Synthesis and biological properties of nitrobenzoxadiazole derivatives as potential nitrogen(ii) oxide donors: SOX induction, toxicity, genotoxicity, and DNA protective activity in experiments using Escherichia coli-based lux biosensors

Chistyakov, V. A.; Semenyuk, Yu. P.; Morozov, P. G.; Празднова, Е. В.; Chmykhalo, Victor; Kharchenko, E. Yu.; Клецкий, М. Е.; Бородкин, Г. С.; Лисовин, Антон В.; Буров, Олег Н.; Kurbatov, S. V.

doi:10.1007/s11172-015-1019-y

Cited by 18 publications

(8 citation statements)

References 37 publications

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“…Besides DNA-protective activity, it was found earlier that substance-1 has an ability to generate nitric oxide (II) in vivo. [12,16] Another feature of this compound is its ability to exist in two isomeric forms, which are in 1 1' equilibrium (Fig.5). This process of dynamic restructuring of the furoxan cycle is called 1,3-N-oxide tautomerism and may potentially facilitate its conformational adjustment to binding sites of biopolymers.…”

Section: Discussionmentioning

confidence: 99%

“…[12,16] To analyze the expression of stress-inducible operons and mutagenesis we used recombinant strain of Escherichia coli MG1655 (pRecA-lux), with a plasmid containing luxCDABE operon from photobacteria Photorhabdus luminescens, put under control of PrecA promoter of E. coli. Biosensors with pRecA plasmids react to factors causing induction of the SOSresponse in the cell.…”

Section: Methodsmentioning

confidence: 99%

“…Confidence intervals for protective activity value were calculated by the described method. [15,16] Determination of spontaneous and induced mutagenesis parameters Cells of E.coli MG1655 (pRecA-lux) strain were inoculated into 4 ml of the LB medium and stirred evenly. The induced culture was divided into four equal aliquots.…”

Section: Bioluminescent Testmentioning

confidence: 99%

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7-(1-Methyl-3-Pyrrolyl-)-4,6-Dinitrobenzofuroxan Reduces the Frequency of Antibiotic Resistance Mutations Induced by Ciprofloxacin in Bacteria

Chistyakov¹,

Празднова²,

Kharchenko³

et al. 2016

Int J Biomed

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The aim of the present study was to investigate biological properties of the novel nitrobenzoxadiazole derivative 7-(1-methyl-3-pyrrolyl-)-4,6-dinitrobenzofuroxan. Materials and Methods:We used a bioluminescent test based on a set of lux-biosensors, which are genetically modified E.coli strains able to react on different types of factors that can induce an SOS-response with light emission. The spontaneous and induced mutation frequencies of antibiotic resistance in E. coli were determined by methods of classical genetics of microorganisms.Results: 7-(1-methyl-3-pyrrolyl-)-4,6-dinitrobenzofuroxan demonstrated inhibition of SOS-response in a biosensor model system and significantly reduced the frequency of spontaneous mutations and mutations induced by ciprofloxacin of antibiotic resistance.Conclusion: Based on our data, we can recommend using compound 1 as a starting point for the development of drugs that block mutagenesis associated with the emergence of antibiotic-resistant bacteria. (Int J Biomed. 2016;6(3):228-232.).

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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7-(1-Methyl-3-Pyrrolyl-)-4,6-Dinitrobenzofuroxan Reduces the Frequency of Antibiotic Resistance Mutations Induced by Ciprofloxacin in Bacteria

Chistyakov¹,

Празднова²,

Kharchenko³

et al. 2016

Int J Biomed

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“…These ndings are in agreement with those previously reported by Chistyakov et al on the reaction between 4 and Nmethylpyrrole that gave two 1,3-N-oxide tautomers. 52…”

Section: Resultsmentioning

confidence: 99%

Intriguing enigma of nitrobenzofuroxan's ‘Sphinx’: Boulton–Katritzky rearrangement or unusual evidence of the N-1/N-3-oxide rearrangement?

et al. 2020

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“…21,22 For example, recent research shows 3-nitropyrrolidine fused with benzoazoles to be potential NO-donors. 23 This class of compound is quite limited and therefore insufficiently studied. In addition, the pyrrolidine moiety (including fused pyrrolidines) is considered as a "privileged" structural fragment and a key component of efficient organocatalysts, 24 enzyme inhibitors, 25 etc.…”

Section: Introductionmentioning

confidence: 99%

Dearomatization of 3,5-dinitropyridines – an atom-efficient approach to fused 3-nitropyrrolidines

Bastrakov¹,

Kucherova²,

Fedorenko³

et al. 2017

Arkivoc

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An efficient and convenient one-step method for the synthesis of decahydrodipyrrolo [3,4-b:3',4'-d]pyridine derivatives was developed on the basis of 1,3-dipolar cycloaddition of unstabilized N-methyl azomethine ylide with 2-substituted 3,5-dinitropyridines. This novel heterocyclic system contains two 3-nitropyrrolidine fragments fused to a partially saturated pyridine ring. Such types of compound, as follows from the literature, can be considered as potential nitric oxide donors.

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Synthesis and biological properties of nitrobenzoxadiazole derivatives as potential nitrogen(ii) oxide donors: SOX induction, toxicity, genotoxicity, and DNA protective activity in experiments using Escherichia coli-based lux biosensors

Cited by 18 publications

References 37 publications

7-(1-Methyl-3-Pyrrolyl-)-4,6-Dinitrobenzofuroxan Reduces the Frequency of Antibiotic Resistance Mutations Induced by Ciprofloxacin in Bacteria

7-(1-Methyl-3-Pyrrolyl-)-4,6-Dinitrobenzofuroxan Reduces the Frequency of Antibiotic Resistance Mutations Induced by Ciprofloxacin in Bacteria

Intriguing enigma of nitrobenzofuroxan's ‘Sphinx’: Boulton–Katritzky rearrangement or unusual evidence of the N-1/N-3-oxide rearrangement?

Dearomatization of 3,5-dinitropyridines – an atom-efficient approach to fused 3-nitropyrrolidines

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