Spectroscopic characterization of the 4-hydroxy catechol estrogen quinones - Derived GSH and N-acetylated Cys conjugates

Chemical Research in Toxicology

Volumn 16, Issue 3, 2003, Pages 304-311

  Jankowiak, Ryszard ^a   Markushin, Yuri ^a   Cavalieri, Ercole L ^b   Small, Gerald J ^a  

^a IOWA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYESTRADIOL; 4 HYDROXYESTRONE; ACETYLCYSTEINE; CARCINOGEN; CATECHOL ESTROGEN QUINONE; DNA; ESTRADIOL; ESTROGEN DERIVATIVE; ESTRONE; GLUTATHIONE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL CARCINOGENESIS; DNA ADDUCT; ELECTROCHEMICAL DETECTION; ENERGY; HUMAN; LUMINESCENCE; MOLECULAR MODEL; QUANTUM MECHANICS; URINALYSIS;

ACETYLCYSTEINE; ESTROGENS, CATECHOL; GLUTATHIONE; LUMINESCENT MEASUREMENTS; MODELS, MOLECULAR; QUINONES; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, FLUORESCENCE; THERMODYNAMICS; TUMOR MARKERS, BIOLOGICAL;

EID: 0037352460     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx020088p     Document Type: Article

References (45)

1. Cavalieri, E. L., Rogan, E. G., and Chakravarti, D. (2002) Initiation of cancer and other diseases by catechol ortho-quinones: a unifying mechanism. Cell. Mol. Life Sci. 59, 665-681.
2. Chakravarti, D., Mailander, P. C., Li, K.-M., Higginbotham, S., Zhang, H. L., Gross, M., Meza, J. L., Cavalieri, E. L., and Rogan, E. G. (2001) Evidence that a burst of DNA depurination in SENCAR mouse skin induces error-prone repair and froms mutations in the H-ras gene. Oncogene 20, 7945-7953.
3. Dwivedy, I., Devanesan, P. D., Cremonosi, P., Rogan, E. G., and Cavalieri, E. L. (1992) Synthesis and characterization of estrogen 2,3- and 3,4-quinons. Comparison of the DNA adducts formed by the quinones versus horseradish peroxidase-activated catechol estrogens. Chem. Res. Toxicol. 5, 828-833.
4. International Agency for Research on Cancer Group (1979) IARC Monographs on Evaluation of Carcinogenic Risk of Chemicals to Humans, Sex Hormones (II), Vol. 21, pp 173-221, International Agency for Research on Cancer, Lyon, France.
5. Liehr, J. G. (2000) Is estradiol a genotoxic mutagenic carcinogen? Endocr. Rev. 21, 4054-4058.
6. Kalyanaraman, B., Sealy, R. C., and Sivarajah, K. (1984) An electron spin resonance study of o-semiquinones formed during the enzymatic and auto-oxidation of catechol estrogens. J. Biol. Chem. 259, 14018-14022.
7. Kalyanaraman, B., Felix, C. C., and Sealy, R. C. (1985) Semiquinone anion radicals of catechol(amine)s, catechol estrogens, and their metal ion complexes. Environ. Health Perspect. 64, 185-198.
8. Liehr, J. G., Ulubelen, A. A., and Strobel, H. W. (1986) Cytochrome P-450-mediated redox cycling of estrogens. J. Biol. Chem. 261, 16865-16870.
9. Liehr, J. G., and Roy, D. (1990) Free radical generation by redox cycling of estrogens. Free Radical Biol. Med. 8, 415-423.
10. Nutter, L. M., Wu, Y.-Y., Ngo, E. O., Sierra, E. E., Gutierrez, P. L., and Abul-Hajj, Y. J. (1994) An o-quinone form of estrogen produces free radicals in human breast cancer cells: Correlation with DNA damage. Chem. Res. Toxicol. 7, 23-28.
11. 2-3,4-quinone with DNA. Proc. Am. Assoc. Cancer Res. 39, 636-643.
12. Stack, D., Byun, J., Gross, M. L., Rogan, E. G., and Cavalieri, E. (1996) Molecular characteristics of catechol estrogen quinones in reactions with deoxyribonucleosides. Chem. Res. Toxicol. 9, 851-859.
13. Jankowiak, R., Zamzow, D., Stack, D. E., Cavalieri, E. L., and Small, G. J. (1998) Spectral characterization of fluorescently labeled catechol estrogen-3,4-quinone derived-N7Gua adducts and their identification in rat mammary gland tissue. Chem. Res. Toxicol. 11, 1339-1345.
14. Cavalieri, E. L., Stack, D. E., Devanesan, P. D., Todorovic, R., Dwivedy, I., Higginbotham, S., Johanson, S., Patil, K., and Rogan, E. (1997) Molecular origin of cancer: catechol estrogen-3,4-quinones as endogeneous tumor initators. Proc. Natl. Acad. Sci. U.S.A. 94, 10937-10942.
15. Devanesan, P., Todorovic, R., Zhao, J., Gross, M. L., Rogan, E. G., and Cavalieri, E. L. (2001) Catechol estrogen conjugates and DNA adducts in the kidney of male Syrian golden hamsters treated with 4-hydroxyestradiol: potential biomarkers for estrogen-initiated cancer. Carcinogenesis 22, 489-497.
16. Todorovic, R., Devanesan, P., Higginbotham, S., Zhao, J., Gross, M. L., Rogan, E. G., and Cavalieri, E. L. (2001) Analysis of potential biomarkers of estrogen-initiated cancer in the urine of Syrian golden hamsters treated with 4-hydroxyestradiol. Carcinogenesis 22, 905-911.
17. Cavalieri, E. L., Kumar, S., Todorovic, R., Higginbotham, S., Badawi, A. F., and Rogan, E. G. (2002) Imbalance of estrogen homeostasis in kidney and liver of hamsters treated with estradiol: implications for estrogen-induced initiation of renal tumors. Chem. Res. Toxicol. 14, 1041-1050.
18. Devanesan, P., Santen, R. J., Bocchinfuso, W. P., Korach, K. S., Rogan, E., and Cavalieri, E. (2001) Catechol estrogen metabolites and conjugates in mammary tumors with hyperplastic tissue from estogen receptor-α knock-out (ERKO)/Wnt-1 mice: implications for initiation of mammary tumors. Carcinogenesis 22, 1573-1576.
19. Cao, K., Devanesan, P. D., Ramanathan, R., Gross, M. L., Rogan, E., and Cavalieri, E. L. (1998) Covalent binding of catechol estrogens to glutathione catalyzed by horseradish peroxidase. Chem. Res. Toxicol. 11, 917-924.
20. Nakagomi, M., and Suzuki, E. (2000) Quantitation of catechol estrogens and their N-acetylcysteine conjugates in urine of rats and hamsters. Chem. Res. Toxicol. 13, 1208-1213.
21. Udenfriend, S. (1962) Fluorescence Assays in Biology and Medicine, Chapter 10, pp 349-365, Academic Press, New York.
22. Roberts, H. R., and Siino, M. R. (1963) Stability Assays of Pharmaceutical Preparations by Quantitative Paper Chromatography II. J. Pharm. Sci. 52, 370.
23. Velury, S., and Howell, S. (1988) Measurements of plasma thiols after derivatization with monobromobimane. J. Chromatogr. 424, 141-146.
24. Houzé, P., Dussaucy, M., Courties, Y., and Bousquet, B. (1999) Evaluation of the bio-red high-performance liquid chromatographic method for plasma total homocysteine assay. Ann. Biol Clin. 57, 611-616.
25. Markushin, Y., Zhong, W., Small, G. J., Yeung, E. S., Cavalieri, E. L., and Jankowiak, R. (2003) Anal. Chem. (to be submitted).
26. Burkert, U., and Allinger, N. L. (1982) Molecular Mechanics, ACS Monograph, Vol. 177, American Chemical Society, Washington, DC.
27. Allinger, N. L. (1977) Conformational analysis 130. MM2: a hydrocarbon force field utilizing V1 and V2 torsional terms. J. Am. Chem. Soc. 99, 8127-8134.
28. Ridley, J. E., and Zerner, M. C. (1976) Triplet states via intermediate neglect of differential overlap: benzene, pyridine, and the diazines. Theor. Chim. Acta 42, 223-236.
29. Del Bene, J., and Jaffé, H. H. (1968) Use of the CNDO method in spectroscopy. I. Benzene, pyridine, and the diazines. J. Chem. Phys. 48, 1807-1813.
30. Del Bene, J., and Jaffé, H. H. (1968) Use of the CNDO method in spectroscopy. II. Five-membered rings. J. Chem. Phys. 48, 4050-4055.
31. Becker, R. S. (1969) Theory and Interpretation of Fluorescence and Phosphorescence, Chapter 12, pp 155-189, Wiley-Interscience, New York.
32. Shimada, J., and Goodman, L. (1965) Polarization of aromatic carbonyl spectra. J. Chem. Phys. 43, 2027-2041.
33. 1 transition of formaldehyde. J. Chem. Phys. 29, 644-652.
34. Vanquickenborne, L., and McGlynn, S. (1966) Spin-orbit coupling in aza-aromatics and carbonyls. J. Chem. Phys. 45, 4755-4756.
35. Lim, E. C. (1986) Proximity Effect in Molecular Photophysics: Dynamical Consequences of Pseudo-Jahn - Teller Interaction. J. Phys. Chem. 90, 6770-6777.
36. Kearns, D., and Case, W. (1966) Investigation of singlet-triplet transitions by the phosphorescence excitation model. III. Aromatic ketones and aldehydes. J. Am. Chem. Soc. 88, 5087-5097.
37. Udenfriend, S. (1969) Fluorescence Assay in Biology and Medicine, Chapter 14, pp 655-472, Academic Press, New York.
38. Klesinger, M., and Michl, J. (1995) Excited States and Photochemistry of Organic Molecules, VCM Publishers, New York.
39. Reichardt, Ch. (1988) Solvents Effects in Organic Chemistry (2nd ed.) VCM, Weinheim.
40. McConnell, H. (1952) Effect of polar solvents on the absorption frequency of n → π* electronic transitions. J. Chem. Phys. 20, 700-704.
41. Kasha, M. (1960) Radiat. Res. 2, 243-248.
42. Hyperchem Computational Chemistry (2002) Publication HC-70-00-04-00, Part 2, Theory and Methods, p 307, Hypercube, Inc.
43. El Sayed, M. A. (1963) Spin-orbit coupling and the radiationless processes in nitrogen heterocyclic. J. Chem. Phys. 38, 2834-2838.
44. Roberts, K. P., Jankowiak, R., and Small, G. J. (2001) High-performance liquid chromatography interfaced with fluorescence line-narrowing spectroscopy for on-line analysis. Anal. Chem. 73, 951-956.
45. Roberts, K. P., Lin, C.-H., Singhal, M., Casale, G. P., Small, G. J., and Jankowiak, R. (2000) On-line identification of depurinating DNA adducts in human urine by capillary electrophoresis-fluorescence line narrowing spectroscopy. Electrophoresis 21, 799-806.