3-Hydroxykynurenine bound to eye lens proteins induces oxidative modifications in crystalline proteins through a type I photosensitizing mechanism

Ávila, Felipe; Ravello, Natalia; Zanocco, Antonio L.; Gamon, Luke F.; Davies, Michael J.; Silva, Eduardo

doi:10.1016/j.freeradbiomed.2019.05.024

Cited by 11 publications

(4 citation statements)

References 62 publications

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“…Methionine has been reported to undergo type I and type II reactions based on the reaction conditions (171). For example, the formation of the endogenous photosensitizer, 3-hydroxykynurenine (from Trp), leads to methionine sulfoxide (from Met) and DOPA (from Tyr), mainly by the type I reaction because Φ Δ values were relatively low (<20%) (172). On the other hand, a di-cyan-hemin sensitized reaction showed evidence for a type II process in the conversion of methionine to methionine sulfoxide, in contrast to cysteine and tryptophan oxidation reactions that involve mixed type I and type II reactions (139,173).…”

Section: Singlet Oxygen Oxidation Of Amino Acidsmentioning

confidence: 99%

Photosensitization Reactions of Biomolecules: Definition, Targets and Mechanisms

Baptista

Cadet

Greer

et al. 2021

Photochem & Photobiology

104

144

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Photosensitization reactions have been demonstrated to be largely responsible for the deleterious biological effects of UV and visible radiation, as well as for the curative actions of photomedicine. A large number of endogenous and exogenous photosensitizers, biological targets and mechanisms have been reported in the past few decades. Evolving from the original definitions of the type I and type II photosensitized oxidations, we now provide physicochemical frameworks, classifications and key examples of these mechanisms in order to organize, interpret and understand the vast information available in the literature and the new reports, which are in vigorous growth. This review surveys in an extended manner all identified photosensitization mechanisms of the major biomolecule groups such as nucleic acids, proteins, lipids bridging the gap with the subsequent biological processes. Also described are the effects of photosensitization in cells in which UVA and UVB irradiation triggers enzyme activation with the subsequent delayed generation of superoxide anion radical and nitric oxide. Definitions of photosensitized reactions are identified in biomolecules with key insights into cells and tissues.

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Section: Singlet Oxygen Oxidation Of Amino Acidsmentioning

confidence: 99%

Photosensitization Reactions of Biomolecules: Definition, Targets and Mechanisms

Baptista

Cadet

Greer

et al. 2021

Photochem & Photobiology

104

144

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“…The increase in the amount of oxygen after the addition of catalase indicates the generation of H 2 O 2 in our system, considering that catalase decompose H 2 O 2 to O 2 and H 2 O [ 44 ]. This approach has been used before to demonstrate the generation of reactive oxygen species [ 45 , 46 ]. Therefore, a contribution of free radical reactions to the protein crosslinking and oxidation cannot be discarded.…”

Section: Discussionmentioning

confidence: 99%

Antiglycating Effect of Phenolics from the Chilean Currant Ribes cucullatum under Thermal Treatment

et al. 2021

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Numerous dietary polyphenols possess antiglicating activity, but the effects of thermal treatment on this activity are mostly unknown. The effect of thermal treatment in the antiglycating activity of polyphenolic enriched extracts (PEEs) from Ribes cucullatum towards glyoxal-induced glycation of sarcoplasmic proteins was assessed. Sarcoplasmic proteins from chicken, beef, salmon, and turkey, were incubated 2 h at 60 °C with and without glyoxal and different concentrations of PEEs (0.25, 0.5, 1, and 5 mg/mL). The antiglycating activity was evaluated by: (1) Lys and Arg consumption, (2) Carboxymethyl lysine (CML) generation, and (3) lipid-derived electrophiles inhibition in a gastric digestion model. Protective effects were observed against CML generation in proteins and a decrease of electrophiles in the gastric digestion model. A dose-dependent consumption of Lys and Arg in proteins/PEEs samples, indicated the possible occurrence of quinoproteins generation from the phenolics. Protein/PEEs incubations were assessed by: (1) High pressure liquid chromatography analysis, (2) Gel electrophoresis (SDS-PAGE), and (3) Redox cycling staining of quinoproteins. Protein/PEEs incubations produced: (1) Decrease in phenolics, (2) increase of protein crosslinking, and (3) dose-dependent generation of quinoproteins. We demonstrate that phenolic compounds from R. cucullatum under thermal treatment act as antiglycating agents, but oxidative reactions occurs at high concentrations, generating protein crosslinking and quinoproteins.

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“…S1c, ESI †) can trigger crystalline proteins' oxidative modification when bound to the eye lens by a type I photosensitized oxidation mechanism. 138 Similarly, RF and RB, two of the most employed PS to assist the photo-crosslinking of biomimetic materials, have been shown to mediate protein crosslinking by a mixture of type I and type II photosensitized oxidation reactions. 44,55 Compelling evidence supports that uncontrolled oxidative environments can harm human health.…”

Section: Photo-reactions Side Effects When Applied In Situmentioning

confidence: 99%

Use of photosensitive molecules in the crosslinking of biopolymers: applications and considerations in biomaterials development

Santos,

Fuentes-Lemus,

Ahumada

2024

J. Mater. Chem. B

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3-Hydroxykynurenine bound to eye lens proteins induces oxidative modifications in crystalline proteins through a type I photosensitizing mechanism

Cited by 11 publications

References 62 publications

Photosensitization Reactions of Biomolecules: Definition, Targets and Mechanisms

Photosensitization Reactions of Biomolecules: Definition, Targets and Mechanisms

Antiglycating Effect of Phenolics from the Chilean Currant Ribes cucullatum under Thermal Treatment

Use of photosensitive molecules in the crosslinking of biopolymers: applications and considerations in biomaterials development

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