&lt;b&gt;Syntheses and spectral studies of novel ciprofloxacin derivatives&lt;/b&gt;

Yadav, Pradeep; Joshi, Yogesh

doi:10.4314/bcse.v22i3.61246

Cited by 6 publications

(4 citation statements)

References 18 publications

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“…The structure-activity relationship (SAR) and the functions of different positions on the quinolone core have been identified (14). The SAR studies indicated that the group at position 7 affects its antibacterial spectrum (15). The substituted 7-piperazinyl derivatives of ciprofloxacin, such as azo (11), Mannich base (16,17), N-alkylated (18) and N-acylated ciprofloxacin derivatives (19) have been synthesized and evaluated for antibacterial activity.…”

Section: Introductionmentioning

confidence: 99%

Ciprofloxacin containing Mannich base and its copper complex induce antitumor activity via different mechanism of action

Yang

Zhou

et al. 2014

International Journal of Oncology

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The Mannich base containing ciprofloxacin and kojic acid structural units was prepared and evaluated in antitumor activity. The enhancement in antitumor activity was observed both from the Mannich base (IC(50): 103.3±5.0 µM for HepG2, 87.9±8.0 µM for HCT-116 cell) and its copper complex (IC(50): 11.5±1.8 µM for HepG2, 44.4±2.5 µM for HCT-116 cell) compared to the ciprofloxacin and kojic acid. The mechanistic studies via RT-PCR, cell cycle analysis, mitochondrial membrane potential measurement, inhibition of topoisomerase and molecular docking indicated that there is a different molecular mechanism between the Mannich base and its copper complex. The cytotoxicity of the Mannich base was involved in apoptosis, cell cycle arrest, depolarization of mitochondrial membrane and weaker topoisomerase II inhibition, but the copper complex exerted its cytotoxicity mainly through dual topoisomerase inhibition, especially stabilizing the intermediate of cleavage DNA-topoisomerase complex.

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Section: Introductionmentioning

confidence: 99%

Ciprofloxacin containing Mannich base and its copper complex induce antitumor activity via different mechanism of action

Yang

Zhou

et al. 2014

International Journal of Oncology

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“…It has been reported by Yadev and Sharma that ciprofloxacin may form a diazotized compound upon reacting with piprazine. 17 This reaction utilizes thionyl chloride as a solvent, and takes place after a 4-h reflux. It utilizes the NH of ciprofloxacin.…”

Section: Theoretical Basis For the Microwave Assisted Diazotization Omentioning

confidence: 99%

“…16 Its reaction with piprazine forms a diazotized compound that is colored in nature. 17 The nature and extent of reactions may depend upon a number of factors, including the way of energy transfer. Among these, the microwave assisted reactions are unique regarding their speed and selectivity.…”

Section: Introductionmentioning

confidence: 99%

Investigation of a New Spectrophotometric Method for the Analysis of Ciprofloxacin Based on Microwave Assisted Diazotization

et al. 2019

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A microwave-assisted diazotization reaction of ciprofloxacin was used for the analysis of ciprofloxacin in pharmaceutical samples. The ciprofloxacin was diazotized with phenol using acidified sodium nitrite in a domestic microwave oven. Faster microwave heating and microwave effects were found to be very effective for the process of diazotization. The microwave-assisted reaction was initiated in an acidic media and the colored product was stabilized in a slightly basic medium using a NaOH solution as a neutralizer. The product was found to exhibit the maximum absorbance at 440 nm. All of the experimental conditions like the concentration of reagents, microwave power and reaction time were optimized. The optimum concentrations for phenol, sodium nitrite, HCl and NaOH were found to be 140 ppm, 300 ppm, 0.006 M and 0.006 M respectively. The optimum reaction time was found to be 2 min and a medium high power of the microwave was found to be most effective. The limit of detection (LOD) and the limit of quantification (LOQ) were found to be 1.08 and 3.61 mg L-1 respectively. The developed method was successfully applied for the determination of ciprofloxacin in pharmaceutical samples. This new spectrophotometric method for the analysis of ciprofloxacin is fast, sensitive, easy and cost effective.

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“…Several quinolones modifications have been shown to improve properties in cancer treatment. Some modifications comprise ß-keto and carboxylic acid moiety that are required for hydrogen-bonding interactions with DNA gyrases or/and DNA bases, and therefore, both two functional group moieties are essential [6]. e proximity of the carboxyl and keto groups on the fluoroquinolone molecule would account for good chelating properties [7], suggesting that the interaction of the quinolone complexed to metal is a major step [8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Hybrid Fluoroquinolone-Boron Complexes and Their Evaluation in Cervical Cancer Cell Lines

Hernández‐López

Sánchez-Miranda

Araujo-Huitrado

et al. 2019

Journal of Chemistry

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Quinolones are a family of antimicrobial agents that have been used in antibacterial and anticancer chemotherapy. Fluoroquinolone targets DNA gyrase and topoisomerase IV enzymes affecting several cellular processes, like cell death and proliferation; the best way to act is in the form of carboxylic acid or, recently, as quinolone-metal complex. In this work, the use of boron is shown as an alternative of metal to form a complex by incorporating to fluoroquinolone as an electron withdrawing substituent to activate the C-7 position chemoselectively for the production of new fluoroquinolone hybrids and test their effects on cell proliferation. Fluoroquinolone-boron complexes were synthesized according to the Gould-Jacobs cyclization method, and five hybrid fluoroquinolone-boron compounds were obtained by S N Ar reaction, yielding 31 to 46%, at 80°C, and in 10 to 25 hours of reaction. e effect of the five fluoroquinolone-boron hybrids was evaluated in cervical cancer cell lines by cell proliferation assay. 7-hydantoin-fluoroquinolone-boron and 7-dihydropyridine-fluoroquinolone-boron complexes showed the strongest effect according to dose-response assay, respectively. e fluoroquinolone-boron hybrid complex showed proliferation inhibition in SiHa and CasKi cells, opening the possibility to use them as potential agents for the treatment of cancer.

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<b>Syntheses and spectral studies of novel ciprofloxacin derivatives</b>

Cited by 6 publications

References 18 publications

Ciprofloxacin containing Mannich base and its copper complex induce antitumor activity via different mechanism of action

Ciprofloxacin containing Mannich base and its copper complex induce antitumor activity via different mechanism of action

Investigation of a New Spectrophotometric Method for the Analysis of Ciprofloxacin Based on Microwave Assisted Diazotization

Synthesis of Hybrid Fluoroquinolone-Boron Complexes and Their Evaluation in Cervical Cancer Cell Lines

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