Study of the forces stabilizing complexes between chlorophylls and heterocyclic amine mutagens

Environmental and Molecular Mutagenesis

Volumn 27, Issue 3, 1996, Pages 211-218

  Dashwood, Roderick ^a   Yamane, Shane ^a   Larsen, Randy ^a  

^a UNIVERSITY OF HAWAII   (United States)

Author keywords

Antimutagenicity; Chlorophylin; Chlorophyll; Heterocyclic amine mutagens; Interceptor molecules; Molecular complex formation

Indexed keywords

ANTIMUTAGENIC AGENT; CHLOROPHYLL; HETEROCYCLIC AMINE; MUTAGENIC AGENT; PORPHYRIN;

ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; MUTAGENICITY; NONHUMAN;

AMINES; ANTIMUTAGENIC AGENTS; CHEMISTRY, PHYSICAL; CHLOROPHYLL; HETEROCYCLIC COMPOUNDS; KINETICS; MODELS, MOLECULAR; MUTAGENICITY TESTS; MUTAGENS; SALMONELLA TYPHIMURIUM; SPECTROPHOTOMETRY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0029964530     PISSN: 08936692     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2280(1996)27:3<211::AID-EM6>3.0.CO;2-H     Document Type: Article

References (28)

1. Arimoto S, Hayatsu H (1989): Role of hemin in the inhibition of mutagenic activity of 3-ammo-1-methyl-5H-pyrido[4,3-b]-indole (Trp-P-2) and other aminoazaarenes. Mutat Res 213:217-226.
2. Arimoto S, Fukuoka S, Itome C, Nakano H, Rai H, Hayatsu H (1993): Binding of polycyclic planar mutagens to chlorophyllin resulting in inhibition of the mutagenic activity. Mutat Res 287:293-305.
3. Breinholt V, Schimerlik M, Dashwood R, Bailey G (1995a): Mechanisms of chlorophyllin anticarcinogenesis against aflatoxin B1: Complex formation with the carcinogen. Chem Res Toxicol 8:506-514.
4. Breinholt V, Hendricks J, Pereira C, Arbogast D, Bailey G (1995b): Dietary chlorophyllin is a potent inhibitor of aflatoxin B1 hepatocarcinogenesis in rainbow trout. Cancer Res 55:57-62.
5. Chemomorsky S, Segelman A (1988): Biological activities of chlorophyll derivatives. NJ Med 85:669-673.
6. Connors KA (1987): "Binding Constants - The Measurement of Molecular Complex Stability." New York: John Wiley and Sons.
7. Dashwood RH (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.
8. Dashwood RH. 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.
9. Dashwood R, Guo D (1993): Antimutagenic potency of chlorophyllin in the Salmonella assay and its correlation with binding constants of mutagen-inhibitor complexes. Environ Mol Mutagen 22:164-171.
10. Dashwood RH, Breinholt V, Bailey GS (1991): Chemopreventive properties of chlorophyllin: Inhibition of aflatoxin B1 (AFB1)-DNA binding in vivo and antimutagenic activity against AFB1 and two heterocyclic amines in the Salmonella mutagenicity assay. Carcinogenesis 12:939-942.
11. Ghosh AK, Sen S, Sharma A, Talukder G (1991): Effect of chlorophyllin on mercuric chloride-induced clastogenicity in mice. Food Chem Toxicol 29:777-779.
12. Guo D, Horio D, Grove J, Dashwood R (1995): Inhibition by chlorophyllin of 2-amino-3-methylimidazo[4,5-f]quinoline-induced tumorigenesis in the male F344 rat. Cancer Lett 95:161-165.
13. Hambright P (1975): Dynamic coordination chemistry of metallo-porphyrins. In Smith KM (ed): "Porphyrins and Metallo-Porphyrins." Amsterdam: Elsevier, pp 233-278.
14. Hartman PE, Shankel D (1990): Antimutagens and anticarcinogens: A survey of putative interceptor molecules. Environ Mol Mutagen 15:145-182.
15. Katoh Y, Nemoto N, Tanaka M (1983): Inhibition of benzo[a]pyrene mutagenesis in Chinese hamster V79 cells by hemin and related compounds. Mutat Res 121:153-157.
16. Kepart JC (1955): Chlorophyll derivatives - Their chemistry, commercial preparation and uses. Econ Bot 9:3-38.
17. Negishi T, Arimoto S, Nishizaki C, 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.
18. Olvera O, Zimmering S, Arceo C, Craces M (1993): The protective effects of chlorophyllin in treatment with chromium (VI) oxide in somatic cells of Drosophila, Mutat Res 301:201-204.
19. Ong T, Whong W-Z, Stewart JD, Brockman HE (1986): Chlorophyllin: A potent antimutagen against environmental and dietary complex mixtures. Mutat Res 173:111-115.
20. Physicians Desk Reference (1992): "PDR, 46th Ed." Montvale, NJ: Medical Economics, pp 1994-1995.
21. Sarkar D, Sharma A, Talukder (1993): Differential protection of chlorophyllin against clastogenic effects of chromium and chlordane in mouse bone marrow in vivo. Mutat Res 301:33-38.
22. Sato M, Fujimoto I, Sakai T, Aimoto T, Kimura R, 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
23. Shelnutt J (1984): Electronic structure of the porphyrin ring in an electrostatically bound π-π complex. J Phys Chem 88:6121-6127.
24. Tachino N, Guo D, Dashwood WM, Yamane S, Larsen R, Dashwood R (1994): Mechanisms of 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 308:191-203.
25. Terwel L, van der Hoeven JCM (1985): Antimutagenic activity of some naturally occurring compounds towards cigarette-smoke condensate and benzo[a]pyrene in the Salmonella/microsome assay. Mutat Res 152:1-4.
26. Warner JR, Nath J, Ong T-M (1991): Antimutagenicity studies of chlorophyllin using the Salmonella arabinose-resistant assay system Mutat Res 262:25-30.
27. Whong WZ, Stewart JD, Brockman HE, Ong T (1988): Comparative antimutagenicity of chlorophyllin and five other agents against aflatoxin B1-induced reversion in Salmonella typhimurium strain TA98. Teratogen Carcinogen Mutagen 8:215-224.
28. Zimmering S, Olvera O, Hernandez ME, Cruces MP, Arceo C, Pimentai E (1990) Evidence for a radioprotective effect of chlorophyllin in Drosophila Mutat Res 245:47-49.