Abstract
DNA's of various AT content, poly[d(A-T)-d(A-T)], and double-stranded RNA were irradiated with UV light at 365 nm in the presence of linear (xanthotoxin) or angular (angelicin) furocoumarins. The covalent photobinding is strongly dependent on the spatial arrangement of furocoumarin molecules at the polymer conformation. CD measurements demonstrate that the bifunctional photochemical binding of xanthotoxin with double-stranded DNA's and poly[d(A-T)-d(A-T)] is accompanied by conformational changes which involve probably decreasing helical twisting of the double helix. This effect is greatly enhanced with increasing AT content. The formation of A-like structures is very unlikely since the B leads to A transition induced by ethanol addition was found to be strongly suppressed in xanthotoxin photoreacted DNA. The B-type helix appears to be the most sensitive conformation with minor restriction to produce photochemically induced cross-links.
Full text
PDF












Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Arnott S., Chandrasekaran R., Hukins D. W., Smith P. J., Watts L. Structural details of double-helix observed for DNAs containing alternating purine and pyrimidine sequences. J Mol Biol. 1974 Sep 15;88(2):523–533. doi: 10.1016/0022-2836(74)90499-9. [DOI] [PubMed] [Google Scholar]
- Bevilacqua R., Bordin F. Photo-C 4 -cycloaddition of psoralen and pyrimidine bases: effect of oxygen and paramagnetic ions. Photochem Photobiol. 1973 Mar;17(3):191–208. doi: 10.1111/j.1751-1097.1973.tb06348.x. [DOI] [PubMed] [Google Scholar]
- Bordin F., Baccichetti F., Bevilacqua R., Musajo L. Inhibition of protein synthesis in Ehrlich ascites tumor cells by irradiation (365 nm) in the presence of skin-photosensitizing furocoumarins. Experientia. 1973 Mar 15;29(3):272–273. doi: 10.1007/BF01926470. [DOI] [PubMed] [Google Scholar]
- Bordin F., Baccichetti F., Bevilacqua R., Musajo L. Inhibition of protein synthesis in Ehrlich ascites tumor cells by irradiation (365 nm) in the presence of skin-photosensitizing furocoumarins. Experientia. 1973 Mar 15;29(3):272–273. doi: 10.1007/BF01926470. [DOI] [PubMed] [Google Scholar]
- Bram S. The secondary structure of DNA in solution and in nucleohistone. J Mol Biol. 1971 May 28;58(1):277–288. doi: 10.1016/0022-2836(71)90246-4. [DOI] [PubMed] [Google Scholar]
- Campbell A. M., Lochhead D. S. Optical rotatory dispersion and circular dichroism of superhelical deoxyribonucleic acid. Biochem J. 1971 Jul;123(4):661–663. doi: 10.1042/bj1230661. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Chandra P., Kraft S., Wacker A., Rodighiero S., Dall'Acqua F., Marciani S. Studies on the reactivation of bacteria photodamaged by psoralen. Biophysik. 1971;7(4):251–258. doi: 10.1007/BF01190236. [DOI] [PubMed] [Google Scholar]
- DAVIES D. R., BALDWIN R. L. X-ray studies on two synthetic DNA copolymers. J Mol Biol. 1963 Apr;6:251–255. doi: 10.1016/s0022-2836(63)80086-8. [DOI] [PubMed] [Google Scholar]
- Dall'Acqua F., Marciani S., Ciavatta L., Rodighiero G. Formation of inter-strand cross-linkings in the photoreactions between furocoumarins and DNA. Z Naturforsch B. 1971 Jun;26(6):561–569. doi: 10.1515/znb-1971-0613. [DOI] [PubMed] [Google Scholar]
- Dall'Acqua F., Marciani S., Vedaldi D., Rodighiero G. Skin photosensitization and cross-linkings formation in native DNA by furocoumarins. Z Naturforsch C. 1974 Sep-Oct;29C(9-10):635–636. doi: 10.1515/znc-1974-9-1031. [DOI] [PubMed] [Google Scholar]
- Dall'Acqua F., Terbojevich M., Benvenuto F. Light scattering and viscosimetric studies on DNA after the photoreaction with some furocoumarins. Z Naturforsch B. 1968 Jul;23(7):943–945. doi: 10.1515/znb-1968-0711. [DOI] [PubMed] [Google Scholar]
- Dall'Aqua F., Marciani S., Vedaldi D., Rodighiero G. Formation of inter-strand cross-linkings on DNA of guinea pig skin after application of psoralen and irradiation at 365 nm. FEBS Lett. 1972 Nov 1;27(2):192–194. doi: 10.1016/0014-5793(72)80617-3. [DOI] [PubMed] [Google Scholar]
- FOWLKS W. L., GRIFFITH D. G., OGINSKY E. L. Photosensitization of bacteria by furocoumarins and related compounds. Nature. 1958 Feb 22;181(4608):571–572. doi: 10.1038/181571a0. [DOI] [PubMed] [Google Scholar]
- Hartmann M., Zimmer C. Investigation of cross-link formation in DNA by the alkylating cytostatic IMET 3106, 3393 and 3943. Biochim Biophys Acta. 1972 Dec 22;287(3):386–389. doi: 10.1016/0005-2787(72)90282-1. [DOI] [PubMed] [Google Scholar]
- Ito T., Zama M., Amagasa J. Induced Cotton effects of tRNA-acridine orange complex and tRNA conformation. Biopolymers. 1972;11(8):1583–1592. doi: 10.1002/bip.1972.360110805. [DOI] [PubMed] [Google Scholar]
- Ivanov V. I., Minchenkova L. E., Schyolkina A. K., Poletayev A. I. Different conformations of double-stranded nucleic acid in solution as revealed by circular dichroism. Biopolymers. 1973;12(1):89–110. doi: 10.1002/bip.1973.360120109. [DOI] [PubMed] [Google Scholar]
- Krauch C. H., Krämer D. M., Wacker A. Zum Wirkungsmechanismus photodynamischer Furocumarine Photoreaktion von Psoralen-(4-14C) mit DNS, RNS, Homopolynucleotiden und Nucleosiden. Photochem Photobiol. 1967 May;6(5):341–354. doi: 10.1111/j.1751-1097.1967.tb08882.x. [DOI] [PubMed] [Google Scholar]
- Krämer D. M., Pathak M. A. Photoaddition of psoralen and of 4,5',8-trimethylpsoralen to DNA. Photochem Photobiol. 1970 Oct;12(4):333–337. doi: 10.1111/j.1751-1097.1970.tb06064.x. [DOI] [PubMed] [Google Scholar]
- MATHEWS M. M. Comparative study of lethal photosensitization of Sarcina lutea by 8-methoxypsoralen and by toluidine blue. J Bacteriol. 1963 Feb;85:322–328. doi: 10.1128/jb.85.2.322-328.1963. [DOI] [PMC free article] [PubMed] [Google Scholar]
- MUSAJO L., RODIGHIERO G., COLOMBO G., TORLONE V., DALLACQUA F. PHOTOSENSITIZING FUROCOUMARINS: INTERACTION WITH DNA AND PHOTO-INACTIVATION OF DNA CONTAINING VIRUSES. Experientia. 1965 Jan 15;21:22–24. doi: 10.1007/BF02136362. [DOI] [PubMed] [Google Scholar]
- Mantulin W. W., Song P. S. Excited states of skin-sensitizing coumarins and psoralens. Spectroscopic studies. J Am Chem Soc. 1973 Aug 8;95(16):5122–5129. doi: 10.1021/ja00797a004. [DOI] [PubMed] [Google Scholar]
- Marciani S., Terbojevic M., Dall'Acqua F. Light scattering and flow dichroism studies on DNA after the photoreaction with psoralen. Z Naturforsch B. 1972 Feb;27(2):196–200. doi: 10.1515/znb-1972-0216. [DOI] [PubMed] [Google Scholar]
- Marciani S., Terbojevich M., Dall'Acqua F., Rodighiero G. Bifunctional photobinding of psoralen to single stranded nucleic acids. Z Naturforsch C. 1973 Jul-Aug;28(7):370–375. doi: 10.1515/znc-1973-7-802. [DOI] [PubMed] [Google Scholar]
- Moore T. A., Mantulin W. W., Song P. S. Excited states and reactivity of carcinogenic benzpyrene; a comparison with skin-sensitizing coumarins. Photochem Photobiol. 1973 Sep;18(3):185–194. doi: 10.1111/j.1751-1097.1973.tb06410.x. [DOI] [PubMed] [Google Scholar]
- Musajo L., Rodighiero G. Mode of photosensitizing action of furocoumarins. Photophysiology. 1972;(7):115–147. [PubMed] [Google Scholar]
- Musajo L., Rodighiero G. Studies on the photo-C4-cyclo-addition reactions between skin-photosensitizing furocoumarins and nucleic acids. Photochem Photobiol. 1970 Jan;11(1):27–35. doi: 10.1111/j.1751-1097.1970.tb05714.x. [DOI] [PubMed] [Google Scholar]
- Musajo L., Visentini P., Bacchinetti F., Razzi M. A. Photoinactivation of Ehrlich ascites tumor cells in vitro obtained with skin-photosensitizing furocoumarins. Experientia. 1967 May 15;23(5):335–336. doi: 10.1007/BF02144498. [DOI] [PubMed] [Google Scholar]
- Parrish J. A., Fitzpatrick T. B., Tanenbaum L., Pathak M. A. Photochemotherapy of psoriasis with oral methoxsalen and longwave ultraviolet light. N Engl J Med. 1974 Dec 5;291(23):1207–1211. doi: 10.1056/NEJM197412052912301. [DOI] [PubMed] [Google Scholar]
- Pathak M. A., Krämer D. M. Photosensitization of skin in vivo by furocoumarins (psoralens). Biochim Biophys Acta. 1969 Nov 19;195(1):197–206. doi: 10.1016/0005-2787(69)90616-9. [DOI] [PubMed] [Google Scholar]
- Pathak M. A., Worden L. R., Kaufman K. D. Effect of structural alterations on the photosensitizing potency of furocoumarins (psoralens) and related compounds. J Invest Dermatol. 1967 Feb;48(2):103–118. doi: 10.1038/jid.1967.17. [DOI] [PubMed] [Google Scholar]
- Pilet J., Brahms J. Dependence of B-A conformational change in DNA on base composition. Nat New Biol. 1972 Mar 29;236(65):99–100. doi: 10.1038/newbio236099a0. [DOI] [PubMed] [Google Scholar]
- Rodighiero G., Chandra P., Wacker A. Structural specificity for the photoinactivation of nucleic acids by furocoumarins. FEBS Lett. 1970 Sep 18;10(1):29–32. doi: 10.1016/0014-5793(70)80408-2. [DOI] [PubMed] [Google Scholar]
- Rodighiero G., Musajo L., Dall'Acqua F., Marciani S., Caporale G., Ciavatta L. Mechanism of skin photosensitization by forucoumarins. Photoreactivity of various furocouma- rins with native DNA and with ribosomal RNA. Biochim Biophys Acta. 1970 Sep 17;217(1):40–49. [PubMed] [Google Scholar]
- Schoentjes M., Fredericq E. Proflavine binding to yeast rRNA and ribosomes as related to structure. Biopolymers. 1972 Feb;11(2):361–374. doi: 10.1002/bip.1972.360110205. [DOI] [PubMed] [Google Scholar]
- Song P. S., Gordon W. H., 3rd A spectroscopic study of the excited states of coumarin. J Phys Chem. 1970 Nov 26;74(24):4234–4240. doi: 10.1021/j100718a010. [DOI] [PubMed] [Google Scholar]
- Song P. S., Harter M. L., Moore T. A., Herndon W. C. Luminescence spectra and photocycloaddition of the excited coumarins to DNA bases. Photochem Photobiol. 1971 Oct;14(4):521–530. doi: 10.1111/j.1751-1097.1971.tb06191.x. [DOI] [PubMed] [Google Scholar]
- Zimmer C., Luck G. Conformation and reactivity of DNA. VI. Circular dichroism studies of salt-induced conformational changes of DNAs of different base composition. Biochim Biophys Acta. 1974 Aug 15;361(1):11–32. [PubMed] [Google Scholar]
