Nucleic Acids Research, Vol 27, Issue 11 2387-2392, Copyright © 1999 by Oxford University Press
K Yamana, R Iwase, S Furutani, H Tsuchida, H Zako, T Yamaoka and A Murakami
Oligonucleotide 9mers containing 2'-O-(1-pyrenylmethyl)uridine [U(pyr)] at
the center position were synthesized by using a protected U(pyr)
phosphoramidite. The UV melting behaviors indicate that the pyrene-
modified oligonucleotides can bind to both their complementary DNA and RNA
in aqueous solution. When compared with the unmodified oligonucleotides,
the pyrene-modified oligonucleotides showed higher affinity for DNA while
exhibiting lower affinity for RNA. The pyrene- modified oligonucleotides in
diluted solution exhibited fluorescence typical of pyrene monomer emission
[lambdamax 378 (band I) and 391 nm (band III)]. When these oligomers bound
to DNA, the fluorescence intensity ratio of band III/band I was increased.
With this fluorescence change, a new broad emission (lambdamax 450 nm) due
to exciplex between the pyrene and an adjacent nucleobase appeared. In
contrast, addition of RNA to the pyrene oligonucleotides resulted in
enhancement of the pyrene monomer emission with decrease in the
fluorescence band ratio. The extent of the emission enhancement was found
to be highly dependent on the nucleobase adjacent to the U(pyr) in the
pyrene oligomers. The pyrene oligonucleotide containing dC at the 3'-site
of the modification showed remarkable increase (approximately 250 times) in
fluorescence (375 nm) upon binding to complementary RNA. The present
findings would open the way to the design of a highly sensitive fluorescent
probe of RNA.
ARTICLES
2'-Pyrene modified oligonucleotide provides a highly sensitive fluorescent probe of RNA
Department of Applied Chemistry, Himeji Institute of Technology, 2167 Shosha, Himeji, Hyogo 671-2201, Japan.
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