The mycotoxin patulin induces intra- and intermolecular protein crosslinks in vitro involving cysteine, lysine, and histidine side chains, and α-amino groups

Chemico-Biological Interactions

Volumn 123, Issue 2, 1999, Pages 85-103

  Fliege, Ralph ^a   Metzler, Manfred ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Electrophile; Mycotoxin; Patulin; Protein crosslinks

Indexed keywords

ALPHA AMINO ACID; CYSTEINE; HISTIDINE; LYSINE; MYCOTOXIN; PATULIN;

ARTICLE; CROSS LINKING; FLUORESCENCE; IN VITRO STUDY; MOLECULAR INTERACTION; NONHUMAN; POLYACRYLAMIDE GEL ELECTROPHORESIS; PROTEIN PROTEIN INTERACTION; PROTEIN TERTIARY STRUCTURE; STRUCTURE ANALYSIS;

ANIMALS; CATTLE; CHICKENS; CROSS-LINKING REAGENTS; CYSTEINE; DANSYL COMPOUNDS; FEMALE; FLUORESCENT DYES; GLUTATHIONE; HISTIDINE; LYSINE; MURAMIDASE; PATULIN; PROTEIN CONFORMATION; PROTEIN STRUCTURE, TERTIARY; SERUM ALBUMIN, BOVINE; SULFHYDRYL COMPOUNDS; TUBULIN;

EID: 0032703307     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(99)00123-4     Document Type: Article

References (21)

1. Palmgren M.S., Ciegler A. Toxicity and carcinogenicity of fungal lactones: patulin and penicillic acid. Keeler R.F., Tu A.T. Handbook of Natural Toxins. Plant and Fungal Toxins. 1:1983;325-341 Marcel Dekker, New York.
2. Thust R., Kneist S., Mendel J. Patulin, a further clastogenic mycotoxin, is negative in the SCE assay in chinese hamster V79-E cells in vitro. Mutat. Res. 10:1982;91-97.
3. Korte A. Chromosomal analysis in bone-marrow cells of chinese hamsters after treatment with mycotoxins. Mutat. Res. 78:1980;41-49.
4. Roll R., Matthiaschk G., Korte A. Embryotoxicity and mutagenicity of mycotoxins. J. Environ. Pathol. Toxicol. Oncol. 10:1990;1-7.
5. Pfeiffer E., Gross K., Metzler M. Aneuploidogenic and clastogenic potential of the mycotoxins citrinin and patulin. Carcinogenesis. 19:1998;1313-1318.
6. Dickens F., Jones H.E.H. Carcinogenic activity of a series of reactive lactones and related substances. Brit. J. Cancer. 15:1961;85-100.
7. Barhoumi R., Burghardt R.C. Kinetic analysis of the chronology of patulin and gossypol-induced cytotoxicity in vitro. Fund. Appl. Toxicol. 30:1996;290-297.
8. Ciegler A. Patulin. Rodricks J.V. Mycotoxins in Human and Animal Health. 1977;609-624 Pathotox Publishers, Park Forest South, USA.
9. Geiger W.B., Conn J.E. The mechanism of the antibiotic action of clavacin and penicillic acid. J. Am. Chem. Soc. 67:1945;112-116.
10. Fliege R., Metzler M. On the thiol-reactivity of patulin: adduct structures and reaction pathways with the thiol model compound 4-bromothiophenol. Rev. Med. Veter. 6:1998;562.
11. Norstadt F.A., McCalla T.M. Patulin production by Penicillium urticae Bainier in batch culture. Appl. Microbiol. 17:1969;193-196.
12. Pohland A.E., Schuller P.L., Steyn P.S., van Egmond H.P. Physicochemical data for some selected mycotoxins. Pure Appl. Chem. 54:1982;2219-2284.
13. Sekiguchi J., Gaucher G.M. Identification of phyllostine as an intermediate of the patulin pathway in Penecilliun urticae. Biochemistry. 17:1978;1785-1791.
14. Scott P.M. Patulin. Purchase J.F.H. Mycotoxins. 1974;383-403 Elsevier, Amsterdam.
15. Bergner-Lange B., Kächele M., Stengel E. Zur Analytik von Patulin in Obstsäften und Obsterzeugnissen. Dt. Lebensm.-Rundsch. 79:1983;400-404.
16. Ellman G. Tissue sulfhydryl groups. Arch. Biochem. Biophys. 82:1959;70-77.
17. Knapp D.R. Handbook of Analytical Derivatization Reactions. 1979;Wiley, New York.
18. Shelanski M.L., Gaskin F., Cantor C.R. Microtubule assembly in the absence of added nucleotides. Proc. Natl Acad. Sci. USA. 70:1973;765-768.
19. Carpenter F.H., Harrington K.T. Intermolecular cross-linking of monomeric proteins and cross-linking of oligomeric proteins as probe of quarternary structure. J. Biol. Chem. 247:1972;5580-5586.
20. 14C]acetamide and N,N′-ethylenebis(iodoacetamide). Biochemistry. 20:1981;4437-4444.
21. Lee K.S. Cytotoxicity of patulin and its effect on lambda DNA cleavage by restriction endonuclease. Korean J. Toxicol. 7:1991;157-163.