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Title: Fluorescence of tetrols, tetrols complexed with DNA, and benzo[a]pyrene-DNA adducts in methanol/water solutions

Abstract

Several solution fluorescence parameters were acquired for the four tetrol hydrolysis products of benzo[a]pyrene-trans-7,8-dihydrodiol-9,10-epoxide (BPDE)-DNA adducts, tetrols complexed with DNA, and BPDE-DNA adducts in several methanol/water solvents. The relative polarity of the environment for the tetrols and BPDE-DNA adducts was determined by using a modified definition of the R value that is commonly employed for pyrene. The R values for the tetrols and BPDE-DNA adducts were calculated by obtaining the ratios of the intensities of the two major fluorescence emission bands at 380 and 400 nm (I{sub 380}/I{sub 400}). The positions of the hydroxyl groups on the hydroaromatic ring of the tetrols were compared in reference to the R values and the changes in the R values as a function of methanol/water composition. This approach resulted in a method for determining whether the hydroxyl groups in the 9 and 10 positions were on the same side or opposite sides of a hydroaromatic ring. The tetrols intercalated between the DNA bases showed quite different fluorescence spectra compared to tetrols not complexed with DNA. Also, the quasi-intercalated BPDE-DNA adducts gave significant changes in the R values with an increase in methanol in the solvent, and excitation spectra showed large shifts and changesmore » in shape with an increase in methanol. The approaches developed provide unique structural and polarity information on tetrols and BPDE-DNA adducts. (c) 2000 Society for Applied Spectroscopy.« less

Authors:
 [1];  [2]
  1. Department of Chemistry, Stephen F. Austin State University, Nacogdoches, Texas 75962 (United States)
  2. Department of Chemistry, University of Wyoming, Laramie, Wyoming 82071 (United States)
Publication Date:
OSTI Identifier:
20217320
Resource Type:
Journal Article
Journal Name:
Applied Spectroscopy
Additional Journal Information:
Journal Volume: 54; Journal Issue: 2; Other Information: PBD: Feb 2000; Journal ID: ISSN 0003-7028
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; FLUORESCENCE SPECTROSCOPY; POLYCYCLIC AROMATIC HYDROCARBONS; DNA; AQUEOUS SOLUTIONS; VISIBLE SPECTRA; EXCITED STATES; ULTRAVIOLET SPECTRA; EXPERIMENTAL DATA

Citation Formats

Steinbach, Paul B, and Hurtubise, Robert J. Fluorescence of tetrols, tetrols complexed with DNA, and benzo[a]pyrene-DNA adducts in methanol/water solutions. United States: N. p., 2000. Web. doi:10.1366/0003702001949249.
Steinbach, Paul B, & Hurtubise, Robert J. Fluorescence of tetrols, tetrols complexed with DNA, and benzo[a]pyrene-DNA adducts in methanol/water solutions. United States. https://doi.org/10.1366/0003702001949249
Steinbach, Paul B, and Hurtubise, Robert J. Tue . "Fluorescence of tetrols, tetrols complexed with DNA, and benzo[a]pyrene-DNA adducts in methanol/water solutions". United States. https://doi.org/10.1366/0003702001949249.
@article{osti_20217320,
title = {Fluorescence of tetrols, tetrols complexed with DNA, and benzo[a]pyrene-DNA adducts in methanol/water solutions},
author = {Steinbach, Paul B and Hurtubise, Robert J},
abstractNote = {Several solution fluorescence parameters were acquired for the four tetrol hydrolysis products of benzo[a]pyrene-trans-7,8-dihydrodiol-9,10-epoxide (BPDE)-DNA adducts, tetrols complexed with DNA, and BPDE-DNA adducts in several methanol/water solvents. The relative polarity of the environment for the tetrols and BPDE-DNA adducts was determined by using a modified definition of the R value that is commonly employed for pyrene. The R values for the tetrols and BPDE-DNA adducts were calculated by obtaining the ratios of the intensities of the two major fluorescence emission bands at 380 and 400 nm (I{sub 380}/I{sub 400}). The positions of the hydroxyl groups on the hydroaromatic ring of the tetrols were compared in reference to the R values and the changes in the R values as a function of methanol/water composition. This approach resulted in a method for determining whether the hydroxyl groups in the 9 and 10 positions were on the same side or opposite sides of a hydroaromatic ring. The tetrols intercalated between the DNA bases showed quite different fluorescence spectra compared to tetrols not complexed with DNA. Also, the quasi-intercalated BPDE-DNA adducts gave significant changes in the R values with an increase in methanol in the solvent, and excitation spectra showed large shifts and changes in shape with an increase in methanol. The approaches developed provide unique structural and polarity information on tetrols and BPDE-DNA adducts. (c) 2000 Society for Applied Spectroscopy.},
doi = {10.1366/0003702001949249},
url = {https://www.osti.gov/biblio/20217320}, journal = {Applied Spectroscopy},
issn = {0003-7028},
number = 2,
volume = 54,
place = {United States},
year = {2000},
month = {2}
}