Recent Progress on the Evolution of Pourbaix Sensors: Molecular Logic Gates for Protons and Oxidants

Magri, David C.

doi:10.3390/chemosensors6040048

Cited by 9 publications

(3 citation statements)

References 51 publications

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“…Molecular logic gates constitute a wide range of molecular switches that respond to diverse input signals according to the rules of Boolean logic. Since the inception of the first molecular AND logic gate (de Silva et al, 1993), a wide range of “digital” optical switches (de Ruiter and van der Boom, 2011; de Silva and Uchiyama, 2011; Magri and Mallia, 2013; Ling et al, 2015; Akkaya et al, 2017; Katz, 2017; Erbas-Cakmak et al, 2018; Pilarczyk et al, 2018) and related pattern-generating devices (Rout et al, 2012, 2013, 2014; Sarkar et al, 2016; Hatai et al, 2017; Lustgarten et al, 2017; Pode et al, 2017) have been developed and used for various applications, including information processing (de Ruiter and van der Boom, 2011; de Silva and Uchiyama, 2011; Ling et al, 2015; Akkaya et al, 2017; Katz, 2017; Erbas-Cakmak et al, 2018; Pilarczyk et al, 2018), user identification (Rout et al, 2013; Lustgarten et al, 2017; Andréasson and Pischel, 2018), cryptography (Sarkar et al, 2016; Lustgarten et al, 2017), and sensing (Ling et al, 2015; Wu et al, 2017; Erbas-Cakmak et al, 2018; Magri, 2018). These input-dependent systems were initially considered as potential alternatives to conventional transistors and circuits (de Silva et al, 1993).…”

Section: Introductionmentioning

confidence: 99%

Molecular Logic as a Means to Assess Therapeutic Antidotes

2019

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An emerging direction in the area of molecular logic and computation is developing molecular-scale devices that can operate in complex biological environments, such as within living cells, which are beyond the reach of conventional electronic devices. Herein we demonstrate, at the proof-of-principle level, how concepts applied in the field of molecular logic gates can be used to convert a simple fluorescent switch (YES gate), which lights up in the presence of glutathione s-transferase (GST), into a medicinally relevant INHIBIT gate that responds to both GST and beta-cyclodextrin (β-CD) as input signals. We show that the optical responses generated by this device indicate the ability to use it as an enzyme inhibitor, and more importantly, the ability to use β-CD as an “antidote” that prevents GST inhibition. The relevance of this system to biomedical applications is demonstrated by using the INHIBIT gate and β-CD to regulate the growth of breast cancer cells, highlighting the possibility of applying supramolecular inputs, commonly used to control the fluorescence of molecular logic gates, as antidotes that reverse the toxic effect of chemotherapy agents. We also show that the effect of β-CD can be prevented by introducing 1-adamantanecarboxylic acid (Ad-COOH) as an additional input signal, indicating the potential of obtaining precise, temporal control over enzyme activity and anticancer drug function.

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Section: Introductionmentioning

confidence: 99%

Molecular Logic as a Means to Assess Therapeutic Antidotes

2019

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“…Photochemical concepts such as PET and ICT are used as the favorite design concepts. This review highlights the evolution of Pourbaix sensors with anthracene, pyrazoline, and naphthalimide fluorophores, while ferrocene is the electron donor mentioned in most molecules [61].…”

Section: Miscellaneous Mlg Systems Using Ferrocenementioning

confidence: 99%

Molecular Logic Gates Based on Ferrocene-Containing Compounds

Tzeliou,

Zois,

Tzeli

2024

Inorganics

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Ferrocene has a unique structure, i.e., a central iron atom neatly sandwiched between two cyclopentadienyl rings, which has revolutionized the chemists’ views about how metals bind to organic π-systems. This structural arrangement leads to some fascinating chemical and photophysical properties. The last three decades, there were reports about receptor molecules that could be considered to perform simple logic operations via coupling ionic bonding or more complex molecular-recognition processes with photonic (fluorescence) signals. In these systems, chemical binding (‘input’) results in a change in fluorescence intensity (‘output’) from the receptor. It has been proven that molecules respond to changes in their environment, such as the presence of various ions, neutral species, pHs, temperatures, and viscosities. Since their first realization by de Silva, molecular logic gates have been intensively experimentally studied, with purely theoretical studies being less common. Here, we present the research that has been conducted on Molecular Logic Gates (MLGs) containing ferrocene and their applications. We categorized such systems into three families of MLGs: long-chain molecules (oligomers or polymers) that incorporate ferrocene, medium-sized molecules that incorporate ferrocene, and systems where ferrocene or its derivatives are used as external additives. Furthermore, MLGs including metal cations without the ferrocene moiety are briefly presented, while computational methodologies for an accurate theoretical study of MLG, including metal cations, are suggested. Finally, future perspectives of MLGs containing ferrocene and their applications are also presented.

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“…The purpose of this study was to investigate NDIs as colorimetric and fluorimetric pH indicators as a platform for the development of Pourbaix sensors [23,24], fluorescent logic gates for acidity (pH) and oxidisability (pE), [25,26] based on photoinduced electron transfer [27]. In a recent study, we synthesized a core unsubstituted NDI molecule with an electron-donor-spacer-fluorophore-spacer-receptor format, with ferrocene as the electron donor and dimethylamino as the proton receptor [28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Spectrophotometric Studies of Heterocyclic Bay-Substituted Naphthalenediimide Colorimetric pH Indicators

Magro,

Camenzuli,

Magri

2023

Chemosensors

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Four naphthalenediimide colorimetric pH indicators were synthesized with N,N-dimethylethyleneamine at the imide positions and with 5- to 7-membered heterocyclic rings at the bay positions, namely pyrrolidine, morpholine, piperidine and azepane. The pH indicators are constructed in a modular receptor–spacer–fluorophore–spacer–receptor format based on a photoinduced electron transfer (PET) design. The compounds were studied by UV–visible absorption and steady-state fluorescence spectroscopy in 1:1 (v/v) methanol/water. Brilliant colour changes are observed between pH 2 and 4 due to an internal charge transfer (ICT) mechanism. Fluorescence turn-on enhancements range from 10–37 fold; however, the maximum fluorescence quantum yield in the presence of acid is <0.004, which is below naked eye detection. Hence, from the viewpoint of a human observer, these chemosensors function as colorimetric YES logic gates, and fluorimetric PASS 0 logic gates.

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Recent Progress on the Evolution of Pourbaix Sensors: Molecular Logic Gates for Protons and Oxidants

Cited by 9 publications

References 51 publications

Molecular Logic as a Means to Assess Therapeutic Antidotes

Molecular Logic as a Means to Assess Therapeutic Antidotes

Molecular Logic Gates Based on Ferrocene-Containing Compounds

Synthesis and Spectrophotometric Studies of Heterocyclic Bay-Substituted Naphthalenediimide Colorimetric pH Indicators

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