Skip to main content
SpringerLink
Log in

Formation of genotoxic 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP) and its kinetics in a model system

  • Research Article
  • Published:
Food Science and Biotechnology Aims and scope Submit manuscript

Abstract

The influence of important precursors (amino acids and sugars) and heating conditions on the formation of 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP), an abundant heterocyclic amine compound, and its formation kinetics were evaluated in a chemical model system. Phenylalanine containing α-amino propenoic acid (NH2CH2CHCOOH) may be involved in PhIP formation whereas glycine is not. Adding different amounts of 4 sugars (glucose, galactose, fructose, and ribose) resulted in significant differences (p<0.05) in PhIP formation in the model system. All sugars used may have been a limiting factor for PhIP formation. The formation of PhIP increased with increasing time and heating temperature and was correlated with browning reaction intensity. The rate constant of PhIP formation also increased with increasing temperature. Based on the values of activation energy, enthalpy, and activation entropy, PhIP formation was assumed to be a temperature-sensitive, endothermic, and bimolecular reaction. The results offer meaningful information for controlling the risk of PhIP formation in cooked foods.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Alaejos MS, Afonso AM. Factors that affect the content of heterocyclic aromatic amines in foods. Compr. Rev. Food Sci. F. 10: 52–108 (2011)

    Article  CAS  Google Scholar 

  2. Kim S, Lee KG. Effect of cooking variables on formation of heterocyclic amines (HCA) in roasted pork and mackerel. J. Toxicol. Env. Heal. A 73: 1599–1609 (2010)

    Article  CAS  Google Scholar 

  3. Wu MC, Ma CY, Yang CC, Kao WC, Shen SC. The formation of IQ type mutagens from Maillard reaction in ethanolic solution. Food Chem. 125: 582–587 (2011)

    Article  CAS  Google Scholar 

  4. Negishi C, Wakabayashi K, Tsuda M, Sato S, Sugimura T, Saito H, Maeda M, Jägerstad M. Formation of 2-amino-3,7,8-trimethylimidazo [4,5-f] quinoxaline, a new mutagen, by heating a mixture of creatinine, glucose, and glycine. Mutat. Res. 140: 55–59 (1984)

    Article  CAS  Google Scholar 

  5. Felton J, Knize MG, Shen N, Lewis P, Andresen B, Happe J, Hatch F. The isolation of a new mutagen from fried ground beef: 2-Amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP). Carcinogenesis 7: 1081–1086 (1986)

    Article  CAS  Google Scholar 

  6. Murkovic M, Weber HJ, Geiszler S, Fröhlich K, Pfannhauser W. Formation of the food associated carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in model systems. Food Chem. 65: 233–237 (1999)

    Article  CAS  Google Scholar 

  7. Puangsombat K, Gadgil P, Houser TA, Hunt MC, Smith JS. Occurrence of heterocyclic amines in cooked meat products. Meat Sci. 90: 739–746 (2012)

    Article  CAS  Google Scholar 

  8. Weisburger JH. Comments on the history and importance of aromatic and heterocyclic amines in public health. Mutat. Res. 506–507: 9–20 (2002)

    Google Scholar 

  9. Sinha R, Rothman N. Exposure assessment of heterocyclic amines (HCAs) in epidemiologic studies. Mutat. Res. 376: 195–202 (1997)

    Article  CAS  Google Scholar 

  10. Zhu JJ, Chang P, Bondy ML, Sahin AA, Singletary SE, Takahashi S, Shirai T, Li D. Detection of 2-amino-1-methyl-6-phenylimidazo [4,5-b]-pyridine-DNA adducts in normal breast tissues and risk of breast cancer. Cancer Epidem. Biomar. 12: 830–837 (2003)

    CAS  Google Scholar 

  11. Skog K, Jägerstad M. Effects of glucose on the formation of PhIP in a model system. Carcinogenesis 12: 2297–2300 (1991)

    Article  CAS  Google Scholar 

  12. Övervik E, Kleman M, Berg I, Gustafsson JÅ. Influence of creatinine, amino acids, and water on the formation of the mutagenic heterocyclic amines found in cooked meat. Carcinogenesis 10: 2293–2301 (1989)

    Article  Google Scholar 

  13. Skog K, Johansson M, Jägerstad M. Carcinogenic heterocyclic amines in model systems and cooked foods: A review on formation, occurrence, and intake. Food Chem. Toxicol. 36: 879–896 (1998)

    Article  CAS  Google Scholar 

  14. Skog K, Jägerstad M. Effects of monosaccharides and disaccharides on the formation of food mutagens in model systems. Mutat. Res. 230: 263–272 (1990)

    Article  CAS  Google Scholar 

  15. Zöchling S, Murkovic M. Formation of the heterocyclic aromatic amine PhIP: Identification of precursors and intermediates. Food Chem. 79: 125–134 (2002)

    Article  Google Scholar 

  16. Arvidsson P, Boekel M, Skog K, Jägerstad M. Kinetics of formation of polar heterocyclic amines in a meat model system. J. Food Sci. 62: 911–916 (1997)

    Article  CAS  Google Scholar 

  17. Arvidsson P, Boekel M, Skog K, Solyakov A, Jägerstad M. Formation of heterocyclic amines in a meat juice model system. J. Food Sci. 64: 216–221 (1999)

    Article  CAS  Google Scholar 

  18. Ahn J, Grün IU. Heterocyclic amines: 1. Kinetics of formation of polar and nonpolar heterocyclic amines as a function of time and temperature. J. Food Sci. 70: C173–C179 (2005)

    Article  CAS  Google Scholar 

  19. Gross GA, Grüter A. Quantitation of mutagenic/carcinogenic heterocyclic amines in food products. J. Chromatogr. A 592: 271–278 (1992)

    Article  CAS  Google Scholar 

  20. Shin HS, Strasburg GM, Gray JI. A model system study of the inhibition of heterocyclic aromatic amine formation by organosulfur compounds. J. Agr. Food Chem. 50: 7684–7690 (2002)

    Article  CAS  Google Scholar 

  21. Hwang DK, Ngadi M. Kinetics of heterocyclic amines formation in meat emulsion at different fat contents. Lebensm.-Wiss. Technol. 35: 600–606 (2002)

    CAS  Google Scholar 

  22. Arrhenius S. About the reaction rate of the inversion of no refined sugar at souring. Z. Phys. Chem. 4: 226–228 (1889)

    Google Scholar 

  23. Lee J, Dong A, Jung K, Shin HS. Influence of extra virgin olive oil on the formation of heterocyclic amines in roasted beef steak. Food Sci. Biotechnol. 20: 159–165 (2011)

    Article  CAS  Google Scholar 

  24. Tai CY, Lee KH, Chen BH. Effects of various additives on the formation of heterocyclic amines in fried fish fibre. Food Chem. 75: 309–316 (2001)

    Article  CAS  Google Scholar 

  25. Jung K, Lee K, Park J, Dong A, Shin HS. Influence of fructooligosaccharides and garlic on formation of heterocyclic amines in fried ground beef patties. Food Sci. Biotechnol. 19: 1159–1164 (2010)

    Article  CAS  Google Scholar 

  26. Jägerstad M, Reutersward AL, Olsson R, Grivas S, Nyhammar T, Olsson K, Dahlqvist A. Creatine and Maillard reaction products as precursors of mutagenic compounds: Effects of various amino acids. Food Chem. 12: 255–264 (1983)

    Article  Google Scholar 

  27. Pais P, Salmon CP, Knize MG, Felton JS. Formation of mutagenic/carcinogenic heterocyclic amines in dry-heated model systems, meats, and meat drippings. J. Agr. Food Chem. 47: 1098–1108 (1999)

    Article  CAS  Google Scholar 

  28. Skog K. Cooking procedures and food mutagens: A literature review. Food Chem. Toxicol. 31: 655–675 (1993)

    Article  CAS  Google Scholar 

  29. Jägerstad M. Chemistry, formation, and occurrence of genotoxic heterocyclic amines identified in model systems and cooked food. Lebensm. Unter. F. A. 207: 419–427 (1998)

    Article  Google Scholar 

  30. Tinoco I, Sauer K, Wang JC, Puglisi JD. Physical Chemistry: Principles and Applications in Biological Sciences. Prentice-Hall, Upper Saddle River, NJ, USA. pp. 398, 740 (2002)

  31. Hill JW, Petrucci RH. General Chemistry. Prentice-Hall, Upper Saddle River, NJ, USA. pp. 168–172 (1996)

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Food Science and Biotechnology and Institute of Lotus Functional Foods Ingredients, Dongguk University-Seoul, Seoul, 100-715, Korea

    Seung-Eun Moon & Han-Seung Shin

Authors
  1. Seung-Eun Moon
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Han-Seung Shin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Han-Seung Shin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Moon, SE., Shin, HS. Formation of genotoxic 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP) and its kinetics in a model system. Food Sci Biotechnol 22 (Suppl 1), 137–145 (2013). https://doi.org/10.1007/s10068-013-0059-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10068-013-0059-z

Keywords

Search

Navigation