TY - JOUR
T1 - Application of 2-amino-6-vinylpurine as an efficient agent for conjugation of oligonucleotides
AU - Ali, Md Monsur
AU - Nagatsugi, Fumi
AU - Sasaki, Shigeki
AU - Nakahara, Ryusuke
AU - Maeda, Minoru
N1 - Funding Information:
This work was supported by a grant-in-aid for scientific research (B) from the Japan Society for the Promotion of Science (JSPS); CREST from Japan Science and Technology Agency; RR2002 Advanced and Innovational Research Program in Life Sciences from the Ministry of Education, Culture, Sports, Science and Technology; the Japanese Government; and Kyushu University P&P “Green Chemistry.” We also thank Professor S. Futaki at Kyoto University for a kind gift of CysArg8.
PY - 2006/1/1
Y1 - 2006/1/1
N2 - Attempts have been made to conjugate a variety of molecules with oligonucleotides to achieve useful functions. In this study, we have established a new efficient method for post-synthetic conjugation of oligonucleotides with the use of the 2-amino-6-vinylpurine nucleoside. Amino nucleophiles form the corresponding conjugates under acidic conditions, whereas thiol nucleophiles reacted efficiently under alkaline conditions. Thus, glutathione and HS-Cys-(Arg)8 without protecting groups were efficiently conjugated to the 2-amino-6-vinylpurine-bearing ODN under alkaline conditions. The use of 2-amino-6-vinylpurine as an agent for conjugation is advantageous in that it is stable during the reaction and may be applied to conjugation of ODNs with multiple functional molecules.
AB - Attempts have been made to conjugate a variety of molecules with oligonucleotides to achieve useful functions. In this study, we have established a new efficient method for post-synthetic conjugation of oligonucleotides with the use of the 2-amino-6-vinylpurine nucleoside. Amino nucleophiles form the corresponding conjugates under acidic conditions, whereas thiol nucleophiles reacted efficiently under alkaline conditions. Thus, glutathione and HS-Cys-(Arg)8 without protecting groups were efficiently conjugated to the 2-amino-6-vinylpurine-bearing ODN under alkaline conditions. The use of 2-amino-6-vinylpurine as an agent for conjugation is advantageous in that it is stable during the reaction and may be applied to conjugation of ODNs with multiple functional molecules.
KW - 2-Amino-6-vinylpurine
KW - Antisense
KW - Conjugation
KW - Oligodeoxynucleotide
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U2 - 10.1080/15257770500446873
DO - 10.1080/15257770500446873
M3 - Article
C2 - 16541959
AN - SCOPUS:31644436268
SN - 1525-7770
VL - 25
SP - 159
EP - 169
JO - Nucleosides, Nucleotides and Nucleic Acids
JF - Nucleosides, Nucleotides and Nucleic Acids
IS - 2
ER -