Efficient cross-linking to cytidine using substituted phenylsulfide derivatives of 2-amino-6-vinylpurine nucleoside via synchronous activation within duplex.
We have previously described that oligonucleotides containing phenylsulfoxide derivative of 2-amino-6-vinyulpurine nucleoside analog (1) are activated within duplex to form cross-link toward cytidine selectively at the target site. The new cross-linking motif with phenylsulfoxide structure (2) is characteristic in that the stable precursor may be transformed automatically within duplex to a reactive species. To search for more stable precursor susceptible for activation, we designed a series of substituted phenylsulfide analogs of 1. It has been demonstrated that introduction of an electron-donating group on the phenyl ring improved the cross-linking reaction. Particularly, 2-carboxyphenyl sulfide derivative exhibited cross-linking as effectively as phenylsulfoxide derivative without chemical oxidation prior to cross-linking.
Kawasaki
T
T
Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan.
Nagatsugi
F
F
Maeda
M
M
Sasaki
S
S
D001483:Base Sequence; D003432:Cross-Linking Reagents; D003562:Cytidine / Q000737:chemistry*; D015195:Drug Design; D008722:Methods; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D011687:Purines / Q000737:chemistry*; D013440:Sulfides; D014753:Vinyl Compounds / Q000737:chemistry*
C432203:2-amino-6-vinylpurine; D003432:Cross-Linking Reagents; D009838:Oligodeoxyribonucleotides; D011687:Purines; D013440:Sulfides; D014753:Vinyl Compounds; D003562:Cytidine