Photochemical Properties of UV Filter Molecules of the Human Eye

Tsentalovich, Yuri P.; Sherin, Peter S.; Kopylova, Lyudmila V.; Cherepanov, Ivan V.; Grilj, Jakob; Vauthey, Eric

doi:10.1167/iovs.11-8120

Cited by 50 publications

(37 citation statements)

References 44 publications

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“…Eqn (2) holds as long as the pseudo-first-order triplet energy transfer reaction is much faster than the second-order triplet annihilation reaction, and the efficiency of triplet KNA formation in the acetone-sensitized photolysis is close to 100%. 35 The laser pulse energy dependence of the A and B parameters shown in Fig. 8B exhibits a deviation from linear dependence which takes place at laser intensities above 0.5 mJ per pulse.…”

Section: 35mentioning

confidence: 86%

“…The early excited-state dynamics of KNY is similar to that of KN. 1 It has been shown that excitation of KN and other UV filters results in a charge transfer from the amino to the carbonyl group; 35 very likely that the same charge transfer occurs during the KNY excitation, which is supported by a large Stokes shift of the fluorescence band relative to the absorption spectrum (Fig. 1).…”

Section: Photophysics and Photochemistry Of Knymentioning

confidence: 93%

“…Slower TA dynamics was recorded with a nanosecond laser flash photolysis (LFP) setup described earlier. 35 Briefly, solutions, placed in a rectangular cell (inner dimensions 10 mm × 10 mm), were irradiated with either a Quanta-Ray LAB-130-10 Nd : YAG laser (355 nm, pulse duration 8 ns, pulse energy up to 135 mJ), or a Lambda Physik EMG 101 excimer laser (308 nm, pulse duration 15-20 ns, pulse energy up to 100 mJ). A fraction of the laser beam was split by a quartz plate and directed to a photodiode for triggering the oscilloscope and to a Newport 1918-C power meter for the permanent monitoring of the laser energy.…”

Section: Transient Absorption (Ta) Measurementsmentioning

confidence: 99%

“…The triplet quantum yields upon KNA photolysis were measured according to the procedure described earlier. 35 Briefly, the triplet quantum yields were determined by comparing the triplet state concentrations upon direct and acetonesensitized photolysis. As an example, Fig.…”

Section: 35mentioning

confidence: 99%

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Photochemistry of aqueous solutions of kynurenic acid and kynurenine yellow

Zelentsova

Sherin

Snytnikova

et al. 2013

Photochem Photobiol Sci

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The photophysics and photochemistry of kynurenic acid (KNA) and kynurenine yellow (KNY) in neutral aqueous solutions were investigated using time-resolved optical spectroscopy. Both molecules have similar quinoline-like structures, the only difference being the absence of conjugation in the nitrogen containing cycle in KNY. The main channel of S 1 excited state decay in the case of partially-unconjugated KNY is the solvent assisted S 1 → S 0 radiationless transition via intermolecular hydrogen bonds (Φ IC = 0.96), whereas, in the case of fully-conjugated KNA, it is intersystem crossing to the triplet state (Φ T = 0.82). The major intermediate products of the singlet excited KNY deactivation are the triplet state (Φ T = 0.022) and, most probably, the enol form (Φ enol = 0.012), which decay with the formation of 2,3-dihydro-4-hydroxyquinoline and 4-hydroxyquinoline, respectively. The results obtained show that KNA and KNY, which are products of the decomposition of the UV filter kynurenine, are significantly more photoactive and less photostable than the parent molecule.

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Section: 35mentioning

confidence: 86%

Section: Photophysics and Photochemistry Of Knymentioning

confidence: 93%

Section: Transient Absorption (Ta) Measurementsmentioning

confidence: 99%

Section: 35mentioning

confidence: 99%

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Photochemistry of aqueous solutions of kynurenic acid and kynurenine yellow

Zelentsova

Sherin

Snytnikova

et al. 2013

Photochem Photobiol Sci

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“…4-Aryl-4-oxobut-2-enoic acids (also considered as β-aroylacrylic acids), their derivatives represent an important class of compounds with wide spectrum of biological activities including antibacterial activity [1][2][3][4][5], anti-ulcer and cytoprotective properties [6,7], kynurenine-3-hydroxylase [8] and antiproliferative activity toward Human cervix carcinoma (HeLa) [9,10]. Moreover, the β-aroylacrylic acids have been attracting increasing attention in view of their high reactivity as building blocks for the synthesis of wide variety of compounds of various classes due to their selective transformations with different reagents.…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis of new fused and non-fused heterocyclic systems from a γ-ketoacid

et al. 2014

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Characterisation of the Kynurenine Pathway in Skin‐Derived Fibroblasts and Keratinocytes

Sheipouri

Grant

Bustamante

et al. 2015

J of Cellular Biochemistry

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Acute UVB exposure triggers inflammation leading to the induction of indoleamine 2,3 dioxygenase (IDO1), one of the first enzymes in the kynurenine pathway (KP) for tryptophan degradation. However, limited studies have been undertaken to determine the catabolism of tryptophan within the skin. The aim of this study was two fold: (1) to establish if the administration of the proinflammatory cytokine interferon-gamma (IFN-γ) and/or UVB radiation elicits differential KP expression patterns in human fibroblast and keratinocytes; and (2) to evaluate the effect of KP metabolites on intracellular nicotinamide adenine dinucleotide (NAD(+) ) levels, and cell viability. Primary cultures of human fibroblasts and keratinocytes were used to examine expression of the KP at the mRNA level using qPCR, and at the protein level using immunocytochemistry. Cellular responses to KP metabolites were assessed by examining extracellular lactate dehydrogenase (LDH) activity and intracellular NAD(+) levels. Major downstream KP metabolites were analyzed using GC/MS and HPLC. Our data shows that the KP is fully expressed both in human fibroblasts and keratinocytes. Exposure to UVB radiation and/or IFN-γ causes significant changes in the expression pattern of downstream KP metabolites and enzymes. Exposure to various concentrations of KP metabolites showed marked differences in cell viability and intracellular NAD(+) production, providing support for involvement of the KP in the de novo synthesis of NAD(+) in the skin. This new information will have a significant impact on our understanding of the pathogenesis of UV related skin damage and the diagnosis of KP related disease states.

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Photochemical Properties of UV Filter Molecules of the Human Eye

Cited by 50 publications

References 44 publications

Photochemistry of aqueous solutions of kynurenic acid and kynurenine yellow

Photochemistry of aqueous solutions of kynurenic acid and kynurenine yellow

Facile synthesis of new fused and non-fused heterocyclic systems from a γ-ketoacid

Characterisation of the Kynurenine Pathway in Skin‐Derived Fibroblasts and Keratinocytes

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