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Structural identification of the major DNA adduct formed by aflatoxin B1 in vitro.
Open accessAbstract
The covalent binding of the hepatocarcinogen aflatoxin B1 by rat liver microsomes to calf thymus DNA resulted in a binding level equal to one aflatoxin residue per 60 DNA nucleotides. An aflatoxin derivative-guanine adduct was efficiently liberated from DNA with formic acid. Analytical reversed-phase high-pressure liquid chromatography of the DNA hydrolysate revealed that approximately 90% of the carcinogen bound to DNA could be accounted for as a single component. Preparative high-pressure liquid chromatography was used to isolate sufficient quantities of the adduct for structural analysis from large quantities (340 mg) of DNA. A combination of spectral and chemical data indicates that the major product of the interaction of metabolically activated aflatoxin B1 and DNA is 2,3-dihydro-2-(N7-guanyl)-3-hydroxyaflatoxin B1 with the guanine and hydroxyl functions possessing a trans configuration. The structural data support the hypothesis that the putative 2,3-oxide of aflatoxin B1 is quantitatively important as an intermediate in the binding of aflatoxin B1 to nucleic acids.
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Citations
Cited by
Mechanisms of DNA damage, repair, and mutagenesis
Chatterjee, N., & Walker, G. C. (2017) · Environmental and Molecular Mutagenesis · doi:10.1002/em.22087 · Cited by 2,039
(1979) · Advances in Cancer Research · doi:10.1016/s0065-230x(08)60848-9 · Cited by 1,163
Rushing, B. R., & Selim, M. I. (2019) · Food and Chemical Toxicology · doi:10.1016/j.fct.2018.11.047 · Cited by 989
Andrade, R. J., Chalasani, N., Björnsson, E. S., Suzuki, A., Kullak-Ublick, G. A., Watkins, P. B., Devarbhavi, H., Merz, M., Lucena, M. I., Kaplowitz, N., et al. (2019) · Nature Reviews Disease Primers · doi:10.1038/s41572-019-0105-0 · Cited by 924
Mechanisms of Aflatoxin Carcinogenesis
Eaton, D. L., & Gallagher, E. P. (1994) · Annual Review of Pharmacology and Toxicology · doi:10.1146/annurev.pa.34.040194.001031 · Cited by 774
Metadata
- Authors
- Essigmann, J. M., Croy, R. G., Nadzan, A. M., Busby, W. F., Reinhold, V. N., Büchi, G., & Wogan, G. N.
- Venue
- Proceedings of the National Academy of Sciences
- Published
- 1977-05
- Volume
- 74
- Issue
- 5
- Pages
- 1870-1874
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- OpenAlex
- W2064752311
- Cited by
- 507
- References
- 0
- FWCI
- 9.33
- Type
- journal article
- Language
- en
- Open access
- green
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- Essigmann, J. M., Croy, R. G., Nadzan, A. M., Busby, W. F., Reinhold, V. N., Büchi, G., & Wogan, G. N. (1977). Structural identification of the major DNA adduct formed by aflatoxin B1 in vitro. Proceedings of the National Academy of Sciences. https://doi.org/10.1073/pnas.74.5.1870
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