Convenient syntheses of dibenzo[c,p]chrysene and its possible proximate and ultimate carcinogens: In vitro metabolism and DNA adduction studies

Journal of Organic Chemistry

Volumn 70, Issue 13, 2005, Pages 4962-4970

  Sharma, Arun K ^a   Lin, Jyh Ming ^a   Desai, Dhimant ^a   Amin, Shantu ^a  

^a PENN STATE MILTON S HERSHEY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; LIVING SYSTEMS STUDIES; METABOLISM; METABOLITES; OLEFINS; ORGANIC COMPOUNDS; PHENOLS; SYNTHESIS (CHEMICAL); TUMORS;

CYCLIZATION; EPOXIDES;

CARCINOGENS;

1,2 DIHYDROXY 1,2 DIHYDROGEN DIBENZO[C,P]CHRYSENE; 1,2 DIHYDROXY 3,4 EPOXIDE; 1,2 DIHYDROXY 3,4 EPOXY 1,2,3,4 TETRAHYDRO DIBENZO[C,P]CHRYSENE; 11 METHOXY DIBENZO[C,P]CHRYSENE; 11,12 DIHYDROXY 11,12 DIHYDRO DIBENZO[C,P]CHRYSENE; 11,12 DIHYDROXY 13,14 EPOXY 11,12,13,14 TETRAHYDRO DIBENZO[C,P]CHRYSENE; 2 METHOXY DIBENZO[C,P]CHRYSENE; 6 [2 (BETA METHOXYETHENYL) 4 METHOXYPHENYL]CHRYSENE; 6 [2 (BETA METHOXYETHENYL)PHENYL]CHRYSENE; ALKENE DERIVATIVE; AROMATIC HYDROCARBON; BETA NAPHTHOFLAVONE; CARCINOGEN; CHRYSENE DERIVATIVE; DIBENZO[C,P]CHRYSENE; DNA; EPOXIDE; PHENOBARBITAL; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CARCINOGENIC ACTIVITY; CHEMICAL ANALYSIS; CHEMICAL ENVIRONMENT; CHEMICAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; LIVER HOMOGENATE; METABOLISM; METABOLITE; NONHUMAN; PHOTOCHEMISTRY; RAT; RAT STRAIN; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

ANIMALS; BETA-NAPHTHOFLAVONE; CARCINOGENS, ENVIRONMENTAL; CHRYSENES; DNA ADDUCTS; LIVER; MOLECULAR STRUCTURE; NEOPLASMS, EXPERIMENTAL; PHENOBARBITAL; RATS; RATS, SPRAGUE-DAWLEY;

EID: 20844437281     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040291k     Document Type: Article

References (60)

1. Harvey, R. G. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity, Cambridge University Press: Cambridge, England, 1991.
2. (a) Gelboin, H. V. Physiol. Rev. 1980, 34, 1107.
3. (b) Conney, A. H. Cancer Res. 1982, 42, 4875.
4. (c) Cooper, C. S.; Grover, P. L.; Sims, P. Prog. Drug. Metab. 1983, 7, 295.
5. (d) Guengerich, F. P. Carcinogenesis 2000, 21, 345-351.
6. (e) Cavalieri, E. L.; Rogan, E. G. One-electron oxidation in aromatic hydrocarbon carcinogenesis. In Polycyclic Hydrocarbons and Carcinogenesis; Harvey, R. G., Ed.; American Chemical Society: Washington, B.C., 1985; pp 289-305.
7. (f) Penning, T. M.; Burczynski, M. E.; Hung, C.-F.; McCoull, K. D.; Palackal, N. T.; Tsuruda, L. S. Chem. Res. Toxicol. 1999, 12, 1.
8. (a) Huggins, C. B.; Pataki, J.; Harvey, R. G. Proc. Natl. Acad. Sci. U.S.A. 1967, 58, 2253.
9. (b) DiGiovanni, J.; Diamond, L.; Harvey, R. G.; Slaga, T. J. Carcinogenesis 1983, 4, 403.
10. (c) Hecht, S. S.; Amin, S.; Huie, K.; Melikan, A. A.; Harvey, R. G. Cancer Res. 1987, 47, 5310.
11. (d) Iyer, R. P.; Lyga, J. W.; Secrist, J. A., III; Daub, G. H.; Slaga, T. J. Cancer Res. 1980, 40, 1073.
12. (a) Hecht, S. S.; El-Bayoumy, K.; Rivenson, A.; Amin, S. Cancer Res. 1994, 54, 21.
13. (b) Levin, W.; Wood, A. W.; Chang, R. L.; Ittah, Y.; Croisy-Delcey, M.; Yagi, H.; Jerina, D. M.; Conney, A. H. Cancer Res. 1980, 40, 3910-3914.
14. (d) Amin, S.; Desai, D.; Dai, W.; Harvey, R. G.; Hecht, S. S. Carcinogenesis 1995, 16, 2813.
15. (d) Amin, S.; Krzeminski, J.; Rivenson, A.; Kurtzke, C.; Hecht, S. S.; El-Bayoumy, K. Carcinogenesis 1995, 16, 1971.
16. (a) Dipple, A. In DNA Adducts: Identification and Biological Significance; Hemminki, K., Dipple, A., Segerback, D., Kadulbar, F., Shuker, D., Bartsch, H., Eds.; IARC: Lyon, France, 1994; pp 107-129.
17. (b) Szeliga, J.; Lee, H.; Harvey, R. G.; Page, J. E.; Ross, H. L.; Routledge, M. N.; Hilton B. D.; Dipple, A. Chem. Res. Toxicol. 1994, 7, 420.
18. (a) Conney, A. H. Cancer Res. 1982, 42, 4875.
19. (b) Geacintov, N. E.; Cosman, M.; Hingerty, B. E.; Amin, S.; Broyde, S.; Patel, D. J. Chem. Res. Toxicol. 1997, 10, 112.
20. (c) Dipple, A.; Moschel, R. C.; Bigger, C. A. H. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph No. 182; American Chemical Society: Washington, DC, 1984; pp 63-84.
21. (d) Harvey, R. G.; Geacintov, N. E. Acc. Chem. Res. 1988, 21, 66.
22. Dipple A.; Pigott, M. A.; Agarwal, S. K.; Yagi, H.; Sayer, J. M.; Jerina, D. M. Nature 1987, 327, 535.
23. Giles, A. S.; Seidel, A.; Phillips, D. H. Chem. Res. Toxicol. 1995, 8, 591.
24. (a) Szeliga, J.; Page, J. E.; Hilton, B. D.; Kiselyov, A. S.; Harvey, R. G.; Dunayevskiy, Y. M.; Vouros, P.; Dipple, A. Chem. Res. Toxicol. 1995, 8, 1014.
25. (b) Herndon, W. C.; Nowal, P. C.; Connor, D. A.; Lin, P. J. Am. Chem. Soc. 1992, 114, 41.
26. (a) Li, K. M.; Todorovic, R.; Rogan, E. G.; Cavalieri, E. L.; Ariese, F.; Suh, M.; Jankowlak, R.; Small, G. J. Biochemistry 1995, 34, 8043.
27. (b) Jankowiak, R.; Ariese, F.; Hewer, A.; Luch, A.; Zamzow, D.; Hughes, N. C.; Phillips, D.; Seidel, A.; Platt, K. L.; Oesch, F.; Small, G. J. Chem. Res. Toxicol. 1998, 11, 674.
28. (c) Ralston, S. L.; Coffing, S. L.; Seidel, A.; Luch, A.; Platt, K. L.; Baird, W. M. Chem. Res. Toxicol. 1997, 10, 687.
29. (d) Baird, W. M.; Ralston, S.; Luch, A.; Platt, K. L.; Seidel, A. Polycyclic Aromat. Compd. 1996, 10, 235.
30. (e) Ralston, S. L.; Seidel, A.; Luch, A.; Platt, K. L.; Baird, W. M. Carcinogenesis 1995, 16, 2899.
31. Buterin, T.; Hess, M. T.; Luneva, N.; Geacintov, N. E.; Amin, S.; Kroth, H.; Seidel, A.; Naegeli, H. Cancer Res. 2000, 60, 1849.
32. Ruan, Q.; Kolbanovskiy, A.; Zhuang, P.; Chen, J.; Krzeminski, J.; Amin, S.; Geacintov, N. E. Chem. Res. Toxicol. 2002, 15, 249.
33. Borosky, G. L. J. Org. Chem. 1999, 64, 7738.
34. Amin, S.; Lin, J.-M.; Krzeminski, J.; Boyiri, T.; Desai, D.; El-Bayoumy, K. Chem. Res. Toxicol. 2003, 16, 227.
35. Harvey, R. G.; Zhang, J.-T.; Pataki, J. J. Org. Chem. 1998, 63, 6405.
36. Harvey, R. G. Polycyclic Aromatic Hydrocarbons; Wiley-VCH: New York, 1997; p 189.
37. (a) Herdon, W. C.; Nowak, P. C.; Connor, D. A.; Lin, P. J. Am. Chem. Soc. 1992, 114, 41.
38. (b) Herdon, W. C.; Connor, D. A.; Lin, P. Pure Appl. Chem. 1990, 62, 435.
39. Burnham, J. W.; Melton, R. G.; Eisenbraun, E. J. J. Org. Chem. 1973, 35, 2783.
40. For recent reviews, see: (a) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lamaire, M. Chem. Rev. 2002, 102, 1359.
41. (b) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
42. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
43. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
44. (e) Suzuki, A Pure Appl. Chem. 1994, 66, 213.
45. (a) Kumar, S. J. Chem. Soc., Perkin Trans. 1 1998, 3157.
46. (b) Zhang, F. J.; Cortez, C.; Harvey, R. G. J. Org. Chem. 2000, 65, 3952.
47. (a) Kumar, S. Synthesis 2001, 841.
48. (a) Kumar, S. J. Org. Chem. 1997, 62, 8535.
49. Rice, J. E.; Cai, Z.-W. J. Org. Chem. 1993, 58, 1415.
50. Desai, D.; Sharma, A. K.; Lin, J.-M.; Krzeminski, J.; Pimental, M.; El-Bayoumy, K.; Nesnow, S.; Amin, S. Chem. Res. Toxicol. 2002, 15, 964.
51. Desai, D.; Sharma, A. K.; Lin, J.-M.; El-Bayoumy, K.; Amin, S.; Pimentel, M.; Nesnow, S. Polycyclic Aromat. Compd. 2002, 22, 267.
52. Sharma, A. K.; Kumar, S.; Amin, S. Polycyclic Aromat. Compd. 2002, 22, 277.
53. Sharma, A. K.; Kumar, S.; Amin, S. J. Org. Chem. 2004, 69, 3979.
54. Krzeminski, J.; Lin, J.-M.; Amin, S.; Hecht, S. S. Chem. Res. Toxicol. 1994, 7, 125.
55. The reaction did not go to completion. However, the olefin mixture was separated easily from the unreacted starting materials by silica gel column chromatography.
56. El-Bayoumy, K.; Desai, D.; Boyiri, T.; Rosa, J.; Krzeminski, J.; Sharma, A. K.; Pittman, B.; Amin, S. Chem. Res. Toxicol. 2002, 15, 972.
57. Mellory, F. B.; Rudolph, M. J.; Oh, S. M. J. Org. Chem. 1989, 54, 4619.
58. Cheng, S. C.; Hilton, B. D.; Roman, J. M.; Dipple, A. Chem. Res. Toxicol. 1989, 2, 334.
59. Desai, D.; Krzeminski, J.; Lin, J.-M.; Chaddha, A.; Miyata, N.; Yagi, H.; Jerina, D. M.; Amin, S. Polycyclic Aromat. Compod. 1999, 16, 255.
60. Baird, W. M.; Brookes, P. Cancer Res, 1973, 33, 2378.