Photoinduced electron transfer and strand cleavage in pyrenyl-DNA complexes and adducts

Nicholas E. Geacintov; Kyril Solntsev; Lawrence W. Johnson; Junxin Chen; Alexander D. Kolbanovskiy; Tongming Liu; Vladimir Ya Shafirovich

doi:10.1002/(sici)1099-1395(199808/09)11:8/9<561::aid-poc61>3.0.co;2-a

Photoinduced electron transfer and strand cleavage in pyrenyl-DNA complexes and adducts

Nicholas E. Geacintov, Kyril Solntsev, Lawrence W. Johnson, Junxin Chen, Alexander D. Kolbanovskiy, Tongming Liu, Vladimir Ya Shafirovich

Chemistry

Research output: Contribution to journal › Review article › peer-review

Abstract

The fluorescence of pyrenyl residues in complexes with the nucleic acid bases G, C and T, but not A, is strongly quenched by photoinduced electron transfer mechanisms. Site-specifically modified 11-mer oligonucleotide duplexes containing a single modified guanosyl base G* bearing a covalently attached pyrenyl residue were prepared in order to probe for photochemical damage associated with these photoinduced electron transfer reactions. When the pyrenyl residue positioned at G* is photoexcited with 355 nm light, direct strand cleavage is observed at that site with low quantum yield. Frank strand breaks are also observed up to five base pairs away from G*, suggesting that intrastrand migration of a reactive intermediate from base to base is occurring.

Original language	English (US)
Pages (from-to)	561-565
Number of pages	5
Journal	Journal of Physical Organic Chemistry
Volume	11
Issue number	8-9
DOIs	https://doi.org/10.1002/(sici)1099-1395(199808/09)11:8/9<561::aid-poc61>3.0.co;2-a
State	Published - 1998

Keywords

Photoinduced electron transfer
Pyrenyl-DNA complexes and adducts
Strand cleavage

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/(sici)1099-1395(199808/09)11:8/9<561::aid-poc61>3.0.co;2-a

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Photoinduced electron transfer and strand cleavage in pyrenyl-DNA complexes and adducts. / Geacintov, Nicholas E.; Solntsev, Kyril; Johnson, Lawrence W.; Chen, Junxin; Kolbanovskiy, Alexander D.; Liu, Tongming; Shafirovich, Vladimir Ya.

In: Journal of Physical Organic Chemistry, Vol. 11, No. 8-9, 1998, p. 561-565.

Research output: Contribution to journal › Review article › peer-review

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title = "Photoinduced electron transfer and strand cleavage in pyrenyl-DNA complexes and adducts",

abstract = "The fluorescence of pyrenyl residues in complexes with the nucleic acid bases G, C and T, but not A, is strongly quenched by photoinduced electron transfer mechanisms. Site-specifically modified 11-mer oligonucleotide duplexes containing a single modified guanosyl base G* bearing a covalently attached pyrenyl residue were prepared in order to probe for photochemical damage associated with these photoinduced electron transfer reactions. When the pyrenyl residue positioned at G* is photoexcited with 355 nm light, direct strand cleavage is observed at that site with low quantum yield. Frank strand breaks are also observed up to five base pairs away from G*, suggesting that intrastrand migration of a reactive intermediate from base to base is occurring.",

keywords = "Photoinduced electron transfer, Pyrenyl-DNA complexes and adducts, Strand cleavage",

author = "Geacintov, {Nicholas E.} and Kyril Solntsev and Johnson, {Lawrence W.} and Junxin Chen and Kolbanovskiy, {Alexander D.} and Tongming Liu and Shafirovich, {Vladimir Ya}",

year = "1998",

doi = "10.1002/(sici)1099-1395(199808/09)11:8/9<561::aid-poc61>3.0.co;2-a",

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TY - JOUR

T1 - Photoinduced electron transfer and strand cleavage in pyrenyl-DNA complexes and adducts

AU - Geacintov, Nicholas E.

AU - Solntsev, Kyril

AU - Johnson, Lawrence W.

AU - Chen, Junxin

AU - Kolbanovskiy, Alexander D.

AU - Liu, Tongming

AU - Shafirovich, Vladimir Ya

PY - 1998

Y1 - 1998

N2 - The fluorescence of pyrenyl residues in complexes with the nucleic acid bases G, C and T, but not A, is strongly quenched by photoinduced electron transfer mechanisms. Site-specifically modified 11-mer oligonucleotide duplexes containing a single modified guanosyl base G* bearing a covalently attached pyrenyl residue were prepared in order to probe for photochemical damage associated with these photoinduced electron transfer reactions. When the pyrenyl residue positioned at G* is photoexcited with 355 nm light, direct strand cleavage is observed at that site with low quantum yield. Frank strand breaks are also observed up to five base pairs away from G*, suggesting that intrastrand migration of a reactive intermediate from base to base is occurring.

AB - The fluorescence of pyrenyl residues in complexes with the nucleic acid bases G, C and T, but not A, is strongly quenched by photoinduced electron transfer mechanisms. Site-specifically modified 11-mer oligonucleotide duplexes containing a single modified guanosyl base G* bearing a covalently attached pyrenyl residue were prepared in order to probe for photochemical damage associated with these photoinduced electron transfer reactions. When the pyrenyl residue positioned at G* is photoexcited with 355 nm light, direct strand cleavage is observed at that site with low quantum yield. Frank strand breaks are also observed up to five base pairs away from G*, suggesting that intrastrand migration of a reactive intermediate from base to base is occurring.

KW - Photoinduced electron transfer

KW - Pyrenyl-DNA complexes and adducts

KW - Strand cleavage

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DO - 10.1002/(sici)1099-1395(199808/09)11:8/9<561::aid-poc61>3.0.co;2-a

M3 - Review article

AN - SCOPUS:0000847661

VL - 11

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JO - Journal of Physical Organic Chemistry

JF - Journal of Physical Organic Chemistry

SN - 0894-3230

IS - 8-9

ER -

Photoinduced electron transfer and strand cleavage in pyrenyl-DNA complexes and adducts

Abstract

Keywords

ASJC Scopus subject areas

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