Photoinduced electron transfer and fluorescence mechanisms in covalently linked polynuclear aromatic-nucleotide complexes

Nicholas E. Geacintov; Bing Mao; Luisa L. France; Rushen Zhao; Junxin Chen; Tong M. Liu; Nai Qi Ya; Leonid A. Margulis; John C. Sutherland

Photoinduced electron transfer and fluorescence mechanisms in covalently linked polynuclear aromatic-nucleotide complexes

Nicholas E. Geacintov, Bing Mao, Luisa L. France, Rushen Zhao, Junxin Chen, Tong M. Liu, Nai Qi Ya, Leonid A. Margulis, John C. Sutherland

Chemistry

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

Abstract

The fluorescence of polycyclic aromatic hydrocarbon-nucleic acid complexes is quenched by photoinduced electron transfer mechanisms in aqueous solutions at ambient temperatures. These effects are illustrated with the biologically important compound benzo[a]pyrene-7,8-diol-9,10-epoxide (BPDE), a mutagenic and carcinogenic metabolite of the environmental pollutant benzo[a]pyrene, which forms covalent mutagenic lesions with 2'-deoxyguanosine (dG) residues in DNA. The dependence of the fluorescence yield and fluorescence decay times of the covalent model adduct (+)-trans- BPDE-N²-dG as a function of temperature and methanol/water composition are described. Because of the sensitivity of the fluorescence of the pyrenyl residue to the polarity of the microenvironment, the magnitude of the fluorescence yield can be used to distinguish between highly hydrophobic (e.g., intercalation) and other more solvent-exposed BPDE- nucleic acid binding sites.

Original language	English (US)
Title of host publication	Proceedings of SPIE - The International Society for Optical Engineering
Publisher	Publ by Int Soc for Optical Engineering
Pages	774-783
Number of pages	10
ISBN (Print)	0819407860
State	Published - 1992
Event	Time-Resolved Laser Spectroscopy in Biochemistry III - Los Angeles, CA, USA Duration: Jan 20 1992 → Jan 22 1992

Publication series

Name	Proceedings of SPIE - The International Society for Optical Engineering
Volume	1640
ISSN (Print)	0277-786X

Other

Other	Time-Resolved Laser Spectroscopy in Biochemistry III
City	Los Angeles, CA, USA
Period	1/20/92 → 1/22/92

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Condensed Matter Physics
Computer Science Applications
Applied Mathematics
Electrical and Electronic Engineering

Cite this

Geacintov, N. E., Mao, B., France, L. L., Zhao, R., Chen, J., Liu, T. M., Ya, N. Q., Margulis, L. A., & Sutherland, J. C. (1992). Photoinduced electron transfer and fluorescence mechanisms in covalently linked polynuclear aromatic-nucleotide complexes. In Proceedings of SPIE - The International Society for Optical Engineering (pp. 774-783). (Proceedings of SPIE - The International Society for Optical Engineering; Vol. 1640). Publ by Int Soc for Optical Engineering.

Photoinduced electron transfer and fluorescence mechanisms in covalently linked polynuclear aromatic-nucleotide complexes. / Geacintov, Nicholas E.; Mao, Bing; France, Luisa L. et al.
Proceedings of SPIE - The International Society for Optical Engineering. Publ by Int Soc for Optical Engineering, 1992. p. 774-783 (Proceedings of SPIE - The International Society for Optical Engineering; Vol. 1640).

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

Geacintov, NE, Mao, B, France, LL, Zhao, R, Chen, J, Liu, TM, Ya, NQ, Margulis, LA & Sutherland, JC 1992, Photoinduced electron transfer and fluorescence mechanisms in covalently linked polynuclear aromatic-nucleotide complexes. in Proceedings of SPIE - The International Society for Optical Engineering. Proceedings of SPIE - The International Society for Optical Engineering, vol. 1640, Publ by Int Soc for Optical Engineering, pp. 774-783, Time-Resolved Laser Spectroscopy in Biochemistry III, Los Angeles, CA, USA, 1/20/92.

Geacintov NE, Mao B, France LL, Zhao R, Chen J, Liu TM et al. Photoinduced electron transfer and fluorescence mechanisms in covalently linked polynuclear aromatic-nucleotide complexes. In Proceedings of SPIE - The International Society for Optical Engineering. Publ by Int Soc for Optical Engineering. 1992. p. 774-783. (Proceedings of SPIE - The International Society for Optical Engineering).

Geacintov, Nicholas E. ; Mao, Bing ; France, Luisa L. et al. / Photoinduced electron transfer and fluorescence mechanisms in covalently linked polynuclear aromatic-nucleotide complexes. Proceedings of SPIE - The International Society for Optical Engineering. Publ by Int Soc for Optical Engineering, 1992. pp. 774-783 (Proceedings of SPIE - The International Society for Optical Engineering).

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title = "Photoinduced electron transfer and fluorescence mechanisms in covalently linked polynuclear aromatic-nucleotide complexes",

abstract = "The fluorescence of polycyclic aromatic hydrocarbon-nucleic acid complexes is quenched by photoinduced electron transfer mechanisms in aqueous solutions at ambient temperatures. These effects are illustrated with the biologically important compound benzo[a]pyrene-7,8-diol-9,10-epoxide (BPDE), a mutagenic and carcinogenic metabolite of the environmental pollutant benzo[a]pyrene, which forms covalent mutagenic lesions with 2'-deoxyguanosine (dG) residues in DNA. The dependence of the fluorescence yield and fluorescence decay times of the covalent model adduct (+)-trans- BPDE-N2-dG as a function of temperature and methanol/water composition are described. Because of the sensitivity of the fluorescence of the pyrenyl residue to the polarity of the microenvironment, the magnitude of the fluorescence yield can be used to distinguish between highly hydrophobic (e.g., intercalation) and other more solvent-exposed BPDE- nucleic acid binding sites.",

author = "Geacintov, {Nicholas E.} and Bing Mao and France, {Luisa L.} and Rushen Zhao and Junxin Chen and Liu, {Tong M.} and Ya, {Nai Qi} and Margulis, {Leonid A.} and Sutherland, {John C.}",

year = "1992",

language = "English (US)",

isbn = "0819407860",

series = "Proceedings of SPIE - The International Society for Optical Engineering",

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AU - Geacintov, Nicholas E.

AU - Mao, Bing

AU - France, Luisa L.

AU - Zhao, Rushen

AU - Chen, Junxin

AU - Liu, Tong M.

AU - Ya, Nai Qi

AU - Margulis, Leonid A.

AU - Sutherland, John C.

PY - 1992

Y1 - 1992

N2 - The fluorescence of polycyclic aromatic hydrocarbon-nucleic acid complexes is quenched by photoinduced electron transfer mechanisms in aqueous solutions at ambient temperatures. These effects are illustrated with the biologically important compound benzo[a]pyrene-7,8-diol-9,10-epoxide (BPDE), a mutagenic and carcinogenic metabolite of the environmental pollutant benzo[a]pyrene, which forms covalent mutagenic lesions with 2'-deoxyguanosine (dG) residues in DNA. The dependence of the fluorescence yield and fluorescence decay times of the covalent model adduct (+)-trans- BPDE-N2-dG as a function of temperature and methanol/water composition are described. Because of the sensitivity of the fluorescence of the pyrenyl residue to the polarity of the microenvironment, the magnitude of the fluorescence yield can be used to distinguish between highly hydrophobic (e.g., intercalation) and other more solvent-exposed BPDE- nucleic acid binding sites.

AB - The fluorescence of polycyclic aromatic hydrocarbon-nucleic acid complexes is quenched by photoinduced electron transfer mechanisms in aqueous solutions at ambient temperatures. These effects are illustrated with the biologically important compound benzo[a]pyrene-7,8-diol-9,10-epoxide (BPDE), a mutagenic and carcinogenic metabolite of the environmental pollutant benzo[a]pyrene, which forms covalent mutagenic lesions with 2'-deoxyguanosine (dG) residues in DNA. The dependence of the fluorescence yield and fluorescence decay times of the covalent model adduct (+)-trans- BPDE-N2-dG as a function of temperature and methanol/water composition are described. Because of the sensitivity of the fluorescence of the pyrenyl residue to the polarity of the microenvironment, the magnitude of the fluorescence yield can be used to distinguish between highly hydrophobic (e.g., intercalation) and other more solvent-exposed BPDE- nucleic acid binding sites.

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M3 - Conference contribution

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SN - 0819407860

T3 - Proceedings of SPIE - The International Society for Optical Engineering

SP - 774

EP - 783

BT - Proceedings of SPIE - The International Society for Optical Engineering

PB - Publ by Int Soc for Optical Engineering

T2 - Time-Resolved Laser Spectroscopy in Biochemistry III

Y2 - 20 January 1992 through 22 January 1992

ER -

Photoinduced electron transfer and fluorescence mechanisms in covalently linked polynuclear aromatic-nucleotide complexes

Abstract

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