Development and Validation of the First Assay Method Coupling Liquid Chromatography with Chemiluminescence for the Simultaneous Determination of Menadione and Its Thioether Conjugates in Rat Plasma

Elgawish, Mohamed Saleh; Shimomai, Chikako; Kishikawa, Naoya; Ohyama, Kaname; Wada, Mitsuhiro; Kuroda, Naotaka

doi:10.1021/tx400253k

Cited by 18 publications

(16 citation statements)

References 35 publications

(57 reference statements)

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“…Therefore, GSTs may prove to be of further interest because of their functional association to cellular protection against oxidative stress-inducing agents ( Mockett et al 1999 ; Whitworth et al 2005 ; Hayes and McLellan 2009 ). In this context, the mechanism by which MSB affects biological systems may be particularly relevant, as it involves reactive oxygen species generation through quinone redox cycling and/or electrophilic attack involving cellular nucleophiles, both of which are modulated by oxidation or conjugation of glutathione ( Akman et al 1985 ; Baker et al 1996 ; Wallace et al 2005 ; Elgawish et al 2013 ). Treatment with menadione has therefore been associated to oxidative damage due to lipid peroxidation, depletion of cellular glutathione, and variation in expression of glutathione metabolic genes ( Chang et al 1992 ; Kavitha and Chandra 2014 ; Thomas et al 2016 ).…”

Section: Discussionmentioning

confidence: 99%

Natural variation in the transcriptional response of Drosophila melanogaster to oxidative stress

Ramnarine

Grath

Parsch

2021

G3 Genes|Genomes|Genetics

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Broadly distributed species must cope with diverse and changing environmental conditions, including various forms of stress. Cosmopolitan populations of Drosophila melanogaster are more tolerant to oxidative stress than those from the species’ ancestral range in sub-Saharan Africa, and the degree of tolerance is associated with an insertion/deletion polymorphism in the 3’ untranslated region of the Metallothionein A (MtnA) gene that varies clinally in frequency. We examined oxidative stress tolerance and the transcriptional response to oxidative stress in cosmopolitan and sub-Saharan African populations of D. melanogaster, including paired samples with allelic differences at the MtnA locus. We found that the effect of the MtnA polymorphism on oxidative stress tolerance was dependent on the genomic background, with the deletion allele increasing tolerance only in a northern, temperate population. Genes that were differentially expressed under oxidative stress included MtnA and other metallothioneins, as well as those involved in glutathione metabolism and other genes known to be part of the oxidative stress response or the general stress response. A gene co-expression analysis revealed further genes and pathways that respond to oxidative stress including those involved in additional metabolic processes, autophagy, and apoptosis. There was significant overlap among the genes induced by oxidative and cold stress, which suggests a shared response pathway to these two stresses. Interestingly, the MtnA deletion was associated with consistent changes in the expression of many genes across all genomic backgrounds, regardless of the expression level of the MtnA gene itself. We hypothesize that this is an indirect effect driven by the loss of microRNA binding sites within the MtnA 3’ untranslated region.

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Section: Discussionmentioning

confidence: 99%

Natural variation in the transcriptional response of Drosophila melanogaster to oxidative stress

Ramnarine

Grath

Parsch

2021

G3 Genes|Genomes|Genetics

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“…The side chains of phylloquinone and MK-4 are shortened by the rat to seven carbon atoms (ω-oxidation followed by β-oxidation), yielding a carboxylic acid group at the end that cyclises to form a γ-lactone which is excreted in the urine, presumably as a glucuronic acid conjugate. Recently, glutathione-and N-acetylcysteine-menadione conjugates were identified in the rat plasma after intraperitoneal administration of menadione (Elgawish et al, 2013).…”

Section: Absorption Distribution Metabolism and Excretionmentioning

confidence: 99%

Scientific Opinion on the safety and efficacy of vitamin K3 (menadione sodium bisulphite and menadione nicotinamide bisulphite) as a feed additive for all animal species

Feed¹

2014

EFS2

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Vitamin K describes a group of lipophilic vitamins that exist naturally in two forms: vitamin K1 (phylloquinone, found in green plants) and vitamin K2 (a group of menaquinones synthesised by bacteria in the intestine). Vitamin K3 (or menadione) is a synthetic form of vitamin K without a side chain. To become active, menadione needs to undergo prenylation. Vitamins K1, K2 and K3 are metabolically activated in the liver to become co‐factors in the activation of vitamin K‐dependent proteins, which are important for normal blood coagulation, and normality of bones and arteries (Gla proteins). Acute toxicity of menadione or its derivatives is reached at levels exceeding the requirements by a factor of at least 1 000. Menadione sodium bisulphite (MSB) and menadione nicotinamide bisulphite (MNB) are safe for all animal species at practical use levels in feed. The use of MSB in water for drinking is likely to increase the exposure of target animals to chromium(VI). Therefore, the FEEDAP Panel has concerns about the safety of MSB when administered by this route. The use of MSB and MNB in animal nutrition does not give rise to safety concerns for consumers. MSB is an eye irritant; in the absence of adequate data, the additive should be considered as a skin sensitiser. In the absence of data, MNB should be considered as irritant to skin and eyes and as a skin sensitiser. Considering the high dusting potential of MSB and MNB, the absence of data on inhalation toxicity and the chromium(VI) content of dust, inhalation exposure resulting from handling of MSB and MNB could be hazardous. The use of MSB and MNB in animal nutrition does not pose a risk to the environment. MSB and MNB are regarded as effective sources of vitamin K in animal nutrition.

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“…19) The HPLC-CL method was based on the phenomenon that the superoxide anion radicals are generated along with the redox cycle of quinone. 20,21) Quinones, including PQQ, are reduced to semiquinone radicals by dithiothreitol (DTT). [22][23][24] The semiquinone radicals convert dissolved oxygen to the superoxide anion radicals that can react with luminol to produce intense CL.…”

Section: Introductionmentioning

confidence: 99%

Determination Method for Pyrroloquinoline Quinone in Food Products by HPLC-UV Detection Using a Redox-Based Colorimetric Reaction

Fukuda

Kishikawa

Samemoto

et al. 2022

CHEMICAL & PHARMACEUTICAL BULLETIN

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We have developed an HPLC-UV method for the determination of pyrroloquinoline quinone (PQQ), which utilizes a redox-based colorimetric reaction. In the proposed colorimetric reaction, the redox reaction between PQQ and dithiothreitol generates superoxide anion radicals that can convert 2-(4-iodophenyl)-3-(4-nitrophenyl)-5-phenyl-2H-tetrazolium chloride (INT) to formazan dye. After PQQ separation on an octadecyl silica column, it was mixed online with dithiothreitol and INT, and the formed formazan dye was monitored by absorbance at 490 nm. The detection limit (S/N 3) of the proposed method was 7.6 nM (152 fmol/injection). The proposed method could selectively detect PQQ in food products without any clean-up procedures.

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Development and Validation of the First Assay Method Coupling Liquid Chromatography with Chemiluminescence for the Simultaneous Determination of Menadione and Its Thioether Conjugates in Rat Plasma

Cited by 18 publications

References 35 publications

Natural variation in the transcriptional response of Drosophila melanogaster to oxidative stress

Natural variation in the transcriptional response of Drosophila melanogaster to oxidative stress

Scientific Opinion on the safety and efficacy of vitamin K3 (menadione sodium bisulphite and menadione nicotinamide bisulphite) as a feed additive for all animal species

Determination Method for Pyrroloquinoline Quinone in Food Products by HPLC-UV Detection Using a Redox-Based Colorimetric Reaction

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