Mechanisms of Chlorophyllin Anticarcinogenesis against Aflatoxin B1: Complex Formation with the Carcinogen

Chemical Research in Toxicology

Volumn 8, Issue 4, 1995, Pages 506-514

  Breinholt, Vibeke ^a   Bailey, George ^a   Schimerlik, Michael ^a   Dashwood, Roderick ^b  

^a OREGON STATE UNIVERSITY   (United States)

^b UNIVERSITY OF HAWAII   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AFLATOXIN B1;

ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER PREVENTION; CHEMICAL CARCINOGENESIS; COMPLEX FORMATION; DRUG MECHANISM; LIVER CANCER; LIVER CARCINOGENESIS; NONHUMAN; TROUT;

AFLATOXIN B1; ANIMAL; ANTIMUTAGENIC AGENTS; CHEMISTRY, PHYSICAL; CHLOROPHYLLIDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; HYDROGEN-ION CONCENTRATION; IN VITRO; KINETICS; LIVER NEOPLASMS, EXPERIMENTAL; MICROSOMES, LIVER; MODELS, MOLECULAR; SPECTROMETRY, FLUORESCENCE; SUPPORT, U.S. GOV'T, P.H.S.; TROUT;

ANIMALIA; SALMONIDAE; SPINACIA OLERACEA; VIRIDIPLANTAE;

EID: 0029063179     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx00046a004     Document Type: Article

References (37)

1. Wattenberg, L. W. (1983) Inhibition of neoplasia by minor dietary constituents. Cancer Res. 43 (Supplement), 2448–2453.
2. Hayatsu, H., Arimoto, S., and Negishi T. (1988) Dietary inhibitors of mutagenesis and carcinogenesis. Mutat. Res. 202, 429–446.
3. Dragsted, L. O., Strube, M., and Larsen, J. C. (1993) Cancer protective factors in fruits and vegetables: Biochemical and biological background. Pharmacol. Toxicol. 72 (Supplement 1), 116-135.
4. 1)-DNA binding in vivo and anti-mutagenic activity against AFBi and two heterocyclic amines in the Salmonella mutagenicity assay. Carcinogenesis 12, 939-942.
5. 1 hepatocarcinogenesis in rainbow trout. Cancer Res. 55, 57–62.
6. Khachik, F., Beecher, G. R., and Whittaker, N. F. (1986) Separation, identification and quantification of the major carotenoid and chlorophyll constituents in extracts of several green vegetables by liquid chromatography. J. Agric. Food Chem. 34, 603–616.
7. Khalyfa, A., Kermasha, S., and Alli, I. (1992) Extraction, purification, and characterization of chlorophyll from spinach leaves. J. Agric. Food Chem. 40, 215–220.
8. Arimoto, S., Negishi, T., and Hayatsu, H. (1980) Inhibitory effect of hemin on the mutagenic activities of carcinogens. Cancer Lett. 11, 29–33.
9. Arimoto, S., and Hayatsu, H. (1989) Role of hemin in the inhibition of mutagenic activity of 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) and other aminoazaarenes. Mutat. Res. 213, 217–226.
10. Dashwood, R. H., and Guo, D. (1992) Inhibition of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)—DNA binding by chlorophyllin: studies of enzyme inhibition and molecular complex formation. Carcinogenesis 13, 1121–1126.
11. Newmark, H. L. (1984) A hypothesis for dietary components as blocking agents of chemical carcinogenesis: Plant phenolics and pyrrole pigments. Nutr. Cancer 6, 58–70.
12. Newmark, H. L. (1987) Plant phenolics as inhibitors of mutational and precarcinogenic events. Can. J. Physiol. Pharm. 65, 461–466.
13. Negishi, T., Arimoto, S., Nishizaki, C., and Hayatsu, H. (1989) Inhibitory effect of chlorophyll on the genotoxicity of 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2). Carcinogenesis 10, 145-149.
14. Katoh, Y., Nemoto, N., Tanaka, M., and Takayama, S. (1983) Inhibition of benzo[a]pyrene-induced mutagenesis in Chinese hamster V79 cells by hemin and related compounds. Mutat. Res. 121, 153–157.
15. Dashwood, R. H. (1992) Protection by chlorophyllin against the covalent binding of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) to rat liver DNA. Carcinogenesis 13, 113–118.
16. International Agency for Cancer Research (1993) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans: Aflatoxins, Vol. 56, pp 245–396, IRAC, Lyon, France.
17. Sato, M., Fujimoto, I., Sakai, T., Aimoto, T., Kimura, R., and Murata, T. (1986) Effect of sodium copper chlorophyllin on lipid peroxidation. IX. On the antioxidative components in commercial preparations of sodium copper chlorophyllin. Chem. Pharm. Bull. 34, 2428–2434.
18. Shelnutt, J. A. (1984) Electronic structure of the porphyrin ring in an electrostatically bound π—π complex. Methylviologenmetalloporphyrin complexes. J. Phys. Chem. 88, 6121–6127.
19. Arimoto, S., Fukuoka, S., Itome, H. C., Nakano, H., Rai, H., and Hayatsu, H. (1993) Binding of polycyclic planar mutagens to chlorophyllin resulting in inhibition of the mutagenic activity. Mutat. Res. 287, 293–305.
20. 1 hepatocarcinoma inhibitor, and other indole analogs on the rainbow trout mixed function oxidase system. Toxicol. Lett. 19, 133–138.
21. Lowry, O. H., Rosebrough, N. J., Far, A. L., and Randall, R. J. (1951) Protein measurements with the Folin phenol reagent. J. Biol. Chem. 193, 265–275.
22. Burton, K. (1956) A study of the conditions and mechanisms of the diphenylamine reaction for the colorimetric estimation of deoxyribonucleic acid. Biochem. J. 62, 315–322.
23. 1. Carcinogenesis 9, 427–432.
24. 1 in the rat and mouse. Toxicol. Appl. Pharmacol. 90, 401–409.
25. Christwell, C. D., and Schilt, A. A. (1975) New and improved techniques for applying the mole ratio method to the identification of weak complexes in solution. Anal. Chem. 47, 1623–1629.
26. 1 hemiacetal. J. Assoc. Offic. Anal. Chem. 51, 907–910.
27. 1-2,3-epoxide. Cancer Res. 43, 4752–4756.
28. Tachino, N., Guo, D., Dashwood, W. M., Yamane, S., Larsen, R., and Dashwood, R. H. (1994) Mechanisms in the in vitro antimutagenic action of chlorophyllin against benzo[a]pyrene: Studies of enzyme inhibition, molecular complex formation and degradation of the ultimate carcinogen. Mutat. Res. 308, 191–302.
29. Sato, M., Konagai, K., Kuwana, T., Kimura, R., and Murata, T. (1984) Effects of sodium copper chlorophyllin on lipid peroxidation. VII. Effects of its administration on the stability of rat liver lysosomes. Chem. Pharm. Bull. 32, 2855–2858.
30. Sato, M., Imai, K., Kimura, R., and Murata, T. (1984) Effect of sodium copper chlorophyllin on lipid peroxidation. VI. Effects of its administration on mitochondrial and microsomal lipid peroxidation in rat liver. Chem. Pharm. Bull. 32, 712–722.
31. Imai, K., Aimoto, T., Sato, M., Watanabe, K., Kimura, R., and Murato, T. (1986) Effects of sodium metallochlorophyllins on the activity and components of the microsomal drug-metabolizing enzyme system in rat liver. Chem. Pharm. Bull. 34, 4287–4293.
32. Oda, T., Yokono, O., Yoshida, A., Miyake, K., and Iino, S. (1971) On the successful treatment of pancreatitis. Gastroenterol. Jpn. 6, 49–54.
33. Wu, Z. L., Chen, J. K., Ong, T., Brockman, H. E., and Whong, W.-Z. (1994) Antitransforming activity of chlorophyllin against selected carcinogens and complex mixtures. Teratog., Carcinog. Mutagen. 14, 75–81.
34. Ghosh, A., Sen, S., Sharma, A., and Talukder, G. (1991) Inhibitions of clastogenic effects of cesium chloride in mice in vivo by chlorophyllin. Toxicol. Lett. 57, 11–17.
35. Ghosh, A., Sen, S., Sharma, A., and Talukder, G. (1991) Effect of chlorophyllin on mercury chloride-induced clastogenicity in mice. Food Chem. Toxicol. 29, 777–779.
36. Robins, E. W., and Nelson, R. L. (1989) Inhibition of 1,2-dimethylhydrazine-induced nuclear damage in rat colonic epithelium by chlorophyllin. Anticancer Res. 9, 981–986.
37. 1-induced reversion in Salmonella typhimurium TA98. Teratog., Carcinog. Mutagen. 8, 215-224.