Phenol derivatives as enhancers and inhibitors of luminol-H2O2-horseradish peroxidase chemiluminescence

Dı́az, A. Navas; Sánchez, Francisco; García, J.A. González

doi:10.1002/(sici)1099-1271(199803/04)13:2<75::aid-bio469>3.0.co;2-7

Cited by 53 publications

(25 citation statements)

References 27 publications

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“…A model compound with an orthosubstituted hydroxyl group to the aromatic ring seems to be adequate for the antioxidant and H 2 O 2 -or DPPH-scavenging activity of phenolic acids [61]. The phenolic compounds act as effective donors or oxygen acceptors in the presence of H 2 O 2 [62,63]. It has been reported that compounds with a hydroxyl group in the ortho position of the phenolic ring have peroxyl radical-and superoxide-scavenging properties [64].…”

Section: Discussionmentioning

confidence: 99%

Hemidesmus indicus Protects against ethanol-induced liver toxicity

Saravanan

Nalini

2008

Cellular and Molecular Biology Letters

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Alcoholic liver disease (ALD) is one of the most common diseases in modern society. A large number of studies are in progress aiming to identify natural substances that would be effective in reducing the severity of ALD. Although there are currently a number of drugs on the market, their long-term use can have numerous side effects. Hemidesmus indicus is an indigenous Ayurvedic medicinal plant used in soft drinks in India. In this study, we examined the effects of its ethanolic root extract on experimental liver damage in order to evaluate its hepatoprotective effects against hepatotoxicity induced in rats by ethanol at a dosage of 5 g/kg body weight for 60 days. The H. indicus root extract was given at a dose of 500 mg/kg body weight for the last 30 days of the experiment. The animals were monitored for food intake and weight gain. The liver was analysed for the degree of lipid peroxidation using thiobarbituric acid reactive substances (TBARS) and antioxidant status using the activities of glutathione-depedendant enzymes. The degree of liver damage was analysed using serum marker enzyme activities, the total protein, albumin, globulin, ceruloplasmin and liver glycogen contents, and the A/G ratio. The Fourier transform infrared spectra (FT-IR) of the liver tissues were recorded in the region of 4000-400 cm -1 . The ethanol-fed rats showed significantly elevated liver marker enzyme activities, lipid peroxidation levels and reduced antioxidant levels as compared to the control rats. Oral administration of H. indicus for the latter 30 days resulted in an increased food intake and weight gain, decreased TBARS levels, near normal levels of glutathione-dependent enzymes, increased total protein, albumin, globulin and liver glycogen contents, an increased A/G ratio, and decreased liver marker enzyme activities and ceruloplasmin levels. The relative intensity of the liver FT-IR bands for the experimental groups were found to be altered significantly (p < 0.05) compared to the control samples. For the group that had H. indicus co-administered with ethanol, the intensity of the bands was near normal. Moreover, the results of the FT-IR study correlated with our biochemical results.

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Section: Discussionmentioning

confidence: 99%

Hemidesmus indicus Protects against ethanol-induced liver toxicity

Saravanan

Nalini

2008

Cellular and Molecular Biology Letters

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“…However, the scavenging activity of formaldehyde, which is used clinically in root canal treatment, as are the phenolic compounds, was much lower than those of the phenolic compounds. It seems likely that the difference of radical scavenging activity is due to the difference between the aromatic and the aldehydic features of these compounds, i.e., due to the fact that the phenolic compounds, but not formaldehyde, act as effective electron donors and oxygen acceptors in the presence of H 2 O 2 (1,18 (18). It seems reasonable that guaiacol acts as an inhibitor of luminol chemiluminescence, because the Hammett constant of guaiacol is approximately − 0.27 (18).…”

Section: Discussionmentioning

confidence: 99%

“…It seems likely that the difference of radical scavenging activity is due to the difference between the aromatic and the aldehydic features of these compounds, i.e., due to the fact that the phenolic compounds, but not formaldehyde, act as effective electron donors and oxygen acceptors in the presence of H 2 O 2 (1,18 (18). It seems reasonable that guaiacol acts as an inhibitor of luminol chemiluminescence, because the Hammett constant of guaiacol is approximately − 0.27 (18). The present results thus strongly demonstrate that the • OH scavenging activity of phenolic compounds, especially guaiacol, was in fact due to their radical scavenging properties, and not to metal-chelating capacity or a direct reaction with H 2 O 2 .…”

Section: Discussionmentioning

confidence: 99%

“…To examine whether guaiacol reacts with H 2 O 2 in a Fenton method, the luminol chemiluminescence reaction using horseradish peroxidase was carried out according to a method described by Navas Díaz et al (18), with some modifications. In a quartz cuvette, 1 mL of 100 mM potassium phosphate buffer (pH 7.5), 20 μL of 10 mM luminol, 60 μL of 100 mM H 2 O 2 , 100 μL of guaiacol at the indicated concentration, and distilled water were added to achieve a final volume of 2950 μL.…”

Section: Reaction Of Guaiacol With H 2 Omentioning

confidence: 99%

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Hydroxyl radical scavenging effects of guaiacol used in traditional dental pulp sedation: Reaction kinetic study

et al. 2005

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Guaiacol, which is a phenolic compound with a methoxy group and used in traditional dental pulp sedation, has the property of inducing cell proliferation. To clarify these mechanisms of guaiacol, this study examined the hydroxyl radical (• OH) scavenging effects of guaiacol in vitro. Generation of• OH was carried out by the Fenton reaction using mixture of ascorbic acid, H 2 O 2 , and Fe(III)-EDTA, and• OH was detected by measuring the • OH-mediated production of degradation products of deoxyribose, which reacts with 2-thiobarbituric acid (TBA) and is relatively stable for a long time. At concentrations of 10 −10 M to 10 −3 M, guaiacol inhibited the TBA reactive substance (TBA-RS) formation in a dose-dependent manner. Phenol and formaldehyde were also found to inhibit the TBA-RS formation, but their inhibitory activities were lower than that of guaiacol. The concentrations of guaiacol, phenol, and formaldehyde needed to cause 50% inhibition of TBA-RS formation were approximately 5 × 10 , and 2 × 10 −3 M, respectively. In this reaction system, guaiacol showed no chelating reaction with ferrous ion and did not directly react with H 2 O 2 . Guaiacol also exhibited radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH) stable free radical, but its scavenging activity was lower than that toward•

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“…However, in the case of piodophenol, the phenoxy radical is thought to play an important role in the enhancing effect. 22,23 The decrease in the enhancing effect of p-iodophenylboronic acid or 4-biphenylboronic acid in the presence of saccharides was attributed to the interaction between the diol group of the saccharide and the boronic acid moiety of the enhancer. The interaction eliminated the possibility of generating such radicals.…”

Section: -Ch(oh)-ch(ch2oh)-mentioning

confidence: 99%

Enhancing Effect of Phenylboronic Acid Compounds and Their Interactions with the Diol Groups of Saccharides in a Capillary Electrophoresis-Chemiluminescence Detection System

et al. 2007

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Capillary electrophoresis(CE) equipped with chemiluminescence (CL) detection has attracted a great deal of attention as a high-performance separation and detection system. [1][2][3][4] We also analyzed many types of sample, including metal ions, metal compounds, amino acids, peptides, proteins, nucleic acids, saccharides, phenolic compounds, fluorescence compounds, and liposomes, using these systems. [5][6][7] We have determined the significant features of CE with CL detection systems through our previous research. 8,9 Naturally, while absorption and fluorescence detection in CE are carried out in an on-capillary manner, CL detection is brought about by endcapillary (postcolumn) detection. That is, CE with CL detection possesses a very interesting and useful "micro-environment area" for reaction/detection at the tip of the capillary outlet. Trace amounts of sample and reagents are delivered quantitatively and mixed reproducibly at the tip of the capillary outlet (micro-environment area), leading to useful and unique CL responses with high sensitivity.Saccharides are among the most important biological molecules in the living body. The compositional formulas of saccharides are simple, as they consist mainly of carbon, hydrogen, and oxygen. However, their molecular structures are very complicated. This complexity in the molecular structure is produced through the various directions of hydroxyl groups in the molecule. There have been many investigations of methodologies to derive information regarding the molecular structures of saccharides, i.e., molecular recognition of saccharides. 10,11 Boronic acids form cyclic esters with saccharides, particularly with those comprising cis-diol groups. [12][13][14] The interaction between boronic acids and saccharides has been used for molecular recognition of saccharides. To derive information regarding the interaction between boronic acids and saccharides, conventional procedures for molecular recognition require specific chemical reactions, such as polymerization and derivatization.In our previous study, 15 we found that the enhancing effect of p-iodophenylboronic acid on luminol-hydrogen peroxidehorseradish peroxidase CL reaction decreased in the presence of saccharide, and we proposed a system to take advantage of the micro-environment area of the CE-CL detection system for molecular recognition of saccharides. The decrease in CL could provide direct information regarding the interaction between piodophenylboronic acids and saccharides without requiring any specific procedures. The method for molecular recognition of saccharides has the following beneficial features in comparison with conventional methods, 16,17 including CD spectra, extraction, and π-A isotherm studies: 1) high sensitivity (a trace amount of a sample specimen is used), 2) rapid analysis, 3) ease of operation, and 4) inexpensive reagents and apparatus.In the present study, to extend our knowledge regarding the molecular recognition of saccharides using the CE with CL detection system, we examined the enh...

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Phenol derivatives as enhancers and inhibitors of luminol-H2O2-horseradish peroxidase chemiluminescence

Cited by 53 publications

References 27 publications

Hemidesmus indicus Protects against ethanol-induced liver toxicity

Hemidesmus indicus Protects against ethanol-induced liver toxicity

Hydroxyl radical scavenging effects of guaiacol used in traditional dental pulp sedation: Reaction kinetic study

Enhancing Effect of Phenylboronic Acid Compounds and Their Interactions with the Diol Groups of Saccharides in a Capillary Electrophoresis-Chemiluminescence Detection System

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