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The Use of Pirkle High-Performance Liquid Chromatography Phases in the Resolution of Enantiomers of Polycyclic Aromatic Hydrocarbon Metabolites

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Chiral Separations

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Summary

Polycyclic aromatic hydrocarbons (PAH) are metabolised within tissues in both a regio- and a stereoselective manner. Enantiomers of PAH metabolites have been resolved on high performance liquid chromatography by one of two methods, either (i) indirectly, following derivatization, or (ii) directly using chiral stationary phases (Pirkle columns). This latter technique has been used to assess, for example, the stereoselectivity of benzo(a)pyrene (BP)-7,8-dihydrodiol formation by samples of human skin following the topical application of [3H]BP and the optical purity of BP-7,8-dihydrodiol and anthracene-1,2-dihydrodiol extracted from incubations of [3H]BP and of [14C]anthracene with rabbit skin and liver microsomal fractions.

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References

  1. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man, Vol. 3: Certain polycyclic aromatic hydrocarbons and heterocyclic compounds, International Agency for Research on Cancer, Lyon (1973).

    Google Scholar 

  2. S. A. Henry, Br.Med.Bull., 4:389 (1947).

    PubMed  CAS  Google Scholar 

  3. D. H. Phillips and P. L. Grover, in: “Monitoring Human Exposure to Carcinogenic and Mutagenic Agents,” A. Berlin, M. Draper, K. Hemminki and H. Vainio, eds., International Agency for Research on Cancer, Lyon, p. 47 (1984).

    Google Scholar 

  4. D. R. Thakker, H. Yagi, W. Levin, A. W. Wood, A. H. Conney and D. M. Jerina, in: “Bioactivation of Foreign Compounds,” M. W. Anders, ed., Academic Press, Inc., New York, ch.7, p. 177 (1985).

    Google Scholar 

  5. P. Sims, P. L. Grover, A. Swaisland, K. Pal and A. Hewer, Nature, 252:326 (1974).

    Article  PubMed  CAS  Google Scholar 

  6. A. H. Conney, Cancer Res., 42:4875 (1982).

    PubMed  CAS  Google Scholar 

  7. S. K. Yang, M. Mushtaq and P.-L. Chiu, in: “ACS Symposium Series No. 283, Polycyclic Hydrocarbons and Carcinogenesis,” R.G. Harvey, ed., American Chemical Society, Washington D.C., p. 19 (1985).

    Chapter  Google Scholar 

  8. P. J. van Bladeren, R. N. Armstrong, D. Cobb, D. R. Thakker, D. E. Ryan, P. E. Thomas, N. D. Sharma, D. R. Boyd, W. Levin and D. M. Jerina, Biochem. Biophys. Res. Commun, 106:602 (1982).

    Article  PubMed  Google Scholar 

  9. S. K. Yang, P. P. Roller and H. V. Gelboin, Biochemistry, 16:3680 (1977).

    Article  PubMed  CAS  Google Scholar 

  10. D. R. Thakker, H. Yagi, W. Levin, A. Y. H. Lu, A. H. Conney and D. M. Jerina, J.Biol.Chem., 252:6328 (1977).

    PubMed  CAS  Google Scholar 

  11. H. Yagi and D. M. Jerina, J.Am.Chem.Soc. 104:4026 (1982).

    Article  CAS  Google Scholar 

  12. D. R. Thakker, W. Levin, H. Yagi, M. Tada, D. E. Ryan, P. E. Thomas, A. H. Conney and D. M. Jerina, J.Biol.Chem., 257:5103 (1982).

    PubMed  CAS  Google Scholar 

  13. M. W. Chou, P.-L. Chiu, P. P. Fu and S. K. Yang, Carcinogenesis, 4:629 (1983).

    Article  PubMed  CAS  Google Scholar 

  14. H. Yagi, D. R. Thakker, Y. Ittah, M. Croisy-Delcey and D. M. Jerina, Tetrahedron Lett., 24:1349(1983).

    Google Scholar 

  15. Y. Ittah, D. R. Thakker, W. Levin, M. Croisy-Delcey, D. E. Ryan, P. E. Thomas, A. H. Conney and D. M. Jerina, Chem.-Biol.Interact., 45:15 (1983).

    Article  PubMed  CAS  Google Scholar 

  16. P. J. van Bladeren, S. K. Balani, J. M. Sayer, D. R. Thakker, D. R. Boyd, D. E. Ryan, P. E. Thomas, W. Levin and D. M. Jerina, Biochem.Biophys.Res.Commun., 145:160 (1987).

    Article  PubMed  Google Scholar 

  17. P. J. van Bladeren, K. P. Vyas, J. M. Sayer, D. E. Ryan, P. E. Thomas, W. Levin and D. M. Jerina, J.Biol.Chem., 259:8966 (1984).

    PubMed  Google Scholar 

  18. P. J. van Bladeren, J. M. Sayer, D. E. Ryan, P. E. Thomas, W. Levin and D. M. Jerina, J.Biol.Chem., 260:10226 (1985).

    PubMed  Google Scholar 

  19. W. Levin, M. K. Buening, A. W. Wood, R. L. Chang, B. Kedzierski, D. R. Thakker, D. R. Boyd, G. S. Gadaginamath, R. N. Armstrong, H. Yagi, J. M. Karle, T. J. Slaga, D. M. Jerina and A. H. Conney, J.Biol.Chem., 255:9067 (1980).

    PubMed  CAS  Google Scholar 

  20. R. N. Armstrong, B. Kedzierski, W. Levin and D. M. Jerina, J.Biol.Chem., 256:4726 (1981).

    PubMed  CAS  Google Scholar 

  21. D. M. Jerina, J. M. Sayer, H. Yagi, P. J. van Bladeren, D. R. Thakker, W. Levin, R. L. Chang, A. W. Wood and A. H. Conney, in: “Microsomes and Drug Oxidations,” A.R. Boobis, J. Caldwell, F. De Matteis and C. R. Elcombe eds., Taylor and Francis, London, p. 310 (1985).

    Google Scholar 

  22. I. W. Wainer and T. D. Doyle, Liq.Chromatogr., 2 (1984).

    Google Scholar 

  23. H. B. Weems and S. K. Yang, Anal.Biochem., 125:156 (1982).

    Article  PubMed  CAS  Google Scholar 

  24. W. H. Pirkle, D. W. House and J. M. Finn, J.Chromatogr., 192:143 (1980).

    Article  CAS  Google Scholar 

  25. W. H. Pirkle and J. M. Finn, J.Org.Chem., 46:2935 (1981).

    Article  CAS  Google Scholar 

  26. S. K. Yang and X.-C. Li, J.Chromatogr., 291:265 (1984).

    Article  PubMed  CAS  Google Scholar 

  27. S. K. Yang, H. B. Weems, M. Mushtaq and P. P. Fu, J.Chromatogr., 316:569 (1984).

    Article  PubMed  CAS  Google Scholar 

  28. H. B. Weems, M. Mushtaq and S. K. Yang, Anal.Biochem., 148:328 (1985).

    Article  PubMed  CAS  Google Scholar 

  29. S. K. Yang, M. Mushtaq, H. B. Weems and P. P. Fu, J.Liq.Chromatogr., 9:473 (1986).

    Article  CAS  Google Scholar 

  30. P.-L. Chiu and S. K. Yang, J.Liq.Chromatogr., 9:701 (1986).

    Article  CAS  Google Scholar 

  31. S. K. Yang, M. Mushtaq and P. P. Fu, J.Chromatogr., 371:195 (1986).

    Article  PubMed  CAS  Google Scholar 

  32. H. B. Weems, M. Mushtaq, P. P. Fu and S. K. Yang, J.Chromatogr., 371:211 (1986).

    Article  PubMed  CAS  Google Scholar 

  33. M. Mushtaq and S. K. Yang, Carcinogenesis, 8:705 (1987).

    Article  PubMed  CAS  Google Scholar 

  34. S. K. Yang, M. Mushtaq and H. B. Weems, Arch.Biochem.Biophys., 255:48 (1987).

    Article  PubMed  CAS  Google Scholar 

  35. L. S. Von Tungeln and P. P. Fu, Carcinogenesis, 7:1135 (1986).

    Article  Google Scholar 

  36. H. B. Weems, P. P. Fu and S. K. Yang, Carcinogenesis, 7:1221 (1986).

    Article  PubMed  CAS  Google Scholar 

  37. S. K. Yang and P. P. Fu, Chem-Biol.Interact., 49:71 (1984).

    Article  PubMed  CAS  Google Scholar 

  38. S. K. Yang, M. Mushtaq, H. B. Weems and P. P. Fu, Tetrahedron Lett., 27:433 (1986).

    Article  CAS  Google Scholar 

  39. S. K. Yang, M. Mushtaq, H. B. Weems, D. W. Miller and P. P. Fu, Biochem.J., 245:191 (1987).

    PubMed  CAS  Google Scholar 

  40. S. K. Yang and H. B. Weems, Anal.Chem, 2658 (1984).

    Google Scholar 

  41. S. K. Yang and P. P. Fu, Biochem.J., 223:775 (1984).

    PubMed  CAS  Google Scholar 

  42. M. Mushtaq, H. B. Weems and S. K. Yang, Biochem.Biophys.Res.Commun., 125:539 (1984).

    Article  PubMed  CAS  Google Scholar 

  43. S. K. Balani, H. J. C. Yeh, D. E. Ryan, P. E. Thomas, W. Levin and D. M. Jerina, Biochem.Biophys.Res.Commun., 130:610 (1985).

    Article  PubMed  CAS  Google Scholar 

  44. P. P. Fu and S. K. Yang, Carcinogenesis, 4:979 (1983).

    Article  PubMed  CAS  Google Scholar 

  45. P. P. Fu, L. S. Von Tungeln and M. W. Chou, Mol.Pharmacol., 28:62 (1985).

    PubMed  CAS  Google Scholar 

  46. A. Weston, R. M. Hodgson, A. J. Hewer, R. Kuroda and P. L. Grover, Chem.-Biol.Interact., 54:223 (1985).

    Article  PubMed  CAS  Google Scholar 

  47. M. Hall and P. L. Grover, Chem-Biollnteract., 59:265 (1986).

    CAS  Google Scholar 

  48. M. Hall, D. K. Parker, M. Christou, C. R. Jefcoate and P. L. Grover in: “Drug Metabolism — From Molecules to Man,” D. Benford, G.G. Gibson and J.W. Bridges, eds., Taylor and Francis, London, p.411 (1987).

    Google Scholar 

  49. K. Yamagiwa and K. Ichikawa, Verh.Jap.Pathol.Ges., 5:142 (1915).

    Google Scholar 

  50. E. Boyland and A. A. Levi, Biochem.J., 29:2679 (1935).

    PubMed  CAS  Google Scholar 

  51. P. Sims, Biochem.J., 92:621 (1964).

    PubMed  CAS  Google Scholar 

  52. A. Weston, P. L. Grover and P. Sims, Chem.-Biol.Interact., 45:359 (1983).

    Article  PubMed  CAS  Google Scholar 

  53. R. Mehta, M. Meredith-Brown and G. M. Cohen, Chem.-Biol.Interact., 28:345 (1979).

    Article  PubMed  CAS  Google Scholar 

  54. A. Weston, P. L. Grover and P. Sims, Chem.-Biol.Interact., 42:233 (1982).

    Article  PubMed  CAS  Google Scholar 

  55. P. H. Chapman, M. D. Rawlins and S. Shuster, Br.J.Clin.Pharmacol., 7:499 (1979).

    PubMed  CAS  Google Scholar 

  56. T. Kuroki, J. Hosomi, K. Chida, J. Hosoi and N. Nemoto, Gann, 78:45 (1987).

    PubMed  CAS  Google Scholar 

  57. W. Levin, A. H. Conney, A. P. Alvares, I. Merkatz and A. Kappas, Science, 176:419 (1972).

    Article  PubMed  CAS  Google Scholar 

  58. T. Eling, J. Curtis, J. Battista and L. J. Marnett, Carcinogenesis, 7:1957 (1986).

    Article  PubMed  CAS  Google Scholar 

  59. G. Ekström, C. von Bahr, H. Glaumann and M. Ingelman-Sundberg, Acta Pharmacol et Toxicol., 50:251 (1982).

    Article  Google Scholar 

  60. R. Ayesh, J. R. Idle, J. C. Ritchie, M. J. Crothers and M. R. Hetzel, Nature, 312:169 (1984).

    Article  PubMed  CAS  Google Scholar 

  61. F. P. Guengerich, M. V. Martin, P. H. Beaune, P. Kremers, T. Wolff and D. J. Waxman, J.Biol.Chem, 261:5051 (1986).

    PubMed  CAS  Google Scholar 

  62. D. E. Ryan, P. E. Thomas, L. M. Reik and W. Levin, Xenobiotica, 12:727 (1982).

    Article  PubMed  CAS  Google Scholar 

  63. D. Sesardic, A. R. Boobis, J. McQuade, S. Baker, E. A. Lock, C. R. Elcombe, R. T. Robson, C. Hayward and D. S. Davies, Biochem.J., 236:569 (1986).

    PubMed  CAS  Google Scholar 

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Authors and Affiliations

  1. Chester Beatty Laboratories, Institute of Cancer Research, Royal Cancer Hospital, Fulham Road, London, SW3 6JB, UK

    Michael Hall & Philip L. Grover

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  1. Michael Hall
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  2. Philip L. Grover
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Editors and Affiliations

  1. The Robens Institute of Industrial and Environmental Health and Safety, University of Surrey, Guildford, Surrey, UK

    D. Stevenson

  2. ICI Pharmaceuticals, Macclesfield, Cheshire, UK

    I. D. Wilson

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© 1988 Plenum Press, New York

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Hall, M., Grover, P.L. (1988). The Use of Pirkle High-Performance Liquid Chromatography Phases in the Resolution of Enantiomers of Polycyclic Aromatic Hydrocarbon Metabolites. In: Stevenson, D., Wilson, I.D. (eds) Chiral Separations. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-6634-2_5

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  • DOI: https://doi.org/10.1007/978-1-4615-6634-2_5

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4615-6636-6

  • Online ISBN: 978-1-4615-6634-2

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