Antioxidative properties of natural coelenterazine and synthetic methyl coelenterazine in rat hepatocytes subjected to tert-butyl hydroperoxide-induced oxidative stress

Dubuisson, Marlène; Wergifosse, Bertrand de; Trouet, André; Baguet, Fernand; Marchand‐Brynaert, Jacqueline; Rees, Jean-François

doi:10.1016/s0006-2952(00)00359-2

Cited by 47 publications

(23 citation statements)

References 40 publications

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“…TBHP is a well-known inducer of ROS-mediated oxidative stress that results in DNA damage [44,45]. In the present study, we have evaluated the antioxidant potential of genistein and biochanin A in providing protection to lymphocytes against TBHP-induced oxidative injury.…”

Section: Antioxidant Activity Of Isoflavones Against Tbhp-induced Oximentioning

confidence: 99%

Cellular DNA breakage by soy isoflavone genistein and its methylated structural analogue biochanin A

Ullah

Shamim

Hanif

et al. 2009

Molecular Nutrition Food Res

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Epidemiological studies have indicated that populations with high isoflavone intake through soy consumption have lower rates of breast, prostate, and colon cancer. The isoflavone polyphenol genistein in soybean is considered to be a potent chemopreventive agent against cancer. In order to explore the chemical basis of chemopreventive activity of genistein, in this paper we have examined the structure-activity relationship between genistein and its structural analogue biochanin A. We show that both genistein and its methylated derivative biochanin A are able to mobilize nuclear copper in human lymphocyte, leading to degradation of cellular DNA. However, the relative rate of DNA breakage was greater in the case of genistein. Further, the cellular DNA degradation was inhibited by copper chelator (neocuproine/bathocuproine) but not by compounds that specifically bind iron and zinc (desferrioxamine mesylate and histidine, respectively). We also compared the antioxidant activity of the two isoflavones against tert-butylhydroperoxide-induced oxidative breakage in lymphocytes. Again genistein was found to be more effective than biochanin A in providing protection against oxidative stress induced by tert-butylhydroperoxide. It would therefore appear that the structural features of isoflavones that are important for antioxidant properties are also the ones that contribute to their pro-oxidant action through a mechanism that involves redox cycling of chromatin-bound nuclear copper.

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Section: Antioxidant Activity Of Isoflavones Against Tbhp-induced Oximentioning

confidence: 99%

Cellular DNA breakage by soy isoflavone genistein and its methylated structural analogue biochanin A

Ullah

Shamim

Hanif

et al. 2009

Molecular Nutrition Food Res

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“…It is known that cells metabolize t-butyl hydroperoxide through two pathways, transforming it by glutathione peroxidase into the corresponding alcohol or cleaving it by cytochrome P-450 into alcoxyl and peroxyl radicals. The first pathway causes an oxidative shift in the cellular glutathione redox state, and the second pathway initiates and propagates lipid peroxidation (71). Products of lipid peroxidation originating from the cytosol can diffuse to mitochondria, causing oxidative damage (72).…”

Section: Fig 2 Effect Of Ca 2؉ On Mitochondrial Function (Respiratimentioning

confidence: 99%

The Characterization of Mitochondrial Permeability Transition in Clonal Pancreatic β-Cells

Koshkin

Bikopoulos

Chan

et al. 2004

Journal of Biological Chemistry

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Mitochondrial permeability transition (MPT), which contributes substantially to the regulation of normal mitochondrial metabolism, also plays a crucial role in the initiation of cell death. It is known that MPT is regulated in a tissue-specific manner. The importance of MPT in the pancreatic ␤-cell is heightened by the fact that mitochondrial bioenergetics serve as the main glucose-sensing regulator and energy source for insulin secretion. In the present study, using MIN6 and INS-1 ␤-cells, we revealed that both Ca 2؉ -phosphate-and oxidant-induced MPT is remarkably different from other tissues. Ca 2؉ -phosphate-induced transition is accompanied by a decline in mitochondrial reactive oxygen species production related to a significant potential dependence of reactive oxygen species formation in ␤-cell mitochondria. Hydroperoxides, which are indirect MPT co-inducers active in liver and heart mitochondria, are inefficient in ␤-cell mitochondria, due to the low mitochondrial ability to metabolize them. Direct cross-linking of mitochondrial thiols in pancreatic ␤-cells induces the opening of a low conductance ion permeability of the mitochondrial membrane instead of the full scale MPT opening typical for liver mitochondria. Low conductance MPT is independent of both endogenous and exogenous Ca 2؉ , suggesting a novel type of nonclassical MPT in ␤-cells. It results in the conversion of electrical transmembrane potential into ⌬pH instead of a decrease in total protonmotive force, thus mitochondrial respiration remains in a controlled state. Both Ca 2؉ -and oxidant-induced MPTs are phosphate-dependent and, through the "phosphate flush" (associated with stimulation of insulin secretion), are expected to participate in the regulation in ␤-cell glucose-sensing and secretory activity.Mitochondrial permeability transition (MPT) 1 is a permeability increase of the inner mitochondrial membrane to solutes of molecular mass up to ϳ1500 Da, which is caused by an opening of specific nonselective proteinaceous pores in the inner mitochondrial membrane (1, 2). Increased permeability of the inner membrane is initiated by an increased level of intramitochondrial Ca 2ϩ and is regulated by multiple effectors, including inorganic phosphate, the redox state of pyridine nucleotides and thiols (oxidative stress), membrane potential, cyclosporin A, and other factors (3). MPT pores are thought to have at least two open conformations and a variable degree of reversibility. Most importantly, MPT in its different forms contributes to both normal cell physiology (regulation of oxidative phosphorylation and Ca 2ϩ metabolism) and to regulatory processes leading to apoptosis (2-4). Specific features of MPT show significant tissue-specific variability (5-8). The most significant and well documented deviation from classical MPT described in liver mitochondria was observed in brain tissue (9). Brain mitochondria demonstrate high resistance to MPT opening (10), low sensitivity to cyclosporin A (5), different responses to MPT modifiers, and a distinctive...

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“…The survival of rat hepatocytes cultured in the presence of tested compounds has been measured with the MTT assay, as previously described [29]. This test determines the mitochondrial succinate dehydrogenase activity that is proportional to cell survival.…”

Section: Toxicity On Hepatocytesmentioning

confidence: 99%

“…Coelenterazine (2-(p-hydroxybenzyl)-6-(p-hydroxyphenyl) -8-benzyl-3,7-dihydroimi-dazolo[1,2-a]pyrazin-3-one; CLZn) has strong antioxidative properties as it is highly reactive with superoxide anion, hydroxyl radical, singlet oxygen, peroxides, lipidic radicals, nitrofurantoin-derived radicals, and peroxynitrite [17][18][27][28][29][30][31][32][33]. It has been previously …”

Section: Introductionmentioning

confidence: 99%

Discovery and Validation of a New Family of Antioxidants: The Aminopyrazine Derivatives

Dubuisson

Rees²,

Marchand‐Brynaert

2004

mrmc

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Coelenteramine (2-amino-1,4-pyrazine derivative), one of the metabolites of the oxidative degradation of coelenterazine (imidazolopyrazinone derivative), is endowed with excellent antioxidative properties towards ROS/RNS, like its mother-compound. This crucial discovery, made during the study of natural bioluminescent compounds (luciferins), has stimulated the development of synthetic aminopyrazine derivatives as new leads in medicinal chemistry in the field of antioxidant-based therapies. Synthetic approaches, theoretical evaluation, radical scavenging properties in acellular and cellular tests, and in vivo evaluation are described, and illustrated with representative aminopyrazines. Tested compounds were inhibitors of lipid peroxidation and good quenchers of peroxynitrite. They efficiently protect isolated LDL against radical-induced damages. They prevent cell constituents (membranes, DNA) against injuries by various oxidative stressors (UV irradiation, hydroperoxide treatment, oxidized LDL toxicity). Lastly, aminopyrazines are remarkably active in the "hamster cheek pouch" assay (in vivo protection against ischemia-reperfusion damages).

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Antioxidative properties of natural coelenterazine and synthetic methyl coelenterazine in rat hepatocytes subjected to tert-butyl hydroperoxide-induced oxidative stress

Cited by 47 publications

References 40 publications

Cellular DNA breakage by soy isoflavone genistein and its methylated structural analogue biochanin A

Cellular DNA breakage by soy isoflavone genistein and its methylated structural analogue biochanin A

The Characterization of Mitochondrial Permeability Transition in Clonal Pancreatic β-Cells

Discovery and Validation of a New Family of Antioxidants: The Aminopyrazine Derivatives

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