Fluorescent Membrane Probes Obey the Israelachvili Rules

Helvetica Chimica Acta, Journal Year: 2024, Volume and Issue: 107(7)

Published: May 9, 2024

Abstract When developing fluorescent membrane probes, we naturally tend to focus on the fluorophore itself. In this study, show that sometimes it can be beneficial shift attention from center periphery, maximize multiple interfacing with complex changing environments. Palmitylation for hydrophobic and glutamate dendrons hydrophilic are combined improve performance of flipper probes. We increase in membranes, solubility water is important, water, hydrophobicity probe. These seemingly paradoxical measures taken satisfy Israelachvili rules. They state only inverted cone amphiphiles form soluble micelles while shaped precipitate into hexagonal 1 supramolecular polymers, intermediate cylindrical behavior dominated by bilayers lamellar precipitates. The normal obtained prevent precipitation prepare efficient transfer lipid bilayer membranes. results flippers break all records set 2016 original regard effective brightness, responsiveness order, anchoring disordered partitioning membranes high stable labeling interest. lessons learned confirm obvious: rules apply also promise literally bright perspectives

Language: Английский

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“Thiophene”: A Sulphur Containing Heterocycle as a Privileged Scaffold

Letters in Drug Design & Discovery, Journal Year: 2023, Volume and Issue: 21(11), P. 1922 - 1935

Published: June 12, 2023

: In the rapidly expanding chemical realm of heterocyclic compounds with interesting therapeutic properties, thiophene nucleus has established itself as a prospective entity. The biological activity comparable substances produced via different pathways is varying magnitudes. Medicinal chemists use their understanding multiple synthetic and various physicochemical properties such to create combinatorial library conduct thorough searches for lead molecules. Due vast spectrum actions, play crucial role in chemistry are extensively researched field drug design development. Thiophene, sulfur- containing scaffold, emerged rather well-explored scaffold synthesis molecules functions, including antibacterial, antipsychotic, anticancer, analgesic, anti-inflammatory, anti-arrhythmic, so on. Depending on kind position substitution, analogues have been shown bind wide cancer-specific protein targets. As result, found exert effects by inhibiting cancerrelated signalling pathways. study resulted that combine moiety traditional components single molecule. This review covers medical nucleus, well information behaviour, synthesis, agents, focus techniques, profiles, structure-activity relationship (SAR) research.

Language: Английский

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Synthesis of N-Sulfinyl Sulfoximines from 5-(Sulfoximido)dibenzothiophenium Triflates and Sodium Sulfinates

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10311 - 10315

Published: July 10, 2024

A transition-metal-free and efficient S-O/S-N bond interconversion reaction has been developed. The protocol facilitates an synthesis of

Language: Английский

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Subphthalocyanine-flipper dyads for selective membrane staining

Physical Chemistry Chemical Physics, Journal Year: 2024, Volume and Issue: 26(5), P. 4759 - 4765

Published: Jan. 1, 2024

To increase responsiveness to membrane tension, subphthalocyanine-flipper dyads combine bright, long-lifetime mechanophores in ordered domains with anisotropically, environment-insensitive, short-lifetime enhancers disordered domains.

Language: Английский

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Core‐Alkynylated Fluorescent Flippers: Altered Ultrafast Photophysics to Track Thick Membranes

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(31)

Published: May 17, 2024

Abstract Fluorescent flippers have been introduced as small‐molecule probes to image membrane tension in living systems. This study describes the design, synthesis, spectroscopic and imaging properties of that are elongated by one two alkynes inserted between push pull dithienothiophene domains. The resulting mechanophores combine characteristics flippers, reporting on physical compression ground state, molecular rotors, torsional motion excited take their photophysics new level sophistication. Intensity ratios broadened excitation bands from differently twisted conformers core‐alkynylated thus report mechanical compression. Lifetime boosts ultrafast excited‐state planarization lifetime drops competitive intersystem crossing into triplet states viscosity. In standard lipid bilayer membranes, too long for leaflet tilt or extend disordered interleaflet space, which preserves rotor‐like disorder weak, blue‐shifted fluorescence. Flipper‐like occurs only highly ordered membranes matching thickness, where they light up selectively these thick with red‐shifted, sharpened maxima, high intensity lifetime.

Language: Английский

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Asparagusic Golgi Trackers

JACS Au, Journal Year: 2024, Volume and Issue: 4(10), P. 3759 - 3765

Published: Aug. 20, 2024

Thiol-mediated uptake (TMU) is thought to occur through dynamic covalent cascade exchange networks. Here we show that the accounting for TMU of asparagusic acid derivatives (AspA) ends in Golgi apparatus (G) and shifts from disulfide thioester with palmitoyl transferases as final partner. As a result, AspA combined pH-sensitive fluoresceins, red-shifted silicon-rhodamines, or mechanosensitive flipper probes selectively labels fluorescence microscopy images living fixed cells. trackers work without cellular engineering excel speed, simplicity, generality, compatibility G/ER cis/trans discrimination, morphological changes, anterograde vesicular trafficking, superresolution imaging by stimulated emission depletion microscopy. flippers particular can image membrane order tension and, if desired, at plasma during TMU.

Language: Английский

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