Excited state properties of the N-(deoxyguanosin-8-yl)-2-aminofluorene adducts.

L. P. van Houte, R. van Grondelle, J. Retèl, J. G. Westra, D. Zinger, J. C. Sutherland, S. K. Kim, Nicholas Geacintov

Research output: Contribution to journalArticle

Abstract

The spectroscopic characteristics of adducts derived from the covalent binding of the carcinogen 2-aminofluorene to the C8 position of deoxyguanosine [N-(deoxyguanosin-8-yl)-2-amino-fluorene, dGuo-C8-AF], and from an adduct of similar structure formed with the synthetic polynucleotide poly(dG-dC).poly(dG-dC), were investigated. At 77 K both adducts are characterized by well-defined and rather narrow fluorescence emission spectra with maxima at 370 and 390 nm characteristic of the aromatic, monomolecular 2-aminofluorene (AF) residue. In contrast, at room temperature, the fluorescence is characterized by a broad, structureless emission band with a maximum at 460 nm in aqueous mixtures, shifting to 415 nm in solvents of lower polarity (100% propanol); the maxima are located at intermediate wavelengths in solutions of different propanol/water compositions, and this emission is attributed to an excited state complex (exciplex). The fluorescence quantum yield decreases when either the solvent polarity or the temperature are increased, varying from 5.4% (100% propanol) to 0.04-0.05% (100% H2O). The fluorescence decay profiles of dGuo-C8-AF adducts (measured at the National Synchrotron Light Source facility at the Brookhaven National Laboratory) can be roughly, but not exactly, modeled in terms of two exponential decay components in the range of about 0.3-1.0 ns with the propanol concentration greater than 60%; at lower propanol concentrations, a single short lifetime is observed and in 100% water solutions its value is 0.08 ns. The shorter lifetime, favored in solvent mixtures of higher polarities, is attributed to an exciplex with significant charge-transfer character.(ABSTRACT TRUNCATED AT 250 WORDS)

Original languageEnglish (US)
Pages (from-to)387-394
Number of pages8
JournalPhotochemistry and Photobiology
Volume49
Issue number4
StatePublished - Apr 1989

Fingerprint

1-Propanol
Excited states
adducts
fluorescence
polarity
Fluorescence
excitation
carcinogens
polynucleotides
life (durability)
decay
Polynucleotides
Synchrotrons
Temperature
Water
water
low concentrations
Quantum yield
light sources
synchrotrons

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biophysics

Cite this

van Houte, L. P., van Grondelle, R., Retèl, J., Westra, J. G., Zinger, D., Sutherland, J. C., ... Geacintov, N. (1989). Excited state properties of the N-(deoxyguanosin-8-yl)-2-aminofluorene adducts. Photochemistry and Photobiology, 49(4), 387-394.

Excited state properties of the N-(deoxyguanosin-8-yl)-2-aminofluorene adducts. / van Houte, L. P.; van Grondelle, R.; Retèl, J.; Westra, J. G.; Zinger, D.; Sutherland, J. C.; Kim, S. K.; Geacintov, Nicholas.

In: Photochemistry and Photobiology, Vol. 49, No. 4, 04.1989, p. 387-394.

Research output: Contribution to journalArticle

van Houte, LP, van Grondelle, R, Retèl, J, Westra, JG, Zinger, D, Sutherland, JC, Kim, SK & Geacintov, N 1989, 'Excited state properties of the N-(deoxyguanosin-8-yl)-2-aminofluorene adducts.', Photochemistry and Photobiology, vol. 49, no. 4, pp. 387-394.
van Houte LP, van Grondelle R, Retèl J, Westra JG, Zinger D, Sutherland JC et al. Excited state properties of the N-(deoxyguanosin-8-yl)-2-aminofluorene adducts. Photochemistry and Photobiology. 1989 Apr;49(4):387-394.
van Houte, L. P. ; van Grondelle, R. ; Retèl, J. ; Westra, J. G. ; Zinger, D. ; Sutherland, J. C. ; Kim, S. K. ; Geacintov, Nicholas. / Excited state properties of the N-(deoxyguanosin-8-yl)-2-aminofluorene adducts. In: Photochemistry and Photobiology. 1989 ; Vol. 49, No. 4. pp. 387-394.
@article{12b6ac80824347848b826477090790c7,
title = "Excited state properties of the N-(deoxyguanosin-8-yl)-2-aminofluorene adducts.",
abstract = "The spectroscopic characteristics of adducts derived from the covalent binding of the carcinogen 2-aminofluorene to the C8 position of deoxyguanosine [N-(deoxyguanosin-8-yl)-2-amino-fluorene, dGuo-C8-AF], and from an adduct of similar structure formed with the synthetic polynucleotide poly(dG-dC).poly(dG-dC), were investigated. At 77 K both adducts are characterized by well-defined and rather narrow fluorescence emission spectra with maxima at 370 and 390 nm characteristic of the aromatic, monomolecular 2-aminofluorene (AF) residue. In contrast, at room temperature, the fluorescence is characterized by a broad, structureless emission band with a maximum at 460 nm in aqueous mixtures, shifting to 415 nm in solvents of lower polarity (100{\%} propanol); the maxima are located at intermediate wavelengths in solutions of different propanol/water compositions, and this emission is attributed to an excited state complex (exciplex). The fluorescence quantum yield decreases when either the solvent polarity or the temperature are increased, varying from 5.4{\%} (100{\%} propanol) to 0.04-0.05{\%} (100{\%} H2O). The fluorescence decay profiles of dGuo-C8-AF adducts (measured at the National Synchrotron Light Source facility at the Brookhaven National Laboratory) can be roughly, but not exactly, modeled in terms of two exponential decay components in the range of about 0.3-1.0 ns with the propanol concentration greater than 60{\%}; at lower propanol concentrations, a single short lifetime is observed and in 100{\%} water solutions its value is 0.08 ns. The shorter lifetime, favored in solvent mixtures of higher polarities, is attributed to an exciplex with significant charge-transfer character.(ABSTRACT TRUNCATED AT 250 WORDS)",
author = "{van Houte}, {L. P.} and {van Grondelle}, R. and J. Ret{\`e}l and Westra, {J. G.} and D. Zinger and Sutherland, {J. C.} and Kim, {S. K.} and Nicholas Geacintov",
year = "1989",
month = "4",
language = "English (US)",
volume = "49",
pages = "387--394",
journal = "Photochemistry and Photobiology",
issn = "0031-8655",
publisher = "Wiley-Blackwell",
number = "4",

}

TY - JOUR

T1 - Excited state properties of the N-(deoxyguanosin-8-yl)-2-aminofluorene adducts.

AU - van Houte, L. P.

AU - van Grondelle, R.

AU - Retèl, J.

AU - Westra, J. G.

AU - Zinger, D.

AU - Sutherland, J. C.

AU - Kim, S. K.

AU - Geacintov, Nicholas

PY - 1989/4

Y1 - 1989/4

N2 - The spectroscopic characteristics of adducts derived from the covalent binding of the carcinogen 2-aminofluorene to the C8 position of deoxyguanosine [N-(deoxyguanosin-8-yl)-2-amino-fluorene, dGuo-C8-AF], and from an adduct of similar structure formed with the synthetic polynucleotide poly(dG-dC).poly(dG-dC), were investigated. At 77 K both adducts are characterized by well-defined and rather narrow fluorescence emission spectra with maxima at 370 and 390 nm characteristic of the aromatic, monomolecular 2-aminofluorene (AF) residue. In contrast, at room temperature, the fluorescence is characterized by a broad, structureless emission band with a maximum at 460 nm in aqueous mixtures, shifting to 415 nm in solvents of lower polarity (100% propanol); the maxima are located at intermediate wavelengths in solutions of different propanol/water compositions, and this emission is attributed to an excited state complex (exciplex). The fluorescence quantum yield decreases when either the solvent polarity or the temperature are increased, varying from 5.4% (100% propanol) to 0.04-0.05% (100% H2O). The fluorescence decay profiles of dGuo-C8-AF adducts (measured at the National Synchrotron Light Source facility at the Brookhaven National Laboratory) can be roughly, but not exactly, modeled in terms of two exponential decay components in the range of about 0.3-1.0 ns with the propanol concentration greater than 60%; at lower propanol concentrations, a single short lifetime is observed and in 100% water solutions its value is 0.08 ns. The shorter lifetime, favored in solvent mixtures of higher polarities, is attributed to an exciplex with significant charge-transfer character.(ABSTRACT TRUNCATED AT 250 WORDS)

AB - The spectroscopic characteristics of adducts derived from the covalent binding of the carcinogen 2-aminofluorene to the C8 position of deoxyguanosine [N-(deoxyguanosin-8-yl)-2-amino-fluorene, dGuo-C8-AF], and from an adduct of similar structure formed with the synthetic polynucleotide poly(dG-dC).poly(dG-dC), were investigated. At 77 K both adducts are characterized by well-defined and rather narrow fluorescence emission spectra with maxima at 370 and 390 nm characteristic of the aromatic, monomolecular 2-aminofluorene (AF) residue. In contrast, at room temperature, the fluorescence is characterized by a broad, structureless emission band with a maximum at 460 nm in aqueous mixtures, shifting to 415 nm in solvents of lower polarity (100% propanol); the maxima are located at intermediate wavelengths in solutions of different propanol/water compositions, and this emission is attributed to an excited state complex (exciplex). The fluorescence quantum yield decreases when either the solvent polarity or the temperature are increased, varying from 5.4% (100% propanol) to 0.04-0.05% (100% H2O). The fluorescence decay profiles of dGuo-C8-AF adducts (measured at the National Synchrotron Light Source facility at the Brookhaven National Laboratory) can be roughly, but not exactly, modeled in terms of two exponential decay components in the range of about 0.3-1.0 ns with the propanol concentration greater than 60%; at lower propanol concentrations, a single short lifetime is observed and in 100% water solutions its value is 0.08 ns. The shorter lifetime, favored in solvent mixtures of higher polarities, is attributed to an exciplex with significant charge-transfer character.(ABSTRACT TRUNCATED AT 250 WORDS)

UR - http://www.scopus.com/inward/record.url?scp=0024652081&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0024652081&partnerID=8YFLogxK

M3 - Article

VL - 49

SP - 387

EP - 394

JO - Photochemistry and Photobiology

JF - Photochemistry and Photobiology

SN - 0031-8655

IS - 4

ER -