Laser spectroscopic studies of DNA adduct structure types from enantiomeric diol epoxides of benzo[a]pyrene

Jankowiak, Ryszard; Lu, Pei Qi; Small, Gerald J.; Geacintov, Nicholas E.

doi:10.1021/tx00013a007

Cited by 29 publications

(76 citation statements)

References 17 publications

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“…The multiple zero phonon lines observed are characteristic of the corresponding vibrational modes. It has also been noted earlier (11,19) that the covalent interactions of the carcinogen benzo[alpyrene with protein and DNA causes large relative changes in the intensities of zero phonon lines but changes the frequency of the vibrational modes only marginally.…”

Section: Pagementioning

confidence: 62%

“…At 368-nm excitation, however, the spectra of adducted H3 appeared to be red shifted and broad ( Figure 4). This anomalous behavior is not well understood but could be the result of a stronger interaction of the pyrene with the protein, leading to broadening and red shifting of the lines (19). These effects are not responsible, though, for the apparent broad peak at 382 nm in Figures 3 and 4, which is a phonon wing.…”

Section: Pagementioning

confidence: 94%

“…These effects are not responsible, though, for the apparent broad peak at 382 nm in Figures 3 and 4, which is a phonon wing. Decrease in intensity of zero phonon lines coupled with increased intensity of the phonon wing has frequently been observed in adducts of anti-BPDE (11,17,19) as compared to other derivatives such as tetrols, especially at longer wavelength excitation. Also leading to the appearance of a spectral peak at 382 nm is the drop in intensity at the end of the spectrum that results from mismatch of the photodiode array and the multichannel analyzer and/or decreased diode sensitivity a t the end of the spectral window.…”

Section: Pagementioning

confidence: 98%

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Characterization of benzo[a]pyrene anti-diol epoxide adducts to human histones

SooHoo

Singh²,

Skipper³

et al. 1994

Chem. Res. Toxicol.

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Nuclei from human lymphoblast cells grown in culture were treated with [7-14C]-(+/-)-r-7,t-8-dihydroxy-t-9,t-10-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene (anti-BPDE), and the nucleosomal core histones were isolated for adduct studies by cryogenic fluorescence line narrowing spectroscopy. The four core histones H2A, H2B, H3, and H4 were separated by sodium dodecyl sulfate-polyacrylamide gel electrophoresis, which yielded each histone free of contamination by the others. Further purification of histones H2A, H2B, and H4 by reversed-phase HPLC also yielded a tetrahydrotetrol of benzo[a]pyrene, indicating that these three histones had some labile adducts. No tetrol was observed upon purification of histone H3. Fluorescence emission spectra of the HPLC-purified histones recorded at 4K after vibronic excitation into the S1 state were generally similar. Fluorescence line-narrowed spectra of model compounds formed by reaction of anti-BPDE with acetic acid, ethylenediamine, cysteamine, and histidine were also recorded. Only the spectra of the ethylenediamine adduct model matched consistently, at different excitation wavelengths, the spectra of the adducted histones. From this it is concluded that the stable human histone adducts of anti-BPDE are formed by reaction with lysine residues and/or the amino groups of the N-termini.

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Section: Pagementioning

confidence: 62%

Section: Pagementioning

confidence: 94%

Section: Pagementioning

confidence: 98%

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Characterization of benzo[a]pyrene anti-diol epoxide adducts to human histones

SooHoo

Singh²,

Skipper³

et al. 1994

Chem. Res. Toxicol.

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“…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%

“…In general,the trans configuration is characterized as site type H, whereas cis adduct is classified as site type I. Even though the carcinogen interacts less strongly with bases of oligonuleotides in (±)-2' than in (±)-3, which were previuosly assigned as site I [171,183], all the basestacking properties of the (-)-2' conformation allow this adduct to be assigned as site type I. This (-)-2' conformation of (-)-franj-BPDE-d(CACATGTACAC)2, identified here for the first time, may be responsible for the disagreement in configuration-conformation relationship observed by Geacintov et al [186], where they observed that the ratio of cis to trans was ~1.7, whereas the ratio of site I to site U was ~9.…”

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

confidence: 99%

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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