Comparative laser spectroscopic study of DNA and polynucleotide adducts from the (+)-anti-diol epoxide of benzo[a]pyrene

Lu, Peiqi; Jeong, Hyunjo; Jankowiak, Ryszard; Small, Gerald J.; Kim, S. K.; Cosman, Monique; Geacintov, Nicholas E.

doi:10.1021/tx00019a008

Cited by 21 publications

(40 citation statements)

References 35 publications

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“…In support of the above conclusion vibronically excited spectra for the cis-and trans-isomers of B[a]P tetrol from (±)-anti-BPDE are presented in Figure 36b and c, reqwctively. The significant differences in vibrational frequencies and vibronic intensity distributions are comparable to those reported for cis-and froMf-isomers of N2-guanine monophosphate adduct formed from (+)-fl«r/-BPDE (see Figure 21) [171]. For comparison, spectrum a (microsomal adduct)…”

Section: Wavelength (Nm)supporting

confidence: 80%

“…Note that the 473, 1385 and 1442 cm"^ bands for the highly purified adduct (c) are weaker than for standard b, see text for discussion known. As discussed elsewhere [171], care must be exercised so as not to mistakenly assign tetrol fluorescence spectra to BPDE adducts. In support of the above conclusion vibronically excited spectra for the cis-and trans-isomers of B[a]P tetrol from (±)-anti-BPDE are presented in Figure 36b and c, reqwctively.…”

Section: Wavelength (Nm)mentioning

confidence: 99%

“…Spectroscopic studies [171,178] show that 80% of the racemic [171]. FLN spectra of intercalated tetrol in solid water host are characterized by two relatively well resolved 757 and 828 cm"^ modes (spectrum a in Fig.…”

Section: F Interaction Between Bpt and Dna In Solid Water And Glass mentioning

confidence: 99%

“…However, the former mode (ZPL) is also slightly contributed to by the BPT in the other configuration, and vise versa. The former configuration (referred to as "free" tetrol [171]) appears to be the more solvent-exposed since its fluorescence is more efficiently quenched by ACR than the latter. The tetrols in the latter configuration interact less strongly with DNA than intercalated tetrols, but more strongly than "free" tetrols.…”

Section: F Interaction Between Bpt and Dna In Solid Water And Glass mentioning

confidence: 99%

“…Furthemiore, the biological activity-structure relationships can be illustrated by using aforementioned methodology [171,183].…”

Section: F Interaction Between Bpt and Dna In Solid Water And Glass mentioning

confidence: 99%

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High resolution fluorescence studies of metabolic pathways of DNA and oligonucleotide adducts from polycyclic aromatic compounds

Jeong

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UMI MICROFILMED 1991 INFORMATION TO USERSThis manuscript has been reproduced from the microfflm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer.The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction.In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion.Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand corner and continuing from left to right in equal sections with small overlaps. Each original is also photographed in one exposure and is included in reduced form at the back of the book.Photographs included in the original manuscript have been reproduced xerographically in this copy. Higher quality 6" x 9" black and white photographic prints are available for any photographs or illustrations appearing in this copy for an additional charge. Contact UMI directly to order. 1991Signature was redacted for privacy.Signature was redacted for privacy.Signature was redacted for privacy.ii Ultraviolet and X-ray light have long beeHxknown to be highly cancer-causing and mutagenic agents [16]. For example, exposure of skin to UV light can induce skin cancer, while X-ray exposure to the thyroid induces thyroid cancer. Electromagnetic radiation, however, may not be assumed to cause all the cells in an exposed population to become cancerous since radiation can also produce many other deleterious changes leading to cell death. A radiation dose sufficient to induce cancer in all cells will virtually kill every cell. Not only can radiation induce simple mutation, it can also produce chromosome fragmentation, resulting in large deletions of genetic material. Thus radiation causes a variety of genetic changes, many of which might contribute to the cancerous state. A well known deleterious effect, xeroderma pigmentosum, is magnified in certain individuals. These people are homozygous for a recessive mutation that inactivates a gene involved in repairing thymine dimers, the major damage caused by UV Similar studies have shown that relatively weak carcinogens are also metabolized by monooxgenation mechanism. In most cases, however, the evidence is much less complete than in the case of B[a]P and rests primarily on comparison of the relative mutagenicities and tumorigenicities of the isomeric dihydrodiols or the corresponding diol epoxides obtained through synthesis. One-electron oxidation and metabolitesThe monooxygenation mechanism, which emphasizes the important role of the bay-region diol epoxide, has been widely accepted during last 15 years...

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Section: Wavelength (Nm)supporting

confidence: 80%

Section: Wavelength (Nm)mentioning

confidence: 99%

Section: F Interaction Between Bpt and Dna In Solid Water And Glass mentioning

confidence: 99%

Section: F Interaction Between Bpt and Dna In Solid Water And Glass mentioning

confidence: 99%

“…Furthemiore, the biological activity-structure relationships can be illustrated by using aforementioned methodology [171,183].…”

Section: F Interaction Between Bpt and Dna In Solid Water And Glass mentioning

confidence: 99%

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High resolution fluorescence studies of metabolic pathways of DNA and oligonucleotide adducts from polycyclic aromatic compounds

Jeong

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Identification of stereoisomeric benzo[a]pyrene tetrols by reversed-phase liquid chromatography coupled semi-ondashline to fluorescence line-narrowing spectroscopy

Kok¹,

Posthumus²,

Bakker³

et al. 1995

Analytica Chimica Acta

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Physical methods for the detection of carcinogen-DNA adducts in humans

Weston

1993

Mutation Research/Fundamental and Molecular Mechanisms of Mutag

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Comparative laser spectroscopic study of DNA and polynucleotide adducts from the (+)-anti-diol epoxide of benzo[a]pyrene

Cited by 21 publications

References 35 publications

High resolution fluorescence studies of metabolic pathways of DNA and oligonucleotide adducts from polycyclic aromatic compounds

High resolution fluorescence studies of metabolic pathways of DNA and oligonucleotide adducts from polycyclic aromatic compounds

Identification of stereoisomeric benzo[a]pyrene tetrols by reversed-phase liquid chromatography coupled semi-ondashline to fluorescence line-narrowing spectroscopy

Physical methods for the detection of carcinogen-DNA adducts in humans

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