Antonio Luis Braga

Federal University of Santa Catarina, Nossa Senhora do Destêrro, Santa Catarina, Brazil

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Publications (10)28.43 Total impact

  • [Show abstract] [Hide abstract]
    ABSTRACT: Organoselenum compounds have been reported to have a wide range of pharmacological properties. Amine-based diselenide, (Z)-N-(4-methylbenzylidene)-1-(2-((2-(1-((E)-4-methyl benzylideneamino)ethyl)phenyl)diselanyl)phenyl)ethanamine ethyl)phenyl) diselanyl) phenyl) ethylimino) methyl)phenol (compound A), and diphenyl diselenide (PhSe)2 were screened for in vitro antioxidant activity. Compound A and (PhSe)2 were tested against sodium nitroprusside (SNP)- and Fe(II)-induced thiobarbituric acid-reactive species (TBARS) in rat brain homogenates. The radical scavenging activity was measured by 1,1-diphenyl-2-picrylhydrazyl assay. Both compounds A and (PhSe)2 decreased Fe(II)- and SNP-stimulated TBARS production in rat brain homogenates. Compound A exhibited the strongest antioxidant activity in the radical scavenging assay, although (PhSe)2, the simplest of the diaryl diselenide, presented no activity. In conclusion, the results of the present investigation indicated that compound A and (PhSe)2 had preventive effects against SNP- and Fe(II)-induced oxidative stress in rat brain homogenates. The amine group in the organic moiety dramatically changed the potency of amine-based diselenide.
    Biological trace element research 05/2012; 149(3). DOI:10.1007/s12011-012-9440-7 · 1.61 Impact Factor
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    ABSTRACT: The reaction mechanism of the GPx-like oxidation of PhSH with H(2)O(2) catalyzed by selenoxides proceeds via formation of the hydroxy perhydroxy selenane, which is a stronger oxidizing agent than selenoxide. A hydroxy perhydroxy selenane intermediate was observed by electrospray ionization mass spectrometry and (77)Se NMR spectroscopy in reactions of selenoxide 8 with H(2)O(2).The initial velocity of oxidation of PhSH by H(2)O(2) with selenoxide 8 is 4 orders of magnitude higher than that of 8 without peroxide. Selenoxide 8 is not reduced to selenide 6 by PhSH in the presence of H(2)O(2). While electronic substituent effects have minimal impact on the catalytic performance of selenoxides, chelating groups increase the rate of catalysis.
    Journal of the American Chemical Society 12/2011; 134(1):138-41. DOI:10.1021/ja209570y · 11.44 Impact Factor
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    ABSTRACT: The use of organoselenium compounds in the copper-catalyzed Huisgen 1,3-dipolar cycloaddition of azido arylselenides with various alkynes is described. Arylseleno-1,2,3-triazoles are prepared in excellent yields via reaction of amino arylselenides with iso-pentylnitrite and trimethylsilyl azide, and subsequent copper-catalyzed 1,3-dipolar cycloaddition of the resulting azido arylselenides with alkynes. The cycloaddition is also performed under mild conditions with several azido arylselenides and phenylacetylene to afford the corresponding arylseleno-1,2,3-triazoles in good to excellent yields. This click chemistry protocol represents an efficient method to produce new selenium-nitrogen compounds.
    ChemInform 11/2011; 42(48). DOI:10.1002/chin.201148139
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    ABSTRACT: Design and synthesis of organoselenium compounds with high thiol peroxidase (TPx) and low thiol oxidase (TOx) activities have been a difficult task and remains a synthetic-activity relationship dilemma. In this regard we are reporting for the first time a detail experimental data (both in vitro and in vivo) about the anti-oxidant and toxicological profile of an Imine (-N) containing organoselenium compound (Compound A). The TPx activity of Compound A was significantly higher than diphenyl diselenide (DPDS). Both Compound A and DPDS protected sodium nitropruside (SNP) induced thiobarbituric acid reactive species (TBARS) production in rats tissue homogenate with significantly higher activity observed for Compound A than DPDS (p<0.05). The Compound A also exhibited strong antioxidant activity in the DPPH and ABTS radical scavenging assays. This study reveals that an imine group close to selenium atom drastically enhances the catalytic activities in the aromatic thiol (PhSH) assay systems. The oxidation of biologically significant thiols reflects the toxicity of the compounds. However, the present data showed that treatment with Compound A at 0, 10, 25 or 50mg/kg was not associated with mortality or body weight loss. Similarly it did not inhibit α-ALA-D and Na(+1)/K(+1) ATPase (sulfhydryl group containing enzymes) activities after acute oral treatment; rather it enhanced non-protein thiols (NPSH) concentration. The Compound A did not cause any oxidative stress as measured by TBARS production in rat's tissue preparation. Our data also indicate that exposure to Compound A did not affect plasma transaminase activities or levels of urea and creatinine in rats. Ascorbic acid is always considered a marker of oxidative stress and the reduction of its content may indicate an increase in oxidative stress. Treatment with Compound A did not alter Ascorbic acid levels in rats. The conducted in vitro and in vivo tests show the versatile therapeutic potential of this compound in the area of free radical induced damages, will undoubtedly enhance our understanding of the mechanism of model compounds and may ultimately yield insights that result in improved GPx mimics.
    Chemico-biological interactions 03/2011; 190(1):35-44. DOI:10.1016/j.cbi.2011.01.012 · 2.98 Impact Factor
  • Antonio L. Braga · Joao V. Comasseto
    Journal of the Brazilian Chemical Society 01/2010; 21(11):2019-2020. · 1.25 Impact Factor
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    ABSTRACT: Diphenyl diselenide (DPDS) is an electrophilic reagent used in the synthesis of a variety of pharmacologically active organoselenium (OS) compounds. The aim of the present study was to investigate the mutagenic effects of three symmetrical derivatives from the prototype DPDS (p-chloride-phenyl-diselenide, p-methyl-phenyl-diselenide and p-methoxy-phenyl-diselenide) in yeast. In summary, the cellular effects of the three OS compounds studied in this work appear to be variable according to the substituent group in the aromatic ring and are concentration-dependent. The presence of methoxyl group in the aromatic ring of DPDS structure results in elevation of the cytotoxic and mutagenic potential while the introduction of a methyl group increases the cytotoxic effect.
    Journal of the Brazilian Chemical Society 12/2009; 21(11):2119-2124. DOI:10.1590/S0103-50532010001100013 · 1.25 Impact Factor
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    Antonio L Braga · João V Comasseto
    Journal of the Brazilian Chemical Society 12/2009; 21(11):I-II. DOI:10.1590/S0103-50532010001100001 · 1.25 Impact Factor
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    ABSTRACT: Thiol oxidation by diphenyl ditelluride is a favorable reaction and may be responsible for alteration in regulatory or signaling pathways. We have measured rate constants for reactions of diphenyl ditelluride with cysteine, dimercaptosuccinic acid, glutathione and dithiothreitol in phosphate buffer. The relative reactivities of the different thiols with diphenyl ditelluride were independent of the pK(a) of the thiol group, such that at pH 7.4, cysteine and dithiothreitol were the most reactive and low reactivity was observed with glutathione and dimercaptosuccinic acid. The reactivity of diphenyl ditelluride was not modified by change in pH. Rate of oxidation increased with increasing pH for all thiols except dimercaptosuccinic acid, where the rate of oxidation was faster at low pH. The lipid peroxidation product malonaldehyde (MDA) was measured in rat brain homogenate and phospholipids extract from egg yolk after incubation in phosphate buffer at various pHs ranging from 7.4 to 5.4. TBARS production increased when homogenates were incubated in the pH (5.4-6.8) medium both in the absence and presence of Fe(II). These data indicate that lipid peroxidation processes, mediated by iron, are enhanced with decreasing pH. The iron mobilization may come from reserves where it is weakly bound. Diphenyl ditelluride significantly protected TBARS production at all studied pH values in a concentration dependent manner in brain homogenate. This study provides in vitro evidence for acidosis induced oxidative stress and anti-oxidant action of diphenyl ditelluride.
    Chemico-biological interactions 06/2009; 180(1):47-53. DOI:10.1016/j.cbi.2008.12.013 · 2.98 Impact Factor
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    ABSTRACT: Iron is more soluble at lower pH values; therefore we hypothesized that decreasing the environmental pH would lead to increased iron-mediated lipid peroxidation. Diphenyl diselenide and ebselen are potential candidates as neuroprotective agent, particularly in situations involving overproduction of free radicals and involving cellular pH fall. The aim of the present study was (a) to investigate the relationship between lipid peroxidation and acidosis in brain homogenate and (b) to test the influence of pH on the antioxidant properties of diphenyl diselenide and ebselen. For the purpose rat brain homogenate was incubated at different pH ranging from physiological to acidic values and extent of lipid peroxidation was measured. Thiobarbituric acid-reactive species (TBARS) production significantly increased when homogenate was incubated in the pH (5.4-6.8) medium both in the absence and presence of Fe (II) as compared with physiological pH (7.4). These data indicate that lipid peroxidation processes, mediated by iron, are enhanced with decreasing extracellular pH. The iron mobilized may come from reserves where it is weakly bound. Diphenyl diselenide significantly protected TBARS production at all studied pH values while ebselen offered only a small statistically non-significant protection. However, calculated IC(50) for TBARS inhibition indicated that pH did not change anti-oxidant activities of the tested compounds. This study provides in-vitro evidence for acidosis induced oxidative stress in brain homogenate and anti-oxidant action of diphenyl diselenide.
    Brain research 03/2009; 1258:71-7. DOI:10.1016/j.brainres.2008.12.046 · 2.83 Impact Factor
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    ABSTRACT: In this study, we evaluated the effects of three simple organochalcogenides (diphenyl diselenide, diphenyl ditelluride and diphenyl telluride) and ebselen on the glutamate-driven 45Ca2+ influx into chick embryonic retinal cells, as well as their effects on the excitotoxic injury in retina cells. None of the compounds tested interfered with basal 45Ca2+ uptake. Diphenyl diselenide and diphenyl ditelluride had no effects on glutamate-driven 45Ca2+ influx. Diphenyl telluride (100-400 microM) decreased and ebselen (100-400 microM) completely blocked the glutamate-driven 45Ca2+ influx (P < 0.01) into chick retinal explants. The assessment of neural injury was made spectrophotometrically by quantification of cellularly reduced MTT (3(4,5-dimethyl-thiazol-2-yl)-2,5-diphenyl tetrazolium bromide) 24 h after the beginning of glutamate exposure (8 h). Ebselen had no effects on retinal MTT reduction when co-incubated with glutamate for 8 h. However, when ebselen (100 and 400 microM) was co-incubated for 8 h with glutamate and remained in the incubation media until MTT evaluation (24 h after the beginning of incubation), it protected retinal cells against the decrease in MTT reduction induced by glutamate. These data indicate that besides its capacity of interacting with Ca2+ channels, other mechanisms are involved in the neuroprotection afforded by ebselen in this work, possibly its antioxidant properties.
    Brain Research 03/2005; 1039(1-2):146-52. DOI:10.1016/j.brainres.2005.01.062 · 2.83 Impact Factor

Publication Stats

82 Citations
28.43 Total Impact Points

Institutions

  • 2009–2012
    • Federal University of Santa Catarina
      • • Departamento de Bioquímica
      • • Departamento de Química
      Nossa Senhora do Destêrro, Santa Catarina, Brazil
  • 2005–2011
    • Universidade Federal de Santa Maria
      • Centre of Natural and Exact Sciences (CCNE)
      Santa Maria da Boca do Monte, Rio Grande do Sul, Brazil