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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

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At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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Controlling Intramolecular Rotation with Five-Membered Heterocycles Facilitates the Design of Highly Cell-Permeable

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Researchers developed new fluorogenic probes using furan or thiophene rings for enhanced live-cell imaging. These probes offer high signal-to-noise ratios and target specificity without washing, enabling visualization of cellular processes and targets like EGFR.

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Area of Science:

  • Chemical Biology
  • Molecular Imaging
  • Biotechnology

Background:

  • Fluorogenic probes are crucial for sensitive, background-free biological imaging.
  • Existing probes face challenges in signal-to-noise ratio, specificity, and cell permeability for wash-free applications.

Purpose of the Study:

  • To engineer a novel class of fluorogenic fluorophores with improved performance for live-cell imaging.
  • To develop versatile probes for various cellular targets and applications.

Main Methods:

  • Incorporation of five-membered heterocycles (furan, thiophene) into the xanthene core to control intramolecular rotation.
  • Design and synthesis of furan/thiophene-substituted carborhodamine and silicon-rhodamine fluorophores.
  • Conjugation of fluorophores with self-labeling protein tags (HaloTag, SNAP-tag, PYP-tag) and targeted inhibitors (JQ1, gefitinib/erlotinib).

Main Results:

  • Achieved fluorescence activation independent of spirolactone equilibrium via controlled intramolecular rotation.
  • Developed wash-free, high-permeability probes for HaloTag, SNAP-tag, and PYP-tag, enabling visualization of endoplasmic reticulum dynamics.
  • Created BRD4- and EGFR-targeting probes demonstrating effective detection of EGFR overexpression.

Conclusions:

  • A versatile design strategy based on controlled intramolecular rotation of heterocycles yields innovative OFF/ON fluorogenic probes.
  • This approach provides a robust platform for selective, wash-free live-cell imaging of diverse biological targets.