Effect of X-Rays on Cytosine in Aerated Aqueous Solution

Ekert, B.; Monier, R.

doi:10.1038/188309a0

Cited by 46 publications

(11 citation statements)

References 2 publications

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“…ESI‐MSMS spectrum of the protonated molecule of the compound 1 (m/z 278.1018, C 9 H 16 N 3 O 7 ), acquired at collision energy of 20 eV, is given in the Supplementary Information (Figure S2). There are reports that the gamma irradiation of aqueous solution of dCyd does not give any detectable levels of hydroxyhydroperoxides . But in the present case in addition to detection and mass spectrometric characterization, a decomposition profile of this compound is also presented.…”

Section: Mass Spectrometric Analysis Of the Transformation Products: mentioning

confidence: 70%

Mass Spectrometric Characterization of Sonochemical Transformation Products of 2’‐Deoxycytidine under Aerated Conditions: Direct Observation of Hydroxyhydroperoxide and Glycol

2017

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The present report profiles the complete ultrasound mediated transformation products of a DNA nucleoside, 2’‐deoxycytidine (dCyd), the second in this series, using high resolution mass spectrometry (UPLC−Q‐ToF‐MS). The compound, dCyd was subjected to sonolysis under four different frequencies (200, 350, 620 and 1000 kHz) at a power density of 24.5 W/ml. The extent of decomposition of dCyd follows the order 620>350>1000>200 kHz. The effect of different gases on sonolysis was also investigated. This clearly indicates the involvement of oxygen radical (O•) in the transformation reactions. The sonochemical transformation products of dCyd were analyzed using UPLC−Q‐ToF‐MS and a total of 8 products were identified and characterized. The identified products include two primary products, 5,6‐dihydro‐5‐hydroxy‐6‐hydroperoxy‐2’‐deoxycytidine (hydroxyhydroperoxide) and 5,6‐dihydro‐5,6‐dihydroxy‐2’‐deoxycytidine (glycol) which are generally difficult to identify in DNA damage studies due to their instability during the work up procedure. The structural identity of all the products was confirmed by the collisionally induced dissociation (CID) pattern. Out of the eight identified products, 5,6‐dihydroxy‐2’‐deoxycytidine, 5,6‐dihydroxy‐2’‐deoxyuridine and 5‐hydroxy‐2’‐deoxyuridine are not observed in radiolysis. The difference in product profile obtained for sonolysis and radiolysis is compared and contrasted.

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Section: Mass Spectrometric Analysis Of the Transformation Products: mentioning

confidence: 70%

Mass Spectrometric Characterization of Sonochemical Transformation Products of 2’‐Deoxycytidine under Aerated Conditions: Direct Observation of Hydroxyhydroperoxide and Glycol

2017

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“…Ten compounds, including unreacted cytosine, are identified. They are urea (IS), formyl urea (14), parabanic acid (12), cytosine ( I ) , isobarbituric acid ( 6 ) , oxaluric acid (13), alloxan monohydrate (9), alloxantin ( l l ) , dialuric acid (7), and uracil glycols (5).…”

Section: Methodsmentioning

confidence: 99%

“…The radiolysis of cytosine has been investigated in aerated aqueous solutions (5)(6)(7)(8)(9). Since the primary reactions in the sonolysis of aqueous solutions (10)(11)(12)(13)(14) are now known to be essentially similar to those produced in radiolytic reactions, the sonolysis and radiolysis are compared and contrasted.…”

Section: Imentioning

confidence: 99%

The sonolysis of cytosine and thymine

Yu¹,

Sutherland²,

Verrall³

1987

Can. J. Chem.

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Sonolysis of cytosine has been studied at 630 kHz in the presence of air and nitrogen. The degradation products were identified by gas chromatographic – mass spectral analysis. Under aerated conditions the following products were found: urea, formyl urea, parabanic acid, isobarbituric acid, oxaluric acid, alloxan monohydrate, alloxantin, dialuric acid, and uracil glycols. Under nitrogen the degradation products were isobarbituric acid, alloxan monohydrate, and uracil glycols. The observed products have been used to develop a possible mechanism for the sonolytic degradation. There appears to be some similarity with the products reported from radiolysis studies of this compound. Sonolysis of thymine in the presence of air was reinvestigated and the gc–ms analysis shows that a previously reported, unidentified, product may be 5-hydroxy-5-methylbarbituric acid.

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“…b 11 t an punne ases. On the basis of these investigations, it has been known that the radiolysis of thymine in aqueous system is preferentially due to the action of OH radicals on the solute molecule at the position of 5,6 double bond of the pyrimidine ring with a loss of its characteristic UV absorption.…”

mentioning

confidence: 98%