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Radical Reactivity: Intramolecular vs Intermolecular01:33

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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this species into...
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Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
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Bio-Photo Dual Action of Intracellular Radical Polymerization.

Chunxiao Wu1, Ze Wei1, Changfeng Li1

  • 1Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research, Ministry of Education, Institute of Interdisciplinary Studies, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, Hunan 410081, China.

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This study introduces a dual-control system for precise intracellular polymerization using stimuli-responsive photocatalysts. This method enables targeted cell death by disrupting endoplasmic reticulum function, advancing synthetic biology and therapeutic discovery.

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Area of Science:

  • Biomedical Engineering
  • Synthetic Biology
  • Chemical Biology

Background:

  • Controlling intracellular polymerization is challenging for merging synthetic chemistry with biological systems.
  • Existing methods lack precise spatiotemporal control over polymerization within living cells.

Purpose of the Study:

  • To develop a stimuli-responsive photocatalyst strategy for biomarker- and light-gated radical polymerization inside cells.
  • To achieve spatiotemporal control over polymerization for targeted cellular intervention.

Main Methods:

  • Engineered 3,4,5,6-tetrabromofluorescein (TBF) photocatalysts with protecting groups responsive to endogenous species (ROS/RSS) or enzymes.
  • Utilized an AND-gated mechanism requiring simultaneous biomarker activation and light irradiation to initiate polymerization.
  • Employed monomer design and dual-control for in situ polymer growth.

Main Results:

  • Achieved exclusive polymerization within target cells through the AND-gated mechanism.
  • Demonstrated that in situ polymer growth selectively disrupts endoplasmic reticulum (ER) integrity.
  • Triggered ER stress, calcium release, and paraptosis (caspase-independent cell death) via ER dilation and cytoplasmic vacuolization.

Conclusions:

  • The developed platform offers a versatile chemical approach for precision organelle intervention.
  • This strategy advances therapeutic discovery by enabling targeted induction of specific cell death pathways.
  • Establishes a new paradigm for synthetic biology applications requiring controlled intracellular chemical reactions.