Research output: Contribution to journal › Article › peer-review
New insights into the nature of short-lived paramagnetic intermediates of ketoprofen. Photo-CIDNP study. / Babenko, Simon V.; Kuznetsova, Polina S.; Polyakov, Nikolay E. et al.
In: Journal of Photochemistry and Photobiology A: Chemistry, Vol. 392, 112383, 01.04.2020.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - New insights into the nature of short-lived paramagnetic intermediates of ketoprofen. Photo-CIDNP study
AU - Babenko, Simon V.
AU - Kuznetsova, Polina S.
AU - Polyakov, Nikolay E.
AU - Kruppa, Aleksandr I.
AU - Leshina, Tatyana V.
PY - 2020/4/1
Y1 - 2020/4/1
N2 - The short-lived paramagnetic particles formed during the UV irradiation of nonsteroidal anti-inflammatory drug - ketoprofen (KP) have been investigated using chemically induced dynamic nuclear polarization (CIDNP). This study answers the questions about the nature of paramagnetic particles which can be responsible for KP phototoxic effects. Phototoxic side effects of NSAIDs, according modern point of view, are associated with the action of free radicals, however, there is insufficient information regarding the nature of the radical species. In contrast, most ketoprofen photodegradation schemes include carbanion as a precursor of products. CIDNP effects analysis has shown that all the major products of KP photodegradation can form via radical pairs (RPs) involving benzyl (2′), ketyl (3′) and CO2H[rad] or CO2 − [rad] free radicals and solvated electron. Radical ways of KP photodegradation include: decarboxylation via RP with benzyl radical formation (I) in non-aqueous solution and both, (I) and photoreduction with formation of ketyl radicals in the presence of water. Moreover, it was found that the photoinduced radical decarboxylation of KP represents a reversible process.
AB - The short-lived paramagnetic particles formed during the UV irradiation of nonsteroidal anti-inflammatory drug - ketoprofen (KP) have been investigated using chemically induced dynamic nuclear polarization (CIDNP). This study answers the questions about the nature of paramagnetic particles which can be responsible for KP phototoxic effects. Phototoxic side effects of NSAIDs, according modern point of view, are associated with the action of free radicals, however, there is insufficient information regarding the nature of the radical species. In contrast, most ketoprofen photodegradation schemes include carbanion as a precursor of products. CIDNP effects analysis has shown that all the major products of KP photodegradation can form via radical pairs (RPs) involving benzyl (2′), ketyl (3′) and CO2H[rad] or CO2 − [rad] free radicals and solvated electron. Radical ways of KP photodegradation include: decarboxylation via RP with benzyl radical formation (I) in non-aqueous solution and both, (I) and photoreduction with formation of ketyl radicals in the presence of water. Moreover, it was found that the photoinduced radical decarboxylation of KP represents a reversible process.
KW - CIDNP
KW - Decarboxylation
KW - Free radicals
KW - Ketoprofen
KW - ELECTRON-SPIN-RESONANCE
KW - ACID
KW - MECHANISM
KW - WATER-RICH
KW - PHOTOSENSITIVITY
KW - RESOLVED RESONANCE RAMAN
KW - BENZOPHENONE
KW - PHOTOCHEMISTRY
KW - HYDROGEN-PEROXIDE
KW - PHOTODECARBOXYLATION
UR - http://www.scopus.com/inward/record.url?scp=85078159689&partnerID=8YFLogxK
U2 - 10.1016/j.jphotochem.2020.112383
DO - 10.1016/j.jphotochem.2020.112383
M3 - Article
AN - SCOPUS:85078159689
VL - 392
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
SN - 1010-6030
M1 - 112383
ER -
ID: 23264589