6
Views
5
CrossRef citations to date
0
Altmetric
Original Article

Identification of the Two cis-syn [2 + 2] Cycloadducts Resulting from the Photoreaction of 3-carbethoxypsoralen with 2′-deoxycytidine and 2′-deoxyuridine

, , , , &
Pages 903-918 | Received 30 Aug 1989, Accepted 06 Nov 1989, Published online: 03 Jul 2009

References

  • Averbeck D. Photochemistry and photobiology of psoralens. Proceedings of the Japanese Society for Investigations in Dermatology 1984; 8: 52–73
  • Boyer V., Moustacchi E., Sage E. Sequence specificity in photoreaction of various psoralen derivatives with DNA: role in biological activity. Biochemistry 1988; 27: 3011–3018
  • Buchanan J.G. Detection of deoxyribonucleosides on paper chromatograms. Nature 1951; 168: 1091–1092
  • Cadet J., Ducolomb R., Hruska F.E. Proton magnetic resonance studies of 5,6-saturated thymidine derivatives produced by ionizing radiation. Conformational analysis of 6-hydroxylated diastereoisomers. Biochimica et Biophysica Acta 1979; 563: 206–215
  • Cadet J., Kan L.-S., Wang S.Y. O6,5′-cyclo-5,6-dihydro-2′-deoxyuridine. Novel deoxyuridine photoproducts. Journal of the American Chemical Society 1978; 100: 6715–6720
  • Cadet J., Voituriez L., Gagoriau F., Vigny P., Della Negra S. Characterization of photocycloaddition products from reaction between thymidine and the monofunctional 3-carbethoxypsoralen. Photochemistry and Photobiology 1983; 37: 363–371
  • Cadet J., Berger M., Decarroz C., Wagner J.R., van Lier J.E., Ginot Y.M., Vigny P. Photosensitized reactions of nucleic acids. Biochimie 1986; 68: 813–834
  • Calvin N.M., Hanawalt P.C. Photoadducts of 8-methoxypsoralen to cytosine in DNA. Photochemistry and Photobiology 1987; 45: 323–330
  • Coq B., Gonnet C., Rocca J.-L. Technique de remplissage de colonnes de chromatographie liquide à haute performance avec des microparticules poreuses. Journal of Chromatography 1975; 106: 244–262
  • Dall'Acqua F. New chemical aspects of the photoreaction between psoralen and DNA. Research in Photobiology, A. Castellani. Plenum Press, New York 1977; 245–255
  • Fisher J., Johns H.E. Pyrimidine photodimers. Photochemistry and Photobiology of Nucleic Acids, S.Y. Wang. Academic Press, New York 1976; I: 225–294
  • Fitzpatrick T.B., Pathak M.A. Historical aspects of methoxsalen and furocoumarins. Journal of Investigative Dermatology 1965; 32: 225–238
  • Gaboriau F., Vigny P., Cadet J., Voituriez L., Bisagni E. Photoreaction of monofunctional 3-carbethoxypsoralen with DNA: Identification and conformational study of the predominant cis-syn furan-side monoadduct to thymine. Photochemistry and Photobiology 1987; 45: 199–207
  • Hahn B.S., Joshi P.C., Kan L.-S., Wang S.Y. Heterodimers of psoralen and thymine derivatives: properties, structure and stereochemistry. Photobiochemistry and Photobiophysics 1981; 3: 113–124
  • Hearst J.E. Psoralen photochemistry and nucleic acid structure. Journal of Investigative Dermatology 1981; 77: 39–44
  • Hruska F.E., Berger M., Cadet J., Remin M. A conformational study of the adduct of 2-deoxythymidine and 2,2,6,6-tetramethyl-1,4-piperidone-N-Oxyl by 1H and 13C nuclear magnetic resonance. Canadian Journal of Chemistry 1985; 63: 15–23
  • Kanne D., Straub K., Hearst J.E., Rapoport H. Isolation and characterization of pyrimidine-psoralen-pyrimidine photodiadducts from DNA. Journal of the American Chemical Society 1982a; 104: 6754–6764
  • Kanne D., Straub K., Rapoport H., Hearst J.E. Psoralendeoxyribonucleic acid photoreaction. Characterization of the monoaddition products from 8-methoxypsoralen and 4,5′,8-trimethylpsoralen. Biochemistry 1982b; 21: 861–871
  • Land E.J., Rushton F.A.P., Beddoes R.L., Bruce J.M., Cernik R.J., Dawson S.C., Mills O.S. A 2 + 2 photoadduct of 8-methoxypsoralen and thymine: X-ray crystal structure; a model for the reaction of psoralen with DNA in the phototherapy of psoriasis. Journal of the Chemical Society, Chemical Communications 1982; 1: 22–23
  • Miolo G., Dall'Acqua F., Moustacchi E., Sage E. Monofunctional angular furocoumarins: sequence specificity in DNA photobinding of 6,6,4′-trimethylangelicin and other angelicins. Photochemistry and Photobiology 1989; 50: 75–84
  • Moysan A., Cazaussus A., Gaboriau F., Blais J.C., Sellier N., Vigny P. Structure of 3-carbethyoxypsoralen photolysis products. Photochemistry and Photobiology 1988; 47: 327–355
  • Moysan A., Gaboriau F., Vigny P., Voituriez L., Cadet J. Chemical structure of 3-carbethoxypsoralen-DNA photoadducts. Biochimie 1986; 68: 787–795
  • Musajo L., Rodighiero G. Mode of photosensitizing action of furocoumarins. Photophysiology, A. Giese. Academic Press, New York 1972a; VII: 115–147
  • Musajo L., Rodighiero G. Photo-C-cycloaddition reaction to nucleic acids. Research Progress in Organic, Biological and Medical Chemistry, U. Gallo, L. Santamaria. North Holland, Amsterdam 1972b; 155–181
  • Musajo L., Rodighiero G., Caporale G., Dall'Acqua F., Marciani S., Bordin F., Baccichetti F.R., Bevilacqua R. Photoreactions between photosensitizing furocoumarins and nucleic acids. Sunlight and Man, M.A. Pathak, L.C. Harber, M. Seiji, A. Kukita. University of Tokyo Press, Tokyo 1974; 369–387
  • Parrish J.A., Fitzpatrick T.B., Tanenbaum L., Pathak M.A. Photochemotherapy of psoriasis with oral methoxsalen and longwave ultraviolet light. New England Journal of Medicine 1974; 291: 1207–1222
  • Peckler S., Graves F., Kanne D., Rapoport H., Hearst J.E., Kim S.H. Structure of a psoralen-thymine monoadduct formed in photoreaction with DNA. Journal of Molecular Biology 1982; 162: 157–172
  • Queval P., Bisagni E. New synthesis of psoralen and related compounds. European Journal of Medicinal Chemistry 1974; 9: 335–340
  • Rabi J.A., Fox J.J. Nucleosides. LXXIX. Facile base-catalyzed hydrogen labeling at position 6 of pyrimidine nucleosides. Journal of the American Chemical Society 1973; 95: 1628–1632
  • Ritchie R.G.S., Perlin A.S. Adenosine-5′-d: rotational conformation of the 5′-carbinol group. Carbohydrate Research 1977; 55: 121–128
  • Shapiro R., DiFate V., Welcher M. Deamination of cytosine derivatives by bisulfite. Mechanism of the reaction. Journal of the American Chemical Society 1974; 96: 906–912
  • Shapiro R., Servis R.E., Welcher M. Reactions of uracil and cytosine derivatives with sodium bisulfite. A specific deamination method. Journal of the American Chemical Society 1970; 92: 422–424
  • Song P.S., Tapley K.J. Photochemistry and photobiology of psoralens. Photochemistry and Photobiology 1979; 29: 1177–1197
  • Straub K., Kanne D., Hearst J.E., Rapoport H. Isolation and characterization of pyrimidine-psoralen photoadducts from DNA. Journal of the American Chemical Society 1981; 103: 2347–2355
  • Viari A., Ballini J.P., Vigny P., Shire D., Dousset P. Sequence analysis of unprotected tri-deoxyribonucleoside diphosphates by 252Cf plasma desorption mass spectrometry. Biomedical and Environmental Mass Spectrometry 1987; 14: 83–90
  • Vigny P., Duquesne M. A spectrofluorimeter for the detection of very weak fluorescences from biological molecules. Photochemistry and Photobiology 1974; 20: 15–25
  • Vigny P., Gaboriau F., Duquesne M., Bisagni E., Averbeck D. Spectroscopic properties of psoralen derivatives substituted by carbethoxy groups at the 3,4 and/or 4′,5′ reaction site. Photochemistry and Photobiology 1979; 30: 557–564
  • Vigny P., Gaboriau F., Voituriez L., Cadet J. Chemical structure of psoralen nucleic acid photoadducts. Biochimie 1985; 67: 317–325
  • Vigny P., Spiro M., Gaboriau F., Le Beyec Y., Della Negra S., Cadet J., Voituriez L. 252Cf-Plasma desorption mass spectrometry of covalently bound nucleic acid adducts: psoralen-nucleoside photoadducts. International Journal of Mass Spectrometry and Ion Physics 1983; 53: 69–83
  • Wolff K., Gschnaīt F., Hönigsmann J., Konrad K., Parrish J.A., Fitzpatrick T.B. Phototesting and dosimetry for photochemotherapy. British Journal of Dermatology 1977; 96: 1–10

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.