Sequence specificity, enantiospecificity and polyelectrolyte effect in the binding to DNA of a 6-(2-pyridyl)phenanthridine chiral photonuclease

Anti-Cancer Drug Design

Volumn 12, Issue 4, 1997, Pages 239-260

  Colmenarejo, Gonzalo ^a   Montero, Francisco ^a   Orellana, Guillermo ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

6 (2 pyridinium)phenanthridinium viologens; Chiral photonucleases; DNA photosensitizers; DNA targeted drugs; Photochemetherapy

Indexed keywords

6 (2 PYRIDYL)PHENANTHRIDINE CHIRAL PHOTONUCLEASE; ANTINEOPLASTIC AGENT; PHENANTHRIDINE DERIVATIVE; POLYELECTROLYTE; POLYNUCLEOTIDE; PROPIDIUM IODIDE; UNCLASSIFIED DRUG;

AFFINITY CHROMATOGRAPHY; ARTICLE; DISSOCIATION CONSTANT; DNA SEQUENCE; DRUG DESIGN; DRUG DNA BINDING; MOLECULAR MODEL; PHOTOCHEMOTHERAPY; PRIORITY JOURNAL;

BASE SEQUENCE; BINDING SITES; CHROMATOGRAPHY, AFFINITY; DNA; DRUG DESIGN; ELECTROLYTES; ENERGY METABOLISM; INTERCALATING AGENTS; KINETICS; MODELS, MOLECULAR; PHENANTHRIDINES; PHOTOSENSITIZING AGENTS; POLYNUCLEOTIDES; SEQUENCE ANALYSIS, DNA; VIOLOGENS;

EID: 0030973441     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (49)

1. AIYAR, J., HITCHCOCK, S A , DENHART, D , LIU, K.K,C , DANISHEFSKY, S.J & CROTHERS, D M (1994). On the DNA recognition role of the carbohydrate sector in calicheamicin: a comparison of DNA cleaving capacity of enantiomeric calicheamicinones. Angewandte Chemie (International Edition in English), 33, 855.
2. ALEXEEV, D G., LIPANOV, A.A. & SKURATOVSKII, I.YA. (1987). Poly(dA)·poly(dT) is a B-type double helix with a distinctively narrow minor groove. Nature, 325, 821.
3. ARNOTT, S. & SELSING, E. (1974). The structure of polydeoxyguanylic acid·polydeoxycytidicil acid. Journal of Molecular Biology, 88, 551.
4. BARCENA, M , COLMENAREJO, C., GUTIERREZ-ALONSO, M.C., MONTERO, F. & ORELLANA, G. (1995). Stereo-specific DNA binding of luminescent atropisomeric viologens. Biochemical and Biophysical Research Communications, 214, 716.
5. BARTON, J K. (1986). Metals and DNA: molecular left-handed complements. Science, 233, 727.
6. BRESLOFF, J.L & CROTHERS, D.M. (1981). Equilibrium studies of ethidium-polynucleotide interactions. Biochemstry, 20, 3547.
7. CADET, J & VIGNY, P (1990). The photochemistry of nucleic acids. In Bioorganic Photochemistry, Vol. 1: Photochemistry and the Nucleic Acids. Morrison, H. (ed.), p. 1. Wiley: New York.
8. CHAIRES, J.B (1983). Equilibrium studies on the interaction of daunomycin with deoxypolynucleotides. Biochemistry, 22, 4204.
9. CHAIRES, J B. (1992). Application of equilibrium binding methods to elucidate the sequence specificity of antibiotic binding to DNA. Advances in DNA Sequence Specific Agents, 1, 3.
10. CHOW, C S & BARTON, J.K. (1992). Transition metal complexes as probes of nucleic acids. Methods in Enzymology, 212, 219.
11. COLL, M., FREDERICK, C.A., WANG, A.H -J. & RICH, A. (1987). A bifurcated hydrogen-bonded conformation in the d(AT) base pairs of the DNA dodecamer d(CGCAAATTTGCG) and its complex with distamycin. Proceedings of the National Academy of Sciences, USA, 84, 8385.
12. COLMENAREJO, G., BARCENA, M., GUTIERREZ-ALONSO, M.C., MONTERO, F & ORELLANA, G. (1995a). DNA photocleavage by novel intercalating 6-(2-pyridinium)phenanthridinium viologens. FEBS Letters, 374, 426.
13. COLMENAREJO, G., GUTIERREZ-ALONSO, M C., BARCENA, M., KELLY, J.M., MONTERO, F. & ORELLANA, G (1995b). Interaction with DNA of photoactive viologens based on the 6-(2-pyridinium) phenanthridinium structure. Journal of Biomolecular Structure and Dynamics, 12, 827.
14. DOUGHERTY, T.J. (1992). Photochemistry in the treatment of cancer. Advances in Photochemistry, 17, 275.
15. GRAND, A G. & GASPARRO, F.P. (1993). Present and future uses of photochemotherapy in medicine. The Spectrum, 6, 28.
16. HEALY, P.C., ENGELHARDT, L.M , PATRICK, V.A. & WHITE, A.H. (1985). Lewis-base adducts of group 1B metal(I) compounds. Part 19. Crystal structures of bis(1,10-phenanthroline)copper(I) perchlorate and dibromocuprate. Journal of the Chemical Society, Dalton Transactions, 2541.
17. JAIN, S C. & SOBELL, H.M. (1984). Visualization of drug-nucleic acid interactions at atomic resolution. VIII. Structures of two ethidium dinucleoside monophosphate crystalline complexes containing ethidium:cytidylyl(3′-5′)guanosine. Journal of Biomolecular Structure and Dynamics, 1, 1179.
18. KAY, E.R., SIMMONS, N.S. & DOUNCE, A L. (1952). An improved preparation of sodium deoxyribonucleotide. Journal of the American Chemical Society, 74, 1724.
19. KNAPP, C., LECOMTE, J.P., KIRSCH-DE MESMAEKER, A & ORELLANA, G. (1996). Photoinduced electron transfer from nucleotides to DNA intercalating viologens: a study by laser-flash photolysis and spectroelectrochemistry. Journal of Photochemistry and Photobiology, B: Biology, 36, 67.
20. KOCHEVAR, I E & DUNN, D A. (1990). Photosensitized reactions of DNA: cleavage and addition. In Bioorganic Photochemistry, Vol. 1: Photochemistry and the Nucleic Acids. Morrison, H. (ed.), p. 273. Wiley: New York.
21. LEUPIN, W., FEIGON, J., DENNY, W A. & KEARNS, D.R (1985). Substituent effects on the binding of ethidium and its derivatives to natural DNA. Biophysical Chemistry, 22, 299.
22. LOHMAN, T.M. (1985). Kinetics of protein-nucleic acid interactions: use of salt effects to probe mechanisms of interaction. CRC Critical Reviews in Biochemistry, 19, 191.
23. LOHMAN, T.M., DEHASETH, P.L. & RECORD, M.T., JR (1978). Analysis of ion concentration effects on the kinetics of protein-nucleic acid interactions. Application to lac represser-operator interactions. Biophysical Chemistry, 8, 281.
24. MANNING, U.S. (1978). The molecular theory of polyelectrolyte solutions with applications to the electrostatic propertites of polynucleotides. Quarterly Review of Biophysics, 11, 179.
25. MARKY, L.A. & MACGREGOR, R.B., JR (1990). Hydration of dA·dT polymers: role of water in the thermodynamics of ethidium and propidium intercalation. Biochemistry, 29, 4805.
26. MCCALL, M., BROWN, T & KENNARD, O (1985). The crystal structure of d(GGGGCCCC). A model for poly(dG)·poly(dC). Journal of Molecular Biology, 183, 385.
27. MCGHEE, J.D. & VON HIPPEL, P.H (1974). Theoretical aspects of DNA-protein interactions: co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice. Journal of Molecular Biology, 86, 469.
28. MEEHAN, T. & STRAUB, K. (1979). Double-stranded DNA stereoselectively binds benzo[a]pyrene diol epoxides. Nature, 277, 410.
29. NELSON, H.C.M , FINCH, J T , LUISI, B F. & KLUG, A (1987). The structure of an oligo(dA)·oligo(dT) tract and its biological implications. Nature, 330, 221.
30. NORDEN, B , LINCOLN, P , AKERMAN, B & TUITE, H (1996). DNA interactions with substitution-inert transition metal ion complexes. In Metal Ions in Biological Systems, Vol. 33. Siegel, A. & Siegel, H. (eds), p. 177. Marcel Dekker, Inc.: New York.
31. MüLLER, W. & CROTHERS, D.M. (1975). Interaction of heteroaromatic compounds with nucleic acids. 1. The influence of heteroatoms and polarizability on the base specificity of intercalating ligands. European Jounal of Biochemistry, 54, 267.
32. OROZCO, M., LAUGHTON, C A , HERZYK, H. & NEIDLE, S. (1990). Molecular-mechanics modelling of drug-DNA structures; the effects of differing dielectric treatment of helix parameters and comparison with a fully solvated structural model. Journal of Biomolecular Structure and Dynamics, 8, 359.
33. RECORD, M.T. &SPOLAR, R.S (1990). Some thermodynamic principles of non-specific and site-specific protein-DNA interactions. In The Biology of Non-Specific DNA-Protein Interactions. Revzin, A. (ed.), p. 33. CRC Press: Boca Raton, FL.
34. RECORD, M T., ANDERSON, C.F. & LOHMAN, T M. (1978). Thermodynamic analysis of ion effects on the binding and conformational equilibria of proteins and nucleic acids: the roles of ion association or release, screening, and ion effects on water activity. Quarterly Review of Biophysics, 11, 103.
35. SAENGER, W. (1984). Principles of Nucleic Acid Structure. Springer-Verlag, New York.
36. SATYANARAYANA, S., DABROWIAK, J.C & CHAIRES, J B (1992). Neither Δ- nor A-tris(phenanthroline) ruthenium(II) binds to DNA by classical intercalation. Biochemistry, 31, 9319.
37. SCARIA, P.V., CRAIG, J C. & SHAFER, R.H. (1993). Differential binding of the enantiomers of chloroquine and quinacrine to polynucleotides: implications for stereoselective metabolism. Biopolymers, 33, 887.
38. SEIDEL, C A.M , SCHULZ, A. & SAUER, M.H.M. (1996). Nucleobase-specific quenching of fluorescent dyes. 1. Nucleobase one-electron redox potentials and their correlation with static and dynamic quenching efficiencies. Journal of Physical Chemistry, 100, 5541.
39. SHAVAROVA, Z. & BOGDANOV, A. (1994) Advances in Organic Chemistry of Nucleic Acids. VCH, Weinheim.
40. 2. Journal of Theoretical Biology, 137, 107.
41. SUMMERS, L A (1980). The Bipyridinium Herbicides. Academic Press, New York.
42. TANIOUS, F.A., VEAL, J M., BUCZAK, H., RATMEYER, L S. & WILSON, W D. (1992). DAPI (4′,6-diamidino-2-phenylindole) binds differently to DNA and RNA: minor-groove binding at AT sites and intercalation at AU sites. Biochemistry, 31, 3103.
43. THOMAS, G.A. & PETICOLAS, W L (1983). Fluctuations in nucleic acids conformations. 2. Raman spectroscopic evidence of varying ring pucker in A-T polynucleotides. Journal of the American Chemical Society, 105, 993.
44. WARING, M.J (1981). DNA modification and cancer. Annual Review of Biochemistry, 50, 159.
45. WEINER, S.J , KOLLMAN, P.A., NGUYEN, D.T. & CASE, D.A. (1986). An all atom force field for simulation of proteins and nucleic acids. Journal of Computational Chemistry, 7, 230.
46. WILSON, W.D. & LOPP, I.G (1979). Analysis of cooperativity and ion effects in the interaction of quinacrine with DNA. Biopolymers, 18, 3025.
47. WILSON, W.D , KRISHNAMOORTHY, C R , WANG, Y.H. & SMITH, J.C (1985a). Mechanism of intercalation: ion effects on the equilibrium and kinetic constants for the interaction of propidium and ethidium with DNA. Biopolymers, 24, 1941.
48. WILSON, W.D., WANG, Y H , KRISHNAMOORTHY, C R. & SMITH, J.C. (1985b). Poly(dA)·poly(dT) exist in an unusual conformation under physiological conditions: propidium binding to poly(dA)·poly(dT) and poly[d(A-T)]·poly[d(A-T)]. Biochemistry, 24, 3991.
49. XODO, L.E., MANZINI, G , RUGGIERO, J & QUADRIFOGLIO, F. (1988). On the interaction of daunomycin with synthetic alternating DNAs: sequence specificity and polyelectrolyte effects on the intercalation equilibrium. Biopolymers, 27, 1839.