Targeting of photooxidative damage on single-stranded DNA representing the bcr-abl chimeric gene using oligonucleotide-conjugates containing [Ru(phen)3]2+-like photosensitiser groups

Photochemical and Photobiological Sciences

Volumn 1, Issue 12, 2002, Pages 1024-1033

  Crean, Conor W ^a   Kavanagh, Yvonne T ^a   O’Keeffe, Clare M ^a   Lawler, Mark P ^b   Stevenson, Clarke ^c   Davies, R Jeremy H ^c   Boyle, Peter H ^a   Kelly, John M ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

^b ST JAMES S HOSPITAL   (Ireland)

^c QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTISENSE OLIGONUCLEOTIDE; GUANINE; ORGANOMETALLIC COMPOUND; PHOTOSENSITIZING AGENT; RUTHENIUM; SINGLE STRANDED DNA; 1,10 PHENANTHROLINE; BCR ABL PROTEIN; BIPYRIDINE DERIVATIVE; CYTOSINE; DEOXYGUANOSINE; DNA BASE; ESTER DERIVATIVE; GUANINE DERIVATIVE; HYDANTOIN DERIVATIVE; METHYL GROUP; OLIGODEOXYNUCLEOTIDE; OXYGEN; PHOSPHORUS 32; RUTHENIUM COMPLEX; SUCCINIMIDE DERIVATIVE;

ARTICLE; AUTORADIOGRAPHY; CHEMISTRY; CHRONIC MYELOID LEUKEMIA; COMPARATIVE STUDY; CONFORMATION; DENSITOMETRY; DNA DAMAGE; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; IN SITU HYBRIDIZATION; NUCLEOTIDE SEQUENCE; ONCOGENE; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; RADIATION EXPOSURE; BINDING SITE; CHEMICAL REACTION; CHIMERA; CONJUGATION; CONTROLLED STUDY; DIASTEREOISOMER; GENE SEQUENCE; GENETIC VARIABILITY; IRRADIATION; MOLECULAR HYBRIDIZATION; NUCLEIC ACID BASE SUBSTITUTION; OXIDATION; PATHOGENESIS; PHOTOLYSIS; PHOTOOXIDATION; PHOTOSENSITIZATION; PRIORITY JOURNAL; SEQUENCE ANALYSIS;

AUTORADIOGRAPHY; BASE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DENSITOMETRY; DNA DAMAGE; DNA, SINGLE-STRANDED; GENES, ABL; GUANINE; HUMANS; IN SITU HYBRIDIZATION; LEUKEMIA, MYELOID, CHRONIC; NUCLEIC ACID CONFORMATION; OLIGONUCLEOTIDES, ANTISENSE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PHOTOCHEMISTRY; PHOTOSENSITIZING AGENTS; RUTHENIUM;

EID: 0038137250     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b207387k     Document Type: Article

References (51)

1. K. E. Erikkila D. T. Odom J. K. Barton Recognition and reaction of metallointercalators with DNA Chem. Rev. 1999 99 2777-2795.
2. B. Nordén, P. Lincoln, B. Akerman and E. Tuite, Probing of nucleic acids by metal ion complexes of small molecules, in Metal Ions in Biological Systems, ed. A. Sigel and H. Sigel, Marcel Dekker, New York, 1996, vol. 33, pp. 177–252.
3. T. Da Ros G. Spalluto A. S. Boutorine R. V. Bensasson M. Prato DNA-photocleavage agents Curr. Pharm. Des. 2001 7 1781-1821.
4. C. Moucheron A. Kirsch-De Mesmaeker J. M. Kelly Photoreactions of ruthenium(II) and osmium(II) complexes with deoxyribonucleic acid (DNA) J. Photochem. Photobiol. B. 1997 40 91-106.
5. C. Moucheron A. Kirsch-De Mesmaeker J. M. Kelly Photophysics and photochemistry of metal polypyridyl and related complexes with nucleic acids Struct. Bonding 1998 92 163-216.
6. J. M. Kelly A. B. Tossi D. J. McConnell C. OhUigin A study of the interactions of some polypyridylruthenium(II) complexes with DNA using fluorescence spectroscopy, topoisomerisation and thermal denaturation Nucleic Acid Research 1985 13 6017-6034.
7. A. B. Tossi J. M. Kelly A study of some polypyridylruthenium(II) complexes as DNA binders and photocleavage reagents Photochem. Photobiol. 1989 49 545-556.
8. A. Aboul-Enein D. Schulte-Frohlinde Biological deactivation and single-strand breakage of plasmid DNA by photosensitization using tris(2,2′-bipyridyl)ruthenium(II) and peroxydisulfate Photochem. Photobiol. 1988 48 27-34.
9. C. Sentage J. C. Chambron J. P. Sauvage N. Paillous Tuning the mechanism of DNA cleavage photosensitized by ruthenium dipyridophenazine complexes by varying the structure of the two non intercalating ligands J. Photochem. Photobiol. B. 1994 26 165-174.
10. J. M. Kelly, A. B. Tossi, D. J. McConnell, C. OhUigin, C. Hélène and T. le Doan, Interaction of ruthenium polypyridyl complexes with DNA and their use as sensitisers for its cleavage, in Free Radicals, Metal Ions and Biopolymers, ed. P. C. Beaumont, D. J. Deeble, B. J. Parsons and C. Rice Evans, Richelieu Press, London, 1989, p. 143.
11. S. Delaney M. Pascaly P. K. Bhattacharya K. Han J. K. Barton Oxidative damage by ruthenium complexes containing the dipyridophenazine ligand or its derivatives: a focus on intercalation Inorg. Chem. 2002 41 1966-1974.
12. 2+ to DNA : A new mode of covalent attachment of metal complexes to duplex DNA J. Am. Chem. Soc. 1997 119 11763-11768.
13. J-P. Lecomte A. Kirsch-De Mesmaeker M. M. Feeney J. M. Kelly Ruthenium(II) complexes with 1,4,5,8,9,12-hexaazatriphenylene and 1,4,5,8-tetraazaphenanthrene ligands: key role played by the photoelectron transfer in DNA cleavage and adduct formation Inorg. Chem. 1995 34 6481-6491.
14. Y. Jenkins J. K. Barton A sequence-specific molecular light switch: tethering of an oligonucleotide to a dipyridophenazine complex of ruthenium(II) J. Am. Chem. Soc. 1992 114 8736-8738.
15. 2+ Inorg. Chem. 2000 39 2500-2504.
16. D. J. Hurley Y. Tor Metal-containing oligonucleotides: solid-phase synthesis and luminescence properties J. Am. Chem. Soc. 1998 120 2194-2195.
17. E. Meggers D. Kusch B. Giese An effective synthesis of enantiomerically pure Δ- and Λ-ruthenium(II) labelled oligonucleotides Helv. Chim. Acta. 1997 80 640-652.
18. 2+-tethered oligo-DNA and studies on the metallointercalation mode into the DNA duplex J. Am. Chem. Soc. 2001 123 3551-3562.
19. W. Bannwarth D. Schmidt R. L. Stallard C. Hornung R. Knorr F. Müller Bathophenanthroline-ruthenium(II) complexes as non-radioactive labels for oligonucleotides which can be measured by time-resolved fluorescence techniques Helv. Chim. Acta. 1988 71 2085-2099.
20. J. Telser A. Cruickshank K. S. Schanze T. L. Netzel DNA oligomers and duplexes containing a covalently attached derivative of tris (2, 2′ -bipyridine) ruthenium(II): synthesis and characterization by thermodynamic and optical spectroscopic measurements J. Am. Chem. Soc. 1989 111 7221-7226.
21. G. N. Grimm A. S. Boutorine P. Lincoln B. Nordén C. Hélène Formation of DNA triple helices by an oligonucleotide conjugated to a fluorescent ruthenium complex ChemBioChem. 2002 3 324-331.
22. D. García-Fresnadillo N. Boutonnet S. Schumm C. Moucheron A. Kirsch-De Mesmaeker E. Defrancq J. F. Constant J. Lhomme Luminescence quenching of Ru-labeled oligonucleotides by targeted complementary strands Biophys. J. 2002 82 978-987.
23. S. Schumm M. Prévost D. García-Fresnadillo O. Lentzen C. Moucheron A. Kirsch-De Mesmaeker Influence of the sequence dependent ionisation potentials of guanines on the luminescence quenching of Ru-labeled oligonucleotides: a theoretical and experimental study J. Phys. Chem. B 2002 106 2763-2768.
24. 2+ with single-stranded DNA – what degree of protection is required for operation of the “light-switch effect”? J. Phys. Chem. B 2001 105 730-735.
25. P. K. Bhattacharya J. K. Barton Influence of intervening mismatches on long-range guanine oxidation in DNA duplexes J. Am. Chem. Soc. 2001 123 8649-8656.
26. I. Ortmans S. Content N. Boutonnet A. Kirsch-De Mesmaeker W. Bannwarth J-F. Constant E. Defrancq J. Lhomme Ru-labeled oligonucleotides for photoinduced reactions on targeted DNA guanines Chem. Eur. J. 1999 5 2712-2721.
27. R. E. Clarke Antisense therapeutics in chronic myeloid leukaemia: the promise, the progress and the problems Leukaemia 2000 14 347-355.
28. A. Hergueta-Bravo M. E. Jiménez-Hernández F. Montero E. Oliveros G. Orellana Singlet oxygen-mediated DNA photocleavage with Ru(II) polypyridyl complexes J. Phys. Chem. B 2002 106 4010-4017.
29. F. Schubert A. Knaf U. Möller D. Cech Covalent attachment of methylene blue to oligonucleotides Nucleosides Nucleotides 1995 14 1437-1443.
30. 2+-deoxyuridine Inorg. Chem. 1999 38 2411-2415.
31. J. Feely P. V. Kavanagh S. M. McNamara J. E. O’Brien Simple preparation of the major urinary metabolites of flunitrazepam and nitrazepam Iran. J. Med. Sci. 1999 168 8-9.
32. B. H. Han D. H. Shin S. Y. Cho Graphite catalysed reduction of aromatic and aliphatic nitro compounds with hydrazine hydrate Tetrahedron Lett. 1985 26 6233-6234.
33. N. Y. Sardesai S. C. Lin K. Zimmermann J. K. Barton Construction of coordinatively saturated rhodium complexes containing appended peptides Bioconjugate Chem. 1995 6 302-312.
34. I. Saito T. Nakamura K. Natatani Mapping of highest occupied molecular orbitals of duplex DNA by cobalt-mediated guanine oxidation J. Am. Chem. Soc. 2000 122 3001-3006.
35. F. Wilkinson W. P. Helman A. B. Ross Rate constants for the decay and reactions of the lowest electronically excited singlet-state of molecular-oxygen in solution-an expanded and revised compliation J. Phys. Chem. Ref. Data 1995 24 663-1021.
36. J. Van Houten R. J. Watts Temperature dependence of the photophysical and photochemical properties of the tris(2,2′-bipyridyl)ruthenium(II) ion in aqueous solution J. Am. Chem. Soc. 1976 98 4853-4858.
37. J-L. Ravanat T. Douki M-F. Incardona J. Cadet HPLC separations of normal and modified nucleobases and nucleosides on an amino-silica gel column J. Liq. Chromatogr. 1993 36 3185-3202.
38. J. Cadet and P. Vigny, in Bioorganic Chemistry, ed. H. Morrison, Wiley, New York, 1990, vol. 1, pp. 1–272.
39. J. C. Niles J. S. Wishnok S. R. Tannenbaum Spiroimino-dihydantoin is the major product of the 8-oxo-7,8-dihydroguanosine reaction with peroxynitrite in the presence of thiols and guanosine photoxidation by methylene blue Org. Lett. 2001 3 963-966.
40. W. Adam M. A. Arnold M. Grüne W. M. Nau U. Pischel C. R. Saha-Müller Spiroiminodihydantoin is a major product in the photooxidation of 2′-deoxyguanosine by the triplet states and oxyl radicals generated from hydroxyacetophenone photolysis and dioxetane thermolysis Org. Lett. 2002 4 537-540.
41. T. Douki J. Cadet Modification of DNA bases by photosensitized one-electron oxidation Int. J. Radiat. Biol. 1999 75 571-581.
42. B. Lewin, Genes V, Oxford University Press Inc., New York, 1994.
43. F. Prat C-C. Hou C. S. Foote Determination of the quenching rate constants of singlet oxygen by derivatized nucleosides in nonaqueous solution J. Am. Chem. Soc. 1997 119 5051-5052.
44. A. S. Boutorine D. Brault M. Takasugi O. Delgado C. Helene Chlorin-oligonucleotide conjugates: synthesis, properties, and red light-induced photochemical sequence-specific DNA cleavage in duplexes and triplexes J. Am. Chem. Soc. 1996 118 9469-9476.
45. I. V. Yang H. H. Thorp Kinetics of metal-mediated one-electron oxidation of guanine in polymeric DNA and in oligonucleotides containing trinucleotide repeat sequences Inorg. Chem. 2000 39 4969-4976.
46. X. Y. Zhang M. A. J. Rodgers Energy and electron-transfer reactions of the MLCT state of ruthenium tris(bipyridyl) with molecular-oxygen – a laser flash-photolysis study J. Phys. Chem. 1995 99 12797-12803.
47. B. P. Sullivan D. J. Salmon T. J. Meyer Mixed phosphine 2,2′-bipyridine complexes of ruthenium Inorg. Chem. 1978 17 3334-3341.
48. G. Sprintschnik H. W. Sprintschnik P. P. Kirsch D. G. Whitten Preparation and photochemical reactivity of surfactant ruthenium(II) complexes in monolayer assemblies and at water-solid interfaces J. Am. Chem. Soc. 1977 15 4947-4954.
49. C. D. Ellis L. D. Margerum R. W. Murray T. J. Meyer Oxidative electropolymerization of polypyridyl complexes of ruthenium Inorg. Chem. 1983 22 1283-1291.
50. E. Koft F. H. Case substituted 1,10-phenanthrolines, benzo and pyrido derivatives J. Org. Chem. 1962 27 865-868.
51. nd edn., Cold Spring Harbour Lab, NY, 1989.