Simple solid-phase synthesis and biological properties of carbohydrate - Oligonucleotide conjugates modified at the 3′-terminus

Bioconjugate Chemistry

Volumn 21, Issue 9, 2010, Pages 1685-1690

  Ikeda, Yutaka ^a   Kubota, Daisuke ^a   Nagasaki, Yukio ^b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATES; GENE EXPRESSION; SYNTHESIS (CHEMICAL);

BIOLOGICAL PROPERTIES; FUNCTIONAL MOIETIES; FUNCTIONALIZATIONS; GLYCOSYLATED; OLIGONUCLEOTIDE CONJUGATES; SIMPLE++; SOLID PHASE SYNTHESIS; SOLID SUPPORTS; SUGAR MOIETY; SYNTHESIS METHOD;

OLIGONUCLEOTIDES;

CARBOHYDRATE; GALACTOSE; PYRANOSIDE; SMALL INTERFERING RNA; UNCLASSIFIED DRUG; [1 (BENZYLOXYMETHYL) 3,4 DIHYDROXYCYCLOPENTYL]METHYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSIDE; [1 (BENZYLOXYMETHYL)CYCLOPENT 3 ENYL]METHANOL; [1 (BENZYLOXYMETHYL)CYCLOPENT 3 ENYL]METHYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSIDE; [3 ACETOXY 1 (BENZYLOXYMETHYL) 4 HYDROXYCYCLOPENTYL]METHYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSIDE; [3 ACETOXY 1 O (4,4' DIMETHOXYTRITYL)METHYL 4 HYDROXY]CYCLOPENTYLMETHYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSIDE; [3 ACETOXY 4 HYDROXY 1 (HYDROXYMETHYL)CYCLOPENTYL]METHYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSIDE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; ENZYME DEGRADATION; GENE EXPRESSION; RNA SYNTHESIS; SOLID PHASE SYNTHESIS; SYNTHESIS;

EID: 77956640516     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc100205v     Document Type: Article

References (26)

1. Moschos, S. A., Spinks, K., Williams, A. E., and Lindsay, M. A. (2008) Targeting the lung using siRNA and antisense based oligonucleotides Curr. Pharm. 14, 3620-3627
2. Que-Gewirth, N. S. and Sullenger, B. A. (2007) Gene therapy progress and prospects: RNA aptamers Gene Ther. 14, 283-291
3. Castanotto, D. and Rossi, J. J. (2009) The promises and pitfalls of RNA-interference-based therapeutics Nature 457, 426-433
4. Juliano, R., Bauman, J., Kang, H., and Ming, X. (2009) Biological barriers to therapy with antisense and siRNA oligonucleotides Mol. Pharm. 6, 686-695
5. Elmén, J., Thonberg, H., Ljungberg, K., Frieden, M., Westergaard, M., Xu, Y., Wahren, B., Liang, Z., Ørum, H., Koch, T., and Wahlestedt, C. (2005) Locked nucleic acid (LNA) mediated improvements in siRNA stability and functionality Nucleic Acids Res. 33, 439-447
6. Soutschek, J., Akinc, A., Bramlage, B., Charisse, K., Constien, R., Donoghue, M., Elbashir, S., Geick, A., Hadwiger, P., Harborth, J., John, M., Kesavan, V., Lavine, G., Pandey, R. K., Racie, T., Rajeev, K. G., Röhl, I., Toudjarska, I., Wang, G., Wuschko, S., Bumcrot, D., Koteliansky, V., Limmer, S., Manoharan, M., and Vornlocher, H. P. (2004) Therapeutic silencing of an endogenous gene by systemic administration of modified siRNAs Nature 432, 173-178
7. Fonseca, S. B., Pereria, M. P., and Kelley, S. O. (2009) Recent advances in the use of cell-penetrating peptides for medical and biological applications Adv. Drug Delivery Rev. 61, 953-964
8. Meade, B. R. and Dowdy, S. F. (2007) Exogenous siRNA delivery using peptide transduction domains/cell penetrating peptides Adv. Drug Delivery Rev. 59, - 40
9. Koppelhus, U., Shiraishi, T., Zachar, V., Pankratova, S., and Nielsen, P. E. (2008) Improved cellular activity of antisense peptide nucleic acids by conjugation to a cationic peptide-lipid (CatLip) domain Bioconjugate Chem. 19, 1526-1534
10. Amantana, A., Moulton, H. M., Cate, M. L., Reddy, M. T., Whitehead, T., Hassinger, J. N., Youngblood, D. S., and Iversen, P. L. (2007) Pharmacokinetics, biodistribution, stability and toxicity of a cell-penetrating peptide-morpholino oligomer conjugate Bioconjugate Chem. 18, 1325-1331
11. Taylor, M. E., and and Drickamer, K. (2003) Introduction to glycobiology, Oxford University Press, United Kingdom.
12. Vasta, G. R. (2009) Roles of galectins in infection Nat. Rev. Microbiol. 7, 424-438
13. Zatsepin, T. S. and Oretskaya, T. S. (2004) Synthesis and applications of oligonucleotide-carbohydrate conjugates Chem. Biodivers. 1, 1401-1417
14. Oishi, M., Nagasaki, Y., Itaka, K., Nishiyama, N., and Kataoka, K. (2005) Lactosylated poly(ethylene glycol)-siRNA conjugate through acid-labile beta-thiopropionate linkage to construct pH-sensitive polyion complex micelles achieving enhanced gene silencing in hepatoma cells J. Am. Chem. Soc. 127, 1624-1625
15. Sheppard, T. L., Wong, C. H., and Joyce, G. F. (2000) Nucleoglycoconjugates: design and synthesis of a new class of DNA-carbohydrate conjugates Angew. Chem., Int. Ed. Engl. 39, 3660-3663
16. Adinolfi, M., Napoli, L. D., Fabio, G. D., Iadonisi, A., Montesarchio, D., and Piccialli, G. (2002) Solid phase synthesis of oligonucleotides tethered to oligo-glucose phosphate tails Tetrahedron 58, 6697-6704
17. Maier, M. A., Yannopoulos, C. G., Mohamed, N., Roland, A., Fritz, H., Mohan, V., Just, G., and Manoharan, M. (2003) Synthesis of antisense oligonucleotides conjugated to a multivalent carbohydrate cluster for cellular targeting Bioconjugate Chem. 14, 18-29
18. Manoharan, M., Rajeev, K. G., Narayanannair, J. K., and Maier, M. U. S. Patent Appl. US 2009/0239814 A1.
19. Reed, M. W., Adams, A. D., Nelson, J. S., and Meyer, R. B., Jr. (1991) Acridine- and cholesterol-derivatized solid supports for improved synthesis of 3′-modified oligonucleotides Bioconjugate Chem. 2, 217-225
20. Kang, J. H., Chung, H. E., Kim, S. Y., Kim, Y., Lee, J., Lewin, N. E., Pearce, L., Blumberg, P. M., and Marquez, V. E. (2003) Conformationally constrained analogues of diacylglycerol (DAG). Effect on protein kinase C (PK-C) binding by the isosteric replacement of Sn-1 and Sn-2 esters in DAG-lactones Bioorg. Med. Chem. 11, 2529-2539
21. Ryan, B. M., O'Donovan, N., and Duffy, M. J. (2009) Survivin: a new target for anti-cancer therapy Cancer Treat. Rev. 35, 553-562
22. Lemarchand, C., Gref, R., and Couvreur, P. (2004) Polysaccharide- decorated nanoparticles Eur. J. Pharm. Biopharm. 58, 327-341
23. Khan, S. H. and O'Neill, R. A. (1996) Modern methods in carbohydrate synthesis, Harwood Academic Publishers, United States.
24. Peng Ho, S., Livanov, V., Zhang, W., Li, J., and Lesher, T. (1998) Mdificatin of phosphorothiate oligonucleotides yields potent analogs with mininmal toxicity for antisensene experiments in the CNS Brain Re. Ml. Brain Res. 62, 1-11
25. Gamper, H. B., Reed, M. W., Cox, T., Virosco, J. S., Adams, A. D., Gall, A. A., Scholler, J. K., and Meyer, R. B., Jr. (1993) Facile preparation of nuclease resistant 3′ modified oligodeoxynucleotides Nucleic Acids Res. 21, 145-150
26. Ueno, Y., Kawada, K., Naito, T., Shibata, A., Yoshikawa, K., Kim, H. S., Wataya, Y., and Kitade, Y. (2008) Synthesis and silencing properties of siRNAs possessing lipophilic groups at their 3′-termini Bioorg. Med. Chem. 16, 7698-7704