Synthesis of carbon-3-substituted 1,5,9-triazacyclododecanes, RNA cleavage agents suitable for oligonucleotide tethering

Bioconjugate Chemistry

Volumn 9, Issue 1, 1998, Pages 132-136

  Hovinen, Jari ^a,b  

^a UNIVERSITY OF TURKU   (Finland)

^b NONE   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CYCLIZATION;

ACID-CATALYZED HYDROLYSIS; AZACROWNS; CYCLIZATION REACTIONS; GUANIDINIUM SALTS; MALONATES; RNA CLEAVAGE; SYNTHESISED; TETHER GROUPS; TITLE COMPOUNDS;

OLIGONUCLEOTIDES;

EID: 0031983119     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc970108c     Document Type: Article

References (33)

1. (1) For reviews, see: (a) Green, P. J., Pines, O., and Inouye, M. (1986) The Role of Antisense RNA and Gene Regulation. Annu. Rev. Biochem. 55, 569-97; (b) Uhlman, E., and Peyman, A. (1990) Antisense Oligonucleotides: a New Therapeutic Principle. Chem. Rev. 90, 543-84; (c) James, W. (1991) Towards Gene-inhibition Therapy: a Review of Progress and Prospects in the Field of Antiviral Antisense Nucleic Acids and Ribozymes. Antiviral Chem. 2, 191-214; (d) Thuong, N. T., and Helene, C. (1993) Sequence-specific Recognition and Modification of Double-helical DNA by Oligonucleotides. Angew. Chem., Int. Ed. Engl. 32, 666-90; (e) Goodchild, J. (1990) Conjugates of Oligonucleotides: a Review of Their Synthesis and Properties. Bioconjugate Chem. 1, 165-87; (f) English, U., and Gauss, D. (1991) Chemically Modified Oligonucleotides as Probes and Inhibitors. Angew. Chem., Int. Ed. Engl. 30, 613-29; (g) De Mesmaeker, A., Häner, R., Martin, P., and Moser, H. E. (1995) Antisense Oligonucleotides. Acc. Chem. Res. 28, 366-74; (h) Eckstein, F. (1985) Nucleoside Phosphorothioates. Annu. Rev. Biochem. 54, 367-402; (i) Lönnberg, H., and Vuorio, E. (1996) Towards Genomic Drug Therapy with Antisense Oligonucleotides. Ann. Med. 28, 511-22.
2. For reviews, see: (a) Green, P. J., Pines, O., and Inouye, M. (1986) The Role of Antisense RNA and Gene Regulation. Annu. Rev. Biochem. 55, 569-97; (b) Uhlman, E., and Peyman, A. (1990) Antisense Oligonucleotides: a New Therapeutic Principle. Chem. Rev. 90, 543-84; (c) James, W. (1991) Towards Gene-inhibition Therapy: a Review of Progress and Prospects in the Field of Antiviral Antisense Nucleic Acids and Ribozymes. Antiviral Chem. 2, 191-214; (d) Thuong, N. T., and Helene, C. (1993) Sequence-specific Recognition and Modification of Double-helical DNA by Oligonucleotides. Angew. Chem., Int. Ed. Engl. 32, 666-90; (e) Goodchild, J. (1990) Conjugates of Oligonucleotides: a Review of Their Synthesis and Properties. Bioconjugate Chem. 1, 165-87; (f) English, U., and Gauss, D. (1991) Chemically Modified Oligonucleotides as Probes and Inhibitors. Angew. Chem., Int. Ed. Engl. 30, 613-29; (g) De Mesmaeker, A., Häner, R., Martin, P., and Moser, H. E. (1995) Antisense Oligonucleotides. Acc. Chem. Res. 28, 366-74; (h) Eckstein, F. (1985) Nucleoside Phosphorothioates. Annu. Rev. Biochem. 54, 367-402; (i) Lönnberg, H., and Vuorio, E. (1996) Towards Genomic Drug Therapy with Antisense Oligonucleotides. Ann. Med. 28, 511-22.
3. For reviews, see: (a) Green, P. J., Pines, O., and Inouye, M. (1986) The Role of Antisense RNA and Gene Regulation. Annu. Rev. Biochem. 55, 569-97; (b) Uhlman, E., and Peyman, A. (1990) Antisense Oligonucleotides: a New Therapeutic Principle. Chem. Rev. 90, 543-84; (c) James, W. (1991) Towards Gene-inhibition Therapy: a Review of Progress and Prospects in the Field of Antiviral Antisense Nucleic Acids and Ribozymes. Antiviral Chem. 2, 191-214; (d) Thuong, N. T., and Helene, C. (1993) Sequence-specific Recognition and Modification of Double-helical DNA by Oligonucleotides. Angew. Chem., Int. Ed. Engl. 32, 666-90; (e) Goodchild, J. (1990) Conjugates of Oligonucleotides: a Review of Their Synthesis and Properties. Bioconjugate Chem. 1, 165-87; (f) English, U., and Gauss, D. (1991) Chemically Modified Oligonucleotides as Probes and Inhibitors. Angew. Chem., Int. Ed. Engl. 30, 613-29; (g) De Mesmaeker, A., Häner, R., Martin, P., and Moser, H. E. (1995) Antisense Oligonucleotides. Acc. Chem. Res. 28, 366-74; (h) Eckstein, F. (1985) Nucleoside Phosphorothioates. Annu. Rev. Biochem. 54, 367-402; (i) Lönnberg, H., and Vuorio, E. (1996) Towards Genomic Drug Therapy with Antisense Oligonucleotides. Ann. Med. 28, 511-22.
4. For reviews, see: (a) Green, P. J., Pines, O., and Inouye, M. (1986) The Role of Antisense RNA and Gene Regulation. Annu. Rev. Biochem. 55, 569-97; (b) Uhlman, E., and Peyman, A. (1990) Antisense Oligonucleotides: a New Therapeutic Principle. Chem. Rev. 90, 543-84; (c) James, W. (1991) Towards Gene-inhibition Therapy: a Review of Progress and Prospects in the Field of Antiviral Antisense Nucleic Acids and Ribozymes. Antiviral Chem. 2, 191-214; (d) Thuong, N. T., and Helene, C. (1993) Sequence-specific Recognition and Modification of Double-helical DNA by Oligonucleotides. Angew. Chem., Int. Ed. Engl. 32, 666-90; (e) Goodchild, J. (1990) Conjugates of Oligonucleotides: a Review of Their Synthesis and Properties. Bioconjugate Chem. 1, 165-87; (f) English, U., and Gauss, D. (1991) Chemically Modified Oligonucleotides as Probes and Inhibitors. Angew. Chem., Int. Ed. Engl. 30, 613-29; (g) De Mesmaeker, A., Häner, R., Martin, P., and Moser, H. E. (1995) Antisense Oligonucleotides. Acc. Chem. Res. 28, 366-74; (h) Eckstein, F. (1985) Nucleoside Phosphorothioates. Annu. Rev. Biochem. 54, 367-402; (i) Lönnberg, H., and Vuorio, E. (1996) Towards Genomic Drug Therapy with Antisense Oligonucleotides. Ann. Med. 28, 511-22.
5. For reviews, see: (a) Green, P. J., Pines, O., and Inouye, M. (1986) The Role of Antisense RNA and Gene Regulation. Annu. Rev. Biochem. 55, 569-97; (b) Uhlman, E., and Peyman, A. (1990) Antisense Oligonucleotides: a New Therapeutic Principle. Chem. Rev. 90, 543-84; (c) James, W. (1991) Towards Gene-inhibition Therapy: a Review of Progress and Prospects in the Field of Antiviral Antisense Nucleic Acids and Ribozymes. Antiviral Chem. 2, 191-214; (d) Thuong, N. T., and Helene, C. (1993) Sequence-specific Recognition and Modification of Double-helical DNA by Oligonucleotides. Angew. Chem., Int. Ed. Engl. 32, 666-90; (e) Goodchild, J. (1990) Conjugates of Oligonucleotides: a Review of Their Synthesis and Properties. Bioconjugate Chem. 1, 165-87; (f) English, U., and Gauss, D. (1991) Chemically Modified Oligonucleotides as Probes and Inhibitors. Angew. Chem., Int. Ed. Engl. 30, 613-29; (g) De Mesmaeker, A., Häner, R., Martin, P., and Moser, H. E. (1995) Antisense Oligonucleotides. Acc. Chem. Res. 28, 366-74; (h) Eckstein, F. (1985) Nucleoside Phosphorothioates. Annu. Rev. Biochem. 54, 367-402; (i) Lönnberg, H., and Vuorio, E. (1996) Towards Genomic Drug Therapy with Antisense Oligonucleotides. Ann. Med. 28, 511-22.
6. For reviews, see: (a) Green, P. J., Pines, O., and Inouye, M. (1986) The Role of Antisense RNA and Gene Regulation. Annu. Rev. Biochem. 55, 569-97; (b) Uhlman, E., and Peyman, A. (1990) Antisense Oligonucleotides: a New Therapeutic Principle. Chem. Rev. 90, 543-84; (c) James, W. (1991) Towards Gene-inhibition Therapy: a Review of Progress and Prospects in the Field of Antiviral Antisense Nucleic Acids and Ribozymes. Antiviral Chem. 2, 191-214; (d) Thuong, N. T., and Helene, C. (1993) Sequence-specific Recognition and Modification of Double-helical DNA by Oligonucleotides. Angew. Chem., Int. Ed. Engl. 32, 666-90; (e) Goodchild, J. (1990) Conjugates of Oligonucleotides: a Review of Their Synthesis and Properties. Bioconjugate Chem. 1, 165-87; (f) English, U., and Gauss, D. (1991) Chemically Modified Oligonucleotides as Probes and Inhibitors. Angew. Chem., Int. Ed. Engl. 30, 613-29; (g) De Mesmaeker, A., Häner, R., Martin, P., and Moser, H. E. (1995) Antisense Oligonucleotides. Acc. Chem. Res. 28, 366-74; (h) Eckstein, F. (1985) Nucleoside Phosphorothioates. Annu. Rev. Biochem. 54, 367-402; (i) Lönnberg, H., and Vuorio, E. (1996) Towards Genomic Drug Therapy with Antisense Oligonucleotides. Ann. Med. 28, 511-22.
7. For reviews, see: (a) Green, P. J., Pines, O., and Inouye, M. (1986) The Role of Antisense RNA and Gene Regulation. Annu. Rev. Biochem. 55, 569-97; (b) Uhlman, E., and Peyman, A. (1990) Antisense Oligonucleotides: a New Therapeutic Principle. Chem. Rev. 90, 543-84; (c) James, W. (1991) Towards Gene-inhibition Therapy: a Review of Progress and Prospects in the Field of Antiviral Antisense Nucleic Acids and Ribozymes. Antiviral Chem. 2, 191-214; (d) Thuong, N. T., and Helene, C. (1993) Sequence-specific Recognition and Modification of Double-helical DNA by Oligonucleotides. Angew. Chem., Int. Ed. Engl. 32, 666-90; (e) Goodchild, J. (1990) Conjugates of Oligonucleotides: a Review of Their Synthesis and Properties. Bioconjugate Chem. 1, 165-87; (f) English, U., and Gauss, D. (1991) Chemically Modified Oligonucleotides as Probes and Inhibitors. Angew. Chem., Int. Ed. Engl. 30, 613-29; (g) De Mesmaeker, A., Häner, R., Martin, P., and Moser, H. E. (1995) Antisense Oligonucleotides. Acc. Chem. Res. 28, 366-74; (h) Eckstein, F. (1985) Nucleoside Phosphorothioates. Annu. Rev. Biochem. 54, 367-402; (i) Lönnberg, H., and Vuorio, E. (1996) Towards Genomic Drug Therapy with Antisense Oligonucleotides. Ann. Med. 28, 511-22.
8. For reviews, see: (a) Green, P. J., Pines, O., and Inouye, M. (1986) The Role of Antisense RNA and Gene Regulation. Annu. Rev. Biochem. 55, 569-97; (b) Uhlman, E., and Peyman, A. (1990) Antisense Oligonucleotides: a New Therapeutic Principle. Chem. Rev. 90, 543-84; (c) James, W. (1991) Towards Gene-inhibition Therapy: a Review of Progress and Prospects in the Field of Antiviral Antisense Nucleic Acids and Ribozymes. Antiviral Chem. 2, 191-214; (d) Thuong, N. T., and Helene, C. (1993) Sequence-specific Recognition and Modification of Double-helical DNA by Oligonucleotides. Angew. Chem., Int. Ed. Engl. 32, 666-90; (e) Goodchild, J. (1990) Conjugates of Oligonucleotides: a Review of Their Synthesis and Properties. Bioconjugate Chem. 1, 165-87; (f) English, U., and Gauss, D. (1991) Chemically Modified Oligonucleotides as Probes and Inhibitors. Angew. Chem., Int. Ed. Engl. 30, 613-29; (g) De Mesmaeker, A., Häner, R., Martin, P., and Moser, H. E. (1995) Antisense Oligonucleotides. Acc. Chem. Res. 28, 366-74; (h) Eckstein, F. (1985) Nucleoside Phosphorothioates. Annu. Rev. Biochem. 54, 367-402; (i) Lönnberg, H., and Vuorio, E. (1996) Towards Genomic Drug Therapy with Antisense Oligonucleotides. Ann. Med. 28, 511-22.
9. For reviews, see: (a) Green, P. J., Pines, O., and Inouye, M. (1986) The Role of Antisense RNA and Gene Regulation. Annu. Rev. Biochem. 55, 569-97; (b) Uhlman, E., and Peyman, A. (1990) Antisense Oligonucleotides: a New Therapeutic Principle. Chem. Rev. 90, 543-84; (c) James, W. (1991) Towards Gene-inhibition Therapy: a Review of Progress and Prospects in the Field of Antiviral Antisense Nucleic Acids and Ribozymes. Antiviral Chem. 2, 191-214; (d) Thuong, N. T., and Helene, C. (1993) Sequence-specific Recognition and Modification of Double-helical DNA by Oligonucleotides. Angew. Chem., Int. Ed. Engl. 32, 666-90; (e) Goodchild, J. (1990) Conjugates of Oligonucleotides: a Review of Their Synthesis and Properties. Bioconjugate Chem. 1, 165-87; (f) English, U., and Gauss, D. (1991) Chemically Modified Oligonucleotides as Probes and Inhibitors. Angew. Chem., Int. Ed. Engl. 30, 613-29; (g) De Mesmaeker, A., Häner, R., Martin, P., and Moser, H. E. (1995) Antisense Oligonucleotides. Acc. Chem. Res. 28, 366-74; (h) Eckstein, F. (1985) Nucleoside Phosphorothioates. Annu. Rev. Biochem. 54, 367-402; (i) Lönnberg, H., and Vuorio, E. (1996) Towards Genomic Drug Therapy with Antisense Oligonucleotides. Ann. Med. 28, 511-22.
10. Magda, D., Miller, R. A., Sessler, J. L., and Iverson, B. L. (1994) J. Am. Chem., Soc. 116, 5891.
11. Bashkin, J. K., Frolova, E. L., and Sampath, U. S. (1994) Sequence-specific Cleavage of HIV mRNA by a Ribozyme Mimic. J. Am. Chem. Soc. 116, 5981-2.
12. Komiyama, M., and Inokawa, T. (1994) Selective Hydrolysis of tRNA by ethylenediamine Bound to a DNA Oligomer. J. Biochem. 116, 719-20.
13. Kazunari, M., Endo, M., and Komiyama, M. (1994) Lanthanide Complex-Oligo-DNA Hybrid for Sequence-selective Hydrolysis of RNA. J. Chem. Soc., Chem. Communn., 2019-20.
14. Hall, J., Husken, D., Pieles, U., Moser, H. E., and Häner, R. (1994) Efficient Sequence-specific Cleavage of RNA Using Novel Europium Complexes Conjugated to Oligonucleotides. Chem. Biol. 1, 185-90.
15. Uchiyama, Y., Inoue, H., and Othsuka, E. (1994) DNA-Linked RNase H for Site-Selective Cleavage of RNA. Bioconjugate Chem. 5, 327-32.
16. Komiyama, M., Inokawa, T., and Yoshinari, K. (1995) Ethylenediamine-oligo DNA Hybrid as Sequence-selective Artificial Ribonuclease. J. Chem. Soc., Chem. Communn., 77-8.
17. Hovinen, J., Guzaev, A., Azhayev, A., and Lönnberg, H. (1995) Imidazole Tethered Oligonucleotides: Synthesis and RNA Cleaving Activity. J. Org. Chem. 60, 2205-9.
18. Kuusela, S., and Lönnberg, H. (1992) Metal Ion-Promoted Hydrolysis of Uridine 2',3'-Cyclic Monophosphate: Effect of Metal Chelates and Uncomplexed Aquo ions. J. Phys. Org. Chem. 50, 803-11.
19. Kuusela, S., and Lönnberg, H. (1994) Metal-ion-promoted Hydrolysis of Polyuridylic Acid. J. Chem. Soc., Perkin Trans. 2, 2301-6.
20. Kuusela, S., Rantanen, M., and Lönnberg, H. (1995) Metal-ion-promoted Hydrolysis of Uridylyl(3',5')uridine: Internal vs. External General Base Catalysis. J. Chem. Soc., Perkin Trans. 2, 2269-73.
21. Hovinen, J., and Salo, H. (1997) C-Glycoside Phosphoramidite Building Block for Versatile Functionalization of Oligonucleotides. J. Chem. Soc., Perkin Trans. 1, 3017-20.
22. Cox, J. P. L., Craig, A. S., Helps, I. M., Jankowski, K. J., Parker, D., Eaton, M. A. W., Millican, A. T., Millar, K., Beeley, N. R. A., and Boyce, B. A. (1990) Synthesis of C-and N-Functionalised Derivatives of 1,4,7-Triazacyclononane-1,4,7-triyltiacetic Acid (NOTA), 1,4,7,10-Tetra-azacyclododecane-1,4,7,10-tetrayltetraacetic Acid (DOTA), and Diethylenetriaminepenta-acetic Acid (DTPA): Bifunctional Complexing Agents for the Derivatization of Antibodies. J. Chem. Soc., Perkin Trans. 1, 2567-76.
23. Hovinen, J., Guzaev, A., Azhayev, A., and Lönnberg, H. (1994) Novel Solid Supports for the Preparation of 3'-Derivatized Oligonucleotides: Introduction of 3'-Alkylphosphate Tether Groups Bearing Amino, Carboxy, Carboxaraido, and Mercapto Functionalities. Tetrahedron 50, 7203-18.
24. Pieles, U., Zürcher, W., Schär, M., and Moser, H. E. (1993) Matrix-assisted Laser Desorption Ionization Time-of-flight Mass Spectrometry: a Powerful Tool for the Mass and Sequence Analysis of natural and Modified Oligonucleotides. Nucleic Acids Res. 21, 3191-6.
25. Carlsen, P. H., Sorbye, K., Ulven, T., and Aasbo, K. (1996) Synthesis of Benzylidene-Protected Dihydroxyacetone. Acta Chem. Scand. 50, 185-7.
26. Brown, H. C., Choi, T. M., and Narasimhan, S. (1982) Selective Reductions. 29. A Simple Technique to Achieve an Enhanced Rate of Reduction of Representative Organic Compounds by Borane-Dimethyl Sulfide. J. Org. Chem. 47, 3153-63.
27. March, J. (1992) Advanced Organic Chemistry, 4th ed., p 1213, Wiley, New York.
28. (20) For reviews, see: (a) Kaden, T. A. (1984) Synthesis and Metal Complexes of Aza-Macrocycles with Pendant Arms having Additional Ligating Groups. Top. Curr. Chem. 121, 157-79; (b) Kimura, E. (1992) Macrocyclic Polyamines with Intelligent Functions. Tetrahedron 48, 6175-217.
29. For reviews, see: (a) Kaden, T. A. (1984) Synthesis and Metal Complexes of Aza-Macrocycles with Pendant Arms having Additional Ligating Groups. Top. Curr. Chem. 121, 157-79; (b) Kimura, E. (1992) Macrocyclic Polyamines with Intelligent Functions. Tetrahedron 48, 6175-217.
30. Alder, R. W., Mowlam, R. W., Vachon, D. J., and Weisman, G. R. (1992) New Synthetic Routes to Macrocyclic Triamines. J. Chem. Soc., Chem. Commun., 507-8.
31. Kim, R. D. H., Wilson, M., and Haseltine, J. (1994) Simple Praparation of Tricyclic Orthoamides and Macrocyclic Triamines. Synth. Commun. 24, 3109-14.
32. Satoh, T., Suzuki, S., Suzuki, Y., Miyaji, Y., and Imai, Z. (1969) Reduction of Organic Compounds with Sodium Borohydride Transition Metal Salt Systems. Reduction of Organic Nitrile, Nitro and Amide Compounds to Primary Amines. Tetrahedron Lett., 4555-8.
33. Misiura, K., Durrant, I. m., Evans, M. R., and Gait, M. J. (1990) Biotinyl and Phosphotyrosinyl Phosphoramidite Derivatives Useful in the Incorporation of Multiple Reporter Groups on Synthetic Oligonucleotides. Nucleic Acids Res. 18, 4345-54.