On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation

Haggi, Ernesto; Blasich, Néstor; Gutierrez, Lihuel Emiliano; Vázquez, Gabriela Co Asesor Martínez; Criado, Susana; Miskoski, Sandra; Ferrari, G; Montaña, M. Paulina; Garcı́a, Norman A.

doi:10.1016/j.jphotobiol.2012.04.010

Cited by 13 publications

(12 citation statements)

References 36 publications

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“…, H 2 O 2 and OH • [36]. As in the present case for Ev, the main reactive pathway is mediated by O 2…”

Section: •-supporting

confidence: 64%

“…Asa, transparent to visible light and currently known as vitamin C, is probably the most extensively studied biologically-relevant substrate in relation to Rf-photosensitized degradations. This pathway has been suggested as the main cause for the in-vivo photodegradation of vitamin C [21,[33][34][35][36].…”

Section: Evaluation Of Ev Photostability Against Ascorbic Acid As a Rmentioning

confidence: 99%

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Vitamin B2-sensitized degradation of the multifunctional drug Evernyl, in the presence of visible light – microbiological implications

Gambetta

Massad

Nesci

et al. 2015

Pure and Applied Chemistry

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Taking into consideration the importance of the photooxidative effects in complex bioenvironments, this paper reports on the visible-light-promoted interactions between Evernyl (methyl 2, 4-dihydroxy-3,6-dimethylbenzoate, Ev) and vitamin B2 (riboflavin, Rf). Ev is a phenolic derivative, transparent to visible light, that possesses important antimicrobial activity. This compound is the first known natural, complete and specific human androgen receptor antagonist. Ev is profusely employed in personal-care products and synthesized as a secondary metabolite by several lichen and plant species. In both sceneries, acting Ev as a cosmetic component for topic applications or as a lichen constituent, may Rf behave as a native visible-light absorber pigment. In this context, kinetic and mechanistic aspects of the Rf-sensitized photooxidation of Ev, has been studied in aqueous solution, irradiating with blue LED light (463-471 nm) and employing stationary and time resolved methods. Results indicate that Ev reacts with the photogenerated reactive oxygen species (ROS) singlet molecular oxygen with a rate constant of k r = 1.1 ± 0.2 × 10 6 M −1 s −1 . In parallel Ev also quenches the electronically excited singlet and triplet excited states of Rf with rate constants close to the difussion limit. As a result the ROS superoxide radical anion and hydrogen peroxide are generated and the latter subsequently reacts with Ev. Possible implications of these photoreactions on the antimicrobial activity of Ev have been investigated employing a Candida albicans (CA) strain, isolated from human skin infection. The simultaneous presence of Rf, Ev in a sub-MIC, and blue-light irradiation produced a significant antimycotic effect, attributed to ROS photogeneration.

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“…, H 2 O 2 and OH • [36]. As in the present case for Ev, the main reactive pathway is mediated by O 2…”

Section: •-supporting

confidence: 64%

Section: Evaluation Of Ev Photostability Against Ascorbic Acid As a Rmentioning

confidence: 99%

Vitamin B2-sensitized degradation of the multifunctional drug Evernyl, in the presence of visible light – microbiological implications

Gambetta

Massad

Nesci

et al. 2015

Pure and Applied Chemistry

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“…In aqueous solution, upon visible-light irradiation both photosensitizers generate the species O 2 ( 1 D g ) with good quantum yields 12,13 ; however, Rf can also generate other ROS and radical species. 19,[26][27][28] Participation of ROS in the Rf-photosensitized oxidation of dCTQ…”

Section: Stationary Photolysismentioning

confidence: 99%

“…The high dependence of k r on the degree of ionization of -OH group has been reported. 28 In these cases, it is postulated the formation of an encounter complex substrate-O 2 ( 1 D g ) with partial charge-transfer character, a formation that is favored by the higher electron-donor ability of the ionized species. The deactivation of this complex could lead to physical quenching or produce the oxidation of the substrate by complete electron transfer.…”

Section: Interaction Of Dctq Withmentioning

confidence: 99%

Antioxidant capacity of (+)-catechin visible-light photoirradiated in the presence of vitamin B₂

et al. 2016

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pH-effect of the medium on radical-scavenging activity comes from the increased electron-donating ability of CTQ upon deprotonation. These results are very interesting due to the fact that the pH of the food products displays important variations. The [Formula: see text]-scavenging ability of CTQ, would be equal to the additive contribution of each reactive center, CTC, and RSC, present at the molecule of CTQ. However, CTQ would have a moderate ability to removal of [Formula: see text]-species at pH 7.

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“…RF, known as vitamin B 2 , is the precursor of biologically important cofactors, FAD and FMN. RF is commonly present in our daily diet, in vegetables, milk, meat products, and so forth, and acts as an effective photosensitizer in food and biological systems . Deficiency of RF causes skin disease and growth retardation.…”

Section: Introductionmentioning

confidence: 99%

Deep ultraviolet initiated excited state dynamics of riboflavin and flavin mononucleotide

Ghosh

Puranik

2018

J Raman Spectroscopy

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Flavins are cofactors in several light-activated enzymes and therefore their excited states are found to involve in many photobiological processes. Excited state dynamics of flavin compounds corresponding to their first singlet state (S 1 ) has been studied using a plethora of techniques, whereas studies related to highly absorbing ultraviolet excited states are lacking. Here, we study the ultrafast excited state dynamics of riboflavin and flavin mononucleotide using resonance Raman intensity analysis upon photoexcitation into their most intense absorption band centered at 266 nm. Resonance Raman cross sections of each flavin band are quantitatively measured across the 266-nm absorption band (257-280 nm), and Raman excitation profiles are constructed. We have used Lee and Heller's time-dependent wave packet theory to simulate the experimental Raman cross sections in a self-consistent manner. The simulation results in instantaneous structural changes along with solvation dynamics, through linewidth broadening within tens of femtoseconds following photoexcitation. Major structural changes were observed through contraction and elongation of several ring stretching coordinates, affecting at a different site when compared with the S 1 excitation. The value of the total reorganization energy was determined to be 1,665 cm −1 (and 1,602 cm −1 for flavin mononucleotide) with a contribution of 1,310 cm −1 from the inertial response of water. We find upon excitation, the first solvation shell inertially responds with an ultrafast timescale of <30 fs for both the molecules. Our results can be useful to determine the structure and dynamics of flavoenzymes by using flavin as a probe following excitation within their 266-nm absorption band.

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On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation

Cited by 13 publications

References 36 publications

Vitamin B2-sensitized degradation of the multifunctional drug Evernyl, in the presence of visible light – microbiological implications

Vitamin B2-sensitized degradation of the multifunctional drug Evernyl, in the presence of visible light – microbiological implications

Antioxidant capacity of (+)-catechin visible-light photoirradiated in the presence of vitamin B₂

Deep ultraviolet initiated excited state dynamics of riboflavin and flavin mononucleotide

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On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation

Cited by 13 publications

References 36 publications

Vitamin B2-sensitized degradation of the multifunctional drug Evernyl, in the presence of visible light – microbiological implications

Vitamin B2-sensitized degradation of the multifunctional drug Evernyl, in the presence of visible light – microbiological implications

Antioxidant capacity of (+)-catechin visible-light photoirradiated in the presence of vitamin B2

Deep ultraviolet initiated excited state dynamics of riboflavin and flavin mononucleotide

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Antioxidant capacity of (+)-catechin visible-light photoirradiated in the presence of vitamin B₂