Translesional Synthesis on a DNA Template Containing a Single Stereoisomer of dG-(+)- or dG-(−)-anti-BPDE (7,8 -Dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene)

Biochemistry

Volumn 32, Issue 29, 1993, Pages 7531-7541

  Shibutani, Shinya ^a   Grollman, Arthur P ^a   Margulis, Leonid A ^b   Geacintov, Nicholas E ^b  

^a STONY BROOK UNIVERSITY   (United States)

^b NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[A]PYRENE; DNA DIRECTED DNA POLYMERASE; PRIMER DNA;

ARTICLE; CONTROLLED STUDY; DELETION MUTANT; DNA ADDUCT; DNA CONFORMATION; DNA FLANKING REGION; DNA TEMPLATE; MUTAGENESIS; NUCLEIC ACID BASE SUBSTITUTION; PRIORITY JOURNAL;

7,8-DIHYDRO-7,8-DIHYDROXYBENZO(A)PYRENE 9,10-OXIDE; BASE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; DNA; DNA DAMAGE; DNA POLYMERASE I; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ESCHERICHIA COLI; GENE DELETION; KINETICS; MOLECULAR SEQUENCE DATA; STEREOISOMERISM; SUPPORT, U.S. GOV'T, NON-P.H.S.; SUPPORT, U.S. GOV'T, P.H.S.; TEMPLATES, GENETIC;

EID: 0027185882     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi00080a027     Document Type: Article

References (76)

1. Autrup, H., & Seremet, T. (1986) Chem.-Biol. Interact. 60, 217–226.
2. Basu, A. K., & Essigmann, J. M. (1988) Chem. Res. Toxicol. 1, 1–18.
3. Benasutti, M., Ezzedine, D., & Loechler, E. L. (1988) Chem. Res. Toxicol. 1, 160–168.
4. Bernelot-Moens, C., Glickman, B. W., & Gordon, A. J. (1990) Carcinogenesis 11, 781–785.
5. Brookes, P., & Osborne, M. R. (1982) Carcinogenesis 3, 1223–1226.
6. Brown, W. C., & Romano, L. J. (1991) Biochemistry 30, 1342–1350.
7. Buening, M. K., Wislocki, P. G., Levin, W., Yagi, H., Thakker, D. R., Akagi, H., Koreeda, M., Jerina, D. M., & Conney, A. H. (1978) Proc. Natl. Acad. Sci. U.S.A. 11, 5358–5361.
8. Burgess, J. A., Stevens, C. W., & Fahl, W. E. (1985) Cancer Res. 45, 4257–4262.
9. Burnouf, D., Koehl, P., & Fuchs, R. P. P. (1989) Proc. Natl. Acad. Sci. U.S.A. 86, 4147–4151.
10. Carothers, A. M., & Grunberger, D. (1990) Carcinogenesis 11, 189–192.
11. Chakrabarti, S., Mizusawa, H., & Seidman, M. (1984) Mutat. Res. 126, 127–137.
12. Chen, R.-H., Maher, V. M., & McCormick, J. J. (1990) Proc. Natl. Acad. Sci. U.S.A. 87, 8680–8684.
13. Chen, R-H., Maher V. M., & McCormick, J. J. (1991) Cancer Res. 51, 2587–2592.
14. Cheng, S. C., Hilton, B. D., Roman, J. M., & Dipple, A. (1989) Chem. Res. Toxicol. 2, 334–340.
15. Cosman, M., Ibanez, V., Geacintov, N. E., & Harvey, R. G. (1990) Carcinogenesis 11, 1667–1672.
16. Cosman, M., Santos, C., Fiala, R., Hingerty, B., Singh, S. B., Ibanez, V., Margulis, L. A., Live, D., Geacintov, N. E., Broyde, S., & Patel, D. J. (1992) Proc. Natl. Acad. Sci. U.S.A. 89, 1914–1918.
17. Cosman, M., de los Santos, C., Fiala, R., Hingerty, B. E., Ibanez, V., Luna, E., Harvey, R. G., Geacintov, N. E., Broyde, S., & Patel, D. (1993) Biochemistry 32, 4145–4155.
18. de los Santos, C., Cosman, M., Hingerty, B. E., Ibanez, V., Margulis, L. A., Geacintov, N. E., Broyde, S., & Patel, D. J. (1992) Biochemistry 31, 5245–5252.
19. Dosanjh, M. K., Galeros, G., Goodman, M. F., & Singer, B. (1991) Biochemistry 30, 11595–11599.
20. Eisenstadt, E., Warren, J., Porter, J., Atkins, D., & Miller, J. H. (1982) Proc. Natl. Acad. Sci. U.S.A. 79, 1945–1949.
21. Geacintov, N. E. (1988) in Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships (Yang, S. K., & Silverman, B. D., Eds.) Vol. II, pp 181–206, CRC Press, Boca Raton, FL.
22. Geacintov, N. E., Gagliano, A. G., Ibanez, V., & Harvey, R. G. (1982) Carcinogenesis 3, 247–253.
23. Geacintov, N. E., Yoshida, H., Ibanez, V., Jacobs, S. A., & Harvey, R. G. (1984) Biochem. Biophys. Res. Commun. 122, 33–39.
24. Geacintov, N. E., Cosman, M., Mao, B., Alfano, A., Ibanez, V., & Harvey, R. G. (1991) Carcinogenesis 12, 2099–2108.
25. Gräslund, A., & Jernström, B. (1989) Q. Rev. Biophys. 22, 1–37.
26. Harvey, R. G., & Geacintov, N. E. (1988) Acc. Chem. Res. 21, 66–73.
27. Hruszkewycz, A. M., & Dipple, A. (1991) Carcinogenesis 12, 2185–2187.
28. Hruszkewycz, A. M., Canella, K. A., & Dipple, A. (1991) Carcinogenesis 12, 1659–1663.
29. Hruszkewycz, A. M., Canella, K. A., Peltonen, K., Kotrappa, L. & Dipple, A. (1992) Carcinogenesis 13, 2347–2352.
30. Hsu, I. C., Bowden, G. T., & Harris, C. C. (1979) Mutat. Res. 63, 351–359.
31. Huberman, E., Sachs, L., Yang, S. K., & Gelboin, H. V. (1976) Proc. Natl. Acad. Sci. U.S.A. 73, 607–611.
32. Jeffrey, A. M., Jennette, K. W., Blobstein, S. H., Weinstein, I. B., Beland, F. A., Harvey, R. G., Kasai, H., Miura, I., & Nakanishi, K. (1976) J. Am. Chem. Soc. 98, 5714–5715.
33. Jeffrey, A. M., Grzeskowiak, K., Weinstein, I. B., Nakanishi, K., Roller, P., & Harvey, R. G. (1979) Science 206, 1309–1311.
34. Kapitulnik, J., Wislocki, P. G., Levin, W., Yagi, H., Thakker, D. R., Akagi, H., Koreeda, M., Jerina, M., & Conney, A. H. (1978). Cancer Res. 38, 2661–2665.
35. Keohavong, P., & Thilly, W. G. (1992) Proc. Natl. Acad. Sci. U.S.A. 89, 4623–4627.
36. King, H. W. S., Osborne, M. R., & Brookes, P. (1979) Chem.- Biol. Interact. 24, 345–353.
37. Koreeda, M., Moore, P. D., Wislocki, P. G., Levin, W., Conney, A. H., Yagi, H., & Jerina, D. M. (1978) Science 199, 778–781.
38. Larson, K. L., & Strauss, B. S. (1987) Biochemistry 26, 2471–2479.
39. Mackay, W., Benasutti, M., Droulin, E., & Loechler, E. L. (1992) Carcinogenesis 13, 1415–1425.
40. Malavelle, C., Kuroki, T., Sims, P., Grover, P. L., & Bartsch, H. (1977) Mutat. Res. 44, 313–326.
41. Maxam, A. M., & Gilbert, W. (1980) Methods Enzymol. 65, 499–560.
42. Mazur, M., & Glickman, B. W. (1988) Somat. Cell Mol. Genet. 14, 393–400.
43. Meehan, T., & Straub, K. (1979) Nature 277, 410–412.
44. Mendelman, L. V., Boosalis, M. S., Petruska, J., & Goodman, M. F. (1989) J. Biol. Chem. 264, 14415–14423.
45. Mendelman, L. V., Petruska, J., & Goodman, M. F. (1990) J. Biol. Chem. 265, 2338–2346.
46. Mizusawa, H., Lee, C-H., Kakefuda, T., McKenney, K., Shimatake, H., & Rosenberg, M. (1981) Proc. Natl. Acad. Sci. U.S.A. 78, 6817–6820.
47. Newbold, R. F., & Brookes, P. (1976) Nature 261, 52–54.
48. Newbold, R. F., Brookes, P., & Harvey, R. G. (1979) Int. J. Cancer 24, 203–209.
49. Osborne, M. R., Harvey, R. G., & Brookes, P. (1978) Chem.- Biol. Interact. 20, 123–130.
50. Osborne, M. R., Jacobs, S., Harvey, R. G., & Brookes, P. (1981) Carcinogenesis 2, 553–558.
51. Reardon, D. B., Bigger, C. A. H., & Dipple, A. (1990) Carcinogenesis 11, 165–168.
52. Rodriguez, H., & Loechler, E. L. (1993) Carcinogenesis 14, 373–383.
53. Roilides, E., Gielen, J. E., Tuteja, N., Levine, A. S., & Dixon, K. (1988) Mutat. Res. 198, 199–206.
54. Sayer, J. M., Chadha, A., Agarwal, S. K., Yeh, H. J. C., Yagi, H., & Jerina, D. M. (1991) J. Org. Chem. 56, 20–29.
55. Shibutani, S., & Grollman, A. P. (1993) J. Biol. Chem. 268, 11703–11710.
56. Shibutani, S., Takeshita, M., & Grollman, A. P. (1991a) Nature 349, 431–434.
57. Shibutani, S., Gentles, R., Johnson, F., & Grollman, A. P. (1991b) Carcinogenesis 12, 813–818.
58. Singer, B., & Essigman, J. M. (1991) Carcinogenesis 12, 949–955.
59. Singh, S. B., Hingerty, B. E., Singh, U. C., Greenberg, J. P., Geacintov, N. E., & Broyde, S. (1991) Cancer Res. 51, 3482–3492.
60. Slaga, T. J., Bracken, W. J., Gleason, G., Levin, W., Yagi, H., Jerina, D. M., & Conney, A. H. (1979) Cancer Res. 394, 67–71.
61. Stevens, C. W., Bouck, N., Burgess, J. A., & Fahl, W. E. (1985) Mutat. Res. 152, 5–14.
62. Strauss, B. S. (1991) BioEssays 13, 79–84.
63. Takeshita, M., Chang, C.-N., Johnson, F., Will, S., & Grollman, A. P. (1987) J. Biol. Chem. 262, 10171–10179.
64. Thakker, D. R., Yagi, H., Lu, A. Y. H., Levin, W., Conney, A. H., & Jerina, D. M. (1976) Proc. Natl. Acad. Sci. U.S.A. 73, 3381–3385.
65. Thakker, D. R., Yagi, H., Akagi, H., Koreeda, M., Lu, A. Y. H., Levin, W., Wood, A. W., Conney, A. H., & Jerina, D. M. (1977a) Chem.-Biol. Interact. 16, 281–300.
66. Thakker, D. R., Yagi, H., Levin, W., Lu, A. Y. H., Conney, A. H., & Jerina, D. M. (1977b) J. Biol. Chem. 252, 6328–6334.
67. Thrall, B. D., Mann, D. B., Smerdon, M. J., & Springer, D. L. (1992) Carcinogenesis 13, 1529–1534.
68. Vousden, K. H., Bos, J. L., Marshall, C. J., & Phillips, D. H. (1986) Proc. Natl. Acad. Sci. U.S.A. 83, 1222–1226.
69. Weems, H. B., & Yang, S. K. (1989) Chirality 1, 276–283.
70. Wei, S. J. C., Chang, R. L., Wong, C.-Q., Bhachech, N., Cui, X. X., Hennig, E., Yagi, H., Sayer, J. M., Jerina, D.M., Preston, B. D., & Conney, A. H. (1991) Proc. Natl. Acad. Sci. U.S.A. 88, 11227–11230.
71. Weinstein, I. B., Jeffrey, A. M., Jennette, K. W., Blobstein, S. H., Harvey, R. G., Harris, C., Autrup, H., Kasai, H., & Nakanishi, K. (1976) Science 193, 592–594.
72. Wood, A. W., Chang, R. L., Levin, W., Yagi, H., Thakker, D. R., Jerina, D. M., & Conney, A. H. (1977) Biochem. Biophys. Res. Commun. 77, 1389–1396.
73. Yang, J-L., Maher, V. M., & McCormick. J. J. (1987) Proc. Natl. Acad. Sci. U.S.A. 84, 3787–3791.
74. Yang, J-L., Chen, R-H., Maher, V. M., & McCormick, J. J. (1991) Carcinogenesis 12, 71–75.
75. Yang, S. K., & Gelboin, H. V. (1976) Biochem. Pharmacol. 25, 2221–2225.
76. Yang, S. K., McCourt, D. W. Roller, P. P., & Gelboin, H. V. (1976) Proc. Natl. Acad. Sci. U.S.A. 73, 2594–2598.