Photochemistry of 2-chloropyrimidine

Photochemical and Photobiological Sciences

Volumn 1, Issue 8, 2002, Pages 600-606

  Lindqvist, Lars ^a   Czochralska, Barbara ^b   Fontaine Aupart, Marie Pierre ^a   Kawczynski, Wieslaw ^b   Tfibel, Francis ^a   Douki, Thierry ^c  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b UNIVERSITY OF WARSAW   (Poland)

^c DSM RESOLVE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLOROPYRIMIDINE; CARBON; CHLORIDE; FREE RADICAL; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; AEROBIC CAPACITY; ANAEROBIC METABOLISM; AQUEOUS SOLUTION; ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PHOTOCHEMISTRY; PHOTODEGRADATION; PHOTOLYSIS; PHOTOSENSITIZATION; POLAROGRAPHY; PRIORITY JOURNAL; QUANTUM YIELD; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 0041408683     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b203620g     Document Type: Article

References (29)

1. G. J. Fisher and H. E. Johns, Pyrimidine photodimers, in Photochemistry and Photobiology of Nucleic Acids, Vol. 1, ed. S. Y. Wang, Academic Press, New York, 1976, pp. 225–294.
2. J. Cadet L. Voituriez A. Grand F. E. Hruska P. Vigny L. S. Kan Recent aspects of the photochemistry of nucleic acids and related model compounds Biochimie 1985 67 277-292.
3. D. Elad, Photochemistry of purins, in Photochemistry and Photobiology of Nucleic Acids, Vol. 1, ed. S. Y. Wang, Academic Press, New York, 1976, pp. 357–378.
4. W. D. Rupp W. H. Prusoff Photochemistry of iodouracil. I. Photoproducts obtained in water Biochem. Biophys. Res. Commun. 1965 18 145-151.
5. W. D. Rupp W. H. Prusoff Photochemistry of iodouracil. II. Effects of sulfur compounds, ethanol and oxygen Biochem. Biophys. Res. Commun. 1965 18 158-164.
6. H. Ishihara S. Y. Wang Photochemistry of 5-bromouracils: isolation of 5,5′-diuracils Nature 1966 210 1222-1225.
7. Z. Kazimierczuk D. Shugar Photochemical transformation of 6-chlorouracil and some alkylated analogues Biochim. Biophys. Acta 1971 254 157-166.
8. E. Beutler Cladribine (2-chlorodeoxyadenosine) Lancet 1992 340 952-956.
9. Z. Kazimierczuk R. Mertens W. Kawczynski F. Seela 2′-Deoxyguanosine and base-modified analogues: chemical and photochemical synthesis Helv. Chim. Acta 1991 74 1742-1748.
10. N. Ramzaeva F. Seela Photochemical conversion of oligonucleotides containing 2-chloro-2′-deoxyadenosine: enhanced UV sensitivity of a modified purine base induced by the nearest neighbor Chem. Res. Toxicol. 1994 7 643-649.
11. B. Czochralska L. Lindqvist Reaction mechanism in the photochemistry of the antileukemic agents 2-chloro- and 2-bromo-2′-deoxyadenosine, studied by nanosecond laser flash photolysis J. Photochem. Photobiol., B 1999 50 28-32.
12. M. P. V. Boarland J. F. W. McOmie Pyrimidines. Part II. The ultraviolet spectra of some monosubstituted pyrimidines J. Chem. Soc. 1952 3716-3722.
13. C. El Hanine-Lmoumene L. Lindqvist Stepwise two-photon excitation of 1,5-dihydroflavin mononucleotide: study of flavosemiquinone properties Photochem. Photobiol. 1997 66 591-595.
14. D. J. Brown E. Hoerger S. F. Mason Simple pyrimidines. Part II. 1,2-Dihydro-1-methylpyrimidines and the configuration of the N-methyluracils J. Chem. Soc. 1955 211-217.
15. D. Shugar, Photochemistry of nucleic acids and their constituents, in The Nucleic Acids, vol. III, ed. E. Chargaff and J. Davidson, Academic Press, New York, 1960, pp. 39–104.
16. M. Charlier C. Hélène Photochemical reactions of aromatic ketones with nucleic acids and their components—III. Chain breakage and thymine dimerization in benzophenone photosensitized DNA Photochem. Photobiol. 1972 51 527-536.
17. A. A. Lamola Triplet photosensitization and the photobiology of thymine dimers in DNA Pure Appl. Chem. 1970 124 599-610.
18. I. G. Gut P. D. Wood R. W. Redmond Interaction of triplet photosensitizers with nucleotides and DNA in aqueous solution at room temperature J. Am. Chem. Soc. 1996 118 2366-2373.
19. P. D. Wood R. W. Redmond Triplet state interactions between nucleic acid bases in solution at room temperature: intermolecular energy and electron transfer J. Am. Chem. Soc. 1996 118 4256-4263.
20. R. Bensasson E. J. Land Triplet–triplet extinction coefficients via energy transfer Trans. Faraday Soc. 1971 67 1904-1915.
21. B. Amand R. Bensasson Determination of triplet quantum yields by laser flash absorption spectroscopy Chem. Phys. Lett. 1975 34 44-48.
22. D. V. Bent E. Hayon P. N. Moorthy Chemistry of the triplet state of diazines in solution studied by laser spectroscopy J. Am. Chem. Soc. 1975 97 5065-5071.
23. H. Görner Transients of uracil and thymine derivatives and the quantum yields of electron ejection and intersystem crossing upon 20 ns photolysis at 248 nm Photochem. Photobiol. 1990 52 935-948.
24. R. V. Bensasson, E. J. Land and T. G. Truscott, Flash photolysis and pulse radiolysis, Pergamon Press, Oxford, UK, 1983.
25. R. V. Bensasson, E. J. Land and T. G. Truscott, Excited states and free radicals in biology and medicine, Oxford University Press, Oxford, UK, 1993.
26. I. Rosenthal J. N. Pitts, Jr Reactivity of purine and pyrimidine bases toward singlet oxygen Biophys. J. 1971 11 963-965.
27. B. Czochralska M. Wrona D. Shugar Electrochemically reduced photoreversible products of pyrimidine and purine analogues Top. Curr. Chem. 1986 130 133-181.
28. Z. B. Alfassi G. L. Khaikin P. Neta Formation and reactivity of pyridylperoxyl radicals in solution J. Phys. Chem. 1995 99 4544-4548.
29. R. O. Rahn Photochemistry of halogen pyrimidines: iodine release studies Photochem. Photobiol. 1992 56 9-15.