Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H20N4 |
| Molecular Weight | 172.2712 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CNCCNCCNCCN1
InChI
InChIKey=QBPPRVHXOZRESW-UHFFFAOYSA-N
InChI=1S/C8H20N4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h9-12H,1-8H2
| Molecular Formula | C8H20N4 |
| Molecular Weight | 172.2712 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
1,4,7,10-Tetraazacyclododecane (Cyclen) is a macro cycle. Cyclen compounds are capable of selectively binding cations. Macrocyclic polyamines are excellent ligands, with high binding affinities towards transition-metal ions, a typical representative being cyclen. They are used as a ligand in chemistry for instance with chemicals used in MRI contrast agents. Lanthanide complexes of cyclen derivatives are widely used in magnetic resonance imaging. Many metal–cyclen complexes have been prepared and used inDNA recognition and cleavage. Zn II–cyclen complexes selectively recognize the DNA bases U and T. Co II–Cyclen complexes were also found to be good DNA-cleaving reagents .
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Efficient cycloreversion of cis,syn-thymine photodimer by a Zn2+ -1,4,7,10-tetraazacyclododecane complex bearing a lumiflavin and tryptophan by chemical reduction and photoreduction of a lumiflavin unit. | 2006-11 |
|
| Peptide-cleaving catalyst selective for melanin-concentrating hormone: Oxidative decarboxylation of N-terminal aspartate catalyzed by Co(III)cyclen. | 2006-10 |
|
| The conjugates of uracil-cyclen Zn(II) complexes: synthesis, characterization, and their interaction with plasmid DNA. | 2006-08-15 |
|
| Angle-dependent electronic effects in 4,4'-bipyridine-bridged Ru3 triangle and Ru4 square complexes. | 2006-08-07 |
|
| Influence of the "innocent" ligands on the MLCT excited-state behavior of mono(bipyridine)ruthenium(II) complexes: a comparison of X-ray structures and 77 K luminescence properties. | 2006-08-07 |
|
| Host-guest interaction between cyclen based macrotricyclic ligands and phosphate anions. A potentiometric investigation. | 2006-07-28 |
|
| Supramolecular self-assembly of mixed f-d metal ion conjugates. | 2006-06-22 |
|
| Monometallic complexes of 1,4,7,10-tetraazacyclododecane containing an imidazolium side: synthesis, characterization, and their interaction with plasmid DNA. | 2006-06-15 |
|
| Radiolytic and cellular reduction of a novel hypoxia-activated cobalt(III) prodrug of a chloromethylbenzindoline DNA minor groove alkylator. | 2006-06-14 |
|
| One- and two-photon absorption and emission properties of a Zn(II) chemosensor. | 2006-05-25 |
|
| Fast water-exchange Gd3+-(DO3A-like) complex functionalized with aza-15-crown-5 showing prolonged residence lifetime in vivo. | 2006-05-18 |
|
| Synthesis and characterisation of bis-cyclen based dinuclear lanthanide complexes. | 2006-04-21 |
|
| Polymethacrylates with a covalently linked CuII-cyclen complex for the in situ generation of nitric oxide from nitrosothiols in blood. | 2006-04-21 |
|
| 166Ho-DOTMP radiation-absorbed dose estimation for skeletal targeted radiotherapy. | 2006-03 |
|
| A europium complex that selectively stains nucleoli of cells. | 2006-02-22 |
|
| Improved biodistribution and radioimmunoimaging with poly(ethylene glycol)-DOTA-conjugated anti-CEA diabody. | 2006-01-19 |
|
| Conformational changes of DNA by photoirradiation of DNA-bis(Zn(II)-cyclen)-azobenzene complex. | 2006 |
|
| Tissue pH measurement by magnetic resonance spectroscopy and imaging. | 2006 |
|
| Towards the rational design of MRI contrast agents: a practical approach to the synthesis of gadolinium complexes that exhibit optimal water exchange. | 2005-12-21 |
|
| The first synthesis of chiral PNA monomer-cyclen conjugates. | 2005-12 |
|
| Positive ion pair cooperativity exhibited for the binding of phosphate under physiological conditions. | 2005-11-07 |
|
| Reliable and cost-effective screening of inherited heterozygosity by Zn2+-cyclen polyacrylamide gel electrophoresis. | 2005-11 |
|
| Asymmetric indolylmaleimide derivatives and their complexation with zinc(II)-cyclen. | 2005-10-27 |
|
| Receptor for anionic pyrene derivatives provides the basis for new biomembrane assays. | 2005-10-26 |
|
| Bis-azamacrocyclic anthracene as a fluorescent chemosensor for cations in aqueous solution. | 2005-10-20 |
|
| Dinuclear macrocyclic polyamine zinc(II) complexes linked with flexible spacers: synthesis, characterization, and DNA cleavage. | 2005-10 |
|
| Cyclen based bis-macrocyclic ligands as phosphates receptors. A potentiometric and NMR study. | 2005-09-21 |
|
| Crystal structures of lanthanide(III) complexes with cyclen derivative bearing three acetate and one methylphosphonate pendants. | 2005-08-08 |
|
| Solvent dependent conformational isomerism and ligand oxidation of novel Ru(II) cyclen complexes. | 2005-08-08 |
|
| Melanoma therapy via peptide-targeted {alpha}-radiation. | 2005-08-01 |
|
| Responsive lanthanide luminescent cyclen complexes: from switching/sensing to supramolecular architectures. | 2005-07-07 |
|
| Artificial metalloprotease with active site comprising aldehyde group and Cu(II)cyclen complex. | 2005-07-06 |
|
| A luminescence sensor of inositol 1,4,5-triphosphate and its model compound by ruthenium-templated assembly of a bis(Zn2+-cyclen) complex having a 2,2'-bipyridyl linker (cyclen = 1,4,7,10-tetraazacyclododecane). | 2005-06-29 |
|
| Angiotensin-cleaving catalysts: conversion of N-terminal aspartate to pyruvate through oxidative decarboxylation catalyzed by Co(III)cyclen. | 2005-06 |
|
| Visual sensing of Ca2+ ion via photoreaction of fluorenyl ester-armed cyclen. | 2005-05-07 |
|
| Imaging of melanoma using 64Cu- and 86Y-DOTA-ReCCMSH(Arg11), a cyclized peptide analogue of alpha-MSH. | 2005-04-21 |
|
| Lewis acid properties of zinc(II) in Its cyclen complex. The structure of [Zn(cyclen)(S=C(NH2)2](ClO4)2 and the bonding of thiourea to metal ions. Some implications for zinc metalloenzymes. | 2005-04-18 |
|
| Synthesis of novel DNA cross-linking antitumour agents based on polyazamacrocycles. | 2005-04-01 |
|
| Design and synthesis of a novel water-soluble NMDA receptor antagonist with a 1,4,7,10-tetraazacyclododecane group. | 2005-04 |
|
| Coumarin-based chemosensors for zinc(II): toward the determination of the design algorithm for CHEF-type and ratiometric probes. | 2005-03-21 |
|
| Cholesterol-armed cyclens for helical metal complexes offering chiral self-aggregation and sensing of amino acid anions in aqueous solutions. | 2005-03-04 |
|
| Peptide-cleaving catalyst selective for peptide deformylase. | 2005-03-02 |
|
| Synthesis and binding properties of hybrid cyclophane-azamacrocyclic receptors. | 2005-01-07 |
|
| Effect on pKa of metal-bound water molecules in lanthanide ion-induced cyclen "cavities". | 2004-12-23 |
|
| Comparative in vivo behavior studies of cyclen-based copper-64 complexes: regioselective synthesis, X-ray structure, radiochemistry, log P, and biodistribution. | 2004-12-16 |
|
| Cyclen-based phenylboronate ligands and their Eu3+ complexes for sensing glucose by MRI. | 2004-11-18 |
|
| Inside or outside a ligand cleft? Synthetic, structural, and kinetic inertness studies of zinc, cadmium, and mercury complexes of cross-bridged cyclam and cyclen. | 2004-11-07 |
|
| A novel design strategy for stable metal complexes of nitrogen mustards as bioreductive prodrugs. | 2004-11-04 |
|
| In vivo evaluation of copper-64-labeled monooxo-tetraazamacrocyclic ligands. | 2004-11 |
|
| Metal chelation-controlled twisted intramolecular charge transfer and its application to fluorescent sensing of metal ions and anions. | 2004-10-20 |
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
964584YO2O
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID60183621
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64963
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629374
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37391
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964584YO2O
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CYCLEN
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m3969
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PRIMARY | Merck Index |