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Related Concept Videos

Crown Ethers02:36

Crown Ethers

Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
Electron Transport Chain: Complex I and II01:46

Electron Transport Chain: Complex I and II

The mitochondrial electron transport chain (ETC) is the main energy generation system in the eukaryotic cells. However, mitochondria also produce cytotoxic reactive oxygen species (ROS) due to the large electron flow during oxidative phosphorylation. While Complex I is one of the primary sources of superoxide radicals, ROS production by Complex II is uncommon and may only be observed in cancer cells with mutated complexes.
ROS generation is regulated and maintained at moderate levels necessary...
The Electron Transport Chain01:30

The Electron Transport Chain

The electron transport chain or oxidative phosphorylation is an exothermic process in which free energy released during electron transfer reactions is coupled to ATP synthesis. This process is a significant source of energy in aerobic cells, and therefore inhibitors of the electron transport chain can be detrimental to the cell's metabolic processes.
Inhibitors of the electron transport chain
Rotenone, a widely used pesticide, prevents electron transfer from Fe-S cluster to ubiquinone or Q in...
Hypersensitivity Reactions: Cytolytic Reactions01:01

Hypersensitivity Reactions: Cytolytic Reactions

Type II hypersensitivity involves IgG and IgM antibodies targeting cell surface antigens, leading to cell destruction. This can occur through complement activation, antibody-dependent cell-mediated cytotoxicity (ADCC), or acting as opsonins for phagocytosis. When excessive, these reactions cause significant tissue damage.Drug-induced hemolytic anemia is a common example, where drugs like penicillin or cephalosporins bind to red blood cells, forming drug-protein complexes. These complexes...
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Bioactivation and Tissue Toxicity01:25

Bioactivation and Tissue Toxicity

Bioactivation is a metabolic process that transforms less reactive substances into highly reactive metabolites, initiating tissue toxicity. This transformation can lead to various toxic effects, including carcinogenesis and teratogenesis. Reactive metabolites are classified into two main types: electrophiles and free radicals.Electrophiles are electron-deficient species and are produced primarily by the enzyme cytochrome P-450 during the metabolism of compounds containing carbon, nitrogen, or...

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Related Experiment Video

Updated: May 12, 2026

An In Vitro Enzymatic Assay to Measure Transcription Inhibition by Gallium(III) and H3 5,10,15-tris(pentafluorophenyl)corroles
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An In Vitro Enzymatic Assay to Measure Transcription Inhibition by Gallium(III) and H3 5,10,15-tris(pentafluorophenyl)corroles

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Crown Ether Host-Rotaxanes as Cytotoxic Agents.

David B Smithrud1, Xiaoyang Wang, Pheruza Tarapore

  • 1Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 452212.

ACS Medicinal Chemistry Letters
|March 30, 2013
PubMed
Summary

Synthetic ionophores, crown ether host-rotaxanes (CEHRs), show high toxicity to cancer cells. Their toxicity is enhanced by calcium ions, suggesting potential for novel cancer therapies.

Keywords:
ApoptosisCalciumCrown EthersMagnesiumRotaxanes

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Last Updated: May 12, 2026

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Area of Science:

  • Medicinal Chemistry
  • Biochemistry
  • Cell Biology

Background:

  • Bacterial ionophores are potent but too toxic for human use due to narrow therapeutic indices.
  • Developing synthetic ionophores with improved safety profiles is crucial for therapeutic applications.

Purpose of the Study:

  • To synthesize novel crown ether host-rotaxanes (CEHRs) with potentially broader therapeutic indices.
  • To evaluate the cytotoxicity of CEHRs against the SKOV-3 cell line.
  • To investigate the influence of magnesium (Mg2+) and calcium (Ca2+) ions on CEHRs' toxicity.

Main Methods:

  • Synthesis of derivatized crown ether host-rotaxanes (CEHRs).
  • Cytotoxicity assays using the SKOV-3 cell line to determine IC50 values.
  • Assessment of ion effects (Mg2+, Ca2+) on CEHRs' toxicity.

Main Results:

  • Boc-CEHR exhibited high toxicity (IC50 = 0.5 μM), and Arg-CEHR showed moderate toxicity (IC50 = 6 μM) in standard medium.
  • Increased extracellular Ca2+ significantly enhanced CEHRs' toxicity.
  • Increased extracellular Mg2+ had a less pronounced effect on reducing CEHRs' IC50 values.

Conclusions:

  • CEHRs demonstrate potent cytotoxicity against SKOV-3 cells.
  • The observed enhancement of toxicity by Ca2+ suggests ion delivery into cells.
  • These findings indicate that CEHRs may induce apoptosis via cation delivery, warranting further investigation for therapeutic potential.