Competitive binding of chlorophyllin and proflavine to DNA
Keywords:
DNA, chlorophyllin, proflavine, competitive binding, protector mechanism, interceptor mechanism, spectrophotometry
Abstract
The effect of chlorophyllin (Chln) on the DNA-proflavine (Pf) interactions has been investigated by spectrophotometry. The absorption spectra were recorded at different DNA-to-ligand molar ratios. Decomposition of the spectra of the Chln-Pf, Pf-DNA and Chln-Pf-DNA mixtures was performed by the principal component analysis, allowing determining the concentrations of the absorbing particles in solutions. The results indicated that chlorophyllin did not interact with DNA. The Chln-Pf heteroassociation constant (K=9×104 М) was calculated using Scatchard isotherm analysis. Furthermore, Chln showed only the interceptor properties in the ternary Chln-Pf-DNA system. Next, spectrophotometric studies of binary and ternary systems were carried out under heating of the solutions from 20 to 90°C. Temperature dependences of the particle concentrations were obtained for Chln-Pf-DNA system. It appeared that Chln interceptor properties increased with the temperature. This is due to the fact that Pf-DNA binding constant decreased under heating, while Chln-Pf heteroassociation constant did not vary significantly with the temperature.Downloads
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References
1. Antimicrobial activity of 9-oxo and 9-thio acridines: correlation with interacalation into DNA and effects on macromolecular biosynthesis / A. Cremieux, J. Chevalier, D. Sharples [et al.] // Res Microbiol. – 1995. – V. 146. – № 1. – P. 73-83.
2. Carlson C. B. Solid-phase synthesis of acridine-based threading intercalator peptides / C. B. Carlson, P. A. Beal // Bioorg Med Chem Lett. – 2000. – V. 10, N 17. – P. 1979-1982.
3. Chlorophyllin intervention reduces aflatoxin-DNA adducts in individuals at high risk for liver cancer / P. A. Egner, J. B. Wang, Y. R. Zhu [et al.] // Proc Natl Acad Sci U S A. – 2001. – V. 98, N 25. – P. 14601-14606.
4. The importance of carcinogen dose in chemoprevention studies: quantitative interrelationships between, dibenzo[a,l]pyrene dose, chlorophyllin dose, target organ DNA adduct biomarkers and final tumor outcome / M. M. Pratt, A. P. Reddy, J. D. Hendricks [et al.] // Carcinogenesis. – 2007. – V. 28, N 3. – P. 611-624.
5. Chlorophyllin Antimutagenesis Mechanisms under Different Treatment Conditions in the Micronucleus Assay in V79 Cells / L. G. L. Rampazo, B. Q. Jordao, V. E. P. Vicentini, M. S. Mantovani // Cytologia. – 2002. – V. 67, N 3. – P. 323-327.
6. Protective effect of curcumin and chlorophyllin against DNA mutation induced by cyclophosphamide or benzo[a]pyrene / M. A. Ibrahim, A. M. Elbehairy, M. A. Ghoneim, H. A. Amer // Z Naturforsch C. – 2007. – V. 62, N 3-4. – P. 215-222.
7. Hernaez J. 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 / J. Hernaez, M. Xu, R. Dashwood // Environ Mol Mutagen. – 1997. – V. 30, N 4. – P. 468-474.
8. Search for compounds that inhibit the genotoxic and carcinogenic effects of heterocyclic aromatic amines / C. E. Schwab, W. W. Huber, W. Parzefall [et al.] // Crit Rev Toxicol. – 2000. – V. 30. - №1. – P. 1-69.
9. Egner P. A. Chemoprevention with chlorophyllin in individuals exposed to dietary aflatoxin / P. A. Egner, A. Munoz, T. W. Kensler // Mutat Res. – 2003. – V. 523-524. – P. 209-216.
10. Garcia-Rodriguez M. C. Effect of chlorophyllin on chromium trioxide-induced micronuclei in polychromatic erythrocytes in mouse peripheral blood / M. C. Garcia-Rodriguez, V. Lopez-Santiago, M. Altamirano-Lozano // Mutat Res. – 2001. – V. 496, N 1-2. – P. 145-151.
11. Inhibition of radiation-induced DNA damage in plasmid pBR322 by chlorophyllin and possible mechanism(s) of action / S. S. Kumar, R. C. Chaubey, T. P. Devasagayam [et al.] // Mutat Res. – 1999. – V. 425, N 1. – P. 71-79.
12. Adsorption of mutagens to chlorophyllin-chitosan, an insoluble form of chlorophyllin / S. Arimoto-Kobayashi, N. Harada, R. Tokunaga [et al.] // Mutat Res. - 1997. - V. 381, N 2. - P. 243-249.
13. Porphyrins as possible preventers of heterocyclic amine carcinogenesis / H. Hayatsu, C. Sugiyama, S. Arimoto-Kobayashi, T. Negishi // Cancer Lett. – 1999. – V. 143, N 2. – P. 185-187.
14. Binding of polycyclic planar mutagens to chlorophyllin resulting in inhibition of the mutagenic activity / S. Arimoto, S. Fukuoka, C. Itome [et al.] // Mutat Res. – 1993. – V. 287, N 2. – P. 293-305.
15. Interactions of chlorophyllin with acridine orange, quinacrine mustard and doxorubicin analyzed by light absorption and fluorescence spectroscopy / M. Pietrzak, Z. Wieczorek, A. Stachelska, Z. Darzynkiewicz // Biophys Chem. – 2003. – V. 104, N 1. – P. 305-313.
16. Attenuation of acridine mutagen ICR-191--DNA interactions and DNA damage by the mutagen interceptor chlorophyllin / M. Pietrzak, H. D. Halicka, Z. Wieczorek [et al.] // Biophys Chem. –2008. – V. 135, N 1-3. – P. 69-75.
17. Neault J. F. Structural analysis of DNA-chlorophyll complexes by Fourier transform infrared difference spectroscopy / J. F. Neault, H. A. Tajmir-Riahi // Biophys J. – 1999. – V. 76, N 4. – P. 2177-2182.
18. The "interceptor" properties of chlorophyllin measured within the three-component system: intercalator-DNA-chlorophyllin / M. Pietrzak, Z. Wieczorek, J. Wieczorek, Z. Darzynkiewicz // Biophys Chem. – 2006. – V. 123, N 1. – P. 11-19.
19. Tajmir-Riahi H. A. DNA adducts with chlorophyll and chlorophyllin as antimutagenic agents: synthesis, stability, and structural features / H. A. Tajmir-Riahi, J. F. Neault, S. Diamantoglou // Methods Mol Biol. – 2004. – V. 274. – P. 159-171.
20. Barcelo F. Thermodynamic characterization of the multivalent binding of chartreusin to DNA / F. Barcelo, D. Capo, J. Portugal // Nucleic Acids Res. – 2002. – V. 30, N 20. – P. 4567-4573.
21. Dourlent M. A quantitative analysis of proflavine binding to polyadenylic acid, polyuridylic acid, and transfer RNA / M. Dourlent, C. Helene // Eur J Biochem. – 1971. – V. 23, N 1. – P. 86-95.
22. Multivariate Data Analysis: In Practice : an Introduction to Multivariate Data Analysis and Experimental Design / K. H. Esbensen, D. Guyot, F. Westad, L. P. Houmoller: CAMO Software, 2002. – 598 p.
23. Traganos F. Caffeine modulates the effects of DNA-intercalating drugs in vitro: a flow cytometric and spectrophotometric analysis of caffeine interaction with novantrone, doxorubicin, ellipticine, and the doxorubicin analogue AD198 / F. Traganos, J. Kapuscinski, Z. Darzynkiewicz // Cancer Res. – 1991. – V. 51, N 14. – P. 3682-3689.
24. Peculiarities of DNA-proflavine binding under different concentration ratios / E. G. Bereznyak, N. A. Gladkovskaya, A. S. Khrebtova [et al.] // Biophysics. – 2009. – V. 54, N 5. – P. 574-580.
25. Basu A. Thermodynamic characterization of proflavine–DNA binding through microcalorimetric studies / A. Basu, G. Suresh Kumar // The Journal of Chemical Thermodynamics. – 2015. – V. 87. – P. 1-7.
26. Determination of ligand to DNA binding parameters from two-dimensional DSC curves / E. V. Dukhopelnikov, E. G. Bereznyak, A. S. Khrebtova [et al.] // Journal of Thermal Analysis and Calorimetry. – 2013. – V. 111, N 3. – P. 1817-1827.
2. Carlson C. B. Solid-phase synthesis of acridine-based threading intercalator peptides / C. B. Carlson, P. A. Beal // Bioorg Med Chem Lett. – 2000. – V. 10, N 17. – P. 1979-1982.
3. Chlorophyllin intervention reduces aflatoxin-DNA adducts in individuals at high risk for liver cancer / P. A. Egner, J. B. Wang, Y. R. Zhu [et al.] // Proc Natl Acad Sci U S A. – 2001. – V. 98, N 25. – P. 14601-14606.
4. The importance of carcinogen dose in chemoprevention studies: quantitative interrelationships between, dibenzo[a,l]pyrene dose, chlorophyllin dose, target organ DNA adduct biomarkers and final tumor outcome / M. M. Pratt, A. P. Reddy, J. D. Hendricks [et al.] // Carcinogenesis. – 2007. – V. 28, N 3. – P. 611-624.
5. Chlorophyllin Antimutagenesis Mechanisms under Different Treatment Conditions in the Micronucleus Assay in V79 Cells / L. G. L. Rampazo, B. Q. Jordao, V. E. P. Vicentini, M. S. Mantovani // Cytologia. – 2002. – V. 67, N 3. – P. 323-327.
6. Protective effect of curcumin and chlorophyllin against DNA mutation induced by cyclophosphamide or benzo[a]pyrene / M. A. Ibrahim, A. M. Elbehairy, M. A. Ghoneim, H. A. Amer // Z Naturforsch C. – 2007. – V. 62, N 3-4. – P. 215-222.
7. Hernaez J. 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 / J. Hernaez, M. Xu, R. Dashwood // Environ Mol Mutagen. – 1997. – V. 30, N 4. – P. 468-474.
8. Search for compounds that inhibit the genotoxic and carcinogenic effects of heterocyclic aromatic amines / C. E. Schwab, W. W. Huber, W. Parzefall [et al.] // Crit Rev Toxicol. – 2000. – V. 30. - №1. – P. 1-69.
9. Egner P. A. Chemoprevention with chlorophyllin in individuals exposed to dietary aflatoxin / P. A. Egner, A. Munoz, T. W. Kensler // Mutat Res. – 2003. – V. 523-524. – P. 209-216.
10. Garcia-Rodriguez M. C. Effect of chlorophyllin on chromium trioxide-induced micronuclei in polychromatic erythrocytes in mouse peripheral blood / M. C. Garcia-Rodriguez, V. Lopez-Santiago, M. Altamirano-Lozano // Mutat Res. – 2001. – V. 496, N 1-2. – P. 145-151.
11. Inhibition of radiation-induced DNA damage in plasmid pBR322 by chlorophyllin and possible mechanism(s) of action / S. S. Kumar, R. C. Chaubey, T. P. Devasagayam [et al.] // Mutat Res. – 1999. – V. 425, N 1. – P. 71-79.
12. Adsorption of mutagens to chlorophyllin-chitosan, an insoluble form of chlorophyllin / S. Arimoto-Kobayashi, N. Harada, R. Tokunaga [et al.] // Mutat Res. - 1997. - V. 381, N 2. - P. 243-249.
13. Porphyrins as possible preventers of heterocyclic amine carcinogenesis / H. Hayatsu, C. Sugiyama, S. Arimoto-Kobayashi, T. Negishi // Cancer Lett. – 1999. – V. 143, N 2. – P. 185-187.
14. Binding of polycyclic planar mutagens to chlorophyllin resulting in inhibition of the mutagenic activity / S. Arimoto, S. Fukuoka, C. Itome [et al.] // Mutat Res. – 1993. – V. 287, N 2. – P. 293-305.
15. Interactions of chlorophyllin with acridine orange, quinacrine mustard and doxorubicin analyzed by light absorption and fluorescence spectroscopy / M. Pietrzak, Z. Wieczorek, A. Stachelska, Z. Darzynkiewicz // Biophys Chem. – 2003. – V. 104, N 1. – P. 305-313.
16. Attenuation of acridine mutagen ICR-191--DNA interactions and DNA damage by the mutagen interceptor chlorophyllin / M. Pietrzak, H. D. Halicka, Z. Wieczorek [et al.] // Biophys Chem. –2008. – V. 135, N 1-3. – P. 69-75.
17. Neault J. F. Structural analysis of DNA-chlorophyll complexes by Fourier transform infrared difference spectroscopy / J. F. Neault, H. A. Tajmir-Riahi // Biophys J. – 1999. – V. 76, N 4. – P. 2177-2182.
18. The "interceptor" properties of chlorophyllin measured within the three-component system: intercalator-DNA-chlorophyllin / M. Pietrzak, Z. Wieczorek, J. Wieczorek, Z. Darzynkiewicz // Biophys Chem. – 2006. – V. 123, N 1. – P. 11-19.
19. Tajmir-Riahi H. A. DNA adducts with chlorophyll and chlorophyllin as antimutagenic agents: synthesis, stability, and structural features / H. A. Tajmir-Riahi, J. F. Neault, S. Diamantoglou // Methods Mol Biol. – 2004. – V. 274. – P. 159-171.
20. Barcelo F. Thermodynamic characterization of the multivalent binding of chartreusin to DNA / F. Barcelo, D. Capo, J. Portugal // Nucleic Acids Res. – 2002. – V. 30, N 20. – P. 4567-4573.
21. Dourlent M. A quantitative analysis of proflavine binding to polyadenylic acid, polyuridylic acid, and transfer RNA / M. Dourlent, C. Helene // Eur J Biochem. – 1971. – V. 23, N 1. – P. 86-95.
22. Multivariate Data Analysis: In Practice : an Introduction to Multivariate Data Analysis and Experimental Design / K. H. Esbensen, D. Guyot, F. Westad, L. P. Houmoller: CAMO Software, 2002. – 598 p.
23. Traganos F. Caffeine modulates the effects of DNA-intercalating drugs in vitro: a flow cytometric and spectrophotometric analysis of caffeine interaction with novantrone, doxorubicin, ellipticine, and the doxorubicin analogue AD198 / F. Traganos, J. Kapuscinski, Z. Darzynkiewicz // Cancer Res. – 1991. – V. 51, N 14. – P. 3682-3689.
24. Peculiarities of DNA-proflavine binding under different concentration ratios / E. G. Bereznyak, N. A. Gladkovskaya, A. S. Khrebtova [et al.] // Biophysics. – 2009. – V. 54, N 5. – P. 574-580.
25. Basu A. Thermodynamic characterization of proflavine–DNA binding through microcalorimetric studies / A. Basu, G. Suresh Kumar // The Journal of Chemical Thermodynamics. – 2015. – V. 87. – P. 1-7.
26. Determination of ligand to DNA binding parameters from two-dimensional DSC curves / E. V. Dukhopelnikov, E. G. Bereznyak, A. S. Khrebtova [et al.] // Journal of Thermal Analysis and Calorimetry. – 2013. – V. 111, N 3. – P. 1817-1827.
Cited
How to Cite
Herus, A. A., Gladkovskaya, N. A., Bereznyak, E. G., & Dukhopelnikov, E. V. (1). Competitive binding of chlorophyllin and proflavine to DNA. Biophysical Bulletin, 2(36), 43-50. https://doi.org/10.26565/2075-3810-2016-36-06
Section
Molecular biophysics
Copyright (c) 2016 A.A. Herus, N.A. Gladkovskaya, E.G. Bereznyak, E.V. Dukhopelnikov
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