Electropolymerization mechanisms of hydroxyphenylacetic acid isomers

Rodrigues, Luciano Pereira; Ferreira, Deusmaque Carneiro; Sonoda, Milton T.; Madurro, Ana G. B.; Abrahão, Odonı́rio; Madurro, João M.

doi:10.1016/j.molstruc.2014.05.031

Cited by 18 publications

(12 citation statements)

References 38 publications

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“…This fact can be attributed to a steeper resonance effect when the benzene ring exhibits para-substitution relative to orthoand meta-substitution, as observed in earlier investigations [9,27]. Hydroxyphenylacetic acid isomers lose the anodizing 1 electron/monomer unit with electronic transfer coefficients(a) of 0.58, 0.64, and 0.65 for 2-HPA, 3-HPA, and 4-HPA, respectively [28]. The higher value of a for 4-HPA is in agreement with it having the lowest oxidation potential required to oxidize it.…”

Section: Detection Of the Genomic Dna Of Neisseria Meningitidissupporting

confidence: 61%

“…These structures were modeled based on electropolymerization mechanisms of hydroxyphenylacetic acid isomers proposed in an earlier work [28]. In that study, Fourier transform infrared spectroscopy (FTIR) investigations show that aromatic ether bonds extend the electron delocalization and expose the free acetic acid group outward.…”

Section: Molecular Modeling Studiesmentioning

confidence: 99%

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Electropolymerization of hydroxyphenylacetic acid isomers and the development of a bioelectrode for the diagnosis of bacterial meningitis

Rodrigues

Ferreira

et al. 2015

J Appl Electrochem

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In this work, three polymeric films derived from hydroxyphenylacetic acid isomers were electropolymerized onto the surfaces of graphite electrodes through cyclic voltammetry. Analysis of electrochemical behaviors and electrical properties of the three polymeric films were investigated and their probably structures were explored by molecular modeling. The best functionalization strategy for the incorporation and retention of adenine and guanine nitrogenous bases was the poly(3-hydroxyphenylacetic acid). It was applied for the immobilization of a nucleotide probe specific to DNA of the bacteria Neisseria meningitidis operated in amperometric and impedimetric indirect modes. The simple protocol of electrochemical detection of DNA by the bioelectrode, developed in this work, could be further enhanced and applied in a low-cost and pain-less platform to diagnose human meningitis infection.

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Section: Detection Of the Genomic Dna Of Neisseria Meningitidissupporting

confidence: 61%

Section: Molecular Modeling Studiesmentioning

confidence: 99%

Electropolymerization of hydroxyphenylacetic acid isomers and the development of a bioelectrode for the diagnosis of bacterial meningitis

Rodrigues

Ferreira

et al. 2015

J Appl Electrochem

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“…21,22,28–30 As the dimer forms, the second electron transfer takes place, which would be responsible for the second oxidation peak. 22 …”

Section: Resultsmentioning

confidence: 99%

“…One explanation for this is that the electrode was scanned at such a high rate that there is not enough time for electrodeposition to occur. 22 …”

Section: Resultsmentioning

confidence: 99%

Simultaneous measurement and quantitation of 4-hydroxyphenylacetic acid and dopamine with fast-scan cyclic voltammetry

Shin

Kaplan

Raider

et al. 2015

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Caged compounds have been used extensively to investigate neuronal function in a variety of preparations, including cell culture, ex vivo tissue samples, and in vivo. As a first step toward electrochemically measuring the extent of caged compound photoactivation while also measuring the release of the catecholamine neurotransmitter, dopamine, fast-scan cyclic voltammetry at carbon-fiber microelectrodes (FSCV) was used to electrochemically characterize 4-hydroxyphenylacetic acid (4HPAA) in the absence and presence of dopamine. 4HPAA is a by-product formed during the process of photoactivation of p-hydroxyphenylacyl-based caged compounds, such as p-hydroxyphenylglutamate (pHP-Glu). Our data suggest that the oxidation of 4HPAA occurs through the formation of a conjugated species. Moreover, we found that a triangular waveform of −0.4 V to +1.3 V to −0.4 V at 600 V/s, repeated every 100 ms, provided an oxidation current of 4HPAA that was enhanced with a limit of detection of 100 nM, while also allowing the detection and quantitation of dopamine within the same scan. Along with quantifying 4HPAA in biological preparations, the results from this work will allow the electrochemical measurement of photoactivation reactions that generate 4HPAA as a by-product as well as provide a framework for measuring the photorelease of electroactive by-products from caged compounds that incorporate other chromophores.

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“…This structural disorganization of the polymer allows the preserved functional groups to be present in the outermost layers of poly(4-HPA). According to the electropolymerization mechanism for poly(4-HPA) proposed by Rodrigues et al [ 39 ], the higher electrostatic repulsion of the anionic pair can be explained by the presence of negative charges of the carboxyl group preserved in the outermost regions of the film.…”

Section: Resultsmentioning

confidence: 99%

Optimization and Application of Electrochemical Transducer for Detection of Specific Oligonucleotide Sequence for Mycobacterium tuberculosis

et al. 2018

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In this study, the electropolymerization of 4-hydroxyphenylacetic acid (4-HPA) over graphite electrodes (GE) was optimized, aiming its application as a functionalized electrochemical platform for oligonucleotides immobilization. It was investigated for the number of potential cycles and the scan rate influence on the monomer electropolymerization by using cyclic voltammetry technique. It was observed that the polymeric film showed a redox response in the region of +0.53/+0.38 V and the increase in the number of cycles produces more electroactive platforms because of the better electrode coverage. On the other hand, the decrease of scan rate produces more electroactive platforms because of the occurrence of more organized coupling. Scanning electron microscopy (SEM) images showed that the number of potential cycles influences the coverage and morphology of the electrodeposited polymeric film. However, the images also showed that at different scan rates a more organized material was produced. The influence of these optimized polymerization parameters was evaluated both in the immobilization of specific oligonucleotides and in the detection of hybridization with complementary target. Poly(4-HPA)/GE platform has shown efficient and sensitive for oligonucleotides immobilization, as well as for a hybridization event with the complementary oligonucleotide in all investigated cases. The electrode was modified with 100 cycles at 75 mV/s presented the best responses in function of the amplitude at the monitored peak current values for the Methylene Blue and Ethidium Bromide intercalators. The construction of the genosensor to detect a specific oligonucleotide sequence for the Mycobacterium tuberculosis bacillus confirmed the results regarding the poly(4-HPA)/GE platform efficiency since it showed excellent sensitivity. The limit of detection and the limit of quantification was found to be 0.56 (±0.05) μM and 8.6 (±0.7) μM, respectively operating with very low solution volumes (15 µL of probe and 10 µL target). The biosensor development was possible with optimization of the probe adsorption parameters and target hybridization, which led to an improvement in the decrease of the Methylene Blue (MB) reduction signal from 14% to 34%. In addition, interference studies showed that the genosensor has satisfactory selectivity since the hybridization with a non-specific probe resulted in a signal decrease (46% lower) when compared to the specific target.

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Electropolymerization mechanisms of hydroxyphenylacetic acid isomers

Cited by 18 publications

References 38 publications

Electropolymerization of hydroxyphenylacetic acid isomers and the development of a bioelectrode for the diagnosis of bacterial meningitis

Electropolymerization of hydroxyphenylacetic acid isomers and the development of a bioelectrode for the diagnosis of bacterial meningitis

Simultaneous measurement and quantitation of 4-hydroxyphenylacetic acid and dopamine with fast-scan cyclic voltammetry

Optimization and Application of Electrochemical Transducer for Detection of Specific Oligonucleotide Sequence for Mycobacterium tuberculosis

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