Electrochemistry of new derivatives of phenothiazine: Electrode kinetics and electropolymerization conditions

Kuzin, Yurii; Khadieva, Alena I.; Padnya, Pavel L.; Khannanov, Artur; Кутырева, М. П.; Стойков, И. И.; Evtugyn, Gennady

doi:10.1016/j.electacta.2021.137985

Cited by 19 publications

(7 citation statements)

References 42 publications

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“…These changes were observed until the 25 th cycle, after which the currents started decreasing due to blocking the GCE surface with the polymerization products, which complicated access of the monomers to the electrode interface. Such non-regular changes in the peak currents are typical for the electropolymerization of the phenothiazine and phenoxazine derivatives [ 58 , 59 ]. The dependence of the oxidation/reduction peak currents on the number of electropolymerization cycles is presented in Figure 2 b.…”

Section: Resultsmentioning

confidence: 99%

Voltammetric Sensor for Doxorubicin Determination Based on Self-Assembled DNA-Polyphenothiazine Composite

Malanina,

Kuzin,

Khadieva

et al. 2023

Nanomaterials

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A novel voltammetric sensor based on a self-assembled composite formed by native DNA and electropolymerized N-phenyl-3-(phenylimino)-3H-phenothiazin-7-amine has been developed and applied for sensitive determination of doxorubicin, an anthracycline drug applied for cancer therapy. For this purpose, a monomeric phenothiazine derivative has been deposited on the glassy carbon electrode from the 0.4 M H2SO4-acetone mixture (1:1 v/v) by multiple potential cycling. The DNA aliquot was either on the electrode modified with electropolymerized film or added to the reaction medium prior to electropolymerization. The DNA entrapment and its influence on the redox behavior of the underlying layer were studied by scanning electron microscopy and electrochemical impedance spectroscopy. The DNA–doxorubicin interactions affected the charge distribution in the surface layer and, hence, altered the redox equilibrium of the polyphenothiazine coating. The voltametric signal was successfully applied for the determination of doxorubicin in the concentration range from 10 pM to 0.2 mM (limit of detection 5 pM). The DNA sensor was tested on spiked artificial plasma samples and two commercial medications (recovery of 90–95%). After further testing on real clinical samples, the electrochemical DNA sensor developed can find application in monitoring drug release and screening new antitumor drugs able to intercalate DNA.

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Section: Resultsmentioning

confidence: 99%

Voltammetric Sensor for Doxorubicin Determination Based on Self-Assembled DNA-Polyphenothiazine Composite

Malanina,

Kuzin,

Khadieva

et al. 2023

Nanomaterials

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“…The synthesis of the target compounds PTZa , PTZ1 , PTZ2 is evidenced in the 1 H NMR spectra by the signals of the aromatic protons of the phenothiazin-5-ium fragment, namely, doublet of protons H1 and H9 with chemical shift 8.05 ppm ( PTZa ), 8.11 ppm ( PTZ2 ), doublet of protons H2 and H8 with chemical shift in the region of 7.68–7.50 ppm and a singlet of protons H4 and H6 in the region of 7.68–7.50 ppm. Vicinal proton–proton coupling constants of phenothiazin-5-ium fragment are 3 J HH = 9.3 Hz, while for the aromatic substituents 3 J HH is always less than 9 Hz [ 17 , 26 , 30 ], which makes it possible to identify the signals of the protons of the phenothiazin-5-ium fragment in 1 H NMR spectra. In the 1 H and 13 C NMR spectra of the target compound PTZ1 , a PTZa hydrolysis product, no signals of protons and carbons of methyl fragments of acetamide groups are observed.…”

Section: Resultsmentioning

confidence: 99%

Arylamine Analogs of Methylene Blue: Substituent Effect on Aggregation Behavior and DNA Binding

Khadieva

Mostovaya

Padnya

et al. 2021

IJMS

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The synthesis of new phenothiazine derivatives, analogs of Methylene Blue, is of particular interest in the design of new drugs, as well as in the development of a new generation of agents for photodynamic therapy. In this study, two new derivatives of phenothiazine, i.e., 3,7-bis(4-aminophenylamino)phenothiazin-5-ium chloride dihydrochloride (PTZ1) and 3,7-bis(4-sulfophenylamino)phenothiazin-5-ium chloride (PTZ2), are synthesized for the first time and characterized by NMR, IR spectroscopy, HRMS and elemental analysis. The interaction of the obtained compounds PTZ1 and PTZ2 with salmon sperm DNA is investigated. It is shown by UV-Vis spectroscopy and DFT calculations that substituents in arylamine fragments play a crucial role in dimer formation and interaction with DNA. In the case of PTZ1, two amine groups promote H-aggregate formation and DNA interactions through groove binding and intercalation. In the case of PTZ2, sulfanilic acid fragments prevent any dimer formation and DNA binding due to electrostatic repulsion. DNA interaction mechanisms are studied and confirmed by UV-vis and fluorescence spectroscopy in comparison with Methylene Blue. The obtained results open significant opportunities for the development of new drugs and photodynamic agents.

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“…The suitable linearity of the last curves indicate that the electrochemical process is controlled by diffusion. Active surface area of the bare and modi ed electrode could be calculated from the slope of the peak currents in terms of the square root of the scan rate utilizing the Randles-Sevcik equation [24,25]:…”

Section: Characterization Of the Ceo 2 -Mwcnts/ccementioning

confidence: 99%

Preparation of cerium oxide–MWCNTs nanocomposite bulk modified carbon ceramic electrode: a sensitive sensor for tamoxifen determination in human serum samples

Shafaei

Hosseinzadeh

Kanberoğlu

et al. 2021

J Mater Sci: Mater Electron

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In this study, cerium oxide and multi-walled carbon nanotubes nanocomposite was incorporated into the carbon ceramic electrode (CeO 2 -MWCNTs/CCE) as a renewable electrode for the electrocatalytic purposes. To demonstrate capability of the fabricated electrode, determination of Tamoxifen as an important anticancer drug with differential pulse voltammetry technique was evaluated. Linear range, limit of detection and sensitivity of the developed sensor were found to be 0.2-40 nM, 0.132 nM and 1.478 µA nM -1 cm -2 , respectively. Ease of production, low cost and high electron transfer rate of CeO 2 -MWCNTs/CCE promise it as a novel electro-analytical tool for determination of important species in real samples.

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Electrochemistry of new derivatives of phenothiazine: Electrode kinetics and electropolymerization conditions

Cited by 19 publications

References 42 publications

Voltammetric Sensor for Doxorubicin Determination Based on Self-Assembled DNA-Polyphenothiazine Composite

Voltammetric Sensor for Doxorubicin Determination Based on Self-Assembled DNA-Polyphenothiazine Composite

Arylamine Analogs of Methylene Blue: Substituent Effect on Aggregation Behavior and DNA Binding

Preparation of cerium oxide–MWCNTs nanocomposite bulk modified carbon ceramic electrode: a sensitive sensor for tamoxifen determination in human serum samples

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