Pulse radiolysis study of the interaction of retinoids with peroxyl radicals

Rozanowska, Malgorzata Barbara; Cantrell, Ann; Edge, Ruth; Land, Edward J.; Sarna, Tadeusz; Truscott, T. G.

doi:10.1016/j.freeradbiomed.2005.07.018

Cited by 39 publications

(54 citation statements)

References 30 publications

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“…The insensitivity of this intermediate to N 2 O and O 2 agrees with retinyl polyene radical cations obtained by pulse radiolysis . Moreover, the generation of ATRA •+ with maximum absorption around 590 nm was confirmed previously by laser flash photolysis study and pulse radiolysis study . Therefore, the absorption band centered at 590 nm herein is assigned as the absorption of ATRA •+ .…”

Section: Resultssupporting

confidence: 86%

“…Pulse radiolysis study by Różanowska et al . showed that ATRA •+ could also be generated via oxidation of ATRA by peroxyl radicals and ATRA •+ had efficient reaction activity to ascorbate . The interaction of ATRA •+ with ascorbate implies that ATRA •+ is a reactive substance which may pose oxidative damage to other biomolecules such as proteins.…”

Section: Introductionmentioning

confidence: 99%

“…Many studies have been made to investigate the transient phenomena in the laser flash photolysis and pulse radiolysis studies of retinoids (12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28). Previous studies on ATRA in methanol showed that 347 nm laser flash photolysis (LFP) of ATRA led to the production of triplet state of ATRA ( 3 ATRA*) via photoexcitation and retinoic acid cation radicals (ATRA •+ ) via photoionization (16).…”

Section: Introductionmentioning

confidence: 99%

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Interaction of Retinoic Acid Radical Cation with Lysozyme and Antioxidants: Laser Flash Photolysis Study in Microemulsion

Wang

et al. 2013

Photochem & Photobiology

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All-trans retinoic acid (ATRA) plays essential roles in the normal biological processes and the treatment of cancer and skin diseases. Considering its photosensitive property, many studies have been focused on the photochemistry of ATRA. In this study, we investigated the transient phenomena in the laser flash photolysis (LFP) of ATRA in microemulsion to further understand the photochemistry of ATRA. Results show that 355 nm LFP of ATRA in both acidic and alkaline conditions leads to the generation of retinoic acid cation radicals (ATRA(•+)) via biphotonic processes. The employment of microemulsion system allows us to investigate the reaction of hydrophobic ATRA(•+) with molecules of different polarity. Therefore, we studied the reaction activity of ATRA(•+) to many hydrophobic and hydrophilic molecules. Results show that ATRA(•+) can efficiently interact with lysozyme, tyrosine, tryptophan and many antioxidants, such as curcumin (Cur), vitamin C (VC) and gallic acid (GA). The apparent rate constants of these reactions were measured and compared. These findings suggest that ATRA(•+) is a reactive transient product which may pose damage to lysozyme, and antioxidants, such as Cur, VC and GA, may inactivate ATRA(•+) by efficient quenching reactions.

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Section: Resultssupporting

confidence: 86%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Interaction of Retinoic Acid Radical Cation with Lysozyme and Antioxidants: Laser Flash Photolysis Study in Microemulsion

Wang

et al. 2013

Photochem & Photobiology

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“…Retinol is one of the active forms of vitamin A; it can promote vision, participate in protein synthesis and cell differentiation, support reproduction and growth [9], and inhibit lipid peroxidation [10]. The two main forms of vitamin E are α-tocopherol and γ-tocopherol; the concentrations of α-tocopherol are reported to be 4–10 times higher than those of γ-tocopherol in the plasma among humans [11].…”

Section: Introductionmentioning

confidence: 99%

Associations of Serum Retinol, α-Tocopherol, and γ-Tocopherol with Biomarkers among Healthy Japanese Men

Zou

Wang

Sakano

et al. 2014

IJERPH

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Retinol, α-tocopherol, and γ-tocopherol are fat-soluble vitamins acting as antioxidants via the prevention of lipid oxidation. Little is known about circulatory levels in healthy individuals. The present cross-sectional study aimed at elucidating the relationship between these antioxidants and clinical biomarkers in 206 male (median age 41 years, range 23–67) employees from companies located in the Okayama Prefecture, Japan. Subjects younger than 40 years (n = 94) showed a positive association of the frequency of alcohol consumption with the circulating retinol (β = 0.344, p = 0.001) and γ-tocopherol levels (β = 0.219, p = 0.041), and an inverse association of fast insulin with serum retinol (β = −0.301, p = 0.009). In participants older than 40 years (n = 112) we found that an inverse association of HOMA-R with serum retinol (β = −0.262, p = 0.021), α-tocopherol (β = −0.236, p = 0.035), and γ-tocopherol levels (β = −0.224, p = 0.052); and cigarette smoking was inversely associated with the levels of serum α-tocopherol (β = −0.286, p = 0.008) and γ-tocopherol (β = −0.229, p = 0.040). We further found negative relationships between serum ferritin and the retinol (β = −0.211, p = 0.032) and α-tocopherol levels (β = −0.223, p = 0.022) in men over 40 years of age. The present study suggests that the circulatory levels of antioxidant vitamins may modulate the action of insulin and that higher levels of iron might decrease the levels of antioxidant vitamins in the blood.

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“…32 By employing competition kinetics using ABTS 2À as reference solute, the bimolecular rate constant (Table 1) for the scavenging of the CCl 3 O 2 c radical by the SeC was in the order of SePA > SeBA > SeEA. 32 By employing competition kinetics using ABTS 2À as reference solute, the bimolecular rate constant (Table 1) for the scavenging of the CCl 3 O 2 c radical by the SeC was in the order of SePA > SeBA > SeEA.…”

Section: Discussionmentioning

confidence: 99%

Effect of alkyl chain length on one-electron oxidation of bis(alkyl carboxylic acid) selenides: implication on their antioxidant ability

et al. 2015

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One-electron redox reactions of three bis(alkyl carboxylic acid) selenide (SeC) derivatives viz., seleno bis(butanoic acid) (SeBA), seleno bis(propanoic acid) (SePA) and seleno bis(ethanoic acid) (SeEA), were carried out in aqueous solutions using nanosecond pulse radiolysis and the resultant transients were detected by absorption spectroscopy. SeC reacted with cOH radicals to form hydroxyl selenouranyl radicals (pSerOH) which subsequently gave different transient species, like the selenium centered radical cation (SeCc + ), dimer radical cation (pSerSe) + , or a selenium-carboxyl oxygen stabilized monomer radical (pSerO). The relative yield of these transient species depended on pH, concentration of SeC and position of the carboxylate functional group. SeEA and SeBA gave exclusively (pSerSe) + absorbing at 490 nm, while in the case of SePA, along with (pSerSe) + , (pSerO) was also formed. The stability of (pSerSe) + was estimated in terms of the equilibrium constant and was in the order SeBA > SeEA > SePA. Secondary electron transfer reactions of the transients were performed with 2,2 0 -azinobis(3-ethylbenzthiazoline-6-sulphonic acid), thionine and methyl viologen. The study showed that SeCc + undergoes decarboxylation with the formation of the corresponding a-(alkylseleno)alkyl radical and the yield of CO 2 formed was in the order SeEA < SeBA < SePA. The formation of a stabilised monomer radical cation in SePA is responsible for its lower yield of CO 2 and the same is reflected in its higher free radical scavenging antioxidant activity, established by comparing the rate constants for scavenging of peroxyl radicals.

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Pulse radiolysis study of the interaction of retinoids with peroxyl radicals

Cited by 39 publications

References 30 publications

Interaction of Retinoic Acid Radical Cation with Lysozyme and Antioxidants: Laser Flash Photolysis Study in Microemulsion

Interaction of Retinoic Acid Radical Cation with Lysozyme and Antioxidants: Laser Flash Photolysis Study in Microemulsion

Associations of Serum Retinol, α-Tocopherol, and γ-Tocopherol with Biomarkers among Healthy Japanese Men

Effect of alkyl chain length on one-electron oxidation of bis(alkyl carboxylic acid) selenides: implication on their antioxidant ability

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