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Griseofulvin

  • Chapter
Mechanism of Action

Part of the book series: Antibiotics ((ANTIBIOTICS,volume 1))

Abstract

Griseofulvin (C17H17O6Cl) was first isolated from Penicillium griseofulvum Dieck by Oxford, Raistrick, and Simonart (1939), In 1946 Brian, Curtis and Hemming isolated a “curling factor” from cultures of P. janczewskii ZAL., which caused abnormal development of fungal hyphae. The chemical and physical properties of the antibiotic were reported by Mcgowan (1946). The identity of “curling factor” with griseofulvin was determined chemically by GROVE and MCGOWAN (1947), and biologically by Brian et al. (1949). Subsequent studies have demonstrated that P. patulum and P. raistrickii also produce the antibiotic (Brian et al., 1949, 1955). The griseofulvin analogs, bromogriseofulvin and dechlorogriseofulvin have also been isolated from fungi (Macmillan, 1951, 1954).

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References

  • Abbott, M. T. J., and J. F. Grove: Uptake and translocation of organic compounds by fungi. II. Griseofulvin. Exptl. Cell Research 17, 105 (1959).

    Article  Google Scholar 

  • Aytoun, R. S. C.: The effects of griseofulvin on certain phytopathogenic fungi. Ann. Botany (London) 20, 297 (1956).

    CAS  Google Scholar 

  • Aytoun, R. S. C., A. H. Campbell, E. J. Napier, and D. A. L. Seiler: Mycological aspects of the action of griseofulvin against dermatophytes. A.M.A. Arch. Dermatol. 81, 650 (1960).

    Article  CAS  Google Scholar 

  • Banbury, G. H.: Physiological studies in the mucorales. Part II. Some observations on growth regulation in the sporongiophore of Phycomyces. J. Exptl. Botany 3, 86 (1952).

    Article  CAS  Google Scholar 

  • Barich, L. L., T. Nakai, J. Schwarz, and D. J. Barich: Tumour promoting effect of excessively large doses of oral griseofulvin on tumours induced in mice by methylcholanthrene. Nature 187, 335 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Barnes, M. J., and B. Boothroyd: The metabolism of griseofulvin in mammals. Biochem. J. 78, 41 (1961).

    PubMed  CAS  Google Scholar 

  • Blank, H., and F. J. Roth: Systemic control of cutaneous fungus infections. Am. J. Med. Sci. 240, 104/466 (1960b).

    Article  Google Scholar 

  • Blank, H., D. Taplin, and F. J. Roth: Electron microscopic observations of the effects of griseofulvin on dermatophytes. A.M.A. Arch. Dermatol. 81, 667 (1960).

    Article  CAS  Google Scholar 

  • Boothroyd, B., E. J. Napier, and G. A. Somerfield: The demethylation of griseofulvin by fungi. Biochem. J. 80, 34 (1961).

    PubMed  CAS  Google Scholar 

  • Brian, P. W.: Studies on the biological activity of griseofulvin. Ann. Botany (London) 13, 59 (1949).

    CAS  Google Scholar 

  • Brian, P. W.: Griseofulvin. Trans. Brit. Myco. Soc. 43, 1 (1960).

    CAS  Google Scholar 

  • Brian, P. W., P. J. Curtis, and H. G. Hemming: A substance causing abnormal development of fungal hyphae produced by Penicillium janczewskii ZAL. I. Biological assay, production, and isolation of “curling factor”. Trans. Brit. Myco. Soc. 29, 173 (1946).

    Article  CAS  Google Scholar 

  • Brian, P. W., P. J. Curtis, and H. G. Hemming: A substance causing abnormal development of fungal hyphae produced by Penicillium janczewskii ZAL. III. Identity of “curling factor” with griseofulvin. Trans. Brit. Myco. Soc. 32, 20 (1949)

    Google Scholar 

  • Brian, P. W., P. J. Curtis, and H. G. Hemming: Production of griseofulvin by Penicillium raistrichii. Trans. Brit. Myco. Soc. 38, 305 (1955).

    Article  Google Scholar 

  • Brian, P. W., J. M. Wright, J. Stubbs, and A. M. Way: Uptake of antibiotic metabolites of soil microorganisms by plants. Nature 167, 347 (1951).

    Article  CAS  Google Scholar 

  • Burgoon, C. F., J. H. Graham, R. J. Keiper, F. Urbach, J. S. Burgoon, and E. B. Helwig: Histopathologic evaluation of griseofulvin in Microsporum andovini infections. A.M.A. Arch. Dermatol. 81, 724 (1960).

    Article  Google Scholar 

  • Crosse, R., R. Mcwilliam, and A. Rhodes: Some relations between chemical structure and antifungal effects of griseofulvin analogues. J. Gen. Microbiol. 34, 51 (1964).

    PubMed  CAS  Google Scholar 

  • Crowdy, S. H., D. Gardner, J. F. Grove, and D. Pramer: The translocation of antibiotics in higher plants. I. Isolation of griseofulvin and chloramphenicol from plant tissue. J. Exptl. Botany 6, 371 (1955).

    Article  CAS  Google Scholar 

  • Crowdy, S. H., A. P. Green, J. F. Grove, P. Mccloskey, and A. Morrison: The translocation of antibiotics in higher plants. 3. The estimation of griseofulvin relatives in plant tissue. Biochem. J. 72, 230 (1959a).

    PubMed  CAS  Google Scholar 

  • Crowdy, S. H., J. F. Grove, H. G. Hemming, and K. C. Robinson: The translocation of antibiotics in higher plants. II. The movement of griseofulvin in broad bean and tomato. J. Exptl. Botany 7, 42 (1956).

    Article  CAS  Google Scholar 

  • Crowdy, S. H., J. F. Grove, and P. Mccloskey: The translocation of antibiotics in higher plants. 4. Systemic fungicidal activity and chemical structure in griseofulvin relatives. Biochem. J. 72, 241 (1959b).

    PubMed  CAS  Google Scholar 

  • Dennis, D. J., M. J. Davis, and J. C. Campbell: The effects of griseofulvin on epithelial cells in tissue culture. J. Invest. Dermatol. 34, 99 (1960).

    Google Scholar 

  • Deyson, G.: Antimitotic properties of griseofulvin. Ann. pharm, franc. 22, 17 (1964a).

    Google Scholar 

  • Deyson, G.: The influence of griseofulvin on the antimitotic properties of colchicine. Ann. pharm, franc. 22, 89 (1964b).

    Google Scholar 

  • El-Nakeeb, M. A., and J. O. Lampen: Formation of complexes of griseofulvin and nucleic acids of fungi and its relation to griseofulvin sensitivity. Biochem. J. 92, 59p (1964a).

    Google Scholar 

  • El-Nakeeb, M. A., and J. O. Lampen: Binding of tritiated-griseofulvin by ribosomes and RNA of Microsporum gypseum. Bacteriol. Proc. 1964, P60 (1964b).

    Google Scholar 

  • El-Nakeeb, M. A., and J. O. Lampen: Uptake of griseofulvin by the sensitive dermatophyte, Microsporum gypseum. J. Bacteriol. 89, 564 (1965a).

    PubMed  CAS  Google Scholar 

  • El-Nakeeb, M. A., and J. O. Lampen: Distribution of griseofulvin taken up by Microsporum gypseum: Complexes of the antibiotic with cell constituents. J. Bacteriol. 89, 1075 (1965b).

    PubMed  CAS  Google Scholar 

  • El-Nakeeb, M. A., W. L. Mclellan, and J. O. Lampen: Antibiotic action of griseofulvin on dermatophytes. J. Bacteriol. 89, 557 (1965c).

    CAS  Google Scholar 

  • El-Nakeeb, M. A., and J. O. Lampen: Uptake of H3-griseofulvin by microorganisms and its correlation with sensitivity to griseofulvin. J. Gen. Microbiol. 39, 285 (1965d).

    PubMed  CAS  Google Scholar 

  • Evans, G.: The antibiotic activity of Cylindrocarpon radicicola. Ph. D. Thesis, University of Sydney 1964.

    Google Scholar 

  • Eveligh, D. E., and S. G. Knight: The effect of griseofulvin on the cell wall composition of Trichophyton mentagrophytes. Bacteriol. Proc. 1965, G 82, p. 27 (1965).

    Google Scholar 

  • Foley, E. J., and G. A. Greco: Studies on the mode of action of griseofulvin. Antibiotics Ann. 1959/60, 670 (1960).

    Google Scholar 

  • Freedman, M. H., R. M. Baxter, and G. C. Walker: In vitro sorption of griseofulvin by keratin substrates. J. Invest. Dermatol. 38, 199 (1962).

    PubMed  CAS  Google Scholar 

  • Goldman, L., A. Beyer, and J. Schwarz: Absence of local cytotoxic change in man from griseofulvin. Nature 187, 335 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Grove, J. F.: Griseofulvin. Quart. Revs. (London) 17, 1 (1963).

    Article  CAS  Google Scholar 

  • Grove, J. F., J. Macmillan, T. P. C. Mulholland, and M. A. T. Rogers: Griseofulvin. Part IV. Structure. J. Chem. Soc. 1952, 3977 (1952).

    Article  Google Scholar 

  • Grove, J. F., and J. C. Mcgowan: Identity of griseofulvin and “curling factor”. Nature 160, 574 (1947).

    Article  CAS  Google Scholar 

  • Huber, F. M., and D. Gottlieb: The mode of action of the antifungal antibiotic griseofulvin (1966). (In Preparation.)

    Google Scholar 

  • Larpent, J. P.: Comparative action of griseofulvin and colchicine on growth and branching of the young thallus of Saprolegnia monoica. Compt. rend. 157, 2219 (Chem. Abstr. 61, 2407f) (1963).

    Google Scholar 

  • Larsen, W. G., and D. J. Demis: Metabolic studies of the effect of griseofulvin and candicidin on fungi. J. Invest. Dermatol. 41, 335 (1963).

    Article  PubMed  CAS  Google Scholar 

  • Macmillan, J.: Griseofulvin. Part 9. Isolation of the bromoanalogue from Penicillium griseofulvum and Penicillium nigricans. J. Chem. Soc. 2585 (1954).

    Google Scholar 

  • Macmillan, J.: Dechlorogriseofulvin — a metabolic product of Penicillium griseofulvum DIERCKX and Penicillium janczewskii ZAL. Chem. & Ind. (London) 179 (1951).

    Google Scholar 

  • Mcgowan, J. C.: A substance causing abnormal development of fungal hyphae produced by Penicillium janczewskii ZAL. II. Preliminary notes on the chemical and physical properties of “curling factor”. Trans. Brit. Myco. Soc. 29, 188 (1946).

    Article  CAS  Google Scholar 

  • Mcnall, E. G.: Biochemical studies on the metabolism of griseofulvin. A.M.A. Arch. Dermatol. 81, 657 (1960a).

    Article  CAS  Google Scholar 

  • Mcnall, E. G.: Metabolic studies on griseofulvin and its mechanism of action. Antibiotics Ann. 1959/60, 674 (1960b).

    Google Scholar 

  • Muntoni, S., and B. Loddo: Griseofulvin — induced budding in cell cultures. Arch. intern, pharmacodynamic 151, 365 (Chem. Abstr. 62, 5755g) (1964).

    CAS  Google Scholar 

  • Napier, E. J., D. I. Turner, and A. Rhodes: The in vitro action of griseofulvin against pathogenic fungi of plants. Ann. Botany (London) 20, 461 (1956).

    CAS  Google Scholar 

  • Oxford, A. E., H. Raistrick, and P. Simonart: Studies on the biochemistry of microorganisms. 60. Griseofulvin, C17H17O6Cl, a metabolic product of Penicillium griseofulvum DIECK. Biochem. J. 33, 240 (1939).

    PubMed  CAS  Google Scholar 

  • Paget, G. E., and S. J. Alcock: Griseofulvin and colchicine: lack of carcinogenic action. Nature 188, 867 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Paget, G. E., and A. L. Walpole: Some cytological effects of griseofulvin. Nature 182, 1320 (1958).

    Article  PubMed  CAS  Google Scholar 

  • Paget, G. E., and A. L. Walpole: The experimental toxicology of griseofulvin. A.M.A. Arch. Dermatol. 81, 750 (1960).

    Article  CAS  Google Scholar 

  • Reiss, F., L. Kornblee, and B. Gordon: Griseofulvin (fulvicin) in the treatment of fungus infections of the hair, skin, and nails with special reference to mycologic changes produced during therapy. J. Invest. Dermatol. 34, 263 (1960).

    PubMed  CAS  Google Scholar 

  • Roth, F. J.: Griseofulvin. Ann. N.Y. Acad. Sci. 89, 81, 750 (1960).

    Google Scholar 

  • Roth, F. J., B. Sallman, and H. Blank: In vitro studies of the antifungal antibiotic griseofulvin. J. Invest. Dermatol. 33, 403 (1959b).

    Article  PubMed  CAS  Google Scholar 

  • Schwarz, J., and J. K. Loutzenhiser: Laboratory experiences with griseofulvin. J. Invest. Dermatol. 34, 295 (1960).

    PubMed  CAS  Google Scholar 

  • Shockman, G. D., and J. O. Lampen: Inhibition by antibiotics of the growth of bacterial and yeast protoplasts. J. Bacteriol. 84, 508 (1962).

    PubMed  CAS  Google Scholar 

  • Srivastava, O. P., and V. C. Vora: Effect of griseofulvin on dermatophytes including locally isolated strains of Trichophyton rubrum and on Microsporum canis grown in keratin. J. Sci. Ind. Research (India) 20C, 163 (1961).

    Google Scholar 

  • Stokes, A.: Uptake and translocation of griseofulvin by wheat seedlings. Plant and Soil 5, 132 (1954).

    Article  CAS  Google Scholar 

  • Thyagarajan, T. R., O. P. Srivastava, and V. V. Vora: Some cytological observations on the effect of griseofulvin on dermatophytes. Naturwissenschaften 50, 524 (1963).

    Article  CAS  Google Scholar 

  • Wright, J. M.: Phytotoxic effects of some antibiotics. Ann. Botany (London) 15, 493 (1951).

    CAS  Google Scholar 

  • Ziegler, H.: Effect of griseofulvin on Microsporum canis. IV. Z. allgem. Mikrobiol. 3, 211 (1963).

    Article  CAS  Google Scholar 

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Authors
  1. Floyd M. Huber
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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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Huber, F.M. (1967). Griseofulvin. In: Gottlieb, D., Shaw, P.D. (eds) Mechanism of Action. Antibiotics, vol 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46051-7_15

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  • DOI: https://doi.org/10.1007/978-3-642-46051-7_15

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-46053-1

  • Online ISBN: 978-3-642-46051-7

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