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Crown Ethers

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.

Structure and Nomenclature of Ethers

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...

Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...

Structure and Nomenclature of Epoxides

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...

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Crown ether functionalized texaphyrin monomers and dimers.

Christian Preihs¹, Darren Magda, Jonathan L Sessler

¹Department of Chemistry & Biochemistry and Institute for Cellular and Molecular Biology, The University of Texas at Austin, 1-University Station A-5300, Austin, Texas 78712-0156, USA.

Journal of Porphyrins and Phthalocyanines

|October 26, 2011

Summary

New gadolinium texaphyrin analogues (2 and 3) functionalized with crown ethers show stability and distinct UV shifts with metal salts. Cytotoxicity studies explored their potential in cancer therapy, particularly concerning zinc(II) regulation of apoptosis.

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Area of Science:

Inorganic Chemistry
Medicinal Chemistry
Biochemistry

Background:

Gadolinium texaphyrin derivatives, like motexafin gadolinium (MGd), are extensively studied compounds.
Crown ether functionalization is a strategy to modify the properties of metal-containing macrocycles.
Zinc(II) ions are crucial in regulating cellular processes, including apoptosis in cancer cells.

Purpose of the Study:

To synthesize and characterize novel 18-crown-6 functionalized analogues of motexafin gadolinium.
To investigate the stability and metal-binding properties of these new compounds.
To evaluate the cytotoxicity of the synthesized analogues, particularly in relation to zinc(II) and apoptosis.

Main Methods:

Synthesis of monomeric (2) and dimeric (3) 18-crown-6 functionalized gadolinium texaphyrins.
Characterization using spectroscopic techniques (UV-Vis).
Cytotoxicity assays on Ramos cell lines in the presence and absence of zinc(II) salts.

Main Results:

Compounds 2 and 3 were successfully synthesized and characterized.
Both analogues demonstrated stability at physiological pH.
Distinct UV spectral shifts were observed upon addition of sodium, potassium, ammonium, and zinc(II) salts, indicating metal-binding interactions.
Cytotoxicity studies revealed differential effects of compounds 2 and 3 on Ramos cells, influenced by zinc(II) presence.

Conclusions:

The synthesized crown ether-functionalized gadolinium texaphyrins (2 and 3) are stable and exhibit selective metal ion interactions.
These compounds show potential for further investigation in cancer therapy, especially considering their interaction with zinc(II) and its role in apoptosis.
The distinct spectral and cytotoxic properties highlight the influence of crown ether functionalization on gadolinium texaphyrin behavior.