Конструирование и синтез низкомолекулярных искусственных рибонуклеаз, объединяющих в своей структуре гидрофобные и поликатионные фрагменты

Список литературы

1. Kolchanov, N.A., Titov, I.I., Vlassova, I.E., Vlassov, V.V. Chemical and computer probing of RNA structure // Prog. Nucleic Acid Res. Mol. Biol. 1996. V. 53. P. 131−196.
2. DNA and RNA cleavers and chemotherapy of Cancer and viral diseases // NATO ASI Ser., Ser. C. 1996. V. 479. 379 p.
3. Zenkova, M.A. Artificial ribonucleases. In Nucleic Acids and Molecular Biology. Heidelberg Varlag. 2004. V. 13.
4. Сильников, B.H., Власов, B.B. Конструирование реагентов для направленного расщепления рибонуклеиновых кислот // Успехи химии. 2001. Т. 70. С. 562−580.
5. Ren, J., Chaires, J.B. Sequence and structural selectivity of nucleic acid binding ligands // Biochemistry. 1999. V. 38. P. 16 067−16 075.
6. Hermann, T. Strategies for the design of drugs targeting RNA and RNA-protein compexes // Angcw. Chem., Int. Ed. 2000. V. 39. P. 1890−1905.
7. Зенгер, В. Принципы структурной организации нуклеиновых кислот. Пер. с англ. Под ред. Б. К. Вайнштейна. М.: Мир, 1987. 584 с.
8. Muller, A., Talbot, F., Leutwyler, S. Hydrogen bond vibrations of 2-aminopyridine*2-pyridone, a Watson-Crick analogue of adenine*uracil // J. Am. Chem. Soc. 2002. V. 124. P. 14 486−14 494.
9. Chow, C., Bogdan, E.M. A structural basis for RNA-ligand interactions // Chem. Rev. 1997. V. 97. P. 1489−1513.
10. Hermann, Т., Westhof, E. RNA as a drug target: chemical, modeling, and evolutionary tools // Curr. Opinion Biotech. 1998. V. 97. P. 66−73.
11. Afshar, M., Prescott, C.D., Varant G. Structure-based and combinatorial search, for new RNA-binding drugs // Curr. Opin. Biotechnol. 1999. V. 10. P. 59−63. '- ¦
12. Wilson, W.D., Li, K. Targeting RNA with small molecules // Curr. Med. Chem. 2000. V. 7. P. 73−98.•j *
13. Charles, I., Xi, H., Arya, D.P. Sequence-specific targeting of RNA with an oligonucleotide-neomycin conjugate// Bioconjugate Chem. 2007. V. 18. P. 160−169.
14. Venkatesan, N., Kim, B.H. Peptide conjugates of oligonucleotides: synthesis andapplications // Chem. Rev. 2006. V. 106. P. 3712−3761. -i 1 3
15. Schmidtchen, F.P., Berger, M. Artificial organic host molecules for anions // Chem: Rev. 1997. V. 97. P. 16 099−16 460.
16. Шабарова, З.А., Богданов, А.А. Химия нуклеиновых кислот и их компонентов. М.: Химия, 1978. 582 с.
17. Carlson, С.В., Stephens, О.М., Beal, P.A. Recognition of double-stranded RNA by proteins and small molecules//Biopolymers. 2003. V. 70. P. 86−102.
18. Neidle, S., Nunn, C.M. Crystal structures of nucleic acids and their drug complexes // Natural Product Rep. 1998. V. 15. P. 1−15.
19. Piantanida, I., Tomisic, V., Zinic, M. 4,9-Diazapyrenium cations. Synthesis, physico-chemical properties and binding of nucleotides in water // J7 Chem. Soc. Perkin Trans. 2. 2000. P. 375−383.
20. Mertz, E., Mattei, S., Zimmerman, S.C. Synthetic receptors for CG base pairs // Org. Letters. i '2000. V. 2. P. 2931−2934.
21. Lecubin, F., Benhida, R., Fourrey, J.-L., Sun, J.-S. NMR recognition studies of CG base pairsi’by new easily accessible heterobicyclic systems // Tetrahedron Lett. 1999. V. 40. P. 8085−8088.
22. Vourloumis, D., Takahashi, M., Simonsen, K.B., Ayida, B.K., Barluenga, S., Winters, G.C., Hermann, T. Solid-phase synthesis of benzimidasole libraries biased for RNA targets // Tetrahedron Lett. 2003. V. 44. P. 2807−2811.
23. Amemiya, S., Buhlmann, P., Umezawa, Y. Fluoresccnce-mediated sensing of guanosine derivatives based on multitopic hydrogen bonding // Chem. Commun. 1997. P. 1027−1028.
24. Lin, K.-Y., Jones, R.J., Matteucci, M. Tricyclic 2'-deoxycytidine analogs: syntheses and incorporation into oligodeoxynucleotides which have enhanced binding to complementary RNA Hi. Am. Chem. Soc. 1995. V. 117. P. 3873−3874.
25. Flanagan, W.M., Wolf, J.J., Olson, P., Grant, D., Lin, K.-Y., Wagner R.W., Matteucci M.D. A cytosine analog that confers enhanced potency to antisense oligonucleotides // Proc. Natl. Acad. Sci. USA. 1999. V. 96. P. 3513−3518.
26. Lin, K.-Y., Matteucci, M.D. A cytosine analogue capable of clamp-like binding in helical nucleic acids//J. Am. Chem. Soc. 1998. V. 120. P. 8531−8532.
27. Frydman, L., Rosomando, P.C., Frydman, V., Fernandez, C.O., Frydman, В., Samejima, K. Interactions between natural polyamines and tRNA: an 15N NMR analysis // Proc. Natl. Acad. Sci. USA. 1992. V. 89. P. 9186−9190.
28. Frydman, B., Westler, W.M., Samejima, K. Spermine binds in solution to the TwC Loop of tRNAphe: evidence from a 750 MHz 'H-NMR analysis // J. Org. Chem. 1996. V. 61. P. 25 882 589. t i
29. Amarantos, I., Kalpaxis, D.L. Photoaffinity polyamines: interactions with AcPhe-tRNA free in solution or bound at the P-site of escherichia coli ribosomes // Nucleic Acids Res. 2000. V. 28. P. 3733−3742.
30. Heerschap, A., Walters, J.A., Hilbers, C.W. Influence of the polyamines spermine and spermidine on yeast tRNAPhe as revealed from its imino proton NMR spectrum // Nucleic Acids Res. 1986. V. 14. P. 983−998.
31. Bibillo, A., Figlerowicz, M., Kierzek R. The non-enzymatic hydrolysis of oligoribonucleotides VI. The role of biogenic polyamines // Nucleic Acids Res. 1999., V. 27. P. 3931−3937.
32. Komiyama, M., Yoshinari, K. Kinetic analysis of diamine-catalyzed RNA hydrolysis // J. Org. Chem. 1997. V. 62. P. 2155−2160.
33. Hammann, C., Hormes, R., Sczakiel, G., Tabler, M. A spermidine-induced conformational change of long-armed hammerhead ribozymes: ionic requirements for fast cleavage kinetics // Nucleic Acids Res. 1997. V. 25. P. 4715−4722.
34. Aguilar, J., Di’az, P., Escarti, F., Garcia-Espana, E., Gil, L., Soriano, C., Verdejo, B. Cation and anion recognition characteristics of open-chain polyamines containing ethyleriic and propylenic chains // Inorg. Chim. Acta. 2002. V. 339. P. 307- 316.
35. Chand, D.K., Schneider, H.-J., Aguilar, J.A., Escarti, F., Garcia-Espana, E., Luis, S.V. Copper complexes of polyazan. cyclophanes and their interaction with DNA and RNA // Inorg. Chim. Acta. 2000. P. 71−78.
36. McConnaughie, A.W., Spychala, J., Zhao, M., Boykin, D., Wilson, W.D. Design and synthesis of RNA-specific groove-binding cations: implications for antiviral drug design // J. Med. Chem. 1994. V. 37. P. 1063−1069. «
37. Lomadze, N., Schneider, H.-J. Reversal of polyamine selectivity for DNA and RNA by steric hindrance // Tetrahedron Lett. 2002. V. 43. P. 4403−4405. «i' i
38. An, H., Haly, B.D., Cook, P.D. New piperazinyl polyazacyclophane scaffolds. Libraries and biological activities // Bioorg. Med. Chem. Lett. 1998. V. 8. P. 2345−2350.
39. Hwang, S., Tamilarasu, N., Ryan, K., Huq, I., Richter, S., Still, W.C., Rana, T.M. Inhibition of gene expression in human cells through small molecule-RNA interactions // Proc. Natl. Acad. Sci. USA. 1999. V. 96. P. 12 997−13 002.
40. Tamilarasu, N., Huq, I., Rana, T.M. Design, synthesis, and biological activity of a cyclic peptide: an inhibitor of HIV-1 Tat-TAR interactions in human cells // Bioorg. Med. Chem. Lett. 2000. V. 10. P. 971−974.
41. Hamy, F., Felder, E.R., Heizmann, G., Lazdins, J., Aboul-ela, F., Varani, G., Karn, J., Klimkait, T. An inhibitor of the Tat/TAR RNA interaction that effectively suppresses HIV-1 replication // Proc. Natl. Acad. Sci. USA. 1997. V. 94. P. 3548−3553. *
42. Wang, X., Huq, I., Rana, T.M. HIV-1 TAR RNA by an unnatural biopolymer // J. Am. Chem. Soc. 1997. V. 119. P. 6444−6445.
43. Tamilarasu, N., Huq, I., Rana, T.M. High affinity and specific binding of HIV-1 TAR RNA by a tat-derived oligourca // J. Am. Chem. Soc. 1999. V. 121. P. 1597−1598.
44. Kesavan, V., Tamilarasu, N., Cao, H., Rana, T.M. A new class of RNA-binding oligomers:'peptoid amide and ester analogues // Bioconjugate Chem. 2002. V. 13. P. 1171−1175.
45. Tamilarasu, N., Huq, I., Rana, T.M. Targeting RNA with peptidomimetic oligomers in human cells // Bioorg. Med. Chem. Lett. 2001. V. 11. P. 505−507.
46. Lawton, G.R., Appella, D.H. Nonionic side chains modulate the affinity and specificity of binding between functionalized polyamines and structured RNA // J. Am. Chem. Soc. 2004. V. 126. P. 12 762−12 763.
47. Dietrich, B., Fyles, T.M., Lehn, J.M., Pease, L.G., Fyles, D.L. Anion receptor molecules. i
48. Synthesis and some anion binding properties of macrocyclic guanidinium salts // J. Chem. Soc. Chem. Commun. 1978. V. 21. P. 934−936.
49. Galan, A., Pueyo, E., Salmeron, A., De Mendoza, J. Selective complexation of adenosine monophosphate nucleotides by rigid bicyclic guanidinium abiotic receptors // Tetrahedron Lett. 1991. V. 32. P. 1827−1830.
50. Jubian, V., Dixon, R.P., Hamilton, A.D. Molecular recognition and catalysis. Acceleration of phosphodiester cleavage by a simple hydrogen-bonding receptor // J. Am. Chem. Soc. 1992. V. 114. P. 1120−1121.
51. He, G.-X., Browne, K.A., Groppe, J.C., Blasko, A., Mei, H.-Y., Bruice, T.C.i .i
52. Microgontropens and their interactions with DNA. 1. Synthesis of the tripyrrole peptides Dien-Microgontropen-a,-b,-c and characterization of their interactions with dsDNA // J. Am.
53. Bando, T., Narita, A., Sugiyama, H. Highly efficient sequence-specific DNA interstrand cross-linking by pyrrole/imidazole CPI conjugates // J. Am. Chem. Soc. 2003. V. 125. P. 34 713 485.
54. Wang, L., Bailly, C., Kumar, A., Ding, D., Bajic, M., Boykin, D.W., Wilson, W.D. Specificj i imolecular recognition of mixed nucleic acid sequences: an aromatic dication that binds in thev '
55. DNA minor groove as a dimmer // Proc. Natl. Acad. Sci. USA. 2000. V. 97. P. 12−16.r
56. Dervan, P.B. Molecular recognition of DNA by small molecules // Bioorg. Med. Chem. 2001. V. 9. P. 2215−2235.
57. Wilson, W.D., Ratmeyer, L., Zhao, M., Strekowski, L., Boykin, D. The search for structure-specific nucleic acid-interactive drugs: effects of compound structure on RNA versus DNA interaction strength // Biochemistry. 1993. V. 32. P. 4098−4104.
58. Tanious, F.A., Veal, J.M., Buczak, H., Ratmeyer, L.S., Wilson, W.D. DAPI (4', 6-diamidino-2-phenylindole) binds differently to DNA and RNA: minor-groove binding at AT sites and intercalation at AU sites // Biochemistry. 1992. V. 31. P. 3103−3112.
59. Rubin, J., Sundaralingam, M. An unexpected major groove binding of netropsin and distamycin A to tRNA (phe) // J. Biomol. Struct. Dyn. 1984. V. 2. P. 165−174.L
60. Zakrzrewska, K., Pullman, B. Theoretical exploration of netropsin binding to tRNA (Phe).// J. Biomol. Struct. Dyn. 1985. V. 2. P. 737−743.
61. Bailly, C., Colson, P., Houssier, C., Hamy, F. The binding mode of drugs to the TAR RNA of HIV-1 studied by electric linear dichroism // Nucleic Acids Res. 1996. V. 24. P. 1460−1464.
62. Sadat-Ebrahimi, S. E., Wilton, A. N., Douglas, K. T. Unique binding site for bis-benzimidazoles on transfer RNA // J. Chem. Soc. Chem. Commun. 1997. P. 385−386.
63. Dassonneville, L., Hamy, F., Colson, P., Houssier, C., Bailly, C. Binding of Hoechst 33 258 to the TAR RNA of HIV-1. Recognition of a pyrimidine bulge-dependent structure // Nucleic Acids Res. 1997. V. 25. P. 4487−4492.
64. Helm, M., Kopka, M.L., Sharma, S.K., Lown, J.W., Giege, R. Rnase activity of DNA minor groove binder with a minimalist catalytic motif from Rnase A // Biochem. Biophys. Res. Comm. 2001. V. 281. P. 1283−1290.
65. Botto, R.E., Coxon, B. Nitrogen-15 nuclear magnetic resonance spectroscopy of neomycin B and related aminoglycosides // J. Am. Chem. Soc. 1983. V. 105. P. 1021−1028.
66. Yoshizawa, S., Fourmy, D., Eason, R. G., Puglisi, D. Sequence-specific recognition of the major groove of RNA by deoxystreptamine // Biochemistry. 2002. V. 41. P. 6263−6270.
67. Recht, M. I., Fourmy, D., Blanchard, S. C., Dahlquist, K. D., Puglisi, J. D. RNA sequence determinants for aminoglycoside binding to an A-site rRNA model oligonucleotide // J. Mol. Biol. 1996. V. 262. P. 421−436.
68. Nature. 1991. V. 353. P. 368−370.
69. Hermann, T., Westhof, E. Aminoglycoside binding to the hammerhead ribozyme: a general model for the interaction of cationic antibiotics with RNA // J. Mol. Biol. 1998. V. 276. P. 903 912.
70. Stage, T.K., Hertel, K.J., Uhlenbeck, O.C. Inhibition of the hammerhead ribozyme by neomycin//RNA. 1995. V. 1. P. 95−101.
71. Clouet-d'Orval, B., Stage, T.K., Uhlenbeck, O.C. Neomycin inhibition of the hammerheadinribozyme involves ionic interactions // Biochemistry. 1995. V. 34. P. 11 186−11 190.
72. Hermann, T., Westhof, E. Saccharide-RNA recognition // Biopolymers. 1998. V. 48. P. 155 166.
73. Zapp, M.L., Stern, S., Green, M.R. Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production // Cell. 1993 V. 74. P. 969−978.
74. Mei, H.-Y., Galan, A.A., Halim, N.S., Mack, D.P., Moreland, D.W., Sanders, K.B.,' fruong, H., Czarnik, A.W. Inhibition of an HIV-1 Tat-derived peptide RNA by aminoglycoside antibiotics // Bioorg. Med. Chem. Lett. 1995. V. 5. P. 2755−2760.
75. Wang, S., Huber, P. W., Cui, M., Czarnik, A. W., Mei, H.-Y. Binding of neomycin to the TAR element of HIV-1 RNA induces dissociation of Tat protein by an allosteric mechanism // Biochemistry. 1998. V. 37. P. 5549−5557.
76. Tassew, N., Thompson, M. Binding affinity and inhibitory potency of neomycin and streptomycin on the Tat peptide interaction with HIV-1 TAR RNA detected by on-line acoustic wave sensor// Org. Med. Biomol. Chem. 2003. V. 1. P. 3268−3270.
77. Faber, C., Sticht, H., Schweimer, K., Rosch, P. Structural rearrangements of HIV-1 Tat-responsive RNA upon binding of neomycin B // J. Biol. Chem. 2000. V. 275. P. 20 660−20 666.
78. Kirk, S.R., Tor, Y. Hydrolysis of an RNA dinucleiside monophosphate by neomicine B // Chem. Commun. 1998. V. l.P. 147−148.
79. Riguet, E., Tripathi, S., Chaubey, B., Desire, J., Pandey, V.N., Dccout, J.-L. A peptide nucleic acid neamine conjugate that targets and cleaves HIV-1 TAR RNA inhibits viral replication // J. Med. Chem. 2004. V. 47. P. 4806−4809.
80. Earnshaw, D.J., Gait, M.J. Hairpin ribozyme cleavage catalyzed by aminoglycosideantibiotics and the polyamine spermine ih the absence of metal ions // Nucleic Acids Res. V. 26.1. P. 5551−5561.
81. Griffey, R.H., Hofstadler, S.A., Sannes-Lowery, K.A., Ecker, D.J., Crooke, S.T. Determinants of aminoglycoside-binding specificity for rRNA by using mass spectrometry // Proc. Natl. Acad. Sei. USA. 1999. V. 96. P. 10 129−10 133.
82. Tor, Y., Hermann, T., Westhof, E. Deciphering RNA recognition: aminoglycoside binding to the hammerhead ribozyme // Chem. Biol. 1998. V. 5. P. R277-R283.>
83. Mikkelsen, N.E., Brannvall, M., Virtanen, A., Kirsebom, L.A. Inhibition of RNase P RNA cleavage by aminoglycosides // Proc. Natl. Acad. Sei. USA. 1999. V. 96. P. 6155−6160. •
84. Blount, K.F., Tor, Y. Using pyrene-labeled HIV-1 TAR to measure RNA-small molecule binding // Nucleic Acids Res. 2003. V. 31. P. 5490−5500.
85. Wang, H., Tor, Y. Electrostatic interactions in RNA aminoglycosides binding // J. Am. Chem. Soc. 1997. V. 119. P. 8734−8735.
86. Chen, Q., Shafer, R.H., Kuntz, I.D. Structure-based discovery of ligands targeted to the RNA double helix // Biochemistry. 1997. V. 36. P. 11 402−11 407.
87. Kuntz, I.D., Meng, E.C., Shoichet, B.K. Receptor-based molecular design // Acc. Chem. Res. 1994. V. 27. P. 117−123.
88. Wallis, M.G., von Ahsen, U., Schroeder, R., Famulok, M. A novel RNA motif for neomycin recognition // Chem. Biol. 1995. V. 2. P. 543−552.
89. Famulok, M., Huttenhofer, A. In vitro selection analysis of neomycin binding RNAs with a mutagenized pool of variants of the 16S rRNA decoding region // Biochemistry. 1996. V. 35. P. 4265−4270.
90. Wang, Y., Rando, R.R. Specific binding of aminoglycoside antibiotics to RNA // Chem. Biol. 1995. V. 2. P. 281−290.
91. Hermann, T. Rational ligand design for RNA: the role of static structure and conformational flexibility in target recognition // Biochimie. 2002. V. 84. P. 869−875.
92. Michael, K., Wang, H., Tor, Y. Enhanced RNA binding of dimerized aminoglycosides // Bioorgan. Med. Chem. 1999. V. 7. P. 1361−1371.i. .
93. Litovchick, A., Evdokimov, A.G., Lapidot, A. Aminoglycoside-arginine conjugates that bind TAR RNA: synthesis, characterization, and antiviral activity // Biochemistry. 2000. y. 39. P. 2838−2852.
94. Baker, T.J., Luedtke, N.W., Tor, Y., Goodman, M. Synthesis and anti-HIV activity of guanidinoglycosides // J. Org. Chem. 2000. V. 65. P. 9054−9058.
95. Luedtke, N.W., Baker, T.J., Goodman, M., Tor, Y. Guanidinoglycosides: a novel family of RNA ligands // J. Am. Chem. Soc. 2000. V. 122. P. 12 035−12 036.
96. Edwards, T.E., Sigurdsson, S.T. Electron paramagnetic resonance dynamics signatures of1. H «* ^
97. TAR RNA-small molecule complexes provide insight into RNA structure and recognition // Biochemistry. 2002. V. 41. P. 14 843−14 847.
98. Wong, C.-H., Hendrix, M., Manning, D.D., Rosenbohm, C., Greenberg, W.A. A- library approach to the discovery of small molecules that recognize RNA: use of a 1,3-hydroxyamine motif as core // J. Am Chem. Soc. 1998. V. 120. P. 8319−8327.
99. Hendrix, M., Priestley, E.S., Joyce, G.F., Wong, C.-H. Direct observation of aminoglycoside-RNA interactions by surface plasmon resonance // J Am. Chem. Soc. 1997. V. 119. P.3641−3648.
100. Wong, C.-H., Hendrix, M., Priestley, E S. Greenberg, W.A. Specificity of aminoglycosideantibiotics for the A-site of the decoding region of ribosomal RNA // Chem. Biol. 1998.V.5. P.1. V ' ¦ 397.406.'i
101. Hendrix, M., Alper, P.B., Priestley, E.S., Wong, C.-H. Hydroxyamines as a new motif for the molecular recognition of phosphodiesters: implications for aminoglycoside-RNA interactions //Angew. Chem., Int. Ed. Engl. 1997. V. 36. 95−98.
102. Wong, C.-H., Bryan, M.C., Nyffeler, P.T., Liu, H., Chapman, E. Synthesis of carbohydrate-based antibiotics // Pure Appl. Chem. 2003. V. 75. P. 179−186.
103. Ding, Y., Hofstadler, S.A., Swayze, E.E., Griffey, R.H. An efficient synthesis of mimetics of neamine for RNA recognition // Org. Lett. 2001. V. 3. P. 1621−1623.. '
104. Vourloumis, D., Winters, G.C., Simonsen, K.B., Takahashi, M., Ayida, B.K., Shandrick, S., Zhao, Q., Han, Q., Hermann, T. Aminoglycoside-hybrid ligands targeting the ribosomal decoding site // ChemBioChem. 2005. V. 6. P. 58−65.
105. Tok, J. B.-H., Rando, R.R. Simple aminols as aminoglycoside surrogates // J. Am. Chem. Soc. 1998. V. 120. P. 8279−8280.
106. Simonsen, K.B., Ayida, B.K., Vourloumis, D., Winters, G.C., Takahashi, M., Shandrick, S., Zhao, Q., Hermann, T. Piperidine glycosides targeting the ribosomal decoding' !site // ChemBioChem. 2003. V. 4. P. 886−890. '
107. Alper, P., Hendrix, M., Sears, P., Wong, C.H. Probing the specificity of aminoglycoside-ribosomal RNA interactions with designed synthetic analogs // J. Am. Chem. Soc. 1998. V. 120. P. 1965−1978.
108. Nunns, C.L., Spence, L.A., Slater, M.J., Berrisford, D.J. Synthesis of neamine libraries for RNA recognition using solution phase chemistry// Tetrahedron Lett. 1999. V. 40. P. 9341−9345.v
109. Hanessian, S., Tremblay, M., Kornienko, A., Moitessier, N. Design, modeling and synthesis of functionalized paromamine analogs // Tetrahedron. 2001. V. 57. P. 3255−3265.
110. Haddad, J., Kotra, L.P., Llano-Sotelo, B., Kim, C., Azucena, E.F., Liu, M., Vakulenko, S.B., Chow, C.S., Mobashery, S. Design of novel. antibiotics that bind to the ribosomal acyltransferase site // J. Am. Chem. Soc. 2002. V. 124. P. 3229−3237.
111. Zhao, M., Janda, L., Nguyen, J., Strekowski, L., Wilson, W.D. The interaction of substituted 2-phenylquinoline intercalators with poly (A)poly (U): classical and:-threading intercalation modes with RNA//Biopolymers. 1994. V. 34. P. 61−73.
112. Ratmeyer, L., Zapp, M.L., Green, M.R., Vinayak, R., Kumar, A., Boykin, D.W., Wilson, W.D. Inhibition of HIV-1 Rev-RRE interaction by diphenylfuran derivatives // Biochemistry. 1996. V. 35. P. 13 689−13 696.
113. Li, K., Davis, T.M., Kumar, A., Singh, R., Boykin, D.W., Wilson, W.D. Heterocyclic inhibitor of the Rev-RRE complex binds to RRE as a dimmer // Biochemistry. 2001. V. 40. P. 1150−1158. '
114. Xiao, G., Kumar, A., Li, K., Rigl, T., Bajic, M., Davis, T.M., Boykin, D.W., Wilsoh, W.D. Inhibition of the HIV-1 Rev-RRE complexformarion by unfused aromatic cations // Biorg. Med. Chem. 2001. V. 9. P. 1097−1113.
115. Gelus, N., Bailly, C., Hamy, F., Klimkait, T., Wilson, W. D., Boykin, D. W. Inhibition of!
116. HIV-1 Tat-TAR interaction by diphenylfuran derivatives: effects of the terminal basic side chains // Bioorg. Med. Chem. Lett. 1999. V. 7. P. 1089−1096. ' !
117. Palm, B.S., Piantanida, I., Zinic, M., Schneider, H.-J. The interaction of new 4,9-diazapyrenium compounds with double stranded nucleic acids // J. Chem. Soc. Perkin Trans. 2. 2000. P. 385−392.
118. Hamy, F., Brondani, V., Florscheimer, A., Stark, W., Blommers, J.J., Klimkait, T. A new class of HIV-1 Tat antogonist acting through Tat-TAR inhibition // Biochemistry. 1998. V. 37. P. 5086−5095., i
119. Gelus, N., Hamy, F., Bailly, C. Molecular basis of HIV-1 TAR RNA specific recognitionby an acridine Tat-antagonist // Bioorg. Med. Chem. Lett. 1999. V. 7. P. 1075−1079.. •i .
120. Kirk, S.R., Luedtke, N.W., Tor, Y. Neomycin-acridine conjugate: a potent inhibitor of Rev-RRE binding // J. Am. Chem. Soc. 2000. V. 122. P. 980−981.
121. Ratmeyer, L., Vinayak, R., Zon, G., Wilson, W.D. An ethidium analog that binds with high specificity to a base-bulged duplex from the TAR RNA region of the HIV-1 genome // J. Med. Chem. 1992. V. 35. P. 966−968. -
122. Gayle, A.Y., Baranger, A.M. Inhibition of the U1A-RNA complex by an aminaacridine derivative // Bioorg. Med. Chem. Lett. 2002. V. 12. P. 2839−2842., f
123. Luedtke, N.W., Liu, Q., Tor, Y. RNA-ligand interactions: affinity and specificity of aminoglycoside dimers and acridine conjugates to the HIV-1 Rev Response Element // Biochemistry. 2003. V. 42. P. 11 391−11 403.
124. Krishnamurthy, M., Gooch, B. D., Beal, P. A. Peptide quinoline conjugates: a new class of RNA-binding molecules // Org. Lett. 2004. V. 6. P. 63−66.
125. Carlson, C.B., Beal, P.A. Solid-phase synthesis of acridine-based threading intercalator peptides // Bioorg. Med. Chem. Lett. 2000. V. 10. P. 1979−1982.
126. Gooch, B.D., Beal, P.A. Recognition of duplex RNA by helix-threading peptides'.// J. Am. j i
127. Chem. Soc. 2004. V. 126. P. 10 603−10 610.
128. Piantanida, I., Palm, B.S., Cudic, P., Zinic, M., Schneider, H.-J. Phenanthridinium cyclobisintercalands. Fluorescence sensing of AMP and selective binding to single-stranded nucleic acids // Tetrahedron Lett. 2001. V. 42. P. 6779−6783.
129. Morin, G.T., Paugam, M.-F., Hughes, M.P., Smith, B.D. Boronic acids mediate glycoside transport through a liquid organic membrane via reversible formation of trigonal boronate esters Hi. Org. Chem. 1994. V. 59. P. 2724−2728.
130. James, T.D., Samankumara, K.R.A.S., Shinkai, S. Saccharide sensing with molecular receptors based on boronic acid // Angew. Chem., Int. Ed. Engl. 1996. V. 35. P. 1910−1922.
131. Riggs, J.A., Hossler, K.A., Smith, B.D., Karpa, M.J., Griffin, G., Duggan, P.J. Nucleotide carrier mixture with transport selectivity for ribonucleoside-5'-phosphates // Tetrahedron Lett. 1996. V. 37. P. 6303−6306.- /
132. Tung, C., Wei, Z. Leibowitz, M.J., Stein, S. Design of peptide-acridine mimics of1» Vribonuclease activity// Proc. Natl. Acad. Sci USA. 1992. V. 89. P. 7114−7118.
133. Lorente, A., Espinosa, J.F., Fernandez-Saiz, M., Lehn, J.-M., Wilson, W.D., Zhong, Y.Y. Synthesis of imidazole-acridine conjugates as ribonuclease A mimics // Tetrahedron Lett. 1996. V. 37. P. 4417−4420.
134. Vlassov V.V., Zuber G., Felden В., Behr J.-P., Giege R. Cleavage of RNA with imidazole constructs: a new approach for probing RNA structure // Nucleic Acids Res. 1995. V. 23. P. 3161−3167. .1.'ll»
135. Hovinen, J., Guzaev, A., Azhayeva, E., Azhayev, A., Lonnberg, H. Imidazole tethered oligodeoxyribonucleotides: synthesis and RNA cleaving activity // J. Org. Chem. 1995. V. 60, 2205−2209.
136. Ждан, H.C., Кузнецова, И.JI., Власов, А.В., Сильников, В.Н., Зенкова, М.А., Власов, f
137. В.В. Синтетические рибонуклеазы. 1. Синтез и свойства искусственных рибонуклеаз, tсодержащих РНК-связывающий фрагмент на основе остатков лизина // Биоорг. Химия. 1999. Т. 25. С. 723−732.
138. Королева, Jl.C., Донина, А.А., Тамкович, Н.В., Ковалев, Н.А., Зенкова, М.А.,
139. Сильников, В.Н. Искусственные рибонуклеазы. Сообщение 6. Рибонуклеазная активность1тетрапептидов на основе аминокислот, формирующих каталитический центр РНКазы Т1 // Изв. АН. Сер. Хим. 2005. Т. 54. С. 2596−2605.
140. Коневец, Д.А., Бекк, И.Э., Сильников, B.H., Зенкова, М.А., Шишкин, Г. В.i I
141. Коневец, Д. А.,. Бекк, И. Э, Шишкин, Г. В., Власов, В.В., Сильников, В. Н. Конструирование и синтез искусственных рибонуклеаз на основе 1, 4-диазабицикло2.2.2.октана и имидазола // Изв. АН. Сер. Хим. 2002. Т. 7. С. 1014−1024.
142. Зенкова, М.А., Чумакова, Н.Л., Власов, А.В., Комарова, Н.И., Веньяминова, А.Г.,• >
143. Власов, В.В., Сильников, В.Н. Синтетические конструкции, функциональноимитирующие рибонуклеазу, А // Мол. Биология. 2000. Т. 34. С. 456−460 •i '
144. Коневец, Д.А., Миронова, Н.Л., Бекк, И.Э., Зенкова, М.А., Шишкин, Г. В., Власов, F
145. В.В., Сильников, В. Н. Химические рибонуклеазы. 4. Анализ доменной структуры-'НО, химических рибонуклеаз на основе конъюгатов 1, 4-диазабицикло2.2.2.октана // Биоорг.
146. Химия. 2002. Т. 28. С. 367−378. • !
147. Soukup, G.A., Breaker, R.R. Relationship between internucleotide linkage geometry and the stability of RNA // RNA. 1999. V. 5. P. 1308−1325. '>',
148. McKay, D.B., Wedekind, J.E. Small Ribozymes // The RNA world / Eds Gesteland R.F., Cech T.R., Atkins J.F. New York: Cold Spring Harbor Lab. Press, 1999. P. 265−286.
149. Tabushu, I., Imuta, J.-I., Seko, N., Kobuke, Y. Highly discriminative binding of nucleoside phosphates by a lipophilic diammonium salt embedded in bicyclic skeleton // J. Am. Chem. Soc. 1978. V. 100. P. 6287−6288.
150. Narlikar, G.J., Hcrschlag, D. Mechanistic aspects of enzymatic catalysis: lessons from comparison of RNA and protein enzymes // Annu. Rev. Biochem. V. 66. 1997. P. 19−59.
151. Shan, S.-O., Herschlag, D. The change in hydrogen bond strength accompanying charge rearrangement: implications for enzymatic catalysis // Proc. Natl. Acad. Sci. USA. V. 93. 1996.p. 14 474−14 479.
152. Katritzky, A.R., Rao, M.S.C., Stevens, J. Compounds with potential 2 -order nonlinear optical-activity// J. Heterocycl. Chem. 1991. V. 28. P. 1115−1119.
153. Garratt, P. J., Ibbett, A.J., Ladbury, J.E., O’Bien, R., Hursthouse, M.B., Abul Malik, K.M.≤>
154. Molecular design using electrostatic interections. 1. Synthesis and properties of flexible tripodand tri- and hexa-cations witn restricted conformations. Molecular selection of ferricyanide from ferrocyanide // Tetrahedron. 1998. V. 54. P. 949−968.
155. Cohen, J.I., Castro, S., Han, J.-a., Behaj, V., Engel, R. Polycations. IX. Polyammonium derivatives of cyclodelxtrins: syntheses and binding to organic oxyanions // Heteroatom Chem. 2000. V. 11. P. 546−555.
156. Giege, R., Felden, В., Silnikov, V.N., Zenkova, M.A., Vlassov, V.V. Cleavage of RNA with synthetic ribonuclease mimics // Methods Enzymol. 2000. V. 318. P. 147−165.. 1
157. Rogoza, A.V. Superlipophilicity (Xenophilicity) and Microlipophilicity of Perfluorinated
158. Saturated Groups. Part 1. Qualitative Selection Criteria for Biologically Active Substances
159. Containing Perfluorinated Fragments // International conference on natural products andiphysiologically active substances (ICNPAS-98). November 30 December 6, 1998. i t
160. Novosibirsk, Russia. P. 149.
161. Jakersman, К. J., Tisdale, M., Russell, S. Efficacy of 2'-fluororiboside against influenza A and В virus inferrets // Antimicrobial agents and chemotherapy. 1994. V. 38. P. 1864−1867.
162. Tisdale, M., Ellis, M., Klumpp, K. Inhibitionof 2'-fluororiboside against influenza A and В virus inferrets // Antimicrobial agents and chemotherapy. 1994. V. 38. P. 1864−1867 —
163. Коваль, И. В. N-Галогенреагенты. N-Галогенсукцинимиды в органическом синтезе и в химии природных соединений // Журн. Орг. Химии. 2002. Т. 38. С. 327−359.
164. Cerichelli, G., Illuminati, G., Lillocci, C. Structural and mechanistic effects on the rates of ring-opening reactions in the 5−16-membered-ring region // J. Org. Chem. 1980. V. 45. P. 39 523 957.
165. Zenkova, M., Beloglazova, N., Sil’nikov, V., Vlassov, V.V., Giege, R. RNA cleavage by l, 4-diazabicyclo2.2.2.octane-imidazole conjugates // Methods Enzymol. 2001. V. 341. P. 468 490.
166. Kierzek, R. Nonenzymatic hydrolysis of oligoribonucleotides // Nucleic Acids Res. 1992. V. 20. P. 5073−5077.
167. Гордон, А., Форд, P. Спутник химика: пер. с англ. М.: Мир, 1976. 541 с. '