Attempted characterisation of phenanthrene-4,5-quinone and electrochemical synthesis of violanthrone-16,17-quinone. How does the stability of bay quinones correlate with structural and electronic parameters?

Wilkinson, D. N.; Cioncoloni, Giacomo; Symes, Mark D.; Bucher, Götz

doi:10.1039/d0ra06519f

Cited by 3 publications

(4 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The spectroelectrochemistry measurements, shown in Figure b, reveal negligible changes in the absorption spectrum of the solid VA79 film, either after initial application of the 2 V bias or for up to 20 min after continual bias application. If the VA79 molecules in the solid film were being permanently oxidized upon the application of the bias, a significant change in the absorption spectrum, in particular, a loss of the peaks between 550 and 750 nm and growth of a new oxidized VA79 absorption peak at 300–400 nm, would be expected, as has been observed previously for this semiconductor . Thus, the release is unlikely to be associated with the oxidation of VA79.…”

Section: Resultsmentioning

confidence: 56%

“…If the VA79 molecules in the solid film were being permanently oxidized upon the application of the bias, a significant change in the absorption spectrum, in particular, a loss of the peaks between 550 and 750 nm and growth of a new oxidized VA79 absorption peak at 300−400 nm, would be expected, as has been observed previously for this semiconductor. 45 Thus, the release is unlikely to be associated with the oxidation of VA79.…”

Section: ■ Methodsmentioning

confidence: 98%

See 1 more Smart Citation

Advanced Control of Drug Delivery for In Vivo Health Applications via Highly Biocompatible Self-Assembled Organic Nanoparticles

Crovador

Heim

Cottam

et al. 2021

ACS Appl. Bio Mater.

View full text Add to dashboard Cite

The use of nanostructured materials for targeted and controlled delivery of bioactive molecules is an attractive alternative to conventional drug administration protocols, enabling selective targeting of diseased cells, lower administered dosages, and reduced systemic side effects. Although a variety of nanocarriers have been investigated in recent years, electroactive organic polymer nanoparticles present several exciting advantages. Here we demonstrate that thin films created from nanoparticles synthesized from violanthrone-79, an n-type semiconducting organic material, can incorporate and release dexamethasone in vitro in a highly controlled manner. By systematically altering the nanoparticle formation chemistry, we successfully tailored the size of the nanoparticles between 30 and 145 nm to control the initial amount of drug loaded into the organic particles. The biocompatibility of the different particles was tested using live/dead assays of dorsal root ganglion neurons isolated and cultured from mice, revealing that elevated levels of the sodium dodecyl sulfate surfactant used to create the smaller nanoparticles are cytotoxic; however, cell survival rates in nanoparticles larger than 45 nm exceed 86% and promote neurite growth and elongation. By manipulating the electrical stimulus applied to the electroactive nanoparticle films, we show an accelerated rate of drug release in comparison to passive release in aqueous media. Furthermore, pulsing the electrical stimulus was successfully used to selectively switch the accelerated release rate on and off. By combining the tuning of drug loading (through tailored nanoparticle synthesis) and drug release rate (through electrical stimulus protocols), we demonstrate a highly advanced control of drug delivery dosage in a biocompatible delivery vehicle. This work highlights the significant potential of electroactive organic nanoparticles for implantable devices that can deliver corticosteroids directly to the nervous system for the treatment of inflammation associated with neurological disorders, presenting a translatable pathway toward precision nanomedicine approaches for other drugs and diseases.

show abstract

Section: Resultsmentioning

confidence: 56%

Section: ■ Methodsmentioning

confidence: 98%

Advanced Control of Drug Delivery for In Vivo Health Applications via Highly Biocompatible Self-Assembled Organic Nanoparticles

Crovador

Heim

Cottam

et al. 2021

ACS Appl. Bio Mater.

View full text Add to dashboard Cite

show abstract

“…It consists of a phenanthrene ring fused with a quinone moiety [ 22 ]. Quinones belong to a class of organic compounds characterized by a conjugated cyclic system with two carbonyl groups [ 23 , 24 ]. They can undergo reversible reductions, both one-electron and two-electron-based, resulting in the generation of a semiquinone radical or a quinone, respectively [ 25 ].…”

Section: Resultsmentioning

confidence: 99%

Glucose Oxidase/Egg White Protein Microparticles with a Redox Mediator for Glucose Biosensors on a Screen-Printed Electrode and a Decomposable Electrode

Rasitanon,

Rattanapan,

Kaewpradub

et al. 2023

Biosensors

View full text Add to dashboard Cite

Glucose oxidase (GOx) is a typical model enzyme used to create biosensors. Exploring a strategy to prepare ready-to-use functional enzymatic microparticles combining GOx and food-based proteins offers compelling advantages. However, no reports exist on the integration of egg white materials to synthesize functional biorecognition particles with glucose oxidation catalytic functions for electrochemical biosensors. Here, we demonstrate functional microparticles combining egg white proteins, GOx, and 9,10-phenanthrenequinone (PQ). The egg white proteins crosslink to form three-dimensional scaffolds to accommodate GOx and redox molecules. The PQ mediator enhances electron transfer between the electrode surface and the GOx enzyme’s flavin adenine dinucleotides. The functional microparticles are directly applied to the printed electrode. The performance of these microparticles is evaluated using a screen-printed carbon nanotube (CNT)-modified electrode coated with GOx/PQ/egg white protein microparticles. The analytical performance of the system exhibits a linear range of 0.125−40 mM, with a maximum current (Imax) and a Michaelis–Menten constant (Km) being 0.2 µA and 4.6 mM, respectively. Additionally, a decomposable electrode composed of CNTs and edible oil conjugated with functional enzyme microparticles is shown to undergo degradation under gastric conditions. Utilizing food-based proteins to accommodate enzymes and to create redox-active microparticles for catalyzing glucose oxidation offers advantages in developing affordable and degradable bioelectrodes. This concept holds promise for advancing biocompatible electrodes in biosensor and bioelectronics applications.

show abstract

“…Firstly, dialdehyde 78 was converted into the corresponding bistosyl hydrazone by the reaction with tosyl hydrazide and subsequently, using sodium hydride, transformed into the desired cyclic alkene 79, but in only 18% yield. 29 Bi et al published a strategy to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles with, among others, arylhydrazines. This work presents an efficient one-pot synthetic route for the functionalization of alkenylboronic acids.…”

Section: Shapiro and Bamford-stevens Reactions -Achievements In Recen...mentioning

confidence: 99%

Shapiro and Bamford-Stevens reactions – revisited

Salamon-Krokosz¹,

Koroniak²,

Koroniak-Szejn³

2022

Arkivoc

View full text Add to dashboard Cite

The Shapiro as well as the Bamford-Stevens reactions are very convenient methods for preparing numerous olefinic compounds from ketones and aldehydes via sulfonylhydrazones. These reactions allow preparation not only simple molecules with a double bond but also larger, complex systems that could have biological activity. Therefore, the synthetical aspects of above-mentioned reactions are of broad interest to organic chemists. This mini review describes the application of Shapiro as well as Bamford-Stevens reactions in the preparation of olefinic compounds.

show abstract

Attempted characterisation of phenanthrene-4,5-quinone and electrochemical synthesis of violanthrone-16,17-quinone. How does the stability of bay quinones correlate with structural and electronic parameters?

Abstract: Bay quinones have the carbonyl oxygen atoms in the bay region of polycyclic aromatic hydrocarbons. This study presents cyclic voltammetry and computational work helping to understand when bay quinones can be expected to be isolable, and when not.

Cited by 3 publications

References 21 publications

Advanced Control of Drug Delivery for In Vivo Health Applications via Highly Biocompatible Self-Assembled Organic Nanoparticles

Advanced Control of Drug Delivery for In Vivo Health Applications via Highly Biocompatible Self-Assembled Organic Nanoparticles

Glucose Oxidase/Egg White Protein Microparticles with a Redox Mediator for Glucose Biosensors on a Screen-Printed Electrode and a Decomposable Electrode

Shapiro and Bamford-Stevens reactions – revisited

Contact Info

Product

Resources

About