Mechanism of radioprotection by dihydroxy-1-selenolane (DHS): Effect of fatty acid conjugation and role of glutathione peroxidase (GPx)

Verma, Prachi; Kunwar, Amit; Arai, Kenichiro; Iwaoka, Michio; Priyadarsini, K. Indira

doi:10.1016/j.biochi.2017.10.021

Cited by 9 publications

(4 citation statements)

References 55 publications

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“…Pharmaceutical inhibition of NRF‐2 leads to an increase in both micronucleus and γ‐H2AX, which abrogate the radioprotective effect of DSNA . Similar results have been revealed for DHS . Furthermore, a study showed that sodium selenite, through stimulation of antioxidant defense, protects against radiation‐induced apoptosis and also stimulates the proliferation of ovarian granulosa cells .…”

Section: Selenium As Radioprotectorsupporting

confidence: 61%

“…51 Similar results have been revealed for DHS. 52 Furthermore, a study showed that sodium selenite, through stimulation of antioxidant defense, protects against radiation-induced apoptosis and also stimulates the proliferation of ovarian granulosa cells. 53 Selenium has also shown ability to restore damages to the ovary via inhibition of oxidative stress and apoptosis.…”

Section: Selenium As Radioprotectormentioning

confidence: 99%

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Selenium as an adjuvant for modification of radiation response

Farhood

Mortezaee

Motevaseli

et al. 2019

J of Cellular Biochemistry

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Ionizing radiation plays a central role in several medical and industrial purposes. In spite of the beneficial effects of ionizing radiation, there are some concerns related to accidental exposure that could pose a threat to the lives of exposed people. This issue is also very critical for triage of injured people in a possible terror event or nuclear disaster. The most common side effects of ionizing radiation are experienced in cancer patients who had undergone radiotherapy. For complete eradication of tumors, there is a need for high doses of ionizing radiation. However, these high doses lead to severe toxicities in adjacent organs. Management of normal tissue toxicity may be achieved via modulation of radiation responses in both normal and malignant cells. It has been suggested that treatment of patients with some adjuvant agents may be useful for amelioration of radiation toxicity or sensitization of tumor cells. However, there are always some concerns for possible severe toxicities and protection of tumor cells, which in turn affect radiotherapy outcomes. Selenium is a trace element in the body that has shown potent antioxidant and radioprotective effects for many years. Selenium can potently stimulate antioxidant defense of cells, especially via upregulation of glutathione (GSH) level and glutathione peroxidase activity. Some studies in recent years have shown that selenium is able to mitigate radiation toxicity when administered after exposure. These studies suggest that selenium may be a useful radiomitigator for an accidental radiation event. Molecular and cellular studies have revealed that selenium protects different normal cells against radiation, while it may sensitize tumor cells. These differential effects of selenium have also been revealed in some clinical studies. In the present study, we aimed to review the radiomitigative and radioprotective effects of selenium on normal cells/tissues, as well as its radiosensitive effect on cancer cells.

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Section: Selenium As Radioprotectorsupporting

confidence: 61%

Section: Selenium As Radioprotectormentioning

confidence: 99%

Selenium as an adjuvant for modification of radiation response

Farhood

Mortezaee

Motevaseli

et al. 2019

J of Cellular Biochemistry

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“…These features are potential merits of DHS when it is applied to medicinal and material Molecules 2023, 28, 3607 2 of 10 sciences. We previously demonstrated that DHS can be an antioxidant against lipid peroxidation [27,28] and a radioprotector [29] by means of adequate chemical modifications of the two hydroxy (OH) groups. In this study, we developed new DHS derivatives with a crown-ether ring fused to the OH groups (DHS-crown-n (n = 4 to 7), 1-4) and investigated their behaviors as host molecules to various alkali metal salts.…”

Section: Introductionmentioning

confidence: 99%

Controlling the Redox Catalytic Activity of a Cyclic Selenide Fused to 18-Crown-6 by the Conformational Transition Induced by Coordination to an Alkali Metal Ion

2023

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trans-3,4-Dihydroxyselenolane (DHS), a water-soluble cyclic selenide, exhibits selenoenzyme-like unique redox activities through reversible oxidation to the corresponding selenoxide. Previously, we demonstrated that DHS can be applied as an antioxidant against lipid peroxidation and a radioprotector by means of adequate modifications of the two hydroxy (OH) groups. Herein, we synthesized new DHS derivatives with a crown-ether ring fused to the OH groups (DHS-crown-n (n = 4 to 7), 1–4) and investigated their behaviors of complex formation with various alkali metal salts. According to the X-ray structure analysis, it was found that the two oxygen atoms of DHS change the directions from diaxial to diequatorial by complexation. The similar conformational transition was also observed in solution NMR experiments. The 1H NMR titration in CD3OD further confirmed that DHS-crown-6 (3) forms stable 1:1 complexes with KI, RbCl and CsCl, while it forms a 2:1 complex with KBPh4. The results suggested that the 1:1 complex (3·MX) exchanges the metal ion with metal-free 3 through the formation of the 2:1 complex. The redox catalytic activity of 3 was evaluated using a selenoenzyme model reaction between H2O2 and dithiothreitol. The activity was significantly reduced in the presence of KCl due to the complex formation. Thus, the redox catalytic activity of DHS could be controlled by the conformational transition induced by coordination to an alkali metal ion.

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“…In our group, a water-soluble cyclic selenide, trans -3,4-dihydroxy-1-selenolane (DHS, 5 ), was developed and utilized as a redox reagent for oxidative folding of various proteins, − a selenoenzyme model, − a radical scavenger, − and so forth with pertinent modifications. As another possible application of 5 , we have planned its transformation to selenothreofuranose derivatives having a trans -2,3-dioxygenated configuration (Scheme c).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4-Selenothreofuranose Derivatives via Pummerer-Type Reactions of trans-3,4-Dioxygenated Tetrahydroselenophenes Mediated by a Selenonium Intermediate

et al. 2021

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Selenosugars are interesting targets of organic synthesis as they would possess potential biological activities. However, 4-selenotherofuranose derivatives, which have trans configuration for the two dihydroxy substituents at the 2,3-positions and a glycoside bond at the anomeric position, are not available in the current selenosugar library. In this study, racemic 4-selenothreofuranose derivatives were synthesized from trans-3,4-dioxygenated tetrahydroselenophenes in 77–99% yields with the α/β selectivity about 7:3 via oxidation and subsequent seleno-Pummerer rearrangement. The acetoxy group introduced at the anomeric position was then substituted with various nucleophiles, including activated 6-chloropurine, which afforded 4′-selenothreonucleoside derivatives, in the presence of BF3·OEt2 or TMSOTf. The stereochemistry of the selenosugar products was established by 1H NMR spectroscopy as well as X-ray analysis. The similar α/β selectivity observed in the latter glycosylation reaction to that in the former seleno-Pummerer rearrangement suggested the mediation of a common selenonium intermediate (−Se+C<). It was also suggested that an unexpected interaction between the ester protecting group at the 3-position of the selenofuranose ring and the anomeric carbon atom decreases the α/β selectivity.

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Mechanism of radioprotection by dihydroxy-1-selenolane (DHS): Effect of fatty acid conjugation and role of glutathione peroxidase (GPx)

Cited by 9 publications

References 55 publications

Selenium as an adjuvant for modification of radiation response

Selenium as an adjuvant for modification of radiation response

Controlling the Redox Catalytic Activity of a Cyclic Selenide Fused to 18-Crown-6 by the Conformational Transition Induced by Coordination to an Alkali Metal Ion

Synthesis of 4-Selenothreofuranose Derivatives via Pummerer-Type Reactions of trans-3,4-Dioxygenated Tetrahydroselenophenes Mediated by a Selenonium Intermediate

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