Chemoselective oxime and thiazolidine bond formation: A versatile and efficient route to the preparation of 3′-peptide-oligonucleotide conjugates

Nucleosides, Nucleotides and Nucleic Acids

Volumn 23, Issue 10, 2004, Pages 1657-1666

  Villien, Mathilde ^a   Defrancq, Eric ^a   Dumy, Pascal ^a  

^a Centre National de la Recherche Scientifique   (France)

Author keywords

Conjugation; DNA; Oxime; Peptide; Thiazolidine

Indexed keywords

1,2 DIOL DERIVATIVE; 3' PEPTIDE OLIGONUCLEOTIDE CONJUGATE; ALDEHYDE; CYSTEINE; OLIGONUCLEOTIDE; OXIME; PEPTIDE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMOSENSITIVITY; CONJUGATION; HYBRIDIZATION; OXIDATION; PROTEIN HYDROLYSIS; PROTEIN STABILITY; PROTEIN SYNTHESIS; REACTION ANALYSIS;

OLIGONUCLEOTIDES; OXIMES; PEPTIDES; SPECTROPHOTOMETRY, ULTRAVIOLET; THIAZOLES;

EID: 9644265266     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-200031467     Document Type: Article

References (23)

1. Buchini, S.; Leumann, C.J. Recent improvements in antigene technology. Curr. Opin. Chem. Biol. 2003, 7, 717-726.
2. Lee, L.K.; Roth, C.M. Antisense technology in molecular and cellular bioengineering. Curr. Opin. Biotechnol. 2003, 14, 505-511.
3. Tuschl, T. RNA interference and small interfering RNAs. Chem. Biochem. 2001, 2, 239-245.
4. Manoharan, M. Oligonucleotide conjugates. In Antisense Drug Technology, Principles, Strategies and Applications; Crooke, S.T., Ed.; M. Dekker: New-York-Basel, 2001; 391-469.
5. Tung, C.-H.; Stein, S. Preparation and applications of peptide-oligonucleotide conjugates. Bioconjug. Chem. 2000, 11, 605-618 and references cited therein.
6. Antopolsky, M.; Azhayeva, E.; Tengvall, U.; Azhayev, A. Towards a general method for the stepwise solid phase synthesis of peptide-oligonucleotide conjugates. Tetrahedron Lett. 2002, 43, 527-530.
7. Truffert, J.-C.; Asseline, U.; Brack, A.; Thuong, N.T. Synthesis, purification and characterization of two peptide-oligonucleotide conjugates as potential artificial nucleases. Tetrahedron 1996, 52, 3005-3016.
8. Harrison, J.G.; Balasubramanian, S. Synthesis and hybridization analysis of a small library of peptide-oligonucleotide conjugates. Nucleic Acids Res. 1998, 26, 3136-3145.
9. Vivès, E.; Lebleu, B. Selective coupling of a highly basic peptide to an oligonucleotide. Tetrahedron Lett. 1997, 38, 1183-1186.
10. Mier, W.; Erijta, R.; Mohammed, A.; Haberkorn, U.; Eisenhut, M. Preparation and evaluation of tumor-targeting peptide-oligonucleotide conjugates. Bioconjug. Chem. 2000, 11, 855-860.
11. Kahl, J.D.; Greenberg, M.M. Solution-phase bioconjugate synthesis using protected oligonucleotides containing 3′-alkyl carboxylic acids. J. Org. Chem. 1999, 64, 507-510.
12. McMinn, D.L.; Greenberg, M.M. Postsynthetic conjugation of protected oligonucleotides containing 3′-alkylamines. J. Am. Chem. Soc. 1998, 120, 3289-3294.
13. Zhang, L.; Torgerson, T.R.; Liu, X.-Y.; Timmons, S.; Colosia, A.D.; Hawiger, J.; Tam, J.P. Preparation of functionally active cell-permeable peptides by single-step ligation of two peptide modules. Proc. Natl. Acad. Sci. U. S. A. 1998, 95, 9184-9189.
14. Cervigny, S.E.; Dumy, P.; Mutter, M. Synthesis of glycopeptides and lipopeptides by chemoselective ligation. Angew. Chem., Int. Ed. Engl. 1996, 35, 1230-1232.
15. Defrancq, E.; Hoang, A.; Vinet, F.; Dumy, P. Oxime bond formation for the covalent attachment of oligonucleotides on glass support. Bioorg. Med. Chem. Lett. 2003, 13, 2683-2686.
16. Salo, H.; Virta, P.; Hakala, H.; Prakash, T.P.; Kawasaki, A.M.; Manoharan, M.; Lönnberg, H. Aminooxy functionalized oligonucleotides: preparation, on-support derivatization, and postsynthetic attachment to polymer support. Bioconjug. Chem. 1999, 10, 815-823.
17. Forget, D.; Boturyn, D.; Defrancq, E.; Lhomme, J.; Dumy, P. Highly efficient synthesis of peptide-oligonucleotide conjugates: chemoselective oxime and thiazolidine formation. Chem. Eur. J. 2001, 7, 3976-3984.
18. Zatsepin, T.S.; Stetsenko, D.A.; Arzumanov, A.A.; Romanova, E.A.; Gait, M.J.; Oretskaya, T.S. Synthesis of peptide-oligonucleotide conjugates with single and multiple peptides attached to 2′-aldehydes through thiazolidine, oxime, and hydrazine linkages. Bioconjug. Chem. 2002, 13, 822-830.
19. 3 integrin for a new cancer therapy. Angew. Chem., Int. Ed. Engl. 1997, 36, 1374-1389.
20. Zanta, M.A.; Belguise-Valladier, P.; Behr, J.-P. Gene delivery: a single nuclear localization signal peptide is sufficient to carry DNA to the cell nucleus. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 91-96.
21. Matsuda, A.; Inada, M.; Nara, H.; Ohtsuka, E.; Ono, A. Incorporation of a mutagenic nucleoside, 5-formyl-2′-deoxyuridine, into an oligodeoxyribonucleotide. Bioorg. Med. Chem. Lett. 1993, 3, 2751-2754.
22. Forget, D.; Renaudet, O.; Boturyn, D.; Defrancq, E.; Dumy, P. 3′-Oligonucleotides conjugation via chemoselective oxime bond formation. Tetrahedron Lett. 2001, 42, 9171-9174.
23. Liu, C.-F.; Tam, J.P. Chemical ligation approach to form a peptide bond between unprotected peptide segments. Concept and model study. J. Am. Chem. Soc. 1994, 116, 4149-4153.