Photochemical reactions of 5-fluorouracil and 5-fluoro-2'-deoxyuridine with N(α)-acetyl-L-tryptophan N-ethylamide in aqueous solution

Journal of Photochemistry and Photobiology B: Biology

Volumn 43, Issue 1, 1998, Pages 66-72

  Celewicz, Lech ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

5 Fluoro 2' deoxyuridine; 5 Fluorouracil; N( ) acetyl L tryptophan N ethylamide; Photocoupling reactions

Indexed keywords

FLOXURIDINE; FLUOROURACIL; N ACETYL 2 (1 (2 DEOXY BETA DEXTRO ERYTHRO PENTOFURANOSYL)URACIL 5 YL)TRYPTOPHAN N ETHYLAMIDE; N ACETYL 2 (URACIL 5 YL)TRYPTOPHAN N ETHYLAMIDE; N ACETYL TRYPTOPHAN N ETHYLAMIDE; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CROSS LINKING; DRUG MECHANISM; DRUG SYNTHESIS; FLUORESCENCE; PHOTOCHEMISTRY; PHOTOREACTIVITY; PRIORITY JOURNAL;

EID: 0032052582     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1011-1344(98)00090-6     Document Type: Article

References (34)

1. [1] R.T. Walker, M.J. Gait, Biosynthesis of nucleotides, in: G.M. Blackburn, M.J. Gait (Eds.), Nucleic Acids in Chemistry and Biology, Oxford University Press, Oxford, 1996, pp. 162-163.
2. [2] C. Périgaud, G. Gosselin, J.-L. Imbach, Nucleoside analogues as chemotherapeutic agents: a review, Nucleosides Nucleotides 11 (1992) 903-945.
3. [3] A. Kornberg, T.A. Baker, DNA Replication, W.H. Freeman, New York, 1992, pp. 445-446.
4. [4] P.V. Sahasrabudhe, R.T. Pon, W.H. Gmeiner, Effects of site-specific substitution of 5-fluorouridine on the stabilities of duplex DNA and RNA, Nucleic Acids Res. 23 (1995) 3916-3921.
5. [5] A.D. Broom, Rational design of enzyme inhibitors: multisubstrate analogue inhibitors, J. Med. Chem. 32 (1989) 2-7.
6. [6] S.Y. Wang, Pyrimidine bimolecular photoproducts, in: S.Y. Wang (Ed.), Photochemistry and Photobiology of Nucleic Acids, vol. 1, Academic Press, New York, 1976, pp. 295-356.
7. [7] J. Cadet, P. Vigny, The photochemistry of nucleic acids, in: H. Morrison (Ed.), Bioorganic Photochemistry, vol. 1, John Wiley. New York, 1990, pp. 1-272.
8. [8] S.C. Shim, S.H. Lee, Photosensitized cyclodimerization of 5-fluorouracil. Photochem. Photobiol. 29 (1979) 1035-1038.
9. [9] J.J. Langer, H. Wojtowicz, K. Golankiewicz, Stacking-controlled phototransformations of the 5-fluorouracil residues in dinucleotide model compounds, J. Photochem. Photobiol. B: Biol. 4 (1989) 15-20.
10. [10] M. Fikus, K.L. Wierzchowski, D. Shugar, Photochemistry of 5-fluorouracil analogues, glycosides and poly-FU. Photochem. Photobiol. 4 (1965) 521-536.
11. [11] H.A. Lozeron, M.P. Gordon, Ultraviolet sensitization and photoreactivation of tobacco mosaic virus ribonucleic acid containing 5-fluorouracil, Biochemistry 3 (1964) 507-510.
12. [12] M.D. Shetlar, Nucleic acid-protein cross-linking induced by UV light: the role of pyrimidine nucleobase-amino acid conjugates. The Spectrum (a quarterly publication of the Center for Photochemical Sciences, Bowling Green State University, OH, USA) 7 (1994) 12-19.
13. [13] K.M. Meisenheimer, T.H. Koch, Photocross-linking of nucleic acids to associated proteins, Crit. Rev. Biochem. Mol. Biol. 32 (1997) 101-140.
14. [14] I. Saito, H. Sugiyama, Photoreactions of nucleic acids and their constituents with amino acids and related compounds, in: H. Morrison (Ed.), Bioorganic Photochemistry, vol. 1, John Wiley, New York, 1990, pp. 317-340.
15. [15] T.M. Dietz, T.H. Koch, Mechanistic studies toward an understanding of photocrosslinking of 5-bromouracil-containing nucleic acids to associated proteins, Trends Photochem. Photobiol. 2 (1991) 121-136.
16. [16] S. Ito, I. Saito, T. Matsuura, Acetone-sensitized photocoupling of 5-bromouridine to tryptophan derivatives via an electron-transfer process, J. Am. Chem. Soc. 102 (1980) 7535-7541.
17. [17] L. Celewicz, Photochemical coupling of 5-bromo-1,3-dimethyluracil and its 6-alkyl derivatives to 3-methylindole and Na-acetyl-L-tryptophan methyl ester, J. Photochem. Photobiol. B: Biol. 3 (1989) 565-574.
18. [18] T.M. Dietz, T.H. Koch, Photochemical coupling of 5-bromouracil to tryptophan, tyrosine and histidine, peptide-like derivatives in aqueous fluid solution, Photochem. Photobiol. 46 (1987) 971-978.
19. [19] C.L. Norris, K.M. Meisenheimer, T.H. Koch, Mechanistic studies relevant to bromouridine-enhanced nucleoprotein photocrosslinking: possible involvement of an excited tyrosine residues of the protein, Photochem. Photobiol. 65 (1997) 201-207.
20. [20] S.L. Murov, I. Carmichael, G.L. Hug, Handbook of Photochemistry, Marcel Dekker. New York. 1993, pp. 307-308 and pp. 315-317.
21. [21] A.S. Plaziak, L. Celewicz, Mass spectrometry of 5-(3-alkyl-1H-indol2-yl)uracils, Org. Mass Spectrom. 24 (1989) 953-955.
22. o acetyl-L-tryptophan N-ethylamide in aqueous solution, J. Photochem. Photobiol. B: Biol. 30 (1995) 129-137.
23. [23] H. Friebolin, Basic One-and Two-Dimensional NMR Spectroscopy, VCH, New York, 1993, pp. 211-216.
24. [24] M.D. Shetlar, R.B. Rose, K. Hom, A.A. Shaw, Ring opening photoreactions of 5-bromouracil and 5-bromo-2′-deoxyuridine with selected alkylamines, Photochem. Photobiol. 53 (1991) 595-609.
25. [25] M. Remin, I. Ekiel, D. Shugar, Proton-magnetic-resonance study of the solution conformation of the α and β anomers of 5-ethyl-2′-deoxyuridine. Eur. J. Biochem. 53 (1975) 197-206.
26. [26] N. Mariaggi, R. Téoule, J. Cadet, H. Dickie, E. Hughes, A new radiolysis mechanism for 2′-deoxyadenosine in aqueous deaerated solution, Radiat. Res. 79 (1979) 431-438.
27. [27] J. Cadet, C. Taïeb, M. Remin, W.P. Niemezura, F.E. Hruska, Conformational studies of α-and β-pyrimidine 2′-deoxyribonucleosides in the syn and anti conformation. Biochim. Biophys. Acta 608 (1980) 435-445.
28. [28] T. Kitamura, C-X bond fission in alkene systems, in: W.M. Horspool, Pill-Soon Song (Eds.), CRC Handbook of Organic Photochemistry and Photobiology, CRC, Boca Raton, FL, 1995, pp. 1171-1180.
29. [29] T.M. Dietz, R.J. Trebra, B.J. Swanson, T.H. Koch, Photochemical coupling of 5-bromouracil (BU) to a peptide linkage. A model for BU-DNA protein photocrosslinking, J. Am. Chem. Soc. 109 (1987) 1793-1797.
30. [30] K. Ohkura, M. Terashima, Y. Kanaoka, K. Seki, New aspects of the aromatic photosubstitution with iodopyridines, Chem. Pharm. Bull. 41 (1993) 1920-1924.
31. [31] T.L. Gilchrist, Heterocyclic Chemistry. Longman Scientific and Technical, New York, 1992, pp. 230-232.
32. [32] E. Kohen, R. Santos, J.G. Hirschberg. Photobiology, Academic Press, San Diego, 1995, pp. 81-83.
33. [33] K. Undheim, T. Benneche, Pyrimidines and their benzo derivatives. in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry II, vol. 6, Elsevier, Oxford, 1996, pp. 93-231.
34. 19F NMR of RNA. The structural and chemical aspects of 5-fluorocytidine and -uridine labeling of oligoribonucleotides, Nucleosides Nucleotides 15 (1996) 477-488.