Electrochemical behavior of dopamine at a 3,3′-dithiodipropionic acid self-assembled monolayers

Codognoto, Lúcia; Winter, Eduardo; Paschoal, Jonas Augusto Rizzato; Suffredini, Hugo B.; Cabral, Murilo F.; Machado, Sérgio Antônio Spínola; Rath, Susanne

doi:10.1016/j.talanta.2006.10.045

Cited by 48 publications

(33 citation statements)

References 28 publications

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“…2a). Moreover, the formation of 5,6-dihydroxyindoline leads to electrode passivation due to the formation of an aminochrome that polymerizes readily to melanin-like products [22,23], as seen when multiple scans are performed without polishing (Fig. 2a).…”

Section: Methodsmentioning

confidence: 99%

Monocopper complex based on N-tripodal ligand immobilized in a Nafion® film for biomimetic detection of catechols: Application to dopamine

Boulkroune

Lemaire

Chibani

et al. 2016

Electrochimica Acta

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complex based on Ntripodal ligand immobilized in a Nafion® film for biomimetic detection of catechols: Application to dopamine. Electrochimica Acta, Elsevier, 2016, 221, pp.80-85 AbstractA complex based on bis-pyrazolyl N-tripodal ligand known to present a good catalytic activity for the oxidation of 3,5-di-tert-butylcatechol is used to prepare a novel biomimetic sensor for the determination of catechol derivatives. The modified electrode prepared by encapsulation of the complex in a Nafion ® film leads to an electrochemical signal 4.4 times higher than with a glassy carbon electrode for dopamine detection in pH 7 medium. After optimization of the conditions used to immobilize the catalyst on the electrode surface, a calibration curve was obtained with linearity in the range of 30 to 320 mol L -1 and a detection limit of 8 mol L -1 .The sensor was not affected by ascorbic acid and uric acid in similar concentrations to dopamine and its electrochemical response was stable after 40 determinations. The biomimetic sensor can also be used for the detection of other catechol derivatives.

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Section: Methodsmentioning

confidence: 99%

Monocopper complex based on N-tripodal ligand immobilized in a Nafion® film for biomimetic detection of catechols: Application to dopamine

Boulkroune

Lemaire

Chibani

et al. 2016

Electrochimica Acta

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“…Standard in vitro activity of succinyl-CoA synthetase in direction of ADP formation was assayed by a continuous spectrophotometric assay according to the method of Cha (11). Measurements of succinate, itaconate, and 3SP were carried out at 30°C in the presence of 50 mM Tris-HCl (pH 7.4), 1 mM ATP, 0.1 mM CoA, 1 mM MgCl 2 , 2 mM phosphoenolpyruvate, and 0.1 mM NADH, together with 6 U of pyruvate kinase and 6 U of lactate dehydrogenase from rabbit muscle (Sigma) as coupling enzymes.…”

Section: Methodsmentioning

confidence: 99%

Novel Reaction of Succinyl Coenzyme A (Succinyl-CoA) Synthetase: Activation of 3-Sulfinopropionate to 3-Sulfinopropionyl-CoA in Advenella mimigardefordensis Strain DPN7 ^T during Degradation of 3,3′-Dithiodipropionic Acid

et al. 2011

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The sucCD gene of Advenella mimigardefordensis strain DPN7 T encodes a succinyl coenzyme A (succinyl-CoA) synthetase homologue (EC 6.2.1.4 or EC 6.2.1.5) that recognizes, in addition to succinate, the structural analogues 3-sulfinopropionate (3SP) and itaconate as substrates. Accumulation of 3SP during 3,3-dithiodipropionic acid (DTDP) degradation was observed in Tn5::mob-induced mutants of A. mimigardefordensis strain DPN7T disrupted in sucCD and in the defined deletion mutant A. mimigardefordensis ⌬sucCD. These mutants were impaired in growth with DTDP and 3SP as the sole carbon source. Hence, it was proposed that the succinyl-CoA synthetase homologue in A. mimigardefordensis strain DPN7T activates 3SP to the corresponding CoA-thioester (3SP-CoA). The putative genes coding for A. mimigardefordensis succinyl-CoA synthetase (SucCD Am ) were cloned and heterologously expressed in Escherichia coli BL21(DE3)/pLysS. Purification and characterization of the enzyme confirmed its involvement during degradation of DTDP. 3SP, the cleavage product of DTDP, was converted into 3SP-CoA by the purified enzyme, as demonstrated by in vitro enzyme assays. The structure of 3SP-CoA was verified by using liquid chromatography-electrospray ionization-mass spectrometry. SucCD Am is Mg 2؉ or Mn 2؉ dependent and unspecific regarding ATP or GTP. In kinetic studies the enzyme showed highest enzyme activity and substrate affinity with succinate (V max ‫؍‬ 9.85 ؎ 0.14 mol min ؊1 mg ؊1 , K m ‫؍‬ 0.143 ؎ 0.001 mM). In comparison to succinate, activity with 3SP was only ca. 1.2% (V max ‫؍‬ 0.12 ؎ 0.01 mol min ؊1 mg ؊1 ) and the affinity was 6-fold lower (K m ‫؍‬ 0.818 ؎ 0.046 mM). Based on the present results, we conclude that SucCD Am is physiologically associated with the citric acid cycle but is mandatory for the catabolic pathway of DTDP and its degradation intermediate 3SP.3,3Ј-Dithiodipropionic acid (DTDP) is an organic disulfide and a precursor for the production of polythioesters (PTEs) by bacteria (25). Further applications for DTDP are thermodynamic studies (40), development of secondary batteries (52), amino acid analysis (53), and the construction of self-assembling monolayers (10). Microbial production of PTEs from simple carbon sources and inorganic sulfur is currently not possible. Knowledge of the catabolism of organic sulfur compounds in bacteria could provide a reasonable strategy to engineer strains suitable for PTE production. A first step in this direction was the isolation of bacteria able to utilize DTDP as the sole source of carbon and energy. Advenella mimigardefordensis strain DPN7T , a betaproteobacterium, found in mature compost in a waste management facility was one of the isolates (15,56

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“…4,49-Dithiodibutyric acid (DTDB), 3,39-dithiodipropionic acid (DTDP) and 3,39-thiodipropionic acid (TDP) are deployed in many different areas of research (Appel et al, 1995;Codognoto et al, 2007;Jang & Keng, 2006;Kanayama & Kitano, 2000;Saxena & Gupta, 1984;Scott, 1968;Tsutsumi et al, 1998;Tuan & Phillips, 1997). However, the biotechnological significance of these organic sulphur compounds (OSCs) is their application in studies for the improvement of polythioester (PTE) production (Lütke-Eversloh & Steinbüchel, 2003).…”

Section: Introductionmentioning

confidence: 99%

Biodegradation of the xenobiotic organic disulphide 4,4′-dithiodibutyric acid by Rhodococcus erythropolis strain MI2 and comparison with the microbial utilization of 3,3′-dithiodipropionic acid and 3,3′-thiodipropionic acid

et al. 2010

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Application of the non-toxic 3,3′-thiodipropionic acid (TDP) and 3,3′-dithiodipropionic acid (DTDP) as precursors for the microbial production of polythioesters (PTEs), a class of biologically persistent biopolymers containing sulphur in the backbone, was successfully established previously. However, synthesis of PTEs containing 4-mercaptobutyrate (4MB) as building blocks could not be achieved. The very harmful 4MB is not used as a PTE precursor or as the carbon source for growth by any known strain. As a promising alternative, the harmless oxidized disulfide of two molecules of 4MB, 4,4′-dithiodibutyric acid (DTDB), was employed for enrichments of bacterial strains capable of biodegradation. Investigation of novel precursor substrates for PTEs and comparison of respective strains growing on TDP, DTDP and DTDB as sole carbon source was accomplished. A broad variety of bacteria capable of using one of these organic sulphur compounds were isolated and compared. TDP and DTDP were degraded by several strains belonging to different genera, whereas all DTDB-utilizing strains were affiliated to the species Rhodococcus erythropolis. Transposon mutagenesis of R. erythropolis strain MI2 and screening of 7500 resulting mutants yielded three mutants exhibiting impaired growth on DTDB. Physiological studies revealed production of volatile hydrogen sulphide and accumulation of significant amounts of 4MB, 4-oxo-4-sulphanylbutanoic acid and succinic acid in the culture supernatants. Based on this knowledge, a putative pathway for degradation of DTDB was proposed: DTDB could be cleaved into two molecules of 4MB, followed by an oxidation yielding 4-oxo-4-sulphanylbutanoic acid. A putative desulphydrase probably catalyses the abstraction of sulphur, thereby generating succinic acid and hydrogen sulphide.

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Electrochemical behavior of dopamine at a 3,3′-dithiodipropionic acid self-assembled monolayers

Cited by 48 publications

References 28 publications

Monocopper complex based on N-tripodal ligand immobilized in a Nafion® film for biomimetic detection of catechols: Application to dopamine

Monocopper complex based on N-tripodal ligand immobilized in a Nafion® film for biomimetic detection of catechols: Application to dopamine

Novel Reaction of Succinyl Coenzyme A (Succinyl-CoA) Synthetase: Activation of 3-Sulfinopropionate to 3-Sulfinopropionyl-CoA in Advenella mimigardefordensis Strain DPN7 ^T during Degradation of 3,3′-Dithiodipropionic Acid

Biodegradation of the xenobiotic organic disulphide 4,4′-dithiodibutyric acid by Rhodococcus erythropolis strain MI2 and comparison with the microbial utilization of 3,3′-dithiodipropionic acid and 3,3′-thiodipropionic acid

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Electrochemical behavior of dopamine at a 3,3′-dithiodipropionic acid self-assembled monolayers

Cited by 48 publications

References 28 publications

Monocopper complex based on N-tripodal ligand immobilized in a Nafion® film for biomimetic detection of catechols: Application to dopamine

Monocopper complex based on N-tripodal ligand immobilized in a Nafion® film for biomimetic detection of catechols: Application to dopamine

Novel Reaction of Succinyl Coenzyme A (Succinyl-CoA) Synthetase: Activation of 3-Sulfinopropionate to 3-Sulfinopropionyl-CoA in Advenella mimigardefordensis Strain DPN7 T during Degradation of 3,3′-Dithiodipropionic Acid

Biodegradation of the xenobiotic organic disulphide 4,4′-dithiodibutyric acid by Rhodococcus erythropolis strain MI2 and comparison with the microbial utilization of 3,3′-dithiodipropionic acid and 3,3′-thiodipropionic acid

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Novel Reaction of Succinyl Coenzyme A (Succinyl-CoA) Synthetase: Activation of 3-Sulfinopropionate to 3-Sulfinopropionyl-CoA in Advenella mimigardefordensis Strain DPN7 ^T during Degradation of 3,3′-Dithiodipropionic Acid