Metastable oxidation states of tetrathiafulvalenes on the surface of liposomes

Kauscher, Ulrike; Bartels, K.; Schrader, Imke; Azov, Vladimir A.; Ravoo, Bart Jan

doi:10.1039/c4tb01627k

Cited by 7 publications

(8 citation statements)

References 45 publications

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“…A comparable anchor design was described by Ravoo et al. showing the suitability of this molecule for membrane incorporation and accessibility for cucurbit[8]uril binding 64…”

Section: Resultsmentioning

confidence: 93%

“…Ac omparable anchord esign was described by Ravoo et al showing the suitability of this molecule for membrane incorporation and accessibility for cucurbit [8]uril binding. [64] First, potential aspecific binding events of the supramolecular buildingb locks and proteins towards ab are dioleoylphosphatidylcholine (DOPC) bilayer were investigated ( Figure S3 in the Supporting Information). FlowingD OPC vesicles over as ilica-coated quartzc rystal resulted in the absorption of the vesicles and formation of as upported lipid bilayer,a s evidenced by ad ecrease in frequency Df and increase in dissipation DD.T he frequencya nd dissipation leveled off at the reported valueso fDfÀ25 Hz and DD 0.5 10…”

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confidence: 99%

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Supramolecular Protein Immobilization on Lipid Bilayers

Bosmans

Hendriksen

Verheijden

et al. 2015

Chemistry A European J

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Protein immobilization on surfaces, and on lipid bilayerss pecifically,h as great potential in biomoleculara nd biotechnological research. Of current special interest is the immobilizationo fp roteins using supramolecular noncovalent interactions. This allows for ar eversible immobilization and obviates the use of harsh ligation conditions that could denature fragile proteins.I nt he work presented here, reversible supramolecular immobilization of proteins on lipid bilayer surfaces was achieved by using the host-guest interaction of the macrocyclic molecule cucurbit[8]uril. Af luorescent protein was successfully immobilized on the lipid bilayer by making use of the property of cucurbit [8]uril to host together am ethylviologen and the indole of at ryptophan positionedo nthe N-terminal of the protein. The supramolecular complex was anchored to the bilayer through ac holesterol moiety that was attached to the methylviologen tethered with asmall polyethylene glycolspacer.Protein immobilization studies using aq uartz crystal microbalance (QCM)s howedt he assembly of the supramolecular complexeso nt he bilayer. Specific immobilization through the protein N-terminus is more efficient than through protein side-chain events. Reversible surfacer eleaseo ft he proteins could be achieved by washing with cucurbit[8]uril or buffer alone.T he described system shows the potentialo fs upramolecular assembly of proteins and providesamethod for site-specific protein immobilization under mild conditions in ar eversible manner.

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“…A comparable anchor design was described by Ravoo et al. showing the suitability of this molecule for membrane incorporation and accessibility for cucurbit[8]uril binding 64…”

Section: Resultsmentioning

confidence: 93%

mentioning

confidence: 99%

Supramolecular Protein Immobilization on Lipid Bilayers

Bosmans

Hendriksen

Verheijden

et al. 2015

Chemistry A European J

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“…of FeCl 3 , following a reported procedure. 36 These measurements could not be performed on TTF-MnMo 6 -TTF because of the formation of a precipitate after addition of Fe 3+ . After addition of 1 equiv of Fe 3+ the solution of SP-MnMo 6 -TTF changed from pink to brown and the solution of TTF-AlMo 6 from orange to green.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The oxidation was performed by addition of 1 eq. of FeCl 3 , following a reported procedure . These measurements could not be performed on TTF-MnMo 6 -TTF because of the formation of a precipitate after addition of Fe 3+ .…”

Section: Resultsmentioning

confidence: 99%

Anderson-Type Polyoxometalates Functionalized by Tetrathiafulvalene Groups: Synthesis, Electrochemical Studies, and NLO Properties

et al. 2018

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Three polyoxometalates (POMs) functionalized by tetrathiafulvalene (TTF) molecules have been synthesized by a coupling reaction between the Anderson-type POMs [MnMoO{(OCH)CNH}] or [AlMoO(OH){(OCH)CNH}] and the TTF carboxylic acid derivative (MeS)TTF(S-CH-COH). The monofunctionalized TTF-AlMo POM contains one TTF group covalently grafted on an Al Anderson platform. The symmetrical TTF-MnMo-TTF POM possesses two TTF groups grafted on each side of a Mn Anderson derivative while the asymmetrical TTF-MnMo-SP POM contains a TTF and a spiropyran groups. These three trianionic species have been characterized by elemental analysis, H andC NMR, FT-IR spectroscopy, ESI-MS spectrometry, and single-crystal X-ray diffraction (for TTF-MnMo-TTF). In the solid state, the grafted TTF molecules of TTF-MnMo-TTF POMs interact via S···S and π···π interactions and form chains. The electrochemical properties of the complexes reflect the contributions of both the inorganic POM and the TTF moieties. Despite adsorption of the oxidized hybrid species on the Pt grid working electrode, UV-vis-NIR spectroelectrochemical investigations evidence peaks characteristic of the oxidation of the TTF units. Finally, hyper-Rayleigh scattering (HRS) measurements show that the three novel TTF derivatives exhibit β values between 20 and 37 × 10 esu. Moreover it is observed that the oxidation of the TTF moieties by Fe ions increases the NLO response. These values are in the order of magnitude of that found for the well-known 4-dimethylamino- N-methyl-4-stilbazolium (DAS) cation (β = 60 × 10 esu).

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“…Although there are many reports about the TTF-based MV crystals or charge transfer complexes, , the direct conversion of the TTF crystal into the TTF MV salt crystal is rarely known. Considering the redox potential of the target TTF crystal, the Fe 3+ ion was chosen as an oxidant, which is relatively more economic than other well-known oxidants, such as gold chloride or silver ion, ,, and has been used to oxidize macromolecules containing the TTF moiety , (Scheme b).…”

mentioning

confidence: 99%

Morphology-Retained Conversion of Neutral to Mixed Valence Tetrathiafulvalene Crystals through a Spontaneous Redox Reaction

Ahn

Koo

Choi

2020

ACS Appl. Electron. Mater.

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Solid-state conversion by the spontaneous redox reaction between tetrathiafulvalene (TTF) and ferric ion is employed to obtain morphology-retained TTF mixed valence (MV) salt crystals. Radical species are formed first at the surface of TTF crystals and then inside of the crystals by diffused ferric ions as revealed by the time-dependent UV−vis absorption and electron spin resonance (ESR) spectroscopy studies. The resulting TTF MV salt crystals exhibit 6 orders of magnitude higher electrical conductivity than the original neutral TTF crystals. By taking advantage of solid-state conversion, TTF neutral-MV heterostructures were demonstrated by selectively contacting TTF crystals to ferric ion solution, and they were applied to selfcontact devices, which showed higher conductivity values than the silver paste devices.

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Metastable oxidation states of tetrathiafulvalenes on the surface of liposomes

Abstract: Redox-active liposomes are prepared by the incorporation of tetrathiafulvalene–cholesterol conjugate 1 in phospholipid vesicles.

Cited by 7 publications

References 45 publications

Supramolecular Protein Immobilization on Lipid Bilayers

Supramolecular Protein Immobilization on Lipid Bilayers

Anderson-Type Polyoxometalates Functionalized by Tetrathiafulvalene Groups: Synthesis, Electrochemical Studies, and NLO Properties

Morphology-Retained Conversion of Neutral to Mixed Valence Tetrathiafulvalene Crystals through a Spontaneous Redox Reaction

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