Tertiary selenoamide compounds are useful superoxide radical scavengers in vitro

Takahashi, H.; Nishina, Atsuyoshi; Kimura, Hirokazu; Motoki, Kenji Freire; Koketsu, Mamoru; Ishihara, Hideharu

doi:10.1016/j.ejps.2004.04.011

Cited by 27 publications

(25 citation statements)

References 18 publications

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“…We have evaluated SOSAs of other selenium compounds including selenocarbamates, selenoureas, thioureas, and tertiary selenoamide compounds using a XOD-MCLA method. [21][22][23] IC 50 of these compounds were about 0.1 to 100 mM. [21][22][23] Thus, 2-amino-1,3-selenazoles had similar SOSAs when compared with previously mentioned synthesized organic selenium compounds.…”

Section: Resultsmentioning

confidence: 65%

“…20) We have showed superoxide anion-scavenging activities (SOSAs) of other organic selenium compounds such as selenocarbamates, selenoureas, and tertiary selenoamide compounds. [21][22][23] In the present study, we synthesized a series of five-membered ring selenium-containing heterocyclic compound, 2-amino-1,3-selenazoles and investigated SOSAs by them in vitro.…”

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confidence: 99%

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Superoxide Anion-Scavenging Effect of 2-Amino-1,3-selenazoles

Sekiguchi

Nishina

Kimura

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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We investigated the superoxide anion scavenging effects of thirteen 2-amino-1,3-selenazoles using a highly sensitive quantitative chemiluminescence method. At 166 m mM, the 2-amino-1,3-selenazoles scavenged in the range of 14.3 to 96.7% of O 2 ؊ . 2-Piperidino-1,3-selenazole and 4-phenyl-2-piperidino-1,3-selenazole exhibited the strongest superoxide anion-scavenging activity among the 2-amino-1,3-selenazoles. The 50% inhibitory concentrations (IC 50 ) of 2-piperidino-1,3-selenazole and 4-phenyl-2-piperidino-1,3-selenazole were determined to be 4.03 m mM and 92.6 m mM, respectively. Thus, these compounds acted in vitro as effective O 2 ؊ scavengers.

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Section: Resultsmentioning

confidence: 65%

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confidence: 99%

Superoxide Anion-Scavenging Effect of 2-Amino-1,3-selenazoles

Sekiguchi

Nishina

Kimura

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Previously, we systematically synthesized various organic selenium compounds, including selenocarbamates, selenoureas, thioureas, tertiary selenoamide compounds, 2-amino-1,3-selenazoles, and bis-(2-amino-5-selenazoyl) ketones, and demonstrated their SOSA by using the same chemiluminescence method. The IC 50 values of these compounds ranged from approximately 0.1 to 100 µM (Takahashi et al, 2004;Sekiguchi et al, 2005;Takahashi et al, 2005a;Takahashi et al, 2005b;Sekiguchi et al, 2006). The SOSA of compound b might be relatively low compared with that of other compounds such as selenocarbamates, selenoureas, thioureas, tertiary selenoamide, and ebselen.…”

Section: Discussionmentioning

confidence: 99%

“…Thus, ebselen is a multifunctional antioxidant having a potential chemopreventive effect on inflammation (Nakamura et al, 2002). On the basis of these facts, various types of organic selenium compounds might be applicable for the reduction of oxidative stresses (Takahashi et al, 2004;Takahashi et al, 2005a;Takahashi et al, 2005b). Morey et al (2001) demonstrated that some selenoproteins, such as selenoprotein P, regulate the redox potential in cells, resulting in modulation of various phosphorylation pathways including Ras/MAP kinase signaling (Morey et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

“…We have synthesized various organic selenium compounds, such as selenoamides (Takahashi et al, 2004), selenoureas, thioureas (Takahashi et al, 2005b), and selenocarbamates (Takahashi et al, 2005a), and found that most of these compounds act as effective scavengers of O 2 -in vitro (Takahashi et al, 2005a;Takahashi et al, 2005b). In the present study, we newly synthesized five-member ring compounds, 1,3-selenazolidin-4-ones, and tested not only their superoxide radical-scavenging activity (SOSA) by using a real-time kinetic chemiluminescence method, but also their suppressive activity toward serum deprivation-induced apoptosis and their ability to induce MAP kinase phosphorylation in PC12 cells.…”

Section: Introductionmentioning

confidence: 99%

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A superoxide anion-scavenger, 1,3-selenazolidin-4-one suppresses serum deprivation-induced apoptosis in PC12 cells by activating MAP kinase

Nishina

Kimura

Kozawa

et al. 2011

Toxicology and Applied Pharmacology

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Synthetic organic selenium compounds, such as ebselen, may show glutathione peroxidaselike antioxidant activity and have a neurotrophic effect. We synthesized 1,3-selenazolidin-4-ones, new types of synthetic organic selenium compounds (five-member ring compounds), to study their possible applications as antioxidants or neurotrophic-like molecules. Their superoxide radical scavenging effects were assessed using the quantitative, highly sensitive method of real-time kinetic chemiluminescence. At 166 M, the O2− scavenging activity of 1,3-selenazolidin-4-ones ranged from 0 to 66.2%. 2-[3-(4-Methoxyphenyl)-4-oxo-1,3-selenazolidin-2-ylidene]malononitrile (compound b) showed the strongest superoxide anion-scavenging activity among the 6 kinds of 2-methylene-1,3-selenazolidin-4-ones examined. Compound b had a 50% inhibitory concentration (IC50) at 92.4 M and acted as an effective and potentially useful O2− scavenger in vitro. The effect of compound b on rat pheochromocytome cell line PC12 cells was compared with that of ebselen or nerve growth factor (NGF) by use of the MTT [3-(4, 5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide] assay. When ebselen was added at 100 M or more, toxicity toward PC12 cells was evident. On the contrary, compound b suppressed serum deprivation-induced apoptosis in PC12 cells more effectively at a concentration of 100 M. The activity of compound b to phosphorylate mitogen-activated protein kinase/extracellular signal-regulated protein kinase (ERK) 1/2 (MAP kinase) in PC12 cells was higher than that of ebselen, and the former at 100 M induced the phosphorylation of MAP kinase to a degree similar to that induced by NGF. From these results, we conclude that this superoxide anion-scavenger, compound b, suppressed serum deprivationinduced apoptosis by promoting the phosphorylation of MAP kinase. (MAP kinase) in PC12 cells was higher than that of ebselen, and the former at 100 μM induced the phosphorylation of MAP kinase to a degree similar to that induced by NGF.From these results, we conclude that this superoxide anion-scavenger, compound b, suppressed serum deprivation-induced apoptosis by promoting the phosphorylation of MAP kinase.

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Organoselenium and organotellurium compounds: Toxicology and pharmacology

Nogueira

Rocha

2011

Patai's Chemistry of Functional Groups

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In the last three decades, the interest in the field of synthesis and reactivity of organoselenium and organotellurium compounds has increased; particularly, in view of the observations that they can exhibit important biological activities. The data presented in this chapter clearly indicate the potential pharmacological and therapeutic uses of organoselenium and organotellurium compounds. Indeed, these classes of molecules exhibit a variety of interesting biological effects, namely antioxidant properties, which can account for their in vitro and in vivo beneficial effects in a wide range of models of different human pathologies. We can conclude that the future of “medicinal chemistry“ of organoselenium and organotellurium compounds will depend on the rational development of new molecules, which can be guided by chemical and biological approaches. Moreover, the structure‐activity relationship for a given class of organoselenium or organotellurium compounds should be used as a toll for screening molecules with high probability of exhibiting low toxicity and high pharmacological activity in mammals.

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Tertiary selenoamide compounds are useful superoxide radical scavengers in vitro

Cited by 27 publications

References 18 publications

Superoxide Anion-Scavenging Effect of 2-Amino-1,3-selenazoles

Superoxide Anion-Scavenging Effect of 2-Amino-1,3-selenazoles

A superoxide anion-scavenger, 1,3-selenazolidin-4-one suppresses serum deprivation-induced apoptosis in PC12 cells by activating MAP kinase

Organoselenium and organotellurium compounds: Toxicology and pharmacology

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