Oxidative degradation of norfloxacin by a lipophilic oxidant, cetyltrimethylammonium permanganate in water–acetonitrile medium: A kinetic and mechanistic study

Garnayak, Sarita; Patel, Sabita

doi:10.1016/j.molliq.2015.06.003

Cited by 12 publications

(5 citation statements)

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“…A moiety of carbonyl and carboxyl from norfloxacin bind with DNA, causing the break of DNA-gyrase complex. This mechanism is responsible for the antibacterial activity of this fluoroquinolone as reported in the literature [4]. Fluorine (F) and the piperazine group give an extra stabilization to the ternary complex norfloxacin-enzyme-DNA because it interacts with the enzyme; this stabilization is responsible for the effectiveness potential antibacterial action.…”

Section: Introductionmentioning

confidence: 58%

“…However, this compound presents poor aqueous solubility that causes a low oral bioavailability, generating a poor metabolization of norfloxacin [5,6]. Garnayak and Patel [4] have reported that less than 10% of the drug containing norfloxacin as active principle is metabolized, part of the drug excreted by renal excretion and a fraction of the drug remained unaltered by the metabolism.…”

Section: Introductionmentioning

confidence: 99%

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Thermal, spectroscopic and antimicrobial activity characterization of some norfloxacin complexes

Nunes

Nascimento

Moura

et al. 2018

J Therm Anal Calorim

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Coordination compounds of transition metals with norfloxacin (Nor) have potential to improve its effectiveness, as already discussed for some compounds found in the literature. The complexes in the solid state were prepared by precipitation of the respective metal cation (M = Mn(II), Co(II), Ni(II), Cu(II) and Zn(II)) with a norfloxacin sodium salt solution. The thermal behavior under oxidative and pyrolysis conditions was investigated employing thermogravimetry and differential thermal analysis (TG/DTG-DTA) and evolved gas analysis (EGA/TG-FTIR), and the complexes were characterized by elemental analysis (EA), EDTA complexometric titration, infrared spectroscopy (FTIR) and X-ray powder diffraction (XRD). By these results, the minimum formula was established as [M(Nor) 2 (H 2 O) 2 ]ÁnH 2 O, where n = 3 (Ni), 2.5 (Mn Co, Zn), or 2 (Cu). The evolved gases identified during thermal decomposition of Ni and Cu complexes were ethylene, CO 2 and CO for Ni; CO 2 and ethane for Cu. Also, antimicrobial activity of the complexes was evaluated by in vitro susceptibility test using the agar diffusion method, and the results were compared with the uncomplexed molecule. It was found that norfloxacin complexation modifies its antibacterial activity. The activity depends on the type of metal ion and microorganism; Mn(II), Co(II) and Zn(II) complexes significantly increased activity against the tested gram-negative bacteria.

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Section: Introductionmentioning

confidence: 58%

Section: Introductionmentioning

confidence: 99%

Thermal, spectroscopic and antimicrobial activity characterization of some norfloxacin complexes

Nunes

Nascimento

Moura

et al. 2018

J Therm Anal Calorim

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“…2 Noroxacin [1-ethyl-6-uoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid] is a representative member of the uoroquinolone family and used in a wide range of gastrointestinal, urinary, respiratory tract, skin and intraabdominal infections. [3][4][5] However, due to the widespread usage of noroxacin in everyday life, large amounts of nor-oxacin are released to the aquatic environment through domestic wastewater, hospital sewage and industrial discharge. 6,7 So far, noroxacin has been detected in various water sources, including sewage treatment plant effluents, surface water, seawater, groundwater and drinking water.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Ti mesh supported N–S–C-tridoped TiO₂ nanosheets to achieve high utilization of optical energy for photocatalytic degradation of norfloxacin

Zhang

Wan

et al. 2016

RSC Adv.

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“…With an objective to develop a new efficient, selective, and mild oxidation protocol, the oxidizing ability of a lipopathic oxidant namely cetyltrimethylammonium dichromate (CTADC), has been explored by our research group using the cetyltrimethylammonium (CTA) ion as the onium counterion for anionic dichromate [3][4][5][6][7][8][9]. The mildness of CTADC is well documented.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of Antitubercular Drug Isoniazid by a Lipopathic Oxidant, Cetyltrimethylammonium Dichromate: A Mechanistic Study

Garnayak

Patel

2015

Int. J. Chem. Kinet.

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The oxidation of an antitubercular drug isoniazid by a lipopathic oxidant cetyltrimethylammonium dichromate (CTADC) in a nonpolar medium generates isonicotinic acid both in the presence and the absence of acetic acid. The conventional UV–vis spectrophotometric method is used to study the reaction kinetics. The occurrence of the Michaelis–Menten–type kinetics with respect to isoniazid confirms the binding of oxidant and substrate to form a complex before the rate‐determining step. The existence of the inverse solvent kinetic isotope effect, k(H2O)/ k(D2O) = 0.7, in an acid‐catalyzed reaction proposes a multistep reaction mechanism. A decrease in the rate constant with an increase in [CTADC] reveals the formation of reverse micellar–type aggregates of CTADC in nonpolar solvents. In the presence of different ionic and nonionic surfactants, CTADC forms mixed aggregates and controls the reaction due to the charge on the interface and also due to partition of oxidant and substrate in two different domains. High negative entropy of activation (ΔS‡ = –145 and –159 J K−1 mol−1 in the absence and presence of acetic acid) proposes a more ordered and highly solvated transition state than the reactants. Furthermore, the solvent polarity‐reactivity relationship reveals (i) the presence of less polar and less ionic transition state compared to the reactants during the oxidation, (ii) differential contribution from nonpolar and dipolar aprotic solvents toward the reaction process, and (iii) the existence of polarity/hydrophobic switch at log P = 0.73. A suitable mechanism has been proposed on the basis of experimental results. These results may provide insight into the mechanism of isoniazid oxidation in hydrophobic environment and may assist in understanding the drug resistance in different location.

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Oxidative degradation of norfloxacin by a lipophilic oxidant, cetyltrimethylammonium permanganate in water–acetonitrile medium: A kinetic and mechanistic study

Cited by 12 publications

References 42 publications

Thermal, spectroscopic and antimicrobial activity characterization of some norfloxacin complexes

Thermal, spectroscopic and antimicrobial activity characterization of some norfloxacin complexes

Preparation of Ti mesh supported N–S–C-tridoped TiO₂ nanosheets to achieve high utilization of optical energy for photocatalytic degradation of norfloxacin

Oxidation of Antitubercular Drug Isoniazid by a Lipopathic Oxidant, Cetyltrimethylammonium Dichromate: A Mechanistic Study

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Oxidative degradation of norfloxacin by a lipophilic oxidant, cetyltrimethylammonium permanganate in water–acetonitrile medium: A kinetic and mechanistic study

Cited by 12 publications

References 42 publications

Thermal, spectroscopic and antimicrobial activity characterization of some norfloxacin complexes

Thermal, spectroscopic and antimicrobial activity characterization of some norfloxacin complexes

Preparation of Ti mesh supported N–S–C-tridoped TiO2 nanosheets to achieve high utilization of optical energy for photocatalytic degradation of norfloxacin

Oxidation of Antitubercular Drug Isoniazid by a Lipopathic Oxidant, Cetyltrimethylammonium Dichromate: A Mechanistic Study

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Preparation of Ti mesh supported N–S–C-tridoped TiO₂ nanosheets to achieve high utilization of optical energy for photocatalytic degradation of norfloxacin