M. Shibata, and K. Nakazawa: Production of tertiomycin A by Streptomyces albireticuli. J. Antibiotics (Japan), Ser. A 12, 59 (1959).

    CAS  Google Scholar 

  • Morin, R. B., and M. Gorman: The partial structure of tylosin, a macrolide antibiotic. Tetrahedron Letters, p. 2339 (1964).

    Google Scholar 

  • Pagano, J. F., M. J. Weinstein, and C. M. McKee: An anti-rickettsial antibiotic from a streptomycete, M-4209. I. Biological caracterizations. Antibiotics Chemotherapy 3, 899 (1953).

    CAS  Google Scholar 

  • Paul, R., et S. Tchelitcheff: Structure de la spiramycine. VI. Etablissement de la formule développée. Bull. soc. chim. France, p. 650 (1965).

    Google Scholar 

  • Pinnert-Sindico, S., L. Ninet, J. Preud’Homme, and C. Cosar: A new antibiotic, spiramycin. Antibiotics Ann. 1954/55, 724.

    Google Scholar 

  • Prelog, V., A. M. Gold, G. Talbot H. A. Zamojski: Stoffwechselprodukte von Actinomyceten. Über die Konstitution der Narbomycins. Hely. Chim. Acta 45, 4 (1962).

    Article  CAS  Google Scholar 

  • Seneca, H., and D. Ides: The effect of magnamycin on protozoa and spermatozoa. Antibiotics Chemotherapy 3, 117 (1953).

    CAS  Google Scholar 

  • Suzuka, I., H. Kaji, and A. Kaji: Binding of specific Rna to 30 S subunits. Comparison with the binding to 70 s ribosomes. Biochem. Biophys. Research Commun. 21, 187 (1965).

    Article  CAS  Google Scholar 

  • Tanner, F. W., A. R. English, T. M. Lees, and J. B. Routien: Some properties of magnamycin, a new antibiotic. Antibiotics Chemotherapy 2, 441 (1952).

    CAS  Google Scholar 

  • Taubman, S. B., F. E. Young, and J. W. Corcoran: Antibiotic glycosides. IV. Studies on the mechanism of erythromycin resistance in Bacillus subtilis. Proc. Natl. Acad. Sci. U.S. 50, 955 (1963).

    Article  CAS  Google Scholar 

  • Umezawa, H.: Recent advances in chemistry and biochemistry of antibiotics. Tokyo 1964. Microbial Chemistry Research Foundation.

    Google Scholar 

  • Vazquez, D.: The binding of chloramphenicol by ribosomes from Bacillus megaterium. Biochem. Biophys. Research Commun. 15, 464 (1964).

    Article  CAS  Google Scholar 

  • Vazquez, D.: Binding of chloramphenicol to ribosomes. The effect of a number of antibiotics. Biochim. et Biophys. Acta 144, 277 (1966a).

    Google Scholar 

  • VazquEZ, D.: Antibiotics affecting chloramphenicol uptake by bacteria. Their effect on amino acid incorporation in a cell-free system. Biochim. et Biophys. Acta 114, 289 (1966b).

    Google Scholar 

  • Videau, D.: Sur le mode d’action des antibiotiques. Cas particulier de la spiramycine. Ann. Inst. Pasteur 94, 709 (1958).

    CAS  Google Scholar 

  • Watanabe, T.: Studies on leucomycin. IV. Isolation of mycaminose from the acid hydrolysate. Bull. Chem. Soc. Japan 34, 15 (1961).

    Article  CAS  Google Scholar 

  • Watanabe, T., H. Nishida, J. Abe, and K. Satake: Studies on leucomycin. Bull. Chem. Soc. Japan 33, 1104 (1960).

    Article  CAS  Google Scholar 

  • Wong, S. C., C. C. James, and A. Finlay: The action of carbomycin (magnamycin) on some viral and rickettsial infectial infections. Antibiotics Chemotherapy 3, 741 (1953).

    CAS  Google Scholar 

  • Woodward, R. B.: Struktur und Biogenese der Makrolide. Eine neue Klasse von Naturstoffen. Angew. Chem. 69, 50 (1957).

    Article  CAS  Google Scholar 

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Authors
  1. D. Vazquez
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Editors and Affiliations

  1. University of Illinois, Urbana, Illinois, USA

    David Gottlieb (Professor of Plant Pathology) & Paul D. Shaw (Associate Professor of Biochemistry) (Professor of Plant Pathology) &  (Associate Professor of Biochemistry)

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Vazquez, D. (1967). Macrolide antibiotics — Spiramycin, Carbomycin, Angolamycin, Methymycin and Lancamycin. In: Gottlieb, D., Shaw, P.D. (eds) Antibiotics. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-38439-8_25

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  • DOI: https://doi.org/10.1007/978-3-662-38439-8_25

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-662-37649-2

  • Online ISBN: 978-3-662-38439-8

  • eBook Packages: Springer Book Archive

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