Conjugation reactions involving maleimides and phosphorothioate oligonucleotides

Bioconjugate Chemistry

Volumn 23, Issue 2, 2012, Pages 300-307

  Saánchez, Albert ^a   Pedroso, Enrique ^a   Grandas, Anna ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDUCTS; DIELS-ALDER; DIESTERS; FULLY COMPATIBLE; MALEIMIDES; MONOESTERS; PHOSPHOROTHIOATE OLIGONUCLEOTIDE; PHOSPHOROTHIOATES; RETRO DIELS-ALDER REACTIONS; RETRO-DIELS-ALDER REACTIONS;

OLIGONUCLEOTIDES;

MALEIMIDE DERIVATIVE; OLIGODEOXYNUCLEOTIDE PHOSPHOROTHIOATE; THIOL DERIVATIVE; TOLUENE;

ARTICLE; CONJUGATION; CONTROLLED STUDY; CYCLOADDITION; DIELS ALDER REACTION;

ALNUS;

EID: 84856887537     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc200598g     Document Type: Article

References (35)

1. Matsukura, M., Shinozuka, K., Zon, G., Mitsuya, H., Reitz, M., Cohen, J. S., and Broder, S. (1987) Phosphorothioate analogs of oligodeoxynucleotides: inhibitors of replication and cytopathic effects of human immunodeficiency virus Proc. Natl. Acad. Sci. U.S.A. 84, 7706-7710
2. Goodchild, J. (1990) Conjugates of oligonucleotides and modified oligonucleotides: A review of their synthesis and properties Bioconjugate Chem. 1, 165-187
3. Diala, I., Osada, A., Maruoka, S., Imanisi, T., Murao, S., Ato, T., Ohba, H., and Fujii, M. (2007) Synthesis of phosphorothioate oligonucleotide-peptide conjugates by solid phase fragment condensation Bioorg. Med. Chem. Lett. 17, 6575-6578
4. Goody, R. S. and Eckstein, F. (1971) Thiophosphate analogs of nucleoside di- and triphosphates J. Am. Chem. Soc. 93, 6252-6257
5. Wettstein, P. J., Borson, N. D., Park, J. G., McNallan, K. T., and Reed, A. M. (2005) Cysteine-tailed class I-binding peptides bind to CpG adjuvant and enhance primary CTL responses J. Immunol. 205, 3681-3689 (Pubitemid 41292028)
6. Antopolsky, M., Azhayeva, E., Tengvall, U., Auriola, S., Jääskeläinen, I, Rönkkö, S., Honkakoski, P., Urtti, A., Lönnberg, H., and Azhayev, A. (1999) Peptide-oligonucleotide phosphorothioate conjugates with membrane translocation and nuclear localization properties Bioconjugate Chem. 10, 598-606 (Pubitemid 29355238)
7. Bongartz, J. P., Aubertin, A.-M., Milhaud, P. G., and Lebleu, B. (1994) Improved biological activity of antisense oligonucleotides conjugated to a fusogenic peptide Nucleic Acids Res. 22, 4681-4688 (Pubitemid 24354801)
8. Stetsenko, D. A., Arzumanov, A. A., Korshun, V. A., and Gait, M. J. (2000) Peptide conjugates of oligonucleotides as enhanced antisense agents Mol. Biol. 34, 852-859 (Pubitemid 33214745)
9. Gait, M. J. (2003) Peptide-mediated cellular delivery of antisense oligonucleotides and their analogues Cell. Mol. Life Sci. 60, 844-853 (Pubitemid 36735115)
10. Fidanza, J. A. and McLaughlin, L. W. (1989) Introduction of reporter groups at specific sites in DNA containing phosphorothioate diesters J. Am. Chem. Soc. 111, 9117-9119 (Pubitemid 20067546)
11. Gryaznov, S. M. and Letsinger, R. L. (1993) Chemical ligation of oligonucleotides in the presence and absence of a template J. Am. Chem. Soc. 115, 3808-3809
12. Lee, J. H., Wong, N. Y., Tan, L. H., Wang, Z., and Lu, Y. (2010) Controlled alignment of multiple proteins and nanoparticles with nanometer resolution via backbone-modified phosphorothioate DNA and bifunctional linkers J. Am. Chem. Soc. 132, 8906-8908
13. Lee, P. and Colman, R. F. (2005) Adenosine 2′-monophosphate, 5′- O -[ S -(4-succinimidylbenzophenone)-thiophosphate]: a new photoaffinity label for the coenzyme site of porcine NADP-specific isocitrate dehydrogenase Bioconjugate Chem. 16, 650-659 (Pubitemid 40696059)
14. Karim, A. S. and Weltman, J. K. (1993) Formation of protein conjugates of phosphorothioate nucleoside diphosphate beta-S Nucleic Acids Res. 21, 5281-5282 (Pubitemid 23342548)
15. Karim, A. S., Johansson, C. S., and Weltman, J. K. (1995) Maleimide-mediated protein conjugates of a nucleoside triphosphate gamma-S and an internucleotide phosphorothioate diester Nucleic Acids Res. 23, 2037-2040
16. Ahn, D.-R., Han, K.-C., Kwon, H. S., and Yang, E. G. (2007) ATP-conjugated peptide inhibitors for calmodulin-dependent protein kinase II Bioorg. Med. Chem. Lett. 17, 147-151 (Pubitemid 44959969)
17. Kaneda, M., Masuda, S., Tomohiro, T., and Hatanaka, Y. (2007) A simple and efficient photoaffinity method for proteomics of GTP-binding proteins ChemBioChem 8, 595-598 (Pubitemid 47194846)
18. Kim, S. H., Jeong, J. H., Mok, H., Lee, S. H., Kim, S. W., and Park, T. G. (2007) Folate receptor targeted delivery of polyelectrolyte complex micelles prepared from ODN-PEG-folate conjugate and cationic lipids Biotechnol. Prog. 23, 232-237 (Pubitemid 46293509)
19. Alam, M. R., Dixit, V., Kang, H., Li, Z.-B., Chen, X., Trejo, J., Fisher, M., and Juliano, R. L. (2008) Intracellular delivery of an anionic antisense oligonucleotide via receptor-mediated endocytosis Nucleic Acids Res. 36, 2764-2776 (Pubitemid 351659588)
20. Rabe, K. S. and Niemeyer, C. M. (2011) Selective covalent conjugation of phosphorothioate DNA oligonucleotides with streptavidin Molecules 16, 6916-6926
21. Hussain, S., Plückthun, A., Allen, T. M., and Zangemeister-Wittke, U. (2006) Chemosensitization of carcinoma cells using epithelial cell adhesion molecule-targeter liposomal antisense against bcl-2/bcl-xL Mol. Cancer Ther. 5, 3170-3180 (Pubitemid 46092060)
22. Sassolas, A., Leca-Bouvier, B. D., and Blum, L. J. (2008) DNA biosensors and microarrays Chem. Rev. 108, 109-139 (Pubitemid 351176406)
23. Williams, B. A. R., Diehnelt, C. W., Belcher, P., Greving, M., Woodbury, N. W., Johnston, S. A., and Chaput, J. C. (2009) Creating protein affinity reagents by combining peptide ligands on synthetic DNA scaffolds J. Am. Chem. Soc. 131, 17233-17241
24. Putta, M. R., Zhu, F.-G., Wang, D.-Q., Bhagat, L., Dai, M., Kandimalla, E. R., and Agrawal, S. (2010) Peptide conjugation at the 5′-end of oligodeoxynucleotides abrogates Toll-like receptor 9-mediated immune stimulatory activity Bioconjugate Chem. 21, 39-45
25. Niemeyer, C. M. (2010) Semisynthetic DNA-protein conjugates for biosensing and nanofabrication Angew. Chem., Int. Ed. 49, 1200-1216
26. Yanai, H., Chiba, S., Ban, T., Nakaima, Y., Onoe, T., Honda, K., Ohdan, H., and Taniguchi, T. (2011) Suppression of immune responses by nonimmunogenic oligodeoxynucleotides with high affinity for high-mobility group box proteins (HMGBs) Proc. Natl. Acad. Sci. U.S.A. 108, 11542-11547
27. Saánchez, A., Pedroso, E., and Grandas, A. (2011) Maleimide-dimethylfuran exo adducts: Effective maleimide protection in the synthesis of oligonucleotide conjugates Org. Lett. 13, 4364-4367
28. Iyer, R. P., Egan, W., Regan, J. B., and Beaucage, S. L. (1990) 3 H -1,2-benzodithiole-3-one 1,1-dioxide as an improved sulfurizing reagent in the solid-phase synthesis of oligodeoxyribonucleoside phosphorothioates J. Am. Chem. Soc. 112, 1253-1254 (Pubitemid 20127085)
29. Hill, K. W., Taunton-Rigby, J., Carter, J. D., Kropp, E., Vagle, K., Pieken, W., McGee, D. P., Husar, G. M., Leuck, M., Anziano, D. J., and Sebesta, D. P. (2001) Diels-Alder bioconjugation of diene-modified oligonucleotides J. Org. Chem. 66, 5352-5358 (Pubitemid 32878885)
30. Pulido, D., Loápez-Alonso, J. P., Marchaán, V., Gonzaález, C., Grandas, A., and Laurents, D. V. (2008) Preparation of ribonuclease S domain-swapped dimers conjugated with DNA and PNA: Modulating the activity of ribonucleases Bioconjugate Chem. 19, 263-270 (Pubitemid 351213858)
31. Marchaán, V., Ortega, S., Pulido, D., Pedroso, E., and Grandas, A. (2006) Diels-Alder cycloadditions in water for the straightforward preparation of peptide-oligonucleotide conjugates Nucleic Acids Res. 34, e24
32. Ellman, G. L (1959) Tissue sulfhydryl groups Arch. Biochem. Biophys. 82, 70-77
33. Ortega, S., Marchaán, V., and Grandas, A. unpublished results.
34. Lo Conte, M., Pacifico, S., Chambery, A., Marra, A., and Dondoni, A. (2010) Photoinduced addition of glycosyl thiols to alkynyl peptides: use of free-radical thiol-yne coupling for post-translational double-glycosylation of peptides J. Org. Chem. 75, 4644-4647
35. Ashley, G. W. and Kushlan, D. M. (1991) Chemical synthesis of oligodeoxynucleotide dumbbells Biochemistry 30, 2927-2933