L-cysteine, N-acetyl-L-cysteine, and glutathione protect xenopus laevis embryos against acrylamide-induced malformations and mortality in the frog embryo teratogenesis assay

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 20, 2010, Pages 11172-11178

  Rayburn, James R ^a   Friedman, Mendel ^b  

^a JACKSONVILLE STATE UNIVERSITY   (United States)

^b WESTERN REGIONAL RESEARCH CENTER   (United States)

Author keywords

Acrylamide; Food safety; Frog embryos; Glycine; L cysteine; N acetyl L cysteine; Protection; Reduced glutathione; Teratogenesis; Toxicity

Indexed keywords

ACRYLAMIDES; FROG EMBRYOS; GLYCINE; L-CYSTEINE; N-ACETYL L-CYSTEINE; PROTECTION; REDUCED GLUTATHIONE; TERATOGENESIS;

AMIDES; CHEMICAL CONTAMINATION; FOOD SAFETY; GLUCOSE; MUTAGENESIS; THERMAL PROCESSING (FOODS); TOXICITY;

AMINO ACIDS;

ANURA; SOLANUM TUBEROSUM; XENOPUS LAEVIS;

ACRYLAMIDE; CYSTEINE; GLUTATHIONE;

ABNORMALITIES, DRUG-INDUCED; ANIMAL; BIOASSAY; CHEMISTRY; DRUG EFFECTS; EMBRYOLOGY; FEMALE; HUMAN; MORTALITY; TERATOGENESIS; TOXICITY; XENOPUS LAEVIS;

ABNORMALITIES, DRUG-INDUCED; ACRYLAMIDE; ANIMALS; BIOLOGICAL ASSAY; CYSTEINE; FEMALE; GLUTATHIONE; HUMANS; TERATOGENESIS; XENOPUS LAEVIS;

EID: 78049244604     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf1023998     Document Type: Article

References (49)

1. Friedman, M. Chemistry, biochemistry, and safety of acrylamide. A review. J. Agric. Food Chem. 2003, 51, 4504-4526.
2. Friedman, M. Biological effects of Maillard browning products that may affect acrylamide safety in food. In Chemistry and Safety of Acrylamide in Food; Friedman, M., Mottram, D. S., Eds.; Springer: New York, 2005; pp 135-155.
3. Friedman, M.; Levin, C. E. Review of methods for the reduction of dietary content and toxicity of acrylamide. J. Agric. Food Chem. 2008, 56, 6113-6140.
4. Vivanti, V.; Finotti, E.; Friedman, M. Level of acrylamide precursors asparagine, fructose, glucose, and sucrose in potatoes sold at retail in Italy and in the United States. J. Food Sci. 2006, 71, C81-C85.
5. Koutsidis, G.; De La Fuente, A.; Dimitriou, C.; Kakoulli, A.; Wedzicha, B. L.; Mottram, D. S. Acrylamide and pyrazine formation in model systems containing asparagine. J. Agric. Food Chem. 2008, 56, 6105-6112.
6. Field, E. A.; Price, C. J.; Sleet, R. B.; Marr, M. C.; Schwetz, B. A.; Morrissey, R. E. Developmental toxicity evaluation of acrylamide in rats and mice. Fundam. Appl. Toxicol. 1990, 14, 502-512.
7. Dearfield, K. L.; Douglas, G. R.; Ehling, U. H.; Moore, M. M.; Sega, G. A.; Brusick, D. J. Acrylamide: A review of its genotoxicity and an assessment of heritable genetic risk. Mutat. Res. 1995, 330, 71-99.
8. Holland, N.; Ahlborn, T.; Turteltaub, K.; Markee, C.; Moore, D., II; Wyrobek, A. J.; Smith, M. T. Acrylamide causes preimplantation abnormalities in embryos and induces chromatin-adducts in male germ cells of mice. Reprod. Toxicol. 1999, 13, 167-178.
9. Fort, D. J.; Paul, R. R. Enhancing the predictive validity of Frog Embryo Teratogenesis Assay - Xenopus (FETAX). J. Appl. Toxicol. 2002, 22, 185-191.
10. Tyl, R. W.; Marr, M. C.; Myers, C. B.; Ross, W. P.; Friedman, M. A. Relationship between acrylamide reproductive and neurotoxicity in male rats. Reprod. Toxicol. 2000, 14, 147-157.
11. Tyl, R. W.; Friedman, M. A. Effects of acrylamide on rodent reproductive performance. Reprod. Toxicol. 2003, 17, 1-13.
12. Dobrzynska, M. M.; Gajewski, A. K. Induction of micronuclei in bone marrow and sperm head abnormalities after combined exposure of mice to low doses of X-rays and acrylamide. Teratog., Carcinog., Mutagen. 2000, 20, 133-140.
13. Lee, K.-Y.; Shibutani, M.; Kuroiwa, K.; Takagi, H.; Inoue, K.; Nishikawa, H.; Miki, T.; Hirose, M. Chemoprevention of acrylamide toxicity by antioxidative agents in rats - Effective suppression of testicular toxicity by phenylethyl isothiocyanate. Arch. Toxicol. 2005, 79, 531-541.
14. Wang, H.; Huang, P.; Lie, T.; Li, J.; Hutz, R. J.; Li, K.; Shi, F. Reproductive toxicity of acrylamide-treated male rats. Reprod. Toxicol. 2010, 29, 225-230.
15. Park, J.; Kamendulis, L. M.; Friedman, M. A.; Klaunig, J. E. Acrylamide-induced cellular transformation. Toxicol. Sci. 2002, 65, 177-183.
16. Klaunig, J. E.; Kamendulis, L. M. Mechanisms of acrylamide induced rodent carcinogenesis. In Chemistry and Safety of Acrylamide in Food; Friedman, M., Mottram, M., Eds.; Springer: New York, 2005; pp 49-62.
17. Sörgel, F.; Weissenbacher, R.; Kinzig-Schippers, M.; Hofmann, A.; Illauer, M.; Skott, A.; Landersdorfer, C. Acrylamide: increased concentrations in homemade food and first evidence of its variable absorption from food, variable metabolism and placental and breast milk transfer in humans. Chemotherapy 2002, 48, 267-274.
18. Annola, K.; Karttunen, V.; Keski-Rahkonen, P.; Myllynen, P.; Segerback, D.; Heinonen, S.; Vahakangas, K. Transplacental transfer of acrylamide and glycidamide are comparable to that of antipyrine in perfused human placenta. Toxicol. Lett. 2008, 182, 50-56.
19. Schettgen, T.;Kütting, B.; Hornig, M.; Beckmann, M. W.; Weiss, T.; Drexler, H.; Angerer, J. Trans-placental exposure of neonates to acrylamide-a pilot study. Int. Arch. Occup. Environ. Health 2004, 77, 213-216.
20. Takahashi, M.; Shibutani, M.; Nakahigashi, J.; Sakaguchi, N.; Inoue, K.; Morikawa, T.; Yoshida, M.; Nishikawa, A. Limited lactational transfer of acrylamide to rat offspring on maternal oral administration during the gestation and lactation periods. Arch. Toxicol. 2009, 83, 785-793.
21. Zödl, B.; Schmid, D.; Wassler, G.; Gundacker, C.; Leibetseder, V.; Thalhammer, T.; Ekmekcioglu, C. Intestinal transport and metabolism of acrylamide. Toxicology 2007, 232, 99-108.
22. Piersma, A. H.; Janer, G.;Wolterink, G.; Bessems, J. G.M.; Hakkert, B. C.; Slob, W. Quantitative extrapolation of in vitro whole embryo culture embryotoxicity data to developmental toxicity in vivo using the benchmark dose approach. Toxicol. Sci. 2008, 101, 91-100.
23. Marchett, F.; Bishop, J.; Lowe, X.; Wyrobek, A. J. Chromosomal mosaicism in mouse two-cell embryos after paternal exposure to acrylamide. Toxicol. Sci. 2009, 107, 194-205.
24. OEHHA-CAL/EPA. Safe Drinking Water and Toxic Enforcement Act of 1986 (Proposition 65): Notice of intent to list acrylamide. Accessed Jun 17, 2010. http://oehha.ca.gov/prop65/CRNR-notices/ admin-listing/intent-to-list/ noil022610.html.
25. ASTM. Standard Guide for Conducting the Frog Embryo Teratogenesis Assay - Xenopus (FETAX), E1439-98; American Society for Testing and Materials: Philadelphia, PA, 1998.
26. Friedman, M.; Rayburn, J. R.; Bantle, J. A. Developmental toxicology of potato glycoalkaloids in the Frog Embryo Teratogenesis Assay - Xenopus (FETAX). Food Chem. Toxicol. 1991, 29, 537-547.
27. Friedman, M.; Rayburn, J. R.; Bantle, J. A. Structural relationships and developmental toxicity of Solanum alkaloids in the frog embryo teratogenesis assay-Xenopus. J. Agric. Food Chem. 1992, 40, 1617-1624.
28. Rayburn, J. R.; Bantle, J. A.; Friedman, M. Role of carbohydrate side chains of potato glycoalkaloids in developmental toxicity. J. Agric. Food Chem. 1994, 42, 1511-1515.
29. Rayburn, J. R.; Bantle, J. A.; Qualls, C. W., Jr.; Friedman, M. Protective effects of glucose-6-phosphate and NADP against R-chaconineinduced developmental toxicity in Xenopus embryos. Food Chem. Toxicol. 1995, 33, 1021-1025.
30. Rayburn, J. R.; Friedman, M.; Bantle, J. A. Synergistic interaction of glycoalkaloids R-chaconine and R-solanine on developmental toxicity in Xenopus embryos. Food Chem. Toxicol. 1995, 33, 1013-1019.
31. Friedman, M.; Burns, C. F.; Butchko, C. A.; Blankemeyer, J. T. Folic acid protects against potato glycoalkaloid R-chaconine-induced disruption of frog embryo cell membranes and developmental toxicity. J. Agric. Food Chem. 1997, 45, 3990-3994.
32. Low, M. Y.; Koutsidis, G.; Parker, J. K.; Elmore, J. S.; Dodson, A. T.; Mottram, D. S. Effect of citric acid and glycine addition on acrylamide and flavor in a potato model system. J. Agric. Food Chem. 2006, 54, 5976-5983.
33. Ou, S.; Lin, Q.; Zhang, Y.; Huang, C.; Sun, X.; Fu, L. Reduction of acrylamide formation by selected agents in fried potato crisps on industrial scale. Innovative Food Sci. Emerging Technol. 2008, 9, 116-121.
34. Zamora, R.; Delgado, R. M.; Hidalgo, F. J. Model reactions of acrylamide with selected amino compounds. J. Agric. Food Chem. 2010, 58, 1708-1713.
35. Boettcher, M. I.; Bolt, H. M.; Drexler, H.; Angerer, J. Excretion of mercapturic acids of acrylamide and glycidamide in human urine after single oral administration of deuterium-labelled acrylamide. Arch. Toxicol. 2006, 80, 55-61.
36. Atkuri, K. R.; Mantovani, J. J.; Herzenberg, L. A.; Herzenberg, L. A. N-Acetylcysteine-a safe antidote for cysteine/glutathione deficiency. Curr. Opin. Pharmacol. 2007, 7, 355-359.
37. Friedman, M. Improvement in the safety of foods by SH-containing amino acids and peptides.Areview. J.Agric. Food Chem. 1994, 42, 3-20.
38. Hidalgo, F. J.; Delgado, R. M.; Zamora, R. Role of mercaptans on acrylamide elimination. Food Chem. 2010, 122, 596-601.
39. Friedman, M. The Chemistry and Biochemistry of the Sulfhydryl Group in Amino Acids, Peptides, and Proteins (Chapter 1: Acid-base equilibria); Pergamon Press: Oxford, 1973.
40. Snow, J. T.; Finley, J. W.; Friedman, M. Relative reactivities of sulfhydryl groups with N-acetyl dehydroalanine and N-acetyl dehydroalanine methyl ester. Int. J. Pept. Protein Res. 1976, 8, 57-64.
41. Friedman, M.; Cavins, J. F.; Wall, J. S. Relative nucleophilic reactivities of amino groups and mercaptide ions in addition to reactions with R, β-unsaturated compounds. J. Am. Chem. Soc. 1965, 87, 3572-3582.
42. LoPachin, R. M.; Gavin, T.; Geohagen, B. C.; Das, S. Neurotoxic mechanisms of electrophilic type-2 alkenes: soft soft interactions described by quantum mechanical parameters. Toxicol. Sci. 2007, 98, 561-570.
43. Ravi, R.; Sai Manohar, R.; Haridas Rao, P. Influence of additives on the rheological characteristics and baking quality of wheat flours. Eur. Food Res. Technol. 2000, 210, 202-208.
44. Friedman, M. Food browning and its prevention: an overview. J. Agric. Food Chem. 1996, 44, 631-653.
45. Friedman, M.; Brandon, D. L. Nutritional and health benefits of soy proteins. J. Agric. Food Chem. 2001, 49, 1069-1086.
46. Stevens, K. L.; Wilson, R. E.; Friedman, M. Inactivation of a tetrachloroimide mutagen from simulated processing water. J. Agric. Food Chem. 1995, 43, 2424-2427.
47. Finley, J. W.; Friedman, M. Chemical methods for available lysine. Cereal Chem. 1973, 50, 101-105.
48. Friedman, M.; Finley, J. W. Reactions of proteins with ethyl vinyl sulfone. Int. J. Pept. Protein Res. 1975, 7, 481-486.
49. Masri, M. S.; Friedman, M. Protein reactions with methyl and ethyl vinyl sulfones. J. Protein Chem. 1988, 7, 49-54.