Horseradish Peroxidase-Catalyzed Oxidation of Rifampicin: Reaction Rate Enhancement by Co-oxidation with Anti-inflammatory Drugs

Santos, Fernanda de Jesus Notário dos; Ximenes, Valdecir Farias; Fonseca, Luiz Marcos da; Oliveira, Olga Maria Mascarenhas de Faria; Brunetti, Iguatemy Lourenço

doi:10.1248/bpb.28.1822

Cited by 19 publications

(12 citation statements)

References 20 publications

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“…Based on the work described in this study as well as other studies of co-oxidation [6,7,10,11], it would appear that AS would be the preferred substrate to react with peroxidase (Fig. 2).…”

Section: Discussionsupporting

confidence: 55%

“…The phenomenon of co-oxidation of phenolics has been an area of intense investigation in the pharmaceutical field where two or more phenolic drugs are prescribed and has revealed effects that could just as likely occur in plants [6,11]. Peroxidases and other redox-active proteins in animals have been shown to metabolize a number of phenolic compounds in vivo, leading to modifications of their bioactivity, which could be either beneficial or detrimental [10,[14][15][16][17]. For example, rifampicin, a broadspectrum antibiotic used in tuberculosis therapy, inhibits bacterial RNA polymerase, but also has immunosuppressive properties in humans that are attributed to its oxidation product, rifampicin quinone [10].…”

Section: Article In Pressmentioning

confidence: 99%

“…Peroxidases and other redox-active proteins in animals have been shown to metabolize a number of phenolic compounds in vivo, leading to modifications of their bioactivity, which could be either beneficial or detrimental [10,[14][15][16][17]. For example, rifampicin, a broadspectrum antibiotic used in tuberculosis therapy, inhibits bacterial RNA polymerase, but also has immunosuppressive properties in humans that are attributed to its oxidation product, rifampicin quinone [10]. The quinone results from the oxidation of rifampicin by ROS at the infection or inflammation site.…”

Section: Article In Pressmentioning

confidence: 99%

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Apoplastic redox metabolism: Synergistic phenolic oxidation and a novel oxidative burst

Baker

Roberts

Mock

et al. 2005

Physiological and Molecular Plant Pathology

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The plant apoplast is an important mediator of communication between the cell cytoplasm and its surroundings. Plant cell suspensions offer a convenient model system to gain insight into apoplastic physiology. Here, we describe a novel phenomenon that took place when two naturally occurring phenolics were added together to either soybean or tobacco cell suspensions. Acetosyringone (AS) and/or hydroxyacetophenone (HAP), phenolics found in the extracellular/apoplast of tobacco cells, were added to soybean or tobacco cell suspensions undergoing an oxidative burst. Individually, AS appeared to be utilized as a typical peroxidase substrate to scavenge hydrogen peroxide, while HAP was utilized at a much lower rate. However, when added together the rate of utilization of both phenolics increased and surprisingly resulted in the production of hydrogen peroxide. We have further characterized this novel phenomenon in suspension cells. This study demonstrates that certain phenolics in plants can cause co-oxidation which, as in animals, could alter the structure and bioactivity of surrounding phenolics.

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“…Based on the work described in this study as well as other studies of co-oxidation [6,7,10,11], it would appear that AS would be the preferred substrate to react with peroxidase (Fig. 2).…”

Section: Discussionsupporting

confidence: 55%

Section: Article In Pressmentioning

confidence: 99%

Section: Article In Pressmentioning

confidence: 99%

See 1 more Smart Citation

Apoplastic redox metabolism: Synergistic phenolic oxidation and a novel oxidative burst

Baker

Roberts

Mock

et al. 2005

Physiological and Molecular Plant Pathology

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“…Rifampicin in solution is prone to oxidation and hydrolysis, especially in acidic medium . The RF release from PLA and PEC:PLA particles was corrected for the amount of RF degradation over time (Figure ).…”

Section: Resultsmentioning

confidence: 99%

“…Rifampicin in solution is prone to oxidation and hydrolysis, especially in acidic medium. [34][35][36][37][38] The RF release from PLA and PEC:PLA particles was corrected for the amount of RF degradation over time (Figure 2). While 43.4 AE 5.4 and 36.4 AE 6.5% of the drug was released from the particles containing 5% and 10% PEC after 60 min, only 14.7 AE 0.8% was released from PLA particles.…”

Section: Drug Releasementioning

confidence: 99%

Poly(ethylene carbonate)-containing polylactic acid microparticles with rifampicin improve drug delivery to macrophages

Priemel

Wang

Bohr

et al. 2018

Journal of Pharmacy and Pharmacology

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Environmentally Friendly Degradation and Detoxification of Rifampicin by a Bacterial Laccase and Hydrogen Peroxide

Durão,

Kis,

Chelo

et al. 2023

ChemBioChem

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Antibiotics are micropollutants accumulating in our rivers and wastewaters, potentially leading to bacterial antibiotic resistance, a worldwide problem to which there is no current solution. Here, we have developed an environmentally friendly two‐step process to transform the antibiotic rifampicin (RIF) into non‐antimicrobial compounds. The process involves an enzymatic oxidation step by the bacterial CotA‐laccase and a hydrogen peroxide bleaching step. NMR identified rifampicin quinone as the main product of the enzymatic oxidation. Growth of Escherichia coli strains in the presence of final degradation products (FP) and minimum inhibitory concentration (MIC) measurements confirmed that FP are non‐anti‐microbial compounds, and bioassays suggest that FP is not toxic to eukaryotic organisms. Moreover, competitive fitness assays between susceptible and RIF‐resistant bacteria show that susceptible bacteria is strongly favoured in the presence of FP. Our results show that we have developed a robust and environmentally friendly process to effectively remediate rifampicin from antibiotic contaminated environments.

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Horseradish Peroxidase-Catalyzed Oxidation of Rifampicin: Reaction Rate Enhancement by Co-oxidation with Anti-inflammatory Drugs

Cited by 19 publications

References 20 publications

Apoplastic redox metabolism: Synergistic phenolic oxidation and a novel oxidative burst

Apoplastic redox metabolism: Synergistic phenolic oxidation and a novel oxidative burst

Poly(ethylene carbonate)-containing polylactic acid microparticles with rifampicin improve drug delivery to macrophages

Environmentally Friendly Degradation and Detoxification of Rifampicin by a Bacterial Laccase and Hydrogen Peroxide

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