Inhibitory effect of ethyl oleate hydroperoxide and alcohol in photosensitized oxidative DNA damage

Adam, Waldemar; Andler, Simone; Saha‐Möller, Chantu R.; Schönberger, André

doi:10.1016/1011-1344(95)07235-7

Cited by 10 publications

(3 citation statements)

References 39 publications

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“…Compared to 13 , the corresponding ethyl esters 14 have been much less investigated. Only reports for the most likely oxidation products 14c ( n = 3, m = 3) and 14i ( n = 4, m = 2) are available (see, for example, [38,39,40]). In summary, from the first fraction of Neurymenia fraxinifolia we have isolated at least three oxidation products of palmitoleic and oleic esters.…”

Section: Resultsmentioning

confidence: 99%

Red Algae (Rhodophyta) from the Coast of Madagascar: Preliminary Bioactivity Studies and Isolation of Natural Products

et al. 2015

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Several species of red algae (Rhodophyta) from the coastal regions of Madagascar have been investigated for their natural products. The most abundant compound was cholesterol (5) in combination with a series of oxidized congeners. The brominated indoles 1–3 along with the sesquiterpene debilone (4) have been isolated from Laurencia complanata. For the first time, debilone (4) has been obtained from a marine plant. From the methanol extract of Calloseris sp., we have achieved the second isolation of the unusual A-ring contracted steroids (−)-2-ethoxycarbonyl-2β-hydroxy-A-nor-cholest-5-en-4-one (9) and phorbasterone B (10). The crude extracts of Laurencia complanata exhibited antimicrobial activity against Bacillus cereus, Staphylococcus aureus, Streptococcus pneumoniae, and Candida albicans.

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Section: Resultsmentioning

confidence: 99%

Red Algae (Rhodophyta) from the Coast of Madagascar: Preliminary Bioactivity Studies and Isolation of Natural Products

et al. 2015

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“…The level of 8-oxodG has been reported to increase dose-dependently in calf thymus DNA treated with singlet O 2 (36). Oxazolone and its precursor imidazolone have been observed as oxidation products of guanine or 8-oxoguanine in oligonucleotides and calf thymus DNA treated with Mn-TMPyP/KHSO 5 (37), ONOO - (11,18), photochemical oxidants (38)(39)(40)(41), and γ radiation (11). Spiroiminodihydantoin has been observed as the final oxidation product of guanine base (likely via 8-oxoguanine) in oligonucleotides by carbonate radical anions (42) and by chromium species (43).…”

Section: Discussionmentioning

confidence: 99%

Quantitation of Four Guanine Oxidation Products from Reaction of DNA with Varying Doses of Peroxynitrite

Venkatarangan

Wishnok

et al. 2005

Chem. Res. Toxicol.

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The oxidation products obtained from the reaction of peroxynitrite (ONOO − ) with dG includeamong others -8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodG)In the present work, the formation of these products from the treatment of calf thymus DNA with varying amounts of ONOO − was studied quantitatively in vitro. 13 C-, 15 N-labeled standards were synthesized for the nucleosides of interest, and calf thymus DNA was reacted with ONOO − and digested enzymatically down to the nucleoside level. Specific modifications in the DNA were measured by HPLC separation followed by electrospray ionization tandem mass spectrometric analysis in the selected reactionmonitoring mode. Artifacts of the above four oxidation products, arising from oxidation of dG and/ or 8-oxodG during DNA digestion and subsequent work-up, were evaluated with 7-15 N-dG and/or stable-isotope labeled 8-oxodG as internal standards. Levels of artifactual 8-oxodG were about 5/10 6 nucleosides. The artifacts of spiroiminodihydantoin and guanidinohydantoin, arising from 8-oxodG, were 3.7% and 0.6% of the measured 8-oxodG values, respectively. No artifacts of oxazolone were detected. 8-OxodG and oxazolone were formed dose-dependently in DNA treated with ONOO − , while the levels of spiroiminodihydantoin and guanidinohydantoin increased significantly at low ONOO − doses, and then dropped off at higher ONOO − doses. The complexity of these doseresponse relationships is likely due to the dual role of peroxynitrite as both an oxidant and a nucleophile in competition with water.

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“…As the most readily oxidized site in DNA, guanine is a major target for DNA oxidants, and its oxidation produces a wide spectrum of end products, including 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodG) spiroiminodihydantoin (Sp) guanidinohydantoin (Gh), 2-amino-5-[2-deoxy-β- d -erythro-pentofuranosyl)amino]-4 H -imidazol-4-one (imidazolone) and its hydrolysis product, 2,2-diamino-4-[(2-deoxy-β- d -erythro-pentofuranosyl)amino]-5(2 H )-oxazolone (Ox) (Scheme ). Although 8-oxodG is produced abundantly in DNA exposed to RNS and ROS, − it is several orders-of-magnitude more susceptible to further oxidation than dG itself, yielding more stable secondary oxidation products, including Sp and Gh (Scheme ). ,, Ox and its precursor imidazolone have been observed as oxidation products of dG or 8-oxodG in oligodeoxynucleotides and calf thymus DNA treated with Mn-TMPyP/KHSO 5 , peroxynitrite (ONOO – ), , and photochemical oxidants − (Scheme ). All of these DNA oxidation products are promutagenic, ,− with both diastereoisomers of Sp strongly inhibiting DNA polymerase , and causing mutation frequencies that are at least an order of magnitude higher than those for 8-oxodG.…”

Section: Introductionmentioning

confidence: 99%

Comparative Analysis of Four Oxidized Guanine Lesions from Reactions of DNA with Peroxynitrite, Singlet Oxygen, and γ-Radiation

Liang

Ye²,

Prestwich³

et al. 2013

Chem. Res. Toxicol.

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Oxidative damage to DNA has many origins, including irradiation, inflammation, and oxidative stress, but the chemistries are not the same. The most oxidizable base in DNA is 2-deoxyguanosine (dG), and the primary oxidation products are 8-oxodG and 2-amino-imidazolone. The latter rapidly converts to 2,2-diamino-oxazolone (Ox), and 8-oxodG is further oxidized to spiroiminodihydantoin (Sp) and guanidinohydantoin (Gh). In this study, we have examined the dose–response relationship for the formation of the above four products arising in calf thymus DNA exposed to gamma irradiation, photoactivated rose bengal, and two sources of peroxynitrite. In order to carry out these experiments, we developed a chromatographic system and synthesized isotopomeric internal standards to enable accurate and precise analysis based upon selected reaction monitoring mass spectrometry. 8-OxodG was the most abundant products in all cases, but its accumulation was highly dependent on the nature of the oxidizing agent and the subsequent conversion to Sp and Gh. Among the other oxidation products, Ox was the most abundant, and Sp was formed in significantly greater yield than Gh.

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Inhibitory effect of ethyl oleate hydroperoxide and alcohol in photosensitized oxidative DNA damage

Cited by 10 publications

References 39 publications

Red Algae (Rhodophyta) from the Coast of Madagascar: Preliminary Bioactivity Studies and Isolation of Natural Products

Red Algae (Rhodophyta) from the Coast of Madagascar: Preliminary Bioactivity Studies and Isolation of Natural Products

Quantitation of Four Guanine Oxidation Products from Reaction of DNA with Varying Doses of Peroxynitrite

Comparative Analysis of Four Oxidized Guanine Lesions from Reactions of DNA with Peroxynitrite, Singlet Oxygen, and γ-Radiation

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