Synthesis of antisense oligonucleotides containing a photocleavable protecting group on a guanine base and their photoinduced duplex formation.
An oligonucleotide containing a photocleavable protecting group at a guanine base was synthesized to induce the duplex formation by photo-irradiation. Alpha-methyl-2-nitropiperonyl (MeNP) group was used for the photocleavable protecting group at O6 position of deoxyguanosine. The oligonucleotide containing MeNP group (MeNP-ODN:5'-dTTCTG(MeNP)TCTGT-3') was synthesized by phosphoramidite method. The MeNP group was found to be removable by UV irradiation at wavelength of 365 nm for 5 min in 98% yield. UV-melting temperature (Tm value) analysis indicated that the duplex of MeNP-ODN with the complementary RNA was significantly unstable compared with the unmodified DNA/RNA duplex (deltaTm = -25 degrees C). After UV irradiation at 365 nm, the Tm value of the mixture increased to the same as that of the unmodified duplex. These results suggest that the RNA binding ability of the MeNP-ODN can be induced by photocleavage of the MeNP group.
Iwase
Reiko
R
Department of Biosciences, Teikyo University of Science and Technology, 2525 Yatsusawa, Uenohara, Yamanashi, 609-0193, Japan.
Fukui
Udai
U
Kobori
Akio
A
Yamaoka
Tetsuji
T
Murakami
Akira
A
D052117:Benzodioxoles / Q000737:chemistry*; D003849:Deoxyguanosine / Q000031:analogs & derivatives*; D006147:Guanine / Q000737:chemistry; D016376:Oligonucleotides, Antisense / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D012313:RNA / Q000737:chemistry; D013696:Temperature; D014466:Ultraviolet Rays
D052117:Benzodioxoles; D016376:Oligonucleotides, Antisense; D006147:Guanine; D012313:RNA; D003849:Deoxyguanosine