Abstract
Recent data on the synthesis of photoactivatable derivatives of nucleic acids and proteins on the basis of aryl(trifluoromethyl)diazirines—analogs of nucleosides, nucleotides, oligonucleotides, as well as amino acids and peptides—are reviewed. The synthesis of bi- and polyfunctional photoactivatable reagents, including those containing a cleavable function, designed for postsynthetic modification of biopolymers is described. Data are given on the use of the photoactivatable derivatives for studying nucleic acid–protein interactions by the method of photoaffinity labeling. Special consideration is paid to the results obtained by the authors" team in cooperation with other researchers as well as graduate students of the Chemistry of Natural Products Chair, Chemical Faculty, Moscow State University and destined to solve various scientific tasks in the domain of nucleic acid–protein recognition with the use of photoaffinity crosslinking.
Similar content being viewed by others
REFERENCES
Singh, A., Thornton, E.R., and Westheimer, F.H., J. Biol. Chem., 1962, vol. 237, pp. 3006–3008.
Bayley, H., Photogenerated Reagents in Biochemistry and Molecular Biology, Work, T. and Burdon, R., Eds., Amsterdam: Elsevier, 1983, vol. 12, p. 187.
Brunner, J., Annu. Rev. Biochem., 1993, vol. 62, pp. 483–514.
Kotzyba-Hilbert, F., Kapfer, I., and Goedner, M., Angew. Chem., Int. Ed., 1995, vol. 34, pp. 1296–1312.
Sheflyan, G.Ya., Kubareva, E.A., and Gromova, E.S., Usp. Khim., 1996, vol. 65, no. 8, pp. 765–780.
Knorre, D.G. and Godovikova, T.S., FEBS Lett., 1998, vol. 433, pp. 9–14.
Fleming, S.A., Tetrahedron, 1995, vol. 51, pp. 12479–12520.
Meisenheimer, K.M. and Koch, T.H., Crit. Rev. Biochem. Mol. Biol., 1997, vol. 32, pp. 101–140.
Dobrikov, M.I., Zarytova, V.F., Komarova, N.I., Levina, A.S., Lokhov, S.A., Prikhod'ko, T.A., Shishkin, G.V., Tabatadze, D.R., and Zaalishvili, M.M., Bioorg. Khim., 1992, vol. 18, pp. 540–549.
Dobrikov, M.I., Dudko, R.Yu., Levina, A.S., Khalimskaya, L.M., and Shishkin, G.V., Bioorg. Khim., 1996, vol. 22, pp. 200–207.
Kanevskii, I.E. and Kuznetsova, S.A., Usp. Khim., 1998, vol. 67, pp. 688–704.
Kolpashchikov, D.M., Zakharenko, A.L., Dezhurov, S.V., Rechkunova, N.I., Khodyreva, S.N., Degtyarev, S.Kh., Litvak, V.V., and Lavrik, O.I., Bioorg. Khim., 1999, vol. 25, pp. 129–136.
Favre, A., Bioorganic Photochemistry, Morrison, H., Ed., New York: John Wiley & Sons, 1990, pp. 379–425.
Smith, R.A.G. and Knowles, J.R., J. Am. Chem. Soc., 1973, vol. 95, pp. 5072–5073.
Bayley, H. and Knowles, J.R., Biochemistry, 1978, vol. 17, pp. 2414–2423.
Brunner, J., Senn, H., and Richards, F.M., J. Biol. Chem., 1980, vol. 255, pp. 3313–3318.
Brunner, J. and Semenza, G., Biochemistry, 1981, vol. 20, pp. 7174–7182.
Nassal, M., Liebigs Ann. Chem., 1983, pp. 1510–1523.
Dolder, M., Michei, H., and Sigrist, H., J. Protein Chem., 1990, vol. 9, pp. 407–415.
Bayley, H. and Staros, J.V., Azides and Nitrenes, Scriven, E., Ed., New York: Academic, 1984, pp. 433–490.
Topin, A.N., Synthesis of Photoactivatable Compounds on the Basis of Aryl(trifluoromethyl)diazirine for the Application in Biological System Studies), Cand. Sci. (Chem.) Dissertation, Moscow: Moscow State Univ., 1996.
Brunner, J. and Richards, F., J. Biol. Chem., 1980, vol. 225, pp. 3319–3329.
Nakayama, H. and Khorana, G., J. Org. Chem., 1990, vol. 55, pp. 4953–4956.
Baldwin, J., Jesudason, C., Moloney, M., Morgan, D., and Pratt, A., Tetrahedron, 1991, vol. 47, pp. 5603–5614.
Barton, D., Jaszberenyi, J., Theodorakis, E., and Reibenspies, J., J. Am. Chem. Soc., 1993, vol. 115, pp. 8050–8059.
Delfino, J., Schreiber, S., and Richards, F., J. Am. Chem. Soc., 1993, vol. 115, pp. 3458–3474.
Rimoldi, J., Kingston, D., Chaudhary, A., Samaranayake, G., Grover, S., and Hamel, E., J. Nat. Prod., 1993, vol. 56, pp. 1313–1330.
Ruhmann, A. and Wentrup, C., Tetrahedron, 1994, vol. 50, pp. 3785–3796.
Hatanaka, Y., Hashimoto, M., Kurihara, H., Nakayama, H., and Kanaoka, Y., J. Org. Chem., 1994, vol. 59, pp. 383–387.
Findlay, J., Fishwick, C., Kersey, I., and Ward, P., Synthesis, 1995, pp. 553–556.
Heck, R.F., J. Am. Chem. Soc., 1968, vol. 90, pp. 5518–5525.
Bigge, C.F. and Mertes, M.P., J. Org. Chem., 1981, vol. 46, pp. 1994–1997.
Chang, G. and Mertes, H., J. Org. Chem., 1987, vol. 52, pp. 3625–3631.
Nasonov, A.F. and Korshunova, G.A., Usp. Khim., 1999, vol. 68, pp. 532–554.
Yamaguchi, T. and Saneyoshi, M., Nucleosides Nucleotides, 1996, vol. 15, pp. 607–618.
Yamaguchi, T. and Saneyoshi, M., Nucleic Acids Res., 1996, vol. 24, pp. 3364–3369.
Yamaguchi, T., Suyama, K., Narita, K., Kohgo, S., Tomikawa, A., and Saneyoshi, M., Nucleic Acids Res., 1997, vol. 25, pp. 2352–2358.
Agapkin, D.V., Vestn. Mosk. Univ., Ser. 2: Khim., 1999, vol. 40, pp. 207–208.
Topin, A.N., Gritsenko, O.V., Brevnov, M.G., Gromova, E.S., and Korshunova, G.A., Nucleosides Nucleotides, 1998, vol. 17, pp. 1163–1175.
Bailly, V., Verly, V.G., O'Connor, T.R., and Laval, J., Biochem. J., 1989, vol. 262, pp. 581–589.
Donehower, L.A. and Varmus, H.E., Proc. Natl. Acad. Sci. USA, 1984, vol. 81, pp. 6461–6465.
Tate, J.J., Persinger, J., and Bartolomew, B., Nucleic Acids Res., 1998, vol. 26, pp. 1421–1426.
Korshunova, G.A., Topin, A.N., Sumbatyan, N.V., Koroleva, O.N., and Drutsa, V.L., XIII International Round Table Nucleosides, Nucleotides and Their Biological Applications, Montpellier, 1998, p. 173.
Korshunova, G.A., Topin, A.N., Sumbatyan, N.V., Koroleva, O.N., and Drutsa, V.L., Nucleosides Nucleotides, 1999, vol. 18, pp. 1097–1098.
Mtchedlidze, M.T., Sumbatyan, N.V., Topin, A.N., Volkov, E.M., and Korshunova, G.A., 7th Ibn Sina International Conference on Pure and Applied Heterocyclic Chemistry, Alexandria, 2000, p. 198.
Korshunova, G.A., Krynetski, E.Y., Mtchedlidze, M.T., Agapkin, D.V., Evans, W.E., and Krynetskaya, N.F., Nucleosides Nucleotides, 1999, vol. 18, pp. 1747–1748.
Krynetskii, E.Yu., Mol. Biol., 1996, vol. 30, pp. 69–80.
Kuznetsova, L.G., Volkov, E.M., Romanova, E.A., Tashlitskii, V.N., Oretskaya, T.S., Krynetskaya, N.F., and Shabarova, Z.A., Bioorg. Khim., 1993, vol. 19, pp. 455–466.
Kachalova, A.V. and Zubin, E.M., Dokl. Akad. Nauk, 1998, vol. 363, pp. 507–509.
Zubin, E.M., Antsypovich, S.I., Oretskaya, T.S., Romanova, E.A., Volkov, E.M., Tashlitsky, V.N., Dolinnaya, N.G., and Shabarova, Z.A., Nucleosides Nucleotides, 1998, vol. 17, pp. 425–440.
Metelev, V.G. and Oretskaya, T.S., Bioorg. Khim., 1999, vol. 25, pp. 474–478.
Hanna, M.M., Methods Enzymol., 1989, vol. 180, pp. 383–409.
Hori, N., Iwai, S., Inoue, H., and Ohtsuka, E., Biol. Chem., 1992, vol. 267, pp. 15591–15594.
Doring, T., Mitchell, P., Osswald, M., Bochkariov, D., and Brimacombe, R., EMBO J., 1994, vol. 13, pp. 2677–2685.
Bochkarev, D.E., Study on the Interaction of tRNA with Ribosome by Pulse Photoaffinity Crosslinking, Cand. Sci. (Chem.) Dissertation, Pushchino: Moscow State Univ., 1993.
Sergiev, P., Dokudovskaya, S., Romanova, E., Topin, A., Bogdanov, A., Brimakombe, R., and Dontsova, O., Nucleic Acids Res., 1998, vol. 26, pp. 2519–2525.
Sylvers, L.A. and Wower, J., Bioconj. Chem., 1993, vol. 4, pp. 411–418.
Braun, B.R., Bartholomew, B., Kassavetis, G.A., and Geiduschek, E.P., J. Mol. Biol., 1992, vol. 228, pp. 1063–1077.
Sergiev, P.V., Lavrik, I.N., Dokudovskaya, S.S., Dontsova, O.A., and Bogdanov, A.A., Biokhimiya, 1998, vol. 63, pp. 1129–1143.
Bhangu, R. and Wollenzien, P., Biochemistry, 1992, vol. 31, pp. 5937–5944.
Dontsova, O., Dokudovskaya, S., Kopylov, A., Bogdanov, A., Rinke-Appel, J., Junke, N., and Brimacombe, R., EMBO J., 1992, vol. 11, pp. 3105–3116.
Brimacombe, R., Mitchell, P., Osswald, M., and Bochkariov, D., FASEB J., 1993, vol. 7, pp. 161–167.
Chen, J.K., Frank, L.A., Hixson, S.S., and Zimmermann, R.A., Biochemistry, 1985, vol. 24, pp. 4777–4784.
Brimacombe, R., Biochimie, 1991, vol. 73, pp. 927–936.
Sergiev, P.V., Lavrik, I.N., Wlasoff, V.A., Dokudovskaya, S.S., Dontsova, O.A., Bogdanov, A.A., and Brimakombe, R., RNA, 1997, vol. 3, pp. 464–475.
Baranov, P.V., Kubarenko, A.V., Gurvich, O.L., Shamolina, T.A., and Brimacombe, R., Nucleic Acids Res., 1999, vol. 27, pp. 184–185.
Nassal, M., J. Am. Chem. Soc., 1984, vol. 106, pp. 7540–7545.
Shih, L. and Bayley, H., Anal. Biochem., 1985, vol. 144, pp. 132–141.
Baldini, G., Martoglio, B., Schachenmann, A., Zugliani, C., and Brunner, J., Biochemistry, 1988, vol. 27, pp. 7951–7959.
Baldwin, J.E., Pratt, A.J., and Moloney, M.G., Tetrahedron, 1987, vol. 43, pp. 2565–2575.
Falchetto, R., Vorherr, T., Brunner, J., and Carafoli, E., J. Biol. Chem., 1991, vol. 266, pp. 2930–2936.
Beck-Sickiger, A.G., Wieland, H.A., and Brunner, J., Recept. Res., 1995, vol. 15, pp. 473–485.
Ploug, M., Ostergaard, S., Hansen, L. B., Holm, A., and Dano, K., Biochemistry, 1998, vol. 37, pp. 3612–3622.
Topin, A.N. and Korshunova, G.A., Vestn. Mosk. Univ., Ser. 2: Khim., 1995, vol. 36, pp. 583–587.
Topin, A.N. and Korshunova, G.A., Programme and Abstracts, 23rd European Peptide Symposium, Braga (Portugal), 1994, no. 3–87, p. 121.
Bondar', D.A., Synthesis and Properties of New Photoactivatable Multifunctional Reagents Containing Aryl(trifluoromethyl)diazirine Group, Graduate Research Work, Moscow: Chemistry Dept., Moscow State Univ., 1999.
Kubarenko, A.V., Study of the Functional Topography of Elongation Factor G on E. coli Ribosome with the Use of Chemical Photoaffinity Modification, Graduate Research Work, Moscow: Chemistry Dept., Moscow State Univ., 2000.
Anthony-Cahill, S., Griffith, M., Noren, C., Suich, D., and Schultz, P., TIBS, 1989, vol. 14, pp. 400–403.
Kurzchalia, T.V., Wiedmann, M., Girshovich, A.S., Bochkareva, E.S., Bielka, H., and Rapoport, T.A., Nature, 1986, vol. 320, pp. 634–636.
Krieg, U.C., Walter, P., and Johnson, A.E., Proc. Natl. Acad. Sci. USA, 1986, vol. 83, pp. 8604–8608.
Kemp, D.S. and Galakatos, N.G., J. Org. Chem., 1986, vol. 51, pp. 1821–1829.
Kogon, A.A., Novel Photoactivatable Reagents for Studying Biological Macromolecules by Fast Photoaffinity Crosslinking, Cand. Sci. (Chem.) Dissertation, Moscow: Moscow State Univ., 1992.
Savage, M.D., Mattson, G., Desai, S., Nielander, G.W., Morgensen, S., and Conklin, E.J., Avidin-Biotin Chemistry: A Handbook, Illinois: Pierce Chemical Co., 1992.
Kogon, A., Peletskaya, E., Quinn, T., and Folk, W., Book of Abstracts, 37th Annual West Central States Biochemistry and Molecular Biology Conference, Research and Education, University of Missouri-Columbia, 1994, p. 60.
Brunner, J., Trends in Cell Biol., 1996, vol. 6, pp. 154–157.
Blanton, M.P., McCardy, E.A., Huggins, A., and Parikh, D., Biochemistry, 1998, vol. 37, pp. 14545–14555.
Bochkarev, D. and Kogon, A., Anal. Biochem., 1992, vol. 204, pp. 90–95.
Kogon, A., Bochkarev, D., Baskunov, B., and Cherpakov, A., Liebigs Ann. Chem., 1992, pp. 879–881.
Kempin, U., Kanoaka, Y., and Hatanaka, Y., Heterocycles, 1998, vol. 49, pp. 465–468.
Rimoldi, J.M., Kingston, D.G.I., Chaudhary, A.G., Samaranayake, G., Grover, S., and Hamel, E., J. Nat. Prod., 1993, vol. 56, pp. 1313–1330.
Hatanaka, Y., Yoshiba, E., Hakayama, H., and Kanaoka, Y., Bioorg. Chem., 1989, vol. 17, pp. 482–485.
Pillai, K., Synthesis, 1980, pp. 1–26.
Lloyd-Williamsetal, F., Tetrahedron, 1993, vol. 49, pp. 11065–11133.
Olejnik, J., Krzymanska-Olejnik, E., and Rothschild, K.J., Nucleic Acids Res., 1998, vol. 26, pp. 3572–3576.
Wei, Y., Yan, Y., Pei, D., and Gong, B., Bioorg. Med. Chem. Letters, 1998, vol. 8, pp. 2419–2422.
Olejnik, J., Ludemann, H.-C., Krzymanska-Olejnik, E., Berkenkamp, S., Hillenkamp, F., and Rothschild, K.J., Nucleic Acids Res., 1999, vol. 27, pp. 4626–4631.
Patchornik, A., Amit, S., and Woodward, R.B., J. Am. Chem. Soc., 1970, vol. 92, pp. 6333–6335.
Fang, K., Hashimoto, M., Jockusch, S., Turro, N.J., and Nakanishi, K., J. Am. Chem. Soc., 1998, vol. 120, pp. 8543–8544.
Hatanaka, Y., Hashimoto, M., Kurihara, H., Nakayama, H., and Kanaoka, Y., J. Org. Chem., 1994, vol. 59, pp. 383–387.
Utkin, Y.N., Hatanaka, Y., Franke, P., Machold, J., Hucho, F., and Tsetlin, V.I., J. Protein Chem., 1995, vol. 14, pp. 197–203.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Korshunova, G.A., Sumbatyan, N.V., Topin, A.N. et al. Photoactivatable Reagents Based on Aryl(trifluoromethyl)diazirines: Synthesis and Application for Studying Nucleic Acid–Protein Interactions. Molecular Biology 34, 823–839 (2000). https://doi.org/10.1023/A:1026671624793
Issue Date:
DOI: https://doi.org/10.1023/A:1026671624793