Electrochemical oxidation of azithromycin and its derivatives

Mandić, Zoran; Weitner, Zlatko; Ilijaš, Marina

doi:10.1016/s0731-7085(03)00315-7

Cited by 37 publications

(20 citation statements)

References 13 publications

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“…For the second oxidation peak (O 2 ), the transferred electron is also calculated to be one. Combining the reported mechanism [20] with our experimental results, we conclude that the peak O 1 is due to the removal of one electron from the nitrogen atom to form an aminium cation radical, and the peak O 2 attributes to the oxidation of the chemical product of aminium cation radical. The possible reactions are suggested as follows:…”

Section: Oxidation Mechanism Of Erythromycinsupporting

confidence: 75%

Enhanced electrochemical detection of erythromycin based on acetylene black nanoparticles

Wang

Yang

et al. 2010

Colloids and Surfaces B: Biointerfaces

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Section: Oxidation Mechanism Of Erythromycinsupporting

confidence: 75%

Enhanced electrochemical detection of erythromycin based on acetylene black nanoparticles

Wang

Yang

et al. 2010

Colloids and Surfaces B: Biointerfaces

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“…The ability to easily and quickly refresh the electrode surface before each measurement allows the Hg(Ag)FE to be applied in adsorptive stripping measurements [39], as in the case of EES [35], doxorubicin [41], closantel [42] and chlornitrofen [54]. When considering the structure of EES and its affinity to the Hg (Ag)FE under optimized measurement conditions [35] and the three semi-synthetic macrolide antibiotic target analytes, it can be noted that -beside of different possible electroactive centers -all of them are amines, with pK a values between 8.1 and 9.5 (for more details see Table 1) [55][56][57][58][59][60][61][62][63][64][65][66][67][68].…”

Section: Loq Was 2á10mentioning

confidence: 99%

Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver – amalgam film electrode

Vajdle

Guzsvány

Škorić

et al. 2017

Electrochimica Acta

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The renewable silver-amalgam film electrode (Hg(Ag)FE) was applied for voltammetric characterization and determination of semi-synthetic macrolide antibiotics azithromycin (AZI), clarithromycin (CLA) and roxithromycin (ROX) in the Britton-Robinson buffer as supporting electrolyte ranging the pH from 4.0 to 11.9. All three macrolides showed reduction signals in fairly negative potential range.During direct cathodic square wave voltammetric (SWV) investigations conducted over the potential range from À0.75 V to À2.00 V vs SCE, either one or two reduction peaks were obtained in the potential range from À1.5 to À1.9 V. The shapes and intensities of the signals depend on the applied pH values in wider pH ranges. For analytical purposes concerning the development of direct cathodic SWV and adsorptive stripping SWV (SW-AdSV) methods the neutral and slightly alkaline media were suitable as pH 7.2, pH 7.4 and pH 7.0 for AZI, CLA and ROX, respectively. Based on the cyclic voltammograms recorded at these pH values, adsorption-controlled electrode kinetics process can be proposed for all three macrolides. Furthermore, the water suppressed 1 H NMR measurements in the pH range between 6.0 and 10.5 indicated that the macrolide molecules at the optimal analytical conditions are predominantly in protonated form via their tertiary amino groups which supported in all three cases their adsorption on the appropriately polarized Hg(Ag)FE electrode. The optimized direct cathodic SWV methods showed good linearity in concentration ranges 4.81-23.3 mg mL À1 , 1.96-28.6 mg mL À1 and 1.48-25.9 mg mL À1 for AZI, CLA and ROX, respectively. The development of the SW-AdSV methods resulted in the linear responses at lower concentration ranges as 1.0-2.46 mg mL À1, 0.05-0.99 mg mL À1 and 0.10-0.99 mg mL À1 , for AZI, CLA and ROX, respectively. The relative standard deviation for all developed methods was not higher than 1.0% except the SWV method for AZI with 4.7%. In the case of all three investigated macrolide antibiotics the protonated form of the tertiary amino group(s) at appropriate accumulation potential and time favored the adsorption of the ionic form of the target molecules offering the opportunity for the development of SW-AdSV methods for their trace level analysis on Hg(Ag)FE. Optimized SW-AdSV method was applied for determination of ROX in pharmaceutical preparation Runac

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“…The progress of the electrolysis was monitored by thin layer chromatography. After the completion of the electrolysis, the anolyte is separated from the reaction cell, evaporated to a dry residue and subjected to chromatography on a slilica gel column (CH 2 Cl 2 -CH 3 OH-NH 4 H and APT NMR spectra were obtained with 4000 Hz and 32000 Hz spectral window, respectively, using 64K data points. Digital resolution was 0.12 Hz and 0.95 Hz per point, respectively.…”

Section: Electrochemical Synthesis Ofmentioning

confidence: 99%

“…As a part of the electrochemical derivatisation of macrolide antibiotics [2][3][4][5][6], we carried out the oxidation of 1 with electrogenerated reactive chlorine species in order to introduce chlorine atom into the lactam nitrogen. N-chlorolactam derivative should exhibit conformational changes in comparison with the starting compound what might in a greater or lesser extent affect biological activity.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Synthesis, Structure Elucidation and Antibacterial Evaluation of 9a-aza-9a-chloro-9a-homoerythromycin A

Mandić

Lazarevski²,

Weitner³

et al. 2014

ADMET DMPK

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Electrochemical oxidation of azithromycin and its derivatives

Cited by 37 publications

References 13 publications

Enhanced electrochemical detection of erythromycin based on acetylene black nanoparticles

Enhanced electrochemical detection of erythromycin based on acetylene black nanoparticles

Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver – amalgam film electrode

Electrochemical Synthesis, Structure Elucidation and Antibacterial Evaluation of 9a-aza-9a-chloro-9a-homoerythromycin A

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