A study of the reaction of different phenol substrates with nitric oxide and peroxynitrite

Yenes, Susana; Messeguer, Ángel

doi:10.1016/s0040-4020(99)00877-7

Cited by 32 publications

(26 citation statements)

References 24 publications

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“…× NO reacts with phenolic compounds (Janzen et al, 1993;Yenes and Messeguer, 1999;Cudic and Ducrocq, 2000), and the initiator in these reactions is believed to be the autoxidation of × NO (Liu et al, 1998;Espey et al, 2001) with the formation of the × NO 2 radical, which can attack the electron-rich phenolic OH group to generate the phenoxyl radical (Hogg et al, 1996;Goss et al, 1999).…”

Section: Discussionmentioning

confidence: 99%

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Effect of Nitric Oxide on the Anticancer Activity of the Topoisomerase-Active Drugs Etoposide and Adriamycin in Human Melanoma Cells

Sinha

Kumar

Bhattacharjee

et al. 2013

J Pharmacol Exp Ther

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Section: Discussionmentioning

confidence: 99%

“…× NO and/or its products react with a wide variety of substrates, including amines, thiols, and phenols (Janzen et al, 1993;Cudic and Ducrocq, 2000;Yenes and Messeguer 1999).…”

Section: No And/or Its Products (mentioning

confidence: 99%

Effect of Nitric Oxide on the Anticancer Activity of the Topoisomerase-Active Drugs Etoposide and Adriamycin in Human Melanoma Cells

Sinha

Kumar

Bhattacharjee

et al. 2013

J Pharmacol Exp Ther

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“…Reaction between •NO and phenolic compounds has been the subject of numerous publications. 25-28 A key initiator in these reactions is the autoxidation of •NO. 49, 50 In the presence of molecular O 2 , •NO autoxidation results in formation of the •NO 2 radical, which can attack the electron rich phenolic OH group to generate the phenoxyl radical.…”

Section: Discussionmentioning

confidence: 99%

“…22-24 •NO or its products have also been shown to react with a wide variety of substrates including amines, thiols and phenols. 25-28 Phenols rapidly react with •NO-derived species to form phenoxy radicals, quinones and nitrated phenols. Thus, tyrosine, a phenolic compound and/or its phenoxyl -free radical reacts with •NO-derived species to form nitrotyrosine, and the formation of nitrotyrosine in cellular proteins has been associated with compromised protein activities.…”

Section: Introductionmentioning

confidence: 99%

Role of Nitric Oxide in the Chemistry and Anticancer Activity of Etoposide (VP-16,213)

Sinha

Bhattacharjee

Chatterjee

et al. 2013

Chem. Res. Toxicol.

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Originally identified as an innate cytotoxin, nitric oxide (•NO) formation in tumors can influence chemotherapy and exacerbate cancer progression. Here, we examined the hypothesis that •NO generation contributes to cancer cell drug resistance towards the widely used anticancer drug Etoposide (VP-16). The UV-V is spectrum of VP-16 was not changed by exposure of VP-16 to •NO in aqueous buffer. In contrast, reddish-orange compound(s) characteristic of o-quinone- and nitroso-VP-16, were readily generated in a hydrophobic medium (chloroform) in an oxygen-dependent manner. Similar products were also formed when the VP-16 radical, generated from VP-16 and horseradish peroxidase/H2O2, was exposed directly to •NO in chloroform in the presence of oxygen. Separation and spectral analysis of VP-16 reaction extracts by electron spin resonance and UV-Vis indicated generation of the phenoxy radical and the o-quinone of VP-16, as well as putative nitroxide, iminoxyl and other nitrogen oxide intermediates. Nitric oxide products of VP-16 displayed significantly diminished topoisomerase II-dependent cleavage of DNA and cytotoxicity to human HL-60 leukemia cells. LPS-mediated induction of nitric oxide synthase in murine macrophages resulted in VP-16 resistance compared to Raw cells. Furthermore, •NO products derived from iNOS rapidly reacted with VP-16 leading to decreased DNA damage and cytotoxicity. Together, these observations suggest that formation of •NO in tumors (associated macrophages) can contribute to VP-16 resistance via detoxification of VP-16.

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“…Another is to provide standard compounds and reliable analytical data for non-α-tocopherol derivatives, the literature being rather ambiguous with regard to those compounds. Five sets of different analytical data (UV and 1 H NMR) existed for 5-nitro-γ-tocopherol, [10][11][12][13][14][15][16] for example, which left the actual identities of the analyzed compounds unclear. This was, of course, unacceptable, especially with regard to medical studies.…”

Section: Introductionmentioning

confidence: 99%

Bromination of Tocopherols: Oxidative Halogenations and Rearrangements

et al. 2011

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The bromination behaviour of all four tocopherols and the corresponding model compounds in acidic and basic aqueous media was studied. Acidic conditions resulted in quinones and brominated quinones, with the bromination of the tocopherol preceeding the oxidation to the quinone. Buffer type and concentration did not influence the reaction results, whereas pH and the ratio of buffer and ethanol used as a cosolvent strongly affected the reaction rates. In alkaline media, two or three major products and a multitude of minor byproducts were obtained, because the combination of oxidizing hypobromite and alkaline conditions allowed for more complex reaction pathways (oxidation, substitution, conden-

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A study of the reaction of different phenol substrates with nitric oxide and peroxynitrite

Cited by 32 publications

References 24 publications

Effect of Nitric Oxide on the Anticancer Activity of the Topoisomerase-Active Drugs Etoposide and Adriamycin in Human Melanoma Cells

Effect of Nitric Oxide on the Anticancer Activity of the Topoisomerase-Active Drugs Etoposide and Adriamycin in Human Melanoma Cells

Role of Nitric Oxide in the Chemistry and Anticancer Activity of Etoposide (VP-16,213)

Bromination of Tocopherols: Oxidative Halogenations and Rearrangements

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