Increased Antioxidant Reactivity of Vitamin C at Low pH in Model MembranesClick to copy article linkArticle link copied!
Abstract
The reactivity of the water-soluble antioxidant vitamin C (l-ascorbic acid) depends on pH. It is generally recognized that the ascorbate monoanion, which predominates at neutral physiological pH, acts as a stronger antioxidant than the protonated form, ascorbic acid. Fluorazophore-L, a long-lived fluorescent probe, was employed as a mimic for lipid peroxyl radicals. The experiments with micellar and bilayer membrane models demonstrate that vitamin C becomes, in fact, a more powerful antioxidant at low pH. This phenomenon may be general for the interception of reactive oxidizing species at the lipid/water interface.
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- Jun Zhu, R. Bruce Lennox. The Role of Iodide in the Formation of Gold Nanotriangles. ACS Applied Nano Materials 2024, Article ASAP.
- Sunil
Paul M. Menacherry, Kitae Kim, Woojin Lee, Cheol Ho Choi, Wonyong Choi. Ligand-Specific Dissolution of Iron Oxides in Frozen Solutions. Environmental Science & Technology 2018, 52
(23)
, 13766-13773. https://doi.org/10.1021/acs.est.8b04484
- Zhigang Cui, Leilei Huang, Yi Ding, Xuechao Zhu, Xinhua Lu, Yuanli Cai. Compartmentalization and Unidirectional Cross-Domain Molecule Shuttling of Organometallic Single-Chain Nanoparticles. ACS Macro Letters 2018, 7
(5)
, 572-575. https://doi.org/10.1021/acsmacrolett.8b00199
- Leonardo Scarabelli, Ana Sánchez-Iglesias, Jorge Pérez-Juste, and Luis M. Liz-Marzán . A “Tips and Tricks” Practical Guide to the Synthesis of Gold Nanorods. The Journal of Physical Chemistry Letters 2015, 6
(21)
, 4270-4279. https://doi.org/10.1021/acs.jpclett.5b02123
- Thomas G. Barclay, Kristina Constantopoulos, and Janis Matisons . Nanotubes Self-Assembled from Amphiphilic Molecules via Helical Intermediates. Chemical Reviews 2014, 114
(20)
, 10217-10291. https://doi.org/10.1021/cr400085m
- Roy N. Dsouza, Uwe Pischel, and Werner M. Nau . Fluorescent Dyes and Their Supramolecular Host/Guest Complexes with Macrocycles in Aqueous Solution. Chemical Reviews 2011, 111
(12)
, 7941-7980. https://doi.org/10.1021/cr200213s
- Cun-Bin An, Ran Liang, Xiao-Hua Ma, Li-Min Fu, Jian-Ping Zhang, Peng Wang, Rui-Min Han, Xi-Cheng Ai, and Leif H. Skibsted . Retinylisoflavonoid as a Novel Membrane Antioxidant. The Journal of Physical Chemistry B 2010, 114
(43)
, 13904-13910. https://doi.org/10.1021/jp106734p
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(18)
, 14723-14729. https://doi.org/10.1021/la101915x
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(5)
, 1977-1983. https://doi.org/10.1021/jo052440k
- Andreas F.-P. Sonnen,, Huseyin Bakirci,, Thomas Netscher, and, Werner M. Nau. Effect of Temperature, Cholesterol Content, and Antioxidant Structure on the Mobility of Vitamin E Constituents in Biomembrane Models Studied by Laterally Diffusion-Controlled Fluorescence Quenching. Journal of the American Chemical Society 2005, 127
(44)
, 15575-15584. https://doi.org/10.1021/ja054367l
- U. Costas-Costas,, Carlos Bravo-Diaz, and, Elisa Gonzalez-Romero. Kinetics and Mechanism of the Reaction between Ascorbic Acid Derivatives and an Arenediazonium Salt: Cationic Micellar Effects. Langmuir 2005, 21
(24)
, 10983-10991. https://doi.org/10.1021/la051564p
- Gabriela Gramlich,, Jiayun Zhang, and, Werner M. Nau. Diffusion of α-Tocopherol in Membrane Models: Probing the Kinetics of Vitamin E Antioxidant Action by Fluorescence in Real Time. Journal of the American Chemical Society 2004, 126
(17)
, 5482-5492. https://doi.org/10.1021/ja039845b
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(4)
, 113-120. https://doi.org/10.22144/ctujos.2024.399
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(7-8)
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(5)
, 106142. https://doi.org/10.1016/j.jece.2021.106142
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(1)
, 71-79. https://doi.org/10.1039/c9pp00439d
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(9)
, 1203-1226. https://doi.org/10.2217/nnm-2018-0409
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(12)
, 3038-3044. https://doi.org/10.1002/chem.201705635
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b
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(60)
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(29)
https://doi.org/10.1002/adfm.201700523
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(3)
, 22. https://doi.org/10.3390/pharmaceutics8030022
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(12)
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(10)
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(6)
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(20)
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(6)
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(2)
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(2-3)
, 204-212. https://doi.org/10.1016/j.jphotochem.2007.06.026
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(17)
, 3585-3590. https://doi.org/10.1016/j.tet.2006.08.108
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(4)
, 1580-1586. https://doi.org/10.1016/j.jpba.2006.11.029
- Werner M. Nau, Andreas Hennig, Apurba L. Koner. Squeezing Fluorescent Dyes into Nanoscale Containers—The Supramolecular Approach to Radiative Decay Engineering. 2007, 185-211. https://doi.org/10.1007/4243_2007_007
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(5)
, 733-737. https://doi.org/10.1002/cbic.200500561
- Shaoying Wen, Dietmar Knoll, Helmut Knoll. Comparison of the characteristic behavior of two azo dyes on temperature dependent microstructure changes in micelles and vesicles. Journal of Colloid and Interface Science 2005, 291
(1)
, 244-250. https://doi.org/10.1016/j.jcis.2005.04.096
- Christian Keithahn, Alexander Lerchl. 5‐Hydroxytryptophan is a more potent in vitro hydroxyl radical scavenger than melatonin or vitamin C. Journal of Pineal Research 2005, 38
(1)
, 62-66. https://doi.org/10.1111/j.1600-079X.2004.00177.x
- Padmaja P. Mishra, Apurba L. Koner, Anindya Datta. Interaction of Lucifer yellow with cetyltrimethyl ammonium bromide micelles and the consequent suppression of its non-radiative processes. Chemical Physics Letters 2004, 400
(1-3)
, 128-132. https://doi.org/10.1016/j.cplett.2004.10.101
- Jyotirmayee Mohanty, Werner M. Nau. Refractive index effects on the oscillator strength and radiative decay rate of 2,3-diazabicyclo[2.2.2]oct-2-ene. Photochemical & Photobiological Sciences 2004, 3
(11-12)
, 1026-1031. https://doi.org/10.1039/b412936a
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(2)
, 488-496. https://doi.org/10.1016/j.jcis.2004.06.033
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(3)
, 305-310. https://doi.org/10.1039/b311416c
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