Solid-supported synthesis and click conjugation of 4′- C -alkyne functionalized oligodeoxyribonucleotides

Bioconjugate Chemistry

Volumn 21, Issue 10, 2010, Pages 1890-1901

  Kiviniemi, Anu ^a   Virta, Pasi ^a   Lönnberg, Harri ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

CHAINS; DNA; LIGANDS; RNA;

ALKYNYL GROUPS; CHAIN ASSEMBLIES; CLICK CHEMISTRY; FUNCTIONALIZED; FUNCTIONALIZED LIGANDS; HIGH SALTS; PHOSPHORAMIDITES; SOLID SUPPORTS; SYNTHESISED; UNIT FORM;

OLIGONUCLEOTIDES;

4' C [N METHYL N (4 PENTYN 1 YL)AMINOMETHYL]THYMIDINE; 4' C [N,N DI(4 PENTYN 1 YL)AMINOMETHYL]THYMIDINE; ALKYNE; ALKYNYL GROUP; AMINE; AMINO ACID; DNA; LIGAND; MANNOSE; MONOMER; NEOMYCIN; OLIGODEOXYRIBONUCLEOTIDE; PAROMAMINE; RNA; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATE; CONJUGATION; DNA DNA HYBRIDIZATION; DNA RNA HYBRIDIZATION; DNA SEQUENCE; MELTING POINT; SOLID; SYNTHESIS; TEMPERATURE;

EID: 77958156328     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc100268w     Document Type: Article

References (55)

1. Jeong, J. H., Mok, H., Oh, Y.-K., and Park, T. G. (2009) siRNA conjugate delivery systems Bioconjugate Chem. 20, 5-14
2. Kurreck, J. (2009) RNA interference: from basic research to therapeutic applications Angew. Chem., Int. Ed. 48, 1378-1398
3. Castanotto, D. and Rossi, J. J. (2009) The promises and pitfalls of RNA-interference-based therapeutics Nature 457, 426-433
4. Grosshans, H. and Filipowicz, W. (2008) Molecular biology: The expanding world of small RNAs Nature 451, 414-416
5. Corey, D. R. (2007) RNA learns from antisense Nat. Chem. Biol. 3, 8-11
6. Kim, D. H. and Rossi, J. J. (2007) Strategies for silencing human disease using RNA interference Nat. Rev. Genetics 8, 173-184
7. de Fougerolles, A., Vornlocher, H.-P., Maraganore, J., and Lieberman, J. (2007) Interfering with disease: a progress report on siRNA-based therapeutics Nat. Rev. Drug Discovery 6, 443-453
8. Yan, H. and Tram, K. (2007) Glycotargeting to improve cellular delivery efficiency of nucleic acids Glycoconj. J. 24, 107-123
9. Wilson, C. and Keefe, A. D. (2006) Building oligonucleotide therapeutics using non-natural chemistries Curr. Opin. Chem. Biol. 10, 607-614
10. Sasaki, S. and Nagatsuki, F. (2006) Application of unnatural oligonucleotides to chemical modification of gene expression Curr. Opin. Chem. Biol. 10, 615-621
11. Bumcrot, D., Manoharan, M., Koteliansky, V., and Sah, D. W. Y. (2006) RNAi therapeutics: a potential new class of pharmaceutical drugs Nat. Chem. Biol. 2, 711-719
12. Dykxhoorn, D. M., Palliser, D., and Lieberman, J. (2006) The silent treatment: siRNAs as small molecule drugs Gene Ther. 13, 541-552
13. Leung, R. K. M. and Whittaker, P. A. (2005) RNA interference: from gene silencing to gene-specific therapeutics Pharm. Ther. 107, 222-239
14. Aboul-Fadl, T. (2005) Antisense oligonucleotides: The state of the art Curr. Med. Chem. 12, 2193-2214
15. Manoharan, M. (2002) Oligonucleotide conjugates as potential antisense drugs with improved uptake, biodistribution, targeted delivery, and mechanism of action Antisense Nucleic Acids Drug Dev. 12, 103-108
16. Ku, K., Duan, Q.-P., Ma, L., and Zhao, D.-X. (2010) Chemical strategies for the synthesis of peptide-oligonucleotide conjugates Bioconjugate Chem. 21, 187-202
17. Singh, Y., Murat, P., and Defrancq, E. (2010) Recent developments in oligonucleotide conjugation Chem. Soc. Rev 39, 2054-2070
18. Lönnberg, H. (2009) Solid-phase synthesis of oligonucleotide conjugates useful for delivery and targeting of potential nucleic acid therapeutics Bioconjugate Chem. 20, 1065-1094
19. Eritja, R. (2007) Solid-phase synthesis of modified oligonucleotides Int. J. Pept. Res. Therapeut. 13, 53-68
20. Venkatesan, N. and Kim, B. H. (2006) Peptide conjugates of oligonucleotides: synthesis and applications Chem. Rev. 106, 3712-3761
21. Zatsepin, T. S. and Oretskaya, T. S. (2004) Synthesis and applications of oligonucleotide-carbohydrate conjugates Chem. Biodivers. 1, 1401-1416
22. Bucior, I. and Burger, M. M. (2004) Carbohydrate-carbohydrate interaction as a major force initiating cell-cell recognition Glycoconj. J. 21, 111-123 (Pubitemid 39382657)
23. Hakomori, S. (2004) Carbohydrate-to-carbohydrate interaction, through glycosynapse, as a basis of cell recognition and membrane organization Glycoconj. J. 21, 125-137
24. Ernst, B. and Magnani, J. L. (2009) From carbohydrate leads to glycomimetic drugs Nat. Rev. Drug Discovery 8, 661-677
25. Gabius, H.-J., Siebert, H.-C., André, S., Jiménez-Barbero, J., and Rüdiger, H. (2004) Chemical biology of the sugar code ChemBioChem 5, 740-764
26. Dwek, R. A. (1996) Glycobiology: Toward understanding the function of sugars Chem. Rev. 96, 683-720
27. Dam, T. K. and Brewer, C. F. (2010) Multivalent lectin-carbohydrate interactions: energetics and mechanisms of binding Adv. Carbohydr. Chem. Biochem. 63, 139-164
28. Kiessling, L. L., Gestwicki, J. E., and Strong, L. E. (2006) Synthetic multivalent ligands as probes of signal transduction Angew. Chem., Int. Ed. 45, 2348-2368
29. Ambrosi, M., Cameron, N. R., and Davis, B. G. (2005) Lectins: tools for the molecular understanding of the glycocode Org. Biomol. Chem. 3, 1593-1608
30. Lundquist, J. J. and Toone, E. J. (2002) The cluster glycoside effect Chem. Rev. 102, 555-578
31. Karskela, M., Helkearo, M., Virta, P., and Lönnberg, H. (2010) Synthesis of oligonucleotide glycoconjugates using sequential click and oximation ligations Bioconjugate Chem. 21, 748-755
32. Pourceau, G., Meyer, A., Vasseur, J.-J., and Morvan, F. (2009) Synthesis of mannose and galactose oligonucleotide conjugates by bi-click chemistry J. Org. Chem. 74, 1218-1222
33. Moni, L., Pourceau, G., Zhang, J., Meyer, A., Vidal, S., Souteyrand, E., Dondoni, A., Morvan, F., Chevolot, Y., Vasseur, J.-J., and Marra, A. (2009) Design of triazole-tethered glycoclusters exhibiting three different spatial arrangements and comparative study of their affinities towards PA-IL and RCA 120 by using a DNA-based glycoarray ChemBioChem 10, 1369-1378
34. Bouillon, C., Meyer, A., Vidal, S., Jochum, A., Chevolot, Y., Cloarec, J.-P., Praly, J.-P., Vasseur, J.-J., and Morvan, F. (2006) Microwave assisted "click" chemistry for the synthesis of multiple labeled-carbohydrate oligonucleotides on solid support J. Org. Chem. 71, 4700-4702
35. Singh, Y., Renaudet, O., Defrancq, E., and Dumy, P. (2005) Preparation of a multitopic glycopeptide-oligonucleotide conjugate Org. Lett. 7, 1359-1362
36. Dubber, M. and Frechet, J. M. J. (2003) Solid-phase synthesis of multivalent glycoconjugates on a DNA synthesizer Bioconjugate Chem. 14, 239-246
37. Matsuura, K., Hibino, M., Ikeda, T., Yamada, Y., and Kobayashi, K. (2004) Self-organized glycoclusters along DNA: Effect of the spatial arrangement of galactoside residues on cooperative lectin recognition Chem.-Eur. J. 10, 352-359
38. Turner, J. J., Meeuwenoord, N. J., Rood, A., Borst, P., van der Marel, G. A., and van Boom, J. H. (2003) Reinvestigation into the synthesis of oligonucleotides containing 5(β-D-glucopyranosyloxymethyl)-2′- deoxyuridine Eur. J. Org. Chem. 3832-3839
39. Matsuura, K., Hibino, M., Yamada, Y., and Kobayashi, K. (2001) Construction of glycol-clusters by self-organization of site-specifically glycosylated oligonucleotides and their cooperative amplification of lectin recognition J. Am. Chem. Soc. 123, 357-358
40. Tona, R., Bertolini, R., and Hunziker, J. (2000) Synthesis of aminoglycoside-modified oligonucleotides Org. Lett. 2, 1693-1696
41. Hunzinker, J. (1999) Synthesis of 5-(2-amino-2-deoxy-β-D- glucopyranosyloxymethyl)-2′-deoxyuridine and its incorporation into oligothymidylates Bioorg. Med. Chem. Lett. 9, 201-204
42. Karskela, M., Virta, P., Malinen, M., Urtti, A., and Lönnberg, H. (2008) Synthesis and cellular uptake of fluorescently labeled multivalent hyaluronan disaccharide conjugates of oligonucleotide phosphorothioates Bioconjugate Chem. 19, 2549-2558
43. Katajisto, J., Heinonen, P., and Lönnberg, H. (2004) Solid-phase synthesis of oligonucleotide glycoconjugates bearing three different glycosyl groups: orthogonally protected bis(hydroxymethyl)- N, N′ -bis(3-hydroxypropyl)malondiamide phosphoramidite as key building block J. Org. Chem. 69, 7609-7615
44. Katajisto, J., Virta, P., and Lönnberg, H. (2004) Solid-phase synthesis of multiantennary oligonucleotide glycoconjugates utilizing on-support oximation Bioconjugate Chem. 15, 890-896
45. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. 41, 2596-2599
46. Tornoe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 67, 3057-3064
47. Kiviniemi, A., Virta, P., and Lönnberg, H. (2008) Utilization of intrachain 4′- C -azidomethylthymidine for preparation of oligonucleotide conjugates by click chemistry in solution and on a solid support Bioconjugate Chem. 19, 1726-1734
48. Gierlich, J., Burley, G. A., Gramlich, P. M. E., Hammond, D. M., and Carell, T. (2006) Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA Org. Lett. 8, 3639-3642
49. Sirivolu, V. R., Chittepu, P., and Seela, F. (2008) DNA with branched internal side chains: Synthesis of 5-tripropargylamine-dU and conjugation by an azide-alkyne double click reaction ChemBioChem 9, 2305-2316
50. Alper, P. B., Hung, S.-C., and Wong, C.-H. (1996) Metal catalyzed diazo transfer Tetrahedron Lett. 37, 6029-6032
51. Simonsen, K. B., Ayida, B. K., Vourloumis, D., Takahashi, M., Winters, G. C., Barluenga, S., Qamar, S., Shandrick, S., Zhao, Q., and Hermann, T. (2002) Novel paromamine derivatives exploring shallow-groove recognition of ribosomal- decoding-site RNA ChemBioChem 3, 1223-1228
52. Subramaniam, C. S., Thomas, P. J., Mamdapur, V. R., and Chadha, M. S. (1979) Simple syntheses of dihydrojasmone and cis -jasmone via 1,4-diketones J. Chem. Soc., Perkin Trans. 1, 2346-2348
53. Ito, Y. and Okuda, T. (1967) 6-Amino-6-deoxy-D-mannose, Jpn. Tokkyo Koho/JP patent 42008003 19670331.
54. Brown, T., Pritchard, C. E., Turner, G., and Salisbury, S. A. (1989) A new base-stable linker for solid-phase oligonucleotide synthesis J. Chem. Soc., Chem. Commun. 891-893
55. Pon, R. T. and Yu, S. (1997) Hydroquinone- O, O ′-diacetic acid ('Q-linker') as a replacement for succinyl and oxalyl linker arms in solid phase oligonucleotide synthesis Nucleic Acids Res. 25, 3629-3635