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Mass Spectrometric Characterization of Sonochemical Transformation Products of 2’‐Deoxycytidine under Aerated Conditions: Direct Observation of Hydroxyhydroperoxide and Glycol
Author(s) -
Chandran Jisha,
Aravind Usha K.,
Aravindakumar Charuvila T.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700925
Subject(s) - chemistry , deoxycytidine , sonochemistry , radiolysis , organic chemistry , aqueous solution , medicine , surgery , chemotherapy , gemcitabine
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.