The Interaction of Hypotaurine and Other Sulfinates with Reactive Oxygen and Nitrogen Species: A Survey of Reaction Mechanisms

Conrado, Alessia Baseggio; D’Angelantonio, Mila; D’Erme, Maria; Pecci, Laura; Fontana, Mario

doi:10.1007/978-94-024-1079-2_45

Cited by 11 publications

(10 citation statements)

References 41 publications

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“…The role of taurine, the oxidative form of hypotaurine, has been shown to have a positive effect on cell survival attributed to its osmolyte activity (19,20) and to have a photoprotective effect against UV‐induced damage via regulating the release of platelet‐activating factor from the membrane of UVB‐irradiated cells (21). To our knowledge, this is the first study that has investigated whether hypotaurine, which has been well studied for its antioxidant effects in vitro , including kinetic experiments using enzyme and radiolysis analysis and ex vivo experiments in rat placental trophoblasts and human skin fibroblasts (14–17), could have photoprotective effects. Approaches to the prevention of photoageing and skin cancer have included a prominent focus on limiting ROS production generated by UVA and counteracting oxidative damage, through the use of antioxidant agents, such as vitamins E and C, β‐carotene and retinoids, which are capable of interacting with ROS and reducing their formation and impact (8,33).…”

Section: Discussionmentioning

confidence: 99%

“…As hypotaurine itself does not absorb radiation in the UVA region (36), this cannot be a consequence of a direct photochemical interaction between hypotaurine and UVA. On the contrary, hypotaurine is well known to interact with ROS and act as an antioxidant (15,27). The taurine level detected did not significantly change in the context of hypotaurine depletion, probably due to lack of sensitivity of detection at these levels, as there were 10‐fold higher levels of intracellular taurine compared to hypotaurine present in the cells after treatment with 5 m M hypotaurine and moreover, taurine levels are reduced at higher UVA doses.…”

Section: Discussionmentioning

confidence: 99%

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Role of Hypotaurine in Protection against UVA‐Induced Damage in Keratinocytes

Conrado

Fanelli

McGuire

et al. 2020

Photochem & Photobiology

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Photoageing and skin cancer are major causes of morbidity and are a high cost to society. Interest in the development of photoprotective agents for inclusion in topical cosmetic and sunscreen products is profound. Recently, amino acids with a sulfinic group, notably hypotaurine, have been included as ingredients in cosmetic preparations. However, the mechanism of action of hypotaurine as a possible anti‐aging agent is unknown, despite its use as a free radical scavenger. To address this issue, we investigated hypotaurine uptake in a human keratinocyte model and examined its effect on UVR‐induced cytotoxicity. Hypotaurine was taken up by keratinocytes in a time‐ and concentration‐dependent manner, with levels remaining significantly above baseline 48 h after washout. A cytoprotective effect of pre‐incubation with 2.5–5 mMhypotaurine was shown as indicated by increased cell viability when keratinocytes were irradiated with UVA at 5 or 10 Jcm‐2, with the level of hypotaurine also significantly reduced. These findings indicate a potential cytoprotective effect of hypotaurine against the deleterious effects of UVA irradiation. This provides support for further studies to evaluate the potential photoprotective benefits of hypotaurine supplementation of topical cosmetic and sunscreen products.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Role of Hypotaurine in Protection against UVA‐Induced Damage in Keratinocytes

Conrado

Fanelli

McGuire

et al. 2020

Photochem & Photobiology

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“…However, no specific enzymatic activity has been detected for this oxidation. Conversely, there is strong evidence that in vivo formation of Tau and CA is the result of sulfinate (RSO 2 – ) interaction with a variety of biologically relevant oxidizing agents [ 153 – 156 ]. The relevance of both CO 3 ·– and · NO 2 in the oxidation of Htau has been recently evidenced by the peroxidase activity of Cu-Zn superoxide dismutase and horseradish peroxidase [ 157 – 159 ].…”

Section: Biochemical Aspects Of Endogenous Sulfurous Metabolitesmentioning

confidence: 99%

“…Noteworthy, Htau is capable of protecting SOD by the H 2 O 2 -mediated inactivation, thus reinforcing the cell defense against oxidative damage [ 176 ]. However, the one-electron oxidative reaction between Htau and various biologically relevant oxidants is accompanied by generation of reactive intermediates, such as sulfonyl radicals, which could promote oxidative chain reactions [ 156 , 157 ].…”

Section: Biochemical Aspects Of Endogenous Sulfurous Metabolitesmentioning

confidence: 99%

Chemistry and Biochemistry of Sulfur Natural Compounds: Key Intermediates of Metabolism and Redox Biology

Francioso

Conrado

Mosca

et al. 2020

Oxidative Medicine and Cellular Longevity

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Sulfur contributes significantly to nature chemical diversity and thanks to its particular features allows fundamental biological reactions that no other element allows. Sulfur natural compounds are utilized by all living beings and depending on the function are distributed in the different kingdoms. It is no coincidence that marine organisms are one of the most important sources of sulfur natural products since most of the inorganic sulfur is metabolized in ocean environments where this element is abundant. Terrestrial organisms such as plants and microorganisms are also able to incorporate sulfur in organic molecules to produce primary metabolites (e.g., methionine, cysteine) and more complex unique chemical structures with diverse biological roles. Animals are not able to fix inorganic sulfur into biomolecules and are completely dependent on preformed organic sulfurous compounds to satisfy their sulfur needs. However, some higher species such as humans are able to build new sulfur-containing chemical entities starting especially from plants’ organosulfur precursors. Sulfur metabolism in humans is very complicated and plays a central role in redox biochemistry. The chemical properties, the large number of oxidation states, and the versatile reactivity of the oxygen family chalcogens make sulfur ideal for redox biological reactions and electron transfer processes. This review will explore sulfur metabolism related to redox biochemistry and will describe the various classes of sulfur-containing compounds spread all over the natural kingdoms. We will describe the chemistry and the biochemistry of well-known metabolites and also of the unknown and poorly studied sulfur natural products which are still in search for a biological role.

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“…[1][2][3] The non-enzymatic oxidation of hypotaurine to taurine by reactive oxygen species (ROS) serves to scavenge ROS. 1,2,4,5) Hypotaurine concentration correlates with the motility of spermatozoa, and reduces their level of ROS. 6,7) Hepatic ischemia-reperfusion induces an increase of cellular hypotaurine.…”

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confidence: 99%

Hypotaurine Is a Substrate of GABA Transporter Family Members GAT2/Slc6a13 and TAUT/Slc6a6

Nishimura

Higuchi

Yoshida

et al. 2018

Biological & Pharmaceutical Bulletin

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Hypotaurine is a precursor of taurine and a physiological antioxidant that circulates in adult and fetal plasma. The purpose of the present study was to clarify whether hypotaurine is a substrate of Slc6a/gammaaminobutyric acid (GABA) transporter family members. Radiolabeled hypotaurine was synthesized from radiolabeled cysteamine and 2-aminoethanethiol dioxygenase. The uptakes of [ 3 H]GABA, [ 3 H]taurine, and [ 14 C]hypotaurine by HEK293 cells expressing mouse GAT1/Slc6a1, TAUT/Slc6a6, GAT3/Slc6a11, BGT1/ Slc6a12, and GAT2/Slc6a13 were measured. TAUT and GAT2 showed strong [ 14 C]hypotaurine uptake activity, while BGT1 showed moderate activity, and GAT1 and GAT3 showed slight but significant activity. Mouse TAUT and GAT2 both showed Michaelis constants of 11 µM for hypotaurine uptake. GAT2-expressing cells pretreated with hypotaurine showed resistance to H 2 O 2-induced oxidative stress. These results suggest that under physiological conditions, TAUT and GAT2 would be major contributors to hypotaurine transfer across the plasma membrane, and that uptake of hypotaurine via GAT2 contributes to the cellular resistance to oxidative stress.

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The Interaction of Hypotaurine and Other Sulfinates with Reactive Oxygen and Nitrogen Species: A Survey of Reaction Mechanisms

Cited by 11 publications

References 41 publications

Role of Hypotaurine in Protection against UVA‐Induced Damage in Keratinocytes

Role of Hypotaurine in Protection against UVA‐Induced Damage in Keratinocytes

Chemistry and Biochemistry of Sulfur Natural Compounds: Key Intermediates of Metabolism and Redox Biology

Hypotaurine Is a Substrate of GABA Transporter Family Members GAT2/Slc6a13 and TAUT/Slc6a6

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