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Title: Base-sequence dependence of emission lifetimes for DNA oligomers and duplexes covalently labeled with pyrene: Relative electron-transfer quenching efficiencies of A, G, C, and T nucleosides toward pyrene

Abstract

This paper reports both continuous and time-resolved spectroscopic studies of the emission properties of photoexcited pyrene labels covalently attached to uridine nucleosides and oligonucleotides. For all nucleic acid systems, uridine is substituted with pyrene at the 2`-oxygen position, 2`-O-[hexyl-N-(1-pyrenepropylcarbonyl)amino]uridine, U(12){sup *} . Three types of nucleic nucleic acid systems are investigated: the 5`-OH (1) and the 5`-ODMT (2) substituted U(12){sup *}-nucleosides; four pentameric oligonucleotides, X{sub 2}U(12){sup *}X{sub 2}, where X is 2`-deoxyadenosine (A), 2`-deoxyguanosine (G), 2`-deoxythymidine (T), or 2`-deoxycytidine (C); and four duplexes with 18 base pairs each containing one strand with a central U(12){sup *} label. The longest {pi},{pi}{sup *} emission lifetimes of U(12){sup *}-labeled DNA duplexes exceed those of the corresponding parameters. A measure of duplex-induced restricted access pyrene{sup *} to base-paired nucleosides in double-strand (ds) versus single-strand (ss) DNA can be obtained. 111 refs., 6 figs., 6 tabs.

Authors:
;  [1]; ; ;  [2]
  1. Isis Pharmaceuticals, Inc., Carlsbad, CA (United States)
  2. Georgia State Univ., Atlanta, GA (United States)
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
174263
Resource Type:
Journal Article
Journal Name:
Journal of Physical Chemistry
Additional Journal Information:
Journal Volume: 99; Journal Issue: 48; Other Information: PBD: 30 Nov 1995
Country of Publication:
United States
Language:
English
Subject:
55 BIOLOGY AND MEDICINE, BASIC STUDIES; 40 CHEMISTRY; 66 PHYSICS; URIDINE; ELECTRON TRANSFER; EMISSION SPECTRA; NUCLEOSIDES; OLIGONUCLEOTIDES; LABELLING; PYRENE; DNA

Citation Formats

Manoharan, M, Tivel, K L, Zhao, M, Nafisi, K, and Netzel, T L. Base-sequence dependence of emission lifetimes for DNA oligomers and duplexes covalently labeled with pyrene: Relative electron-transfer quenching efficiencies of A, G, C, and T nucleosides toward pyrene. United States: N. p., 1995. Web. doi:10.1021/j100048a024.
Manoharan, M, Tivel, K L, Zhao, M, Nafisi, K, & Netzel, T L. Base-sequence dependence of emission lifetimes for DNA oligomers and duplexes covalently labeled with pyrene: Relative electron-transfer quenching efficiencies of A, G, C, and T nucleosides toward pyrene. United States. doi:10.1021/j100048a024.
Manoharan, M, Tivel, K L, Zhao, M, Nafisi, K, and Netzel, T L. Thu . "Base-sequence dependence of emission lifetimes for DNA oligomers and duplexes covalently labeled with pyrene: Relative electron-transfer quenching efficiencies of A, G, C, and T nucleosides toward pyrene". United States. doi:10.1021/j100048a024.
@article{osti_174263,
title = {Base-sequence dependence of emission lifetimes for DNA oligomers and duplexes covalently labeled with pyrene: Relative electron-transfer quenching efficiencies of A, G, C, and T nucleosides toward pyrene},
author = {Manoharan, M and Tivel, K L and Zhao, M and Nafisi, K and Netzel, T L},
abstractNote = {This paper reports both continuous and time-resolved spectroscopic studies of the emission properties of photoexcited pyrene labels covalently attached to uridine nucleosides and oligonucleotides. For all nucleic acid systems, uridine is substituted with pyrene at the 2`-oxygen position, 2`-O-[hexyl-N-(1-pyrenepropylcarbonyl)amino]uridine, U(12){sup *} . Three types of nucleic nucleic acid systems are investigated: the 5`-OH (1) and the 5`-ODMT (2) substituted U(12){sup *}-nucleosides; four pentameric oligonucleotides, X{sub 2}U(12){sup *}X{sub 2}, where X is 2`-deoxyadenosine (A), 2`-deoxyguanosine (G), 2`-deoxythymidine (T), or 2`-deoxycytidine (C); and four duplexes with 18 base pairs each containing one strand with a central U(12){sup *} label. The longest {pi},{pi}{sup *} emission lifetimes of U(12){sup *}-labeled DNA duplexes exceed those of the corresponding parameters. A measure of duplex-induced restricted access pyrene{sup *} to base-paired nucleosides in double-strand (ds) versus single-strand (ss) DNA can be obtained. 111 refs., 6 figs., 6 tabs.},
doi = {10.1021/j100048a024},
journal = {Journal of Physical Chemistry},
number = 48,
volume = 99,
place = {United States},
year = {1995},
month = {11}
}