Alpha tocopherol quinone (αTQ): A potent inhibitor of platelet function

Rao, Gundu H. R.; Cox, Chadwick A.; Gerrard, Jonathan M.; White, James G.

doi:10.1016/0163-7827(81)90097-7

Cited by 10 publications

(1 citation statement)

References 12 publications

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“…(ii) The inhibition of platelet aggregation by 2-alkoxy-1,4-naphthoquinone increases with 2-alkoxy chain length (Lien et al, 2002 ). (iii) The inclusion of a free amino group in the thiosulfonate moiety of quinone (4-aminobenzenesulfonothioic acid S-[(9,10-dihydro-1,4-dimethoxy-9,10-dioxo2-anthracenyl)methyl] ester) increased its antiplatelet activity (Bolibrukh et al, 2015 ), (iv) The inhibition of platelet activation by alpha-tocopherol quinone is greater than that of vitamin E (Rao et al, 1981 ), and (v) gem -diethyl/methyl substitutions and the addition/modifications of the third ring of ortho -carbonyl hydroquinone scaffold influence on the selective index (IC 50 TRAP-6/IC 50 Collagen) and the inhibitory capacity of platelet aggregation (Mendez et al, 2020 ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Thio-Derivatives of 2-Hydroxy-1,4-Naphthoquinone (Lawsone) as Novel Antiplatelet Agents

et al. 2020

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We designed and synthesized in water, using conventional heating and microwave irradiation, new thio-derivatives of 2-hydroxy-1,4-naphthoquinone, a naturally occurring pigment known as lawsone or hennotannic acid, thus improving their antiplatelet activity with relevance to their potential future use in thrombus formation treatment. The structure-activity relationship showed that the thiophenyl moiety enhances the antiplatelet activity. Moreover, the position and nature of the substituent at the phenyl ring have a key effect on the observed biological activity. Compound 4 (2-((4-bromophenyl)thio)-3-hydroxynaphthalene-1,4-dione) was the most active derivative, presenting IC 50 values for platelet aggregation inhibition of 15.03 ± 1.52 µM for TRAP-6, and 5.58 ± 1.01 µM for collagen. Importantly, no cytotoxicity was observed. Finally, we discussed the structure-activity relationships of these new lawsone thio-derivatives on inhibition of TRAP-6-and collagen-induced platelet aggregation.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Thio-Derivatives of 2-Hydroxy-1,4-Naphthoquinone (Lawsone) as Novel Antiplatelet Agents

et al. 2020

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Ubiquinones and Other Bioquinones

Jacini¹

1985

Fette, Seifen, Anstrichm.

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The biochinones, of which a large number is well‐known, can be classified into four groups: ubichinones, vitamins K, plastochinones and tocopherylchinones. Among these the ubichinones are the most commons in nature. By means of selected statements in literature occurrence, formation and importance of the biochinones are discussed in biological red‐ox‐reactions. Furthermore industrial syntheses of ubichinone Q10 are reported. Because of the biological importance of the ubichinones the determination of ubichinones, too, besides vitamin E during routine investigations is to recommend.

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Tocopheryl quinones and mitochondria

Gille

Staniek

Rosenau

et al. 2010

Molecular Nutrition Food Res

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In the past, the role of tocopherols and tocopheryl hydroquinones as antioxidants in mitochondria has been examined. However, structural properties of tocopherols and tocopheryl quinones (arrangement of polar/apolar moieties) have also been recognized as being crucial for the selective transport of RRR-alpha-congeners compared with other tocopherols in the cell, suggesting that these properties might be generally important for the binding of vitamin E-related compounds to proteins and enzymes in mitochondria. Therefore, direct modulation of mitochondrial activities, such as bioenergetics, production of reactive oxygen species and apoptosis, not exclusively related to the redox activity of these compounds is increasingly studied. This overview focuses on the influence of alpha-/gamma-tocopheryl quinones and their parent alpha-/gamma-tocopherols on mitochondrial functions, including formation of tocopheryl quinones, their analytical aspects, their potential as alternative substrates and their inhibitory activity for some mitochondrial functions. It is shown that the understanding of how tocopheryl quinones and tocopherols interfere with mitochondrial functions on the molecular level is still incomplete and that a better comprehension requires further research activities.

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Alpha tocopherol quinone (αTQ): A potent inhibitor of platelet function

Cited by 10 publications

References 12 publications

Synthesis and Biological Evaluation of Thio-Derivatives of 2-Hydroxy-1,4-Naphthoquinone (Lawsone) as Novel Antiplatelet Agents

Synthesis and Biological Evaluation of Thio-Derivatives of 2-Hydroxy-1,4-Naphthoquinone (Lawsone) as Novel Antiplatelet Agents

Ubiquinones and Other Bioquinones

Tocopheryl quinones and mitochondria

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