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On the fungitoxicity of some new thiocyanatopyrazole derivatives: Electron microscopical study in trichophyton mentagrophytes

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Abstract

Four thiocyanatopyrazole derivatives were synthesized and their fungistatic activity was demonstrated in vitro against a number of dermatophytic fungi. In Trichophyton mentagrophytes, the most active compound induced an unusual increase of the plasma membrane with production of intra and extracytoplasmic complexes, a deterioration of nuclear and mitochondrial membranes and a formation of autophagic-like vacuoles. Plasmolysis, accompanied by an almost complete disorganization of cytoplasmic structures, seemed to be the final event. A possible mechanism of action of the compounds was discussed.

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References

  1. Baugham, A. D. & R. W. Horne. 1964. Negative staining of phospholipids and their structural modifications by surface-active agents as observed in the electron microscope. J. Mol. Biol. 8: 660–668.

    Google Scholar 

  2. Carmichael, J. W. 1956. The cellophane technique for studying morphology and hyphal fusions in fungi. Mycologia 48: 450–453.

    Google Scholar 

  3. Dall'Olio, G., G. L. Vannini & D. Mares. 1974. The effects of coumarin on Trichophyton mentagrophytes: light and electron microscopic studies. (Preliminary report). Ann. Univ. Ferrara, Sez. IV-Bot. 4: 151–158.

    Google Scholar 

  4. Djaczenko, W. & A. Cassone. 1971. Visualization of new ultrastructural components in the cell wall of Candida albicans with fixatives containing TAPO. J. Cell Biol. 52: 186–190.

    Google Scholar 

  5. Giori, P., M. Guarneri & C. Branca. 1971. Sintesi ed attività antifungina di solfuri pirazolici. Nota II Farm. (Ed. Sci.) 26: 276–293.

    Google Scholar 

  6. Gordee, R. S. & T. R. Matthews. 1968. Evaluation of the in vitro and in vivo antifungal activity of pyrrolnitrin. Antimicrob. Agents Chemother.-1967: 378–387.

    Google Scholar 

  7. Guarneri, M., P. Giori & R. Tomatis. 1968. Derivati pirazolo-[4,3-b][1,4]-tiazinici. Ann. Chim. 58: 697–708.

    Google Scholar 

  8. Horsfall, J. G. & S. Rich. 1953. Fungitoxicity of sulfurbridged compounds. Indian Phytopathol. 6: 1–14.

    Google Scholar 

  9. Iwata, K., Y. Kanda, H. Yamaguchi & M. Osumi. 1973. Electron microscopic studies on the mechanism of action of clotrimazole on Candida albicans. Sabouraudia 11: 205–209.

    Google Scholar 

  10. Iwata, K., H. Yamaguchi & T. Hiratani. 1973. Mode of action of clotrimazole. Sabouraudia 11: 158–166.

    Google Scholar 

  11. Kinsky, S. C., S. A. Luse, D. Zopf, L. L. M. Van Deenen & J. Haxby. 1967. Interaction of filipin and derivatives with erythrocyte membrane lipid dispersions: electron microscopic observations. Biochim. Biophys. Acta 135: 844–861.

    Google Scholar 

  12. Kinugawa, J., M. Ochiai, C. Matsumura & H. Yamamoto. 1964. Studies on fungicides. VII. Synthesis and antifungal activity of some pyrazole derivatives. Chem. Pharm. Bull. 12: 182–191.

    Google Scholar 

  13. Kosuge, T. & H. Okeda. 1954. Nonylpyrazole, a new antimicrobial substance. J. Biochem. 41: 183–186.

    Google Scholar 

  14. Lampen, J. O. 1969. Amphotericin B and other polyenic antifungal antibiotics. Am. J. Clin. Pathol. 52: 138–146.

    Google Scholar 

  15. Lucy, J. A. & A. M. Glauert. 1964. Structure and assembly of macromolecular lipid complexes composed of globular micelles. J. Mol. Biol. 8: 660–668.

    Google Scholar 

  16. McNew, G. L. & N. K. Sundholm. 1949. The fungicidal activity of substituted pyrazoles and related compounds. Phytopathology 39: 721–751.

    Google Scholar 

  17. Pock-Steen, B. & T. Kobayasi. 1970. Ultrastructure of the hyphal wall and septum of Trichophyton mentagrophytes. J. Invest. Dermatol. 55: 404–409.

    Google Scholar 

  18. Scannerini, S., G. L. Vannini & G. Dall'Olio. 1971. Sulle alterazioni ultrastrutturali indotte in vitro da micostatici nei funghi dermatofiti. I. Stimolazione dell'autofagia in Trichophyton mentagrophytes (Rob.) Blanchard CBS 560.66 trattato con N-(5-nitro-2-furfurilidene)-3-amino-5-metilmercaptometil-2-ossazolidinone. G. Batteriol. Virol. Immunol. 64: 31–43.

    Google Scholar 

  19. Scannerini, S., G. L. Vannini & G. Dall'Olio. 1974. Dimostrazione ultrastrutturale di un componente parietale anomalo in Trichophyton mentagrophytes trattato con Phosfon D. G. Bot. Ital. 108: 311–320.

    Google Scholar 

  20. Tsukahara, T., A. Sato & R. Okada. 1964. Electron microscopic studies on the cytological structure of Trichophyton mentagrophytes. Jpn. J. Microbiol. 8: 83–96.

    Google Scholar 

  21. Urabe, H. & T. Izu. 1969. The ultrastructure of Trichophyton and a double cell wall in the hypha. J. Invest. Derm. 52: 508–513.

    Google Scholar 

  22. Vannini, G. L. & G. Dall'Olio. 1973. Ulteriori osservazioni sulle alterazioni parietali in Trichophyton mentagrophytes trattato con Phosfon D. Ann. Univ. Ferrara, Sez. IV — Bot. 4: 127–133.

    Google Scholar 

  23. Vannini, G. L., G. Dall'Olio. & A. Bonora. 1974. Pigment formation in a colourless strain of Trichophyton mentagrophytes after Phosfon D treatment. Experientia 30: 203–205.

    Google Scholar 

  24. Vannini, G. L. & D. Mares. 1975. Fine structural characterization of microbodies and Woronin bodies in Trichophyton mentagrophytes. Experientia 31: 949–951.

    Google Scholar 

  25. Williams, N. E. & J. H. Luft. 1968. Use of a nitrogen mustard derivative in fixation for electron microscopy and observation on the ultrastructure of Tetrahymena. J. Ultrastruct. Res. 25: 271–292.

    Google Scholar 

  26. Yamaguchi, H., Y. Kanda & M. Iwata. 1973. Electronmicroscopical studies on the fungitoxicity of bisphenyl-[2-chlorophenyl]-1-imidazolyl methane (BAY b 5097): preferential effect on the nuclear envelope in Candida albicans cells. J. Electron. Micros. 22: 167–172.

    Google Scholar 

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Authors and Affiliations

  1. Istituto di Botanica dell'Università di Ferrara, Corso Porta Mare, 2., Italia

    Gian Luigi Vannini & Giuseppe Dall'Olio

  2. Istituto di Chimica Farmaceutica dell'Università di Ferrara, Via Scandiana, 21., Italia

    Paolo Giori

Authors
  1. Gian Luigi Vannini
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  2. Giuseppe Dall'Olio
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  3. Paolo Giori
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Additional information

Investigation supported by a grant from Consiglio Nazionale delle Ricerche of Italy (Contract No. 7500536).

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Vannini, G.L., Dall'Olio, G. & Giori, P. On the fungitoxicity of some new thiocyanatopyrazole derivatives: Electron microscopical study in trichophyton mentagrophytes. Mycopathologia 58, 39–47 (1976). https://doi.org/10.1007/BF00493592

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