Phenothiazine and Derivatives

Taurand, G.

doi:10.1002/14356007.a19_387

Cited by 10 publications

(7 citation statements)

References 109 publications

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“…The history of the phenothiazines began in 1876 upon the synthesis of methylene blue by Henrich Caro (Varga et al 2017). While methylene blue itself is a therapeutically relevant compound, used as an antimalarial drug, its derivatives have amassed significant therapeutic importance due to their wide functional diversity (Taurand et al 2012). The first of these derivatives, phenothiazine, was synthesised in 1883 by Heinrich August Berntthsen (Bernthsen and Laboratorium von A. Bernthsen 1883); its insecticidal (Smith 1937), antihelminthic (Swales 1939, Gordon andSydney 1945) and antibacterial properties (Deeds et al 1939) were noted in the 1930s and 1940s.…”

Section: History Of Phenothiazinesmentioning

confidence: 99%

Do phenothiazines possess antimicrobial and efflux inhibitory properties?

Grimsey

Piddock

2019

FEMS Microbiology Reviews

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Antibiotic resistance is a global health concern; the rise of drug-resistant bacterial infections is compromising the medical advances that resulted from the introduction of antibiotics at the beginning of the 20th century. Considering that the presence of mutations within individuals in a bacterial population may allow a subsection to survive and propagate in response to selective pressure, as long as antibiotics are used in the treatment of bacterial infections, development of resistance is an inevitable evolutionary outcome. This, combined with the lack of novel antibiotics being released to the clinical market, means the need to develop alternative strategies to treat these resistant infections is critical. We discuss how the use of antibiotic adjuvants can minimise the appearance and impact of resistance. To this effect, several phenothiazine-derived drugs have been shown to potentiate the activities of antibiotics used to treat infections caused by Gram-positive and Gram-negative bacteria. Outside of their role as antipsychotic medications, we review the evidence to suggest that phenothiazines possess inherent antibacterial and efflux inhibitory properties enabling them to potentially combat drug resistance. We also discuss that understanding their mode of action is essential to facilitate the design of new phenothiazine derivatives or novel agents for use as antibiotic adjuvants.

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Section: History Of Phenothiazinesmentioning

confidence: 99%

Do phenothiazines possess antimicrobial and efflux inhibitory properties?

Grimsey

Piddock

2019

FEMS Microbiology Reviews

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“…Heterocycles, which are cyclic hydrocarbons embedding one or more heteroatoms, are well established as key building blocks in biostructures and functional materials. Phenothiazine is an anthracene-shaped heterocyclic compound including a nitrogen and sulfur atom at the central ring. , Unlike similar heterocycles such as dihydrophenazine and phenoxazine, phenothiazine can adopt three different states, namely neutral, radical, and oxygenated states (Figure a). These characteristic properties expand its usage for pharmaceutical ingredients as well as electro/photochemical materials and catalysts. , However, the application of phenothiazine in supramolecular host–guest systems has remained almost unexplored so far. , We presumed that the construction of a capsular framework with multiple phenothiazine panels would provide us with a redox-active nanocontainer.…”

Section: Introductionmentioning

confidence: 99%

A Redox-Active Heterocyclic Capsule: Radical Generation, Oxygenation, and Guest Uptake/Release

et al. 2019

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For the development of a redox-active supramolecular capsule with host function, we synthesized a bent heterocyclic amphiphile using phenothiazine panels capable of adopting three different states, i.e., neutral, radical, and oxygenated states. In water, the new amphiphiles spontaneously and quantitatively assemble into a heterocycle-based capsule with an average diameter of ∼2 nm, through the hydrophobic effect and π-stacking interactions. The product structure was confirmed by the combination of NMR, UV−visible, DLS, AFM, and molecular modeling studies. Electrochemical and chemical oxidation of the capsule generates relatively stable radical cation capsules at room temperature in a reversible fashion. The neutral capsule efficiently takes up large hydrophobic compounds (e.g., pigment blue 15 and fullerene C 60 ) into the heterocyclic cavity through a grinding protocol and subsequent chemical oxidation of the products generates radical host−guest complexes. Moreover, chemical oxygenation of the host−guest complexes was shown to induce guest release in water via disassembly of the capsular structure through dioxygenation of the phenothiazine panels.

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“…Most of the current drugs that act on the nervous system, launched in the past 50 years, at a time when only very few things were known about the functioning of the human brain, would not come out today because of their side effects. Many drugs as useful as nerve sedatives and neuroleptics, such as phenothiazine ( 11 ), or drugs such as aspirin, digitalin, and morphine would probably not receive approval to day from the FDA or the EMA, if the value of these drugs had to be assessed on the premise of the current regulatory standards concerning safety.…”

Section: Specific Impact Of the Precautionary Principle On Drug Discomentioning

confidence: 99%

And if the discovery of new drugs for the treatment of brain diseases depends on Asian countries?

Kraus

2014

Journal of Market Access & Health Policy

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At the present time, developed countries are making a huge financial effort to support neuroscience research programs, particularly in the fields of advanced research and treatment of brain diseases and mental disorders. A part of this financial support is devoted to drug discovery programs. The purpose of this communication is to focus on the different parameters (economic, social, and scientific) allowing for the prominent belief that the discovery of new efficient drugs to treat brain disease to an increasing extent is likely to emanate from the Asian countries. A special focus on drug research and discovery in France reveals that, due to the current social context, the lack of small pharmaceutical ventures, the Mediator drug scandal, and the economic situation, the potential for discovering and developing new drugs is dramatically declining.

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Phenothiazine and Derivatives

Abstract: The article contains sections titled: 1. Introduction 2. Uses and Biological Activity … Show more

Cited by 10 publications

References 109 publications

Do phenothiazines possess antimicrobial and efflux inhibitory properties?

Do phenothiazines possess antimicrobial and efflux inhibitory properties?

A Redox-Active Heterocyclic Capsule: Radical Generation, Oxygenation, and Guest Uptake/Release

And if the discovery of new drugs for the treatment of brain diseases depends on Asian countries?

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