Attenuation of acridine mutagen ICR-191 - DNA interactions and DNA damage by the mutagen interceptor chlorophyllin

Biophysical Chemistry

Volumn 135, Issue 1-3, 2008, Pages 69-75

  Pietrzak, Monika ^a   Halicka, H Dorota ^b   Wieczorek, Zbigniew ^a   Wieczorek, Jolanta ^a   Darzynkiewicz, Zbigniew ^b  

^a UNIVERSITY OF WARMIA AND MAZURY IN OLSZTYN   (Poland)

^b NEW YORK MEDICAL COLLEGE   (United States)

Author keywords

Chlorophyllin; Competitive interactions; DNA damage; Histone H2AX phosphorylation; Intercalation; Mutagen interceptor

Indexed keywords

6 CHLORO 9 [3 (2 CHLOROETHYL)AMINOPROPYLAMINO] 2 METHOXYACRIDINE; CHLOROPHYLL; DNA; HISTONE H2AX;

ARTICLE; DNA DAMAGE; HUMAN; HUMAN CELL; LEUKEMIA CELL; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION;

AMINACRINE; ANTIMUTAGENIC AGENTS; BINDING, COMPETITIVE; CHEMOPREVENTION; CHLOROPHYLLIDES; DNA; DNA DAMAGE; HL-60 CELLS; HUMANS; MACROMOLECULAR SUBSTANCES; MUTAGENS; NITROGEN MUSTARD COMPOUNDS;

EID: 43049123082     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2008.03.004     Document Type: Article

References (51)

1. Arimoto S., Kan-yama K., Rai H., and Hayatsu H. Inhibitory effect of hemin, chlorophyllin and related pyrrole pigments on the mutagenicity of benzo[a]pyrene and its metabolites. Mutat. Res. 345 (1995) 127-135
2. Reddy A.P., Harttig U., Barth M.C., Baird W.M., Schimerlik M., Hendricks J.D., and Bailey G.S. Inhibition of dibenzo[a,l]pyrene-induced multi-organ carcinogenesis by dietary chlorophyllin in rainbow trout. Carcinogenesis 20 (1999) 1919-1926
3. Ibrahim M.A., Elbehairy A.M., Ghoneim M.A., and Amer H.A. Protective effect of curcumin and chlorophyllin against DNA mutation induced by cyclophosphamide or benz[a]pyrene. Z. Naturforsch. 62 (2007) 215-222
4. Pratt M.M., Reddy A.P., Hendricks J.D., Pereira C., Kensler T.W., and Bailey G.S. The importance of carcinogen dose in chemoprevention studies: quantitative interrelationships between, dibenzo[a,1] pyrene dose, chlorophyllin dose, target organ DNA adduct biomarkers and final tumor outcome. Carcinogenesis 28 (2007) 611-624
5. Dashwood R.H., and Guo D. 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 (1992) 1121-1126
6. Dashwood R.H., and Guo D. Antimutagenic potency of chlorophyllin in the Salmonella assay and its correlation with binding constants of mutagen - inhibitor complexes. Environ. Mol. Mutagen. 22 (1993) 164-171
7. Hernaez J., Xu M., and Dashwood R.H. Effects of tea and chlorophyllin on the mutagenicity of N-hydroxy - IQ: studies of enzyme inhibition, molecular complex formation, and degradation/scavenging of the active metabolites. Environ. Mol. Mutagen. 30 (1997) 468-474
8. Breinholt V., Hendricks J., Pereira C., Arbogast D., and Bailey G. Dietary chlorophyllin is a potent inhibitor of aflatoxin B1 hepatocarcinogenesis in rainbow trout. Cancer Res. 55 (1995) 57-62
9. Dashwood R.H., Negishi T., Hayatsu H., Breinholt V., Hendricks J., and Bailey G. Chemopreventive properties of chlorophylls towards aflatoxin B1 a review of the antimutagenicity and anticarcinogenicity data in rainbow trout. Mutat. Res. 399 (1998) 245-253
10. Kensler T.W., Groopman J.D., and Roebuck B.D. Use of aflatoxin adducts as intermediate endpoints to assess the efficacy of chemopreventive interventions in animals and man. Mutat. Res. 402 (1998) 165-172
11. Hayashi T., Schimerlik M., and Bailey G. Mechanisms of chlorophyllin anticarcinogenesis: dose-responsive inhibition of aflatoxin uptake and biodistribution following oral co-administration in rainbow trout. Toxicol. Appl. Pharmacol. 158 (1999) 132-140
12. Egner P.A., Muñoz A., and Kensler T.W. Chemoprevention with chlorophyllin in individuals exposed to dietary aflatoxin. Mutat. Res. 523-524 (2003) 209-216
13. García-Rodríguez M.C., López-Satniago V., and Altamirano-Lozano M. Effect of chlorophyllin on chromium trioxide-induced micronuclei in polychromatic erythrocytes in mouse peripheral blood. Mutat. Res. 496 (2001) 145-151
14. Kumar S.S., Chaubey R.C., Devasagayam T.P., Priyadarsini K.I., and Chauhan P.S. Inhibition of radiation-induced DNA damage in plasmid pBR322 by chlorophyllin and possible mechanism(s) of action. Mutat. Res. 425 (1999) 71-79
15. Kumar S.S., Shankar B., and Sainis K.B. Effect of chlorophyllin against oxidative stress in splenic lymphocytes in vitro and in vivo. Biochim. Biophys. Acta. 1673 (2004) 100-111
16. Park K.K., Park J.H., Jung Y.J., and Chung W.Y. Inhibitory effect of chlorophyllin, hemin and tetrakis(4-benzoicacid)porphyrin on oxidative DNA damage and mouse skin inflammation induced by 12-O-tetradecanoylphorbol-13-acetate as a possible antitumor promoting mechanism. Mutat. Res. 542 (2003) 89-97
17. Arimoto S., Fukuoka S., Itome C., Nakano H., Rai H., and Hayatsu H. Binding of polycyclic planar mutagens to chlorophyllin resulting in inhibition of the mutagenic activity. Mutat. Res. 287 (1993) 293-305
18. Arimoto-Kobayashi S., Harada N., Tokunaga R., Odo J., and Hayatsu H. Adsorption of mutagens to chlorophyllin-chitosan, an insoluble form of chlorophyllin. Mutat. Res. 381 (1997) 243-249
19. Hayatsu H., Sugiyama C., Arimoto-Kobayashi S., and Negishi T. Porphirins as possible preventers of heterocyclic amine carcinogenesis. Cancer Lett. 143 (1999) 185-187
20. Hartman P.E., and Shankel D. Antimutagens and anticarcinogens: a survey of putative interceptor molecules. Environ. Mol. Mutagen. 5 (1990) 145-182
21. Ardelt B., Kunicki J., Traganos F., and Darzynkiewicz Z. Chlorophyllin protects cells from the cytostatic and cytotoxic effects of quinacrine mustard but not nitrogen mustard. Int. J. Oncol. 18 (2001) 849-853
22. Pietrzak M., Wieczorek Z., Stachelska A., and Darzynkiewicz Z. Interaction of chlorophyllin with acridine orange, quinacrine mustard and doxorubicin analyzed by light absorption and fluorescence spectroscopy. Biophys. Chemist. 104 (2003) 305-313
23. Pietrzak M., Wieczorek Z., Wieczorek J., and Darzynkiewicz Z. The "interceptor" properties of chlorophyllin measured within the three-component system: intercalator-DNA-chlorophyllin. Biophys. Chemist. 123 (2006) 11-19
24. Ferruzzi M.G., and Blakeslee J. Digestion, absorption, and cancer preventative activity of dietary chlorophyll derivatives. Nutr. Res. 27 (2007) 1-12
25. Kapuscinski J., Ardelt B., Piosik J., Zdunek M., and Darzynkiewicz Z. The modulation of the DNA-damaging effect of polycyclic aromatic agents by xanthines. Part I. Reduction of cytostatic effects of quinacrine mustard by caffeine. Biochem. Pharmacol. 63 (2002) 625-634
26. Traganos F., Kapuscinski J., Gong J.P., Ardelt B., Darzynkiewicz R.J., and Darzynkiewicz Z. Caffeine prevents apoptosis and cell cycle effects induced by camptothecin or topotecan in HL-60 cells. Cancer Res. 53 (1993) 4613-4618
27. Bedner E., Du L., Traganos F., and Darzynkiewicz Z. Caffeine dissociates complexes between DNA and intercalating dyes. Application for bleaching fluorochrome-stained cells for their subsequent re-staining and analysis by laser scanning cytometry. Cytometry 43 (2001) 38-45
28. Piosik J., Ulanowska K., Gwizdek-Wiśniewska A., Czyż A., Kapuściński J., and We{ogonek}grzyn G. Alleviation of mutagenic effects of polycyclic aromatic agents (quinacrine mustard, ICR-191 and ICR-170) by caffeine and pentoxifiline. Mutat. Res. 530 (2003) 47-57
29. Evstigneev M.P., Khomich V.V., and Davies D.B. Complexation of anthracycline drugs with DNA in the presence of caffeine. Eur. Biophys. J. 36 (2006) 1-11
30. Sahasrabudhe S.R., Luo X., and Humayun M.Z. Specificity of base substitutions induced by the acridine mutagen ICR-191: mispairing by guanine N7 adducts as a mutagenic mechanism. Genetics 129 (1991) 981-989
31. Herman R.K., and Dworkin N.B. Effect of gene induction on the rate of mutagenesis by ICR-191 in Escherichia coli. J. Bacteriol. 106 (1971) 543-550
32. Rogakou E.P., Pilch D.R., Orr A.H., Ivanova V.S., and Bonner W.M. DNA double-stranded breaks induce histone H2AX phosphorylation on serine 139. J. Biol. Chem. 273 (1998) 5858-5868
33. 125IUdr-induced DNA double-strand breaks with γ-H2AX antibody. Radiat. Res. 158 (2002) 486-492
34. MacPhail S.H., Banath J.P., Yu T.Y., Chu E.H., Lambur H., and Olive P.L. Expression of phosphorylated histone H2AX in cultured cell lines following exposure to X-rays. Int. J. Radiat. Biol. 79 (2003) 351-358
35. Halicka H.D., Huang X., Traganos F., King M.A., Dai W., and Darzynkiewicz Z. Histone H2AX phosphorylation after cell irradiation with UV-B: relationship to cell cycle phase and induction of apoptosis. Cell Cycle 4 (2005) 339-345
36. Huang X., Okafuji M., Traganos F., Luther E., Holden E., and Darzynkiewicz Z. Assessment of histone H2AX phosphorylation induced by DNA topoisomerase I and II inhibitors topotecan and mitoxantrone and by DNA crosslinking agent cisplatin. Cytometry A 58A (2004) 99-110
37. Tanaka T., Halicka H.D., Traganos F., Seiter K., and Darzynkiewicz Z. Induction of ATM activation, histone H2AX phosphorylation and apoptosis by etoposide: relation to the cell cycle phase. Cell Cycle 6 (2007) 371-376
38. Zhao H., Tanaka T., Halicka H.D., Traganos F., Zarebski M., Dobrucki J., and Darzynkiewicz Z. Cytometric assessment of DNA damage by exogenous and endogenous oxidants reports the aging-related processes. Cytometry A 71A (2007) 905-914
39. Albino A.P., Huang X., Yang J., Gietl D., Jorgensen E., Traganos F., and Darzynkiewicz Z. Induction of histone H2AX phosphorylation in A549 human pulmonary epithelial cells by tobacco smoke and in human bronchial epithelial cells by smoke condensate: a new assay to detect the presence of potential carcinogens in tobacco. Cell Cycle 3 (2004) 1062-1068
40. Wieczorek Z., Stepinski J., Darzynkiewicz E., and Lönnberg H. Association of nucleosides and their 5′-monophosphates with a tryptophan-containing tripeptide, Trp-Leu-Glu, by fluorescence spectroscopy. Biophys. Chemist. 47 (1993) 233-240
41. McGhee J.D., and von Hippel P.H. Theoretical aspects of DNA - protein interactions: co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice. J. Mol. Biol. 86 (1974) 469-489
42. Larsen R.W., Jasuja R., Heltzer R.K., Muraoka P.T., Andrada V.G., and Jameson D.M. Spectroscopic and molecular modeling study of caffeine complexes with DNA intercalators. Biophys. J. 70 (1996) 443-452
43. Hernaez J., Meirong X., and Dashwood R. Effects of tea and chlorophyllin on the mutagenicity of N-hydroxy - IQ: studies of enzyme inhibition molecular complex formation, and degradation /scavenging of the active metabolites. Environ. Mol. Mutagen. 30 (1997) 468-474
44. Yamazaki H., Fujieda M., Togashi M., Saito T., Preti G., Cashman J.R., and Kamataki T. Effects of the dietary supplements, activated charcoal and copper chlorophyllin, on urinary excretion of trimethylamine in Japanese trimethylaminuria patients. Life Sci. 74 (2004) 2739-2747
45. Kapuscinski J., and Darzynkiewicz Z. Interactions of acridine orange with double stranded nucleic acids. Spectral and affinity studies. J. Biomol. Struct. Dyn. 5 1 (1987) 127-143
46. Chaires J.B., Dattagupta N., and Crothers D.M. Studies on interaction of anthracycline antibiotics and deoxyribonucleic acid: equilibrium binding studies on interaction of daunomycin with deoxyribonucleic acid. Biochemistry 21 (1982) 3933-3940
47. Evstigneev M.P., Mykhina Y.V., and Davies D.B. Complexation of daunomycin with DNA oligomer in the presence of an aromatic vitamin (B2) determined by NMR spectroscopy. Biophys. Chemist. 118 (2005) 118-127
48. Tanaka T., Halicka H.D., Traganos F., and Darzynkiewicz Z. Phosphorylation of histone H2AX on Ser 139 and activation of ATM during oxidative burst in phorbol ester-treated human leukocytes. Cell Cycle 5 (2006) 2671-2675
49. Hsiang Y.H., Lihou M.G., and Liu L.F. Arrest of replication forks by drug stabilized topoisomerase I-DNA cleavable complexes as a mechanism of cell killing by camptothecin. Cancer Res. 49 (1989) 5077-5082
50. Del Bino G., Lassota P., and Darzynkiewicz Z. The S-phase cytotoxicity of camptothecin. Exp. Cell Res. 193 (1991) 27-35
51. Kapuscinski J., and Darzynkiewicz Z. Relationship between the pharmacological activity of antitumor drugs Ametantrone and Mitoxantrone (Novantrone) and their ability to condense nucleic acids. Proc. Natl. Acad. Sci. U. S. A. 83 (1986) 6302-6306