Gliotoxin and related epipolythiodioxopiperazines

General Pharmacology

Volumn 27, Issue 8, 1996, Pages 1311-1316

  Waring, Paul ^a   Beaver, Joanne ^a,b  

^a Australian National University   (Australia)

^b UNIVERSITY OF CANBERRA   (Australia)

Author keywords

a poptosis; aspergillosis; enzyme inhibition; epipolythiodioxopiperazine; gliotoxin; immunosuppression

Indexed keywords

CALCIUM; DISULFIDE; GLIOTOXIN; PIPERAZINE DERIVATIVE;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTIVIRAL ACTIVITY; APOPTOSIS; ASPERGILLOSIS; CELL DEATH; DRUG ACTIVITY; DRUG MECHANISM; ENZYME INHIBITION; GRAFT REJECTION; HUMAN; IMMUNOMODULATION; LYMPHOCYTE; MYCOSIS; NONHUMAN; PRIORITY JOURNAL; REVIEW;

ADJUVANTS, IMMUNOLOGIC; ANIMALS; APOPTOSIS; CALCIUM; DISULFIDES; FEMALE; GLIOTOXIN; HUMANS; IMMUNOSUPPRESSIVE AGENTS; MYCOSES; REACTIVE OXYGEN SPECIES; SPORIDESMINS;

EID: 0030561529     PISSN: 03063623     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0306-3623(96)00083-3     Document Type: Review

References (66)

1. Bauer J., Gareis A., Bott A. and Gedek B. (1989) Isolation of gliotoxin from bovine udder infected with Aspergillus fumigatus. J. Med. Vet. Mycol. 27, 45-50.
2. Beaver J. and Waring P. (1994) Lack of correlation between early intracellular cellular calcium ion rises and the onset of apoptosis in thymocytes. Immunol. and Cell Biol. 72, 489-499.
3. Beecham A. F., Fridrichsons J. and Mathieson A. (1966) The structure and absolute configuration of gliotoxin and sporidesmin. Tetrahedron Lett. 3131-3138.
4. Bellomo G., Perotti M., Taddei F., Mirabelli F., Finardi G., Nicotera P. and Orrenius S. (1992) Tumor necrosis factor induces apoptosis in mouse mammary adenocarcinoma cells by an increase in free calcium and DNA fragmentation. Cancer Res. 52, 1342-1346.
5. Bodley G., Bueltmann B., Duguid W., Gibbs D., Hanak H., Hotchi M., Mall G., Martino P., Meunier F., Millikin S., Naoe S., Okudaira M., Scevola D. and van't Wout J. (1992) Fungal infections in cancer patients: an international autopsy study. Eur. J. Clin. Microbiol. Infect. Dis. 11, 99-109.
6. Braithwaite A., Eichner R. D., Waring P. and Mullbacher A. (1987) The immunomodulating agent gliotoxin causes genomic DNA fragmentation. Molec. Immunol. 24, 47-55.
7. Cordiner S. J. and Jordan T. W. (1983) Inhibition by sporidesmin of hepatocyte bile acid transport. Biochem. J. 212, 197-204.
8. De Clercq E., Billiau A., Ottenheijm H. C. J. and Herscheid J. D. M. (1978) Anti reverse transcriptase activity of gliotoxin analogs. Biochem. Pharmacol. 27, 635-639.
9. Duvall E. and Wyllie A. H. (1985) Macrophage recognition of cells undergoing apoptosis. Immunol. 56, 351-358.
10. Eichner R. D., Al Salami M., Wood P. R. and Mullbacher A. (1986) The effect of gliotoxin upon macrophage function. Int. J. Immunopharmac. 8, 789-797.
11. Eichner R. D., Tiwari-Palni U., Waring P. and Mullbacher A. (1988) Detection of the immunomodulating agent gliotoxin in experimental aspergillosis. In Proceedings of the 10th Congress of the International Society for Human and Animal Mycology (Edited by Torres-Rodriguez, J. M.) pp. 133-137. J. R. Prous Science, Barcelona, Spain.
12. Eichner R. D., Waring P., Geue A., Braithwaite A. W. and Mullbacher A. (1988) Gliotoxin causes oxidative damage to plasmid and cellular DNA. J. Biol. Chem. 263, 3772-3777.
13. el-Kady I., el-Maraghy S. and Zohri A. N. (1994) Mycotoxin producing potential of some isolates of Aspergillus flavus and Eurotium groups from meat products. Microbiol. Res. 149, 297-307.
14. Gilman A. G. (1987) G proteins: transducers of receptor generated signals. Ann. Rev. Biochem. 65, 615-649.
15. Hara M. and Han M. (1995) Ras farnesyl transferase inhibitors suppress the phenotype resulting from an activated ras mutation in Caenorhabditis Elegans. Proc. Natl. Acad. Sci. USA 92, 3333-3337.
16. Hasan H. A. H. and Bagy M. M. K. (1993) The incidence of fungi in human axillary hair and their toxigenic potentials. Cryptogamie Mycologia 14, 297-306.
17. Johnson J. R., Bruce W. F. and Dutcher J. D. (1943) Gliotoxin, the antibiotic principle of Gliocladium fimbriatum. Production, physical and biological properties. J. Amer. Chem. Soc. 65, 2005-2009.
18. Jordan T. W. and Cordiner S. J. (1987) Fungal epipolythiodioxopiperazine toxins have therapeutic potential and roles in disease. TIPS 8, 144-149.
19. Kerr J. F. R., Searle J., Harmon B. V. and Bishop C. J. (1987) Apoptosis. In Perspectives on Mammalian Cell Death, (Edited by C. S. Potten) pp. 93-128. Oxford University Press, Oxford.
20. Kobayashi M., Mullbacher A., Waring P. and Hapel A. J. (1991) Gliotoxin treatment selectively spares M-CSF-plus IL-3-responsive multipotent hemopoietic progenitor cells in bone marrow. Eur. J. Haematol. 46, 205-211.
21. Kopp E. E. and Ghosh S. (1995) NF-kB and rel proteins in innate immunity. Adv. Immunol. 58, 1-27.
22. Korbel R., Bauer J. and Gedek B. (1993) Pathological, anatomical and mycotoxicological studies of aspergillosis in birds. Tierarztl-Prax. 21, 134-139.
23. Lissing J. R., Tuch B. E. and Suranyi M. G. (1988) The use of gliotoxin in human fetal pancreas transplantation. Transplant. Proc. 20, 76-78.
24. Martin S. J., Lennon S. V., Bonham A. M. and Cotter T. G. (1990) Induction of apoptosis (programmed cell death) in human leukemic HL-60 cells by inhibition of RNA and protein synthesis. J. Immunol. 145, 1859-1867.
25. Mason J. W. and Kidd J. G. (1951) Effects of gliotoxin and other sulphur containing compounds on tumor cells in vitro, with observations on mechanisms of action of gliotoxin. J. Immunol. 66, 99-106.
26. McConkey D. J., Orrenius S. and Jondal M. (1990) Agents that stimulate c-AMP stimulate DNA fragmentation in thymocytes. J Immunol. 145, 1227-1230.
27. McMinn P. C., Halliday G. M. and Muller H. K. (1990) Effects of gliotoxin on langerhans' cell function: contact hypersensitivity responses and skin graft survival. Immunology 71, 46-51.
28. McMinn P. C., Halliday G. M., Waring P. and Muller H. K. (1991) Langerhans cell depletion in gliotoxin treated murin epidermis. Pathology 23, 39-44.
29. Middleton M. C. (1974) The involvement of the disulphide group of sporidesmin in the action of the toxin on the swelling and respiration of liver mitochondria. Biochem. Pharmacol. 23, 811-820.
30. Mullbacher A. and Eichner R. D. (1984) Hypothesis: Fungal toxins are involved in aspergillosis and AIDS. Aust. J. Exp. Biol. Med. Sci. 62, 479-484.
31. Mullbacher A. and Eichner R. D. (1984) Immunosuppression in vitro by a metabolite of a human pathogenic fungus. Proc. Natl. Acad. Sci. USA 81, 3835-3837.
32. Mullbacher A., Waring P., Tiwari-Palni U. and Eichner R. D. (1986) Structural relationships of epipolythiodixoxpiperazines and their immunomodulating activity. Molec. Immunol. 23, 231-235.
33. Mullbacher A., Hume D., Braithwaite A. W., Waring P. and Eichner R. D. (1987) Selective resistance of bone marrow derived hemopoietic progenitor cells to gliotoxin. Proc. Natl. Acad. Sci. USA, 84, 3822-3825.
34. Mullbacher A., Moreland A. F., Waring P., Sjaarda A. and Eichner, R. D. (1988) Prevention of graft versus host disease by treatment of bone marrow with gliotoxin in fully allogeneic chimeras and their cyctoxic T cell repertoire. Transplanation 46, 120-125.
35. Mullbacher A., Waring P. and Eichner R. D. (1985) Identification of an agent of Aspergillus fumigatus displaying anti-phagocytic and immunomodulating activity in vitro. J. Gen. Microbiol. 131, 1251-1258.
36. Munday R. (1984) Studies on the mechansim of toxicity of the mycotoxin sporidesmin. Evidence for intracellular generation of superoxide radical from sporidesmin. J. Appl. Toxicol. 4, 176-181.
37. Munday R. (1987) Studies on the mechanism of toxicity of the mycotoxin sporidesmin. Generation of hydroxyl radicals by sporidesmin. J. Appl. Toxicol. 7, 17-22.
38. Munday R. (1989) Toxicity of thiols and disulphides ; involvement of free radical species. Free Radical Biol. Med. 7, 659-673.
39. Nagarajan R. (1984) Gliotoxin and epipolythiodioxopiperazines. In Mycotoxins-Production, Isolation and Purification (Edited by Betina U.) pp. 351-385. New York, Elsevier Science Publishing.
40. Orrenius S., McConkey D. J., Bellomo G. and Nicotera P. (1989) Role of Ca+2 in toxic cell killing. Trends Pharm. Sci. 10, 281-285.
41. Pahl H. L., Kraub B., Schulze-Osthoff K., Decker T., Traencker E. B-M., Myers C., Parks T., Waring P., Mullbacher A., Czernilofsky A.-P. and Baeuerle P. (1996) The immunosuppressive fungal metabolite gliotoxin specifically inhibits transcription factor NF-kB, J. Ex. Med. 83, 1829-1840.
42. Petty H. R. (1987) Specific inhibition of macrophage anti-body dependent endocytosis by p-chloromercuribenzenesulphonic acid: identification of sensitive membrane proteins. Immunology 60, 269-273.
43. Richard J. L., Dehey M. C., Chermette R., Pier A. C., Hasegawa A., Lund A., Bratberg A. M., Padhye A. A. and Connole M. D. (1994) Advances in veterinary mycology. J. Med Vet. Mycol. 32, 169-187.
44. Rodriguez P. L. and Carrasco L. (1992) Gliotoxin: inhibitor of poliovirus RNA synthesis that blocks the viral RNA polymerase 3Dpol. J. Virol. 66, 1971-1976.
45. +2 release from intact rat liver mitochondria. Biochemistry 33, 13401-13405.
46. Shah D. T. and Larsen B. (1991) Clinical isolates of yeast produce a gliotoxin like substance. Mycopathologia 116, 203-208.
47. Shah D. T., Glover D. D. and Larsen B. (1995) In situ mycotoxin production by candida albicans in women with vaginitis. Gynecol Obstet. Invest. 39, 67-69.
48. Sutton P., Beaver J. and Waring P. (1995) Evidence that gliotoxin enhances lymphocyte activation and induces apoptosis by effects on cyclic AMP level. Biochem. Pharmacol. 50, 2009-2014.
49. Sutton P., Newcombe N. R., Waring P. and Mullbacher A. (1994) In vivo immunosuppressive activity of gliotoxin, a metabolite produced by human pathogenic fungi. Infect Immun, 62, 1192-1198.
50. Taylor A. (1971) The toxicology of sporidesmins and other epipolythiodioxopiperazines. In Microbial Toxins (Edited by Kadis S., Ciegler A. and Ajl S. J.) Vol. 7, pp. 337-376 New York, Academic Press.
51. Towers N. R. (1978) The incidence of subclinical facial eczema in selected Waikato dairy herds. NZ Vet. J. 26, 142-145.
52. Tuch B. E., Lissing J. R. and Suranyi M. G. (1988) Immunomodulation of human fetal cells by the fungal metabolite gliotoxin. Immunol. Cell. Biol. 66, 307-312.
53. Upreti G. C. and Jain M. K. (1993) Interaction of sporidesmin, a mycotoxin from Pithomyces chartarum, with lipid bilayers. Biosci. Rep. 13, 233-243.
54. Van der Pyl D., Inokoshi J., Shiomi K., Yang H., Takeshima H. and Omura S. (1992) Inhibition of farnesyl protein transferase by gliotoxin and acetylgliotoxin. J. Antibiot. Res. 45, 1802-1805.
55. Waring P. (1990) DNA fragmentation induced in macrophages by gliotoxin does not require protein synthesis and is preceded by raised inositol triphosphate levels. J. Biol. Chem. 265, 14476-14480.
56. Waring P. and Sjaarda A. (1995) Extracellular calcium is not required for gliotoxin or dexamethasone induced DNA fragmentation: a reappraisal of the use of EGTA. Int. J. Immunopharmacol. 17, 403-410.
57. Waring P., Eichner R. D., Tiwari-Palni U. and Mullbacher A. (1987) Gliotoxin E: a new biologically active epipolythiodioxopiperazine from Penicillium terlikowskii. Aust. J. Chem. 40, 991-997.
58. Waring P., Eichner R. D., Mullbacher A. and Sjaarda A. (1988a) Gliotoxin induces apoptosis in macrophages unrelated to its antiphagocytic properties. J. Biol. Chem. 263, 18493-18499.
59. Waring P., Eichner R. and Mullbacher A. (1988b) The chemistry and biology of the immunomodulating agent gliotoxin and related epipolythiodioxopiperazines. Med. Res. Rev. 8, 499-524.
60. Waring P., Egan M., Braithwaite A. W., Mullbacher A. and Sjaarda A. (1990) Apoptosis induced in macrophages and T blasts by the mycotoxin sporidesmin and protection by Zinc salts. Int. J. Immunopharmac. 12, 445-457.
61. Waring P., Kos F. J. and Mullbacher A. (1991) Apoptosis or programmed cell death. Med. Res. Rev. 11, 219-236.
62. Waring P., Newcombe N., Edel M., Lin Q. H., Jiang H., Sjaarda A., Piva T. and Mullbacher A. (1994) Cellular uptake and release of the immunomodulating fungal toxin gliotoxin. Toxicon 32, 491-504.
63. Waring P., Mamchak A., Khan T., Sjaarda A. and Sutton P. (1995a) DNA synthesis precedes gliotoxin induced apoptosis. Cell Death Differentiation 2, 201-210.
64. Waring P., Sjaarda A. and Lin Q. H. (1995b) Gliotoxin inactivates alcohol dehydrogenase by either covalent modification or free radical damage mediated by redox cycling. Biochem. Pharmacol. 49, 1195-1201.
65. Wyllie A. H., Morris R. G., Smith A. L. and Dunlop D. (1984) Chromatin cleavage in apoptosis: association with condensed chromatin morphology and dependence on macromolecular synthesis. J. Pathol. 142, 67-77.
66. +2 release from sarcoplasmic reticulum via an oxidation reaction. J. Biol. Chem. 264, 21725-21736.