Skip to main content
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1988 Aug 11;16(15):7221–7231. doi: 10.1093/nar/16.15.7221

Preparation and characterization of biotinylated psoralen.

W A Saffran 1, J T Welsh 1, R M Knobler 1, F P Gasparro 1, C R Cantor 1, R L Edelson 1
PMCID: PMC338404  PMID: 3412885

Abstract

Biotinylated psoralen (BPsor), a psoralen derivative containing a biotin moiety attached via a long-chain, positively charged linker, has been synthesized and its interactions with DNA and avidin have been studied. As do other psoralen derivatives, BPsor photoreacts with DNA to form interstrand crosslinks. The biotin binds to streptavidin after the reaction of BPsor with DNA, and this property has been used to measure low levels of BPsor modified DNA by ELISA with streptavidin and biotinylated alkaline phosphatase. In addition, BPsor retains the biological activity of psoralen, as shown by its ability to inhibit lymphocyte proliferation at a level of 10 ng/ml.

Full text

PDF
7222

Images in this article

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Bayer E. A., Wilchek M. The use of the avidin-biotin complex as a tool in molecular biology. Methods Biochem Anal. 1980;26:1–45. doi: 10.1002/9780470110461.ch1. [DOI] [PubMed] [Google Scholar]
  2. Berger C. L., Cantor C., Welsh J., Dervan P., Begley T., Grant S., Gasparro F. P., Edelson R. L. Comparison of synthetic psoralen derivatives and 8-MOP in the inhibition of lymphocyte proliferation. Ann N Y Acad Sci. 1985;453:80–90. doi: 10.1111/j.1749-6632.1985.tb11800.x. [DOI] [PubMed] [Google Scholar]
  3. Chollet A., Kawashima E. H. Biotin-labeled synthetic oligodeoxyribonucleotides: chemical synthesis and uses as hybridization probes. Nucleic Acids Res. 1985 Mar 11;13(5):1529–1541. doi: 10.1093/nar/13.5.1529. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Cimino G. D., Gamper H. B., Isaacs S. T., Hearst J. E. Psoralens as photoactive probes of nucleic acid structure and function: organic chemistry, photochemistry, and biochemistry. Annu Rev Biochem. 1985;54:1151–1193. doi: 10.1146/annurev.bi.54.070185.005443. [DOI] [PubMed] [Google Scholar]
  5. Edelson R., Berger C., Gasparro F., Jegasothy B., Heald P., Wintroub B., Vonderheid E., Knobler R., Wolff K., Plewig G. Treatment of cutaneous T-cell lymphoma by extracorporeal photochemotherapy. Preliminary results. N Engl J Med. 1987 Feb 5;316(6):297–303. doi: 10.1056/NEJM198702053160603. [DOI] [PubMed] [Google Scholar]
  6. Forster A. C., McInnes J. L., Skingle D. C., Symons R. H. Non-radioactive hybridization probes prepared by the chemical labelling of DNA and RNA with a novel reagent, photobiotin. Nucleic Acids Res. 1985 Feb 11;13(3):745–761. doi: 10.1093/nar/13.3.745. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Gasparro F. P., Chan G., Edelson R. L. Phototherapy and photopharmacology. Yale J Biol Med. 1985 Nov-Dec;58(6):519–534. [PMC free article] [PubMed] [Google Scholar]
  8. Green N. M. Avidin. Adv Protein Chem. 1975;29:85–133. doi: 10.1016/s0065-3233(08)60411-8. [DOI] [PubMed] [Google Scholar]
  9. Guesdon J. L., Ternynck T., Avrameas S. The use of avidin-biotin interaction in immunoenzymatic techniques. J Histochem Cytochem. 1979 Aug;27(8):1131–1139. doi: 10.1177/27.8.90074. [DOI] [PubMed] [Google Scholar]
  10. Hearst J. E., Isaacs S. T., Kanne D., Rapoport H., Straub K. The reaction of the psoralens with deoxyribonucleic acid. Q Rev Biophys. 1984 Feb;17(1):1–44. doi: 10.1017/s0033583500005242. [DOI] [PubMed] [Google Scholar]
  11. Isaacs S. T., Shen C. K., Hearst J. E., Rapoport H. Synthesis and characterization of new psoralen derivatives with superior photoreactivity with DNA and RNA. Biochemistry. 1977 Mar 22;16(6):1058–1064. doi: 10.1021/bi00625a005. [DOI] [PubMed] [Google Scholar]
  12. Kempe T., Sundquist W. I., Chow F., Hu S. L. Chemical and enzymatic biotin-labeling of oligodeoxyribonucleotides. Nucleic Acids Res. 1985 Jan 11;13(1):45–57. doi: 10.1093/nar/13.1.45. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Langer P. R., Waldrop A. A., Ward D. C. Enzymatic synthesis of biotin-labeled polynucleotides: novel nucleic acid affinity probes. Proc Natl Acad Sci U S A. 1981 Nov;78(11):6633–6637. doi: 10.1073/pnas.78.11.6633. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. 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]
  15. Parsons B. J. Psoralen photochemistry. Photochem Photobiol. 1980 Dec;32(6):813–821. doi: 10.1111/j.1751-1097.1980.tb04061.x. [DOI] [PubMed] [Google Scholar]
  16. Richardson R. W., Gumport R. I. Biotin and fluorescent labeling of RNA using T4 RNA ligase. Nucleic Acids Res. 1983 Sep 24;11(18):6167–6184. doi: 10.1093/nar/11.18.6167. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Saffran W. A., Goldenberg M., Cantor C. R. Site-directed psoralen crosslinking of DNA. Proc Natl Acad Sci U S A. 1982 Aug;79(15):4594–4598. doi: 10.1073/pnas.79.15.4594. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Scherer R., Kern B., Braun-Falco O. UVA-induced inhibition of proliferation of PHA-stimulated lymphocytes from humans treated with 8-methoxypsoralen. Br J Dermatol. 1977 Nov;97(5):519–528. doi: 10.1111/j.1365-2133.1977.tb14129.x. [DOI] [PubMed] [Google Scholar]
  19. Sheldon E. L., Kellogg D. E., Watson R., Levenson C. H., Erlich H. A. Use of nonisotopic M13 probes for genetic analysis: application to HLA class II loci. Proc Natl Acad Sci U S A. 1986 Dec;83(23):9085–9089. doi: 10.1073/pnas.83.23.9085. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. Song P. S., Tapley K. J., Jr Photochemistry and photobiology of psoralens. Photochem Photobiol. 1979 Jun;29(6):1177–1197. doi: 10.1111/j.1751-1097.1979.tb07838.x. [DOI] [PubMed] [Google Scholar]
  21. Urdal D. L., Hakomori S. Tumor-associated ganglio-N-triosylceramide. Target for antibody-dependent, avidin-mediated drug killing of tumor cells. J Biol Chem. 1980 Nov 10;255(21):10509–10516. [PubMed] [Google Scholar]

Articles from Nucleic Acids Research are provided here courtesy of Oxford University Press

RESOURCES