Mutagenesis by photoaffinity labeling using selected azidofluorenes

Brown, Brenda R.; Yielding, Lerena W.; White, William E.

doi:10.1016/0027-5107(80)90054-8

Cited by 18 publications

(8 citation statements)

References 12 publications

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“…Samples of 4-methoxyphenyl azide and 4-ethoxyphenyl azide were synthesized according to literature methods, and further details of the synthesis and characterization are given in the Supporting Information. The 4-methoxyphenyl azide and 4-ethoxyphenyl azide samples were prepared with concentrations in the 2.3−2.4 mM range in acetonitrile solvent for the time-resolved resonance Raman experiments.…”

Section: Experimental and Calculations Sectionmentioning

confidence: 99%

Time-Resolved Resonance Raman Study of Triplet Arylnitrenes and Their Dimerization Reaction

et al. 2003

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Time-resolved resonance Raman spectra for triplet 4-methoxyphenyl nitrene and 4-ethoxyphenyl nitrene and their dimerization reaction to form azo dimer products in acetonitrile solution on the nanosecond time scale are reported. As the 4-methoxyphenyl nitrene and 4-ethoxyphenyl nitrene Raman bands decay, the Raman bands for the azo dimer products increase in intensity. The triplet 4-methoxyphenyl nitrene and 4-ethoxyphenyl nitrene species and their reaction to produce azo products are compared to a recent study of the 2-fluorenyl nitrene species and its reaction to form dehydroazepine ring-expansion products. The properties of the singlet and triplet arylnitrenes and their reaction mechanisms to form azo dimer and ring-expansion products are briefly discussed.

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Section: Experimental and Calculations Sectionmentioning

confidence: 99%

Time-Resolved Resonance Raman Study of Triplet Arylnitrenes and Their Dimerization Reaction

et al. 2003

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“…4-Methoxyphenyl azide and 4-ethoxyphenyl azide were prepared following a previously reported method for the synthesis of azide compounds. , The 4-methoxyphenyl azide was prepared as follows. In a 200 mL round-bottom flask, 4-methoxyaniline (4.92 g, 40 mmol) was dissolved in water (10 mL) that contained concentrated HCl (20 mL).…”

Section: Experimental and Computational Sectionmentioning

confidence: 99%

Transient Resonance Raman and Density Functional Theory Investigation of 4-Methoxyphenylnitrenium and 4-Ethoxyphenylnitrenium Ions

et al. 2003

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This paper presents a transient resonance Raman and density functional theory study of 4-methoxyphenylnitrenium and 4-ethoxyphenylnitrenium ions in a largely aqueous environment. The transient Raman bands observed in conjunction with the (U)BPW91/cc-PVDZ calculation results indicates these nitrenium ions are singlet state species. Both the 4-methoxyphenylnitrenium and the 4-ethoxyphenylnitrenium ions have significant iminocyclohexadienyl character to a degree very similar to that previously found for the 2-fluorenylnitrenium ion. The 4-methoxyphenylnitrenium and the 4-ethoxyphenylnitrenium ions also have significant oxocarbocation character and this influences both their properties and chemical reactivity. We compare the properties of the 4-methoxyphenylnitrenium and the 4-ethoxyphenylnitrenium ions to those previously found for other arylnitrenium ions.

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“…In the late 1970s, the aryl azide from 2-aminofluorene was used in photoaffinity labeling assays in bacteria (). Additional reports have indicated that mutagenic intermediates are formed by irradiating aryl azides at 360 nm ( , ). Later studies established that aryl azides from polyaromatic amines do not require enzymatic activation but produce, upon UV irradiation, unstable electrophiles that bind covalently to DNA ( − ).…”

Section: Introductionmentioning

confidence: 99%

New Syntheses of DNA Adducts from Methylated Anilines Present in Tobacco Smoke

Branco¹,

Antunes²,

Marques³

et al. 1999

Chem. Res. Toxicol.

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A new synthetic pathway for the formation of deoxyguanosine-monoarylamine adducts is described, involving the generation and use of arylnitrenes as electrophilic synthons. Photolysis of aryl azides, the most common method for generating arylnitrenes, was tested in the presence of 2'-deoxyguanosine. N-(2'-Deoxyguanosin-8-yl)monoarylamine (dG-C8-Ar) adducts were obtained, but the yields were typically low. Deoxygenation of nitro- and nitrosoarenes by triethyl phosphite in the presence of 2'-deoxyguanosine proved to be an effective method, by which dG-C8-Ar, (2'-deoxyguanosin-N1-yl)monoarylamine (dG-N1-Ar), and (2'-deoxyguanosin-O(6)-yl)monoarylamine (dG-O(6)-Ar) adducts were obtained in acceptable yields.

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Mutagenesis by photoaffinity labeling using selected azidofluorenes

Cited by 18 publications

References 12 publications

Time-Resolved Resonance Raman Study of Triplet Arylnitrenes and Their Dimerization Reaction

Time-Resolved Resonance Raman Study of Triplet Arylnitrenes and Their Dimerization Reaction

Transient Resonance Raman and Density Functional Theory Investigation of 4-Methoxyphenylnitrenium and 4-Ethoxyphenylnitrenium Ions

New Syntheses of DNA Adducts from Methylated Anilines Present in Tobacco Smoke

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