Page last updated: 2024-12-06

cyclen

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Cyclen, also known as 1,4,7,10-tetraazacyclododecane, is a macrocyclic tetraamine. It is a versatile ligand used in coordination chemistry and serves as a chelating agent for various metal ions. Cyclen's structure allows it to form stable complexes with transition metals due to its ability to bind through all four nitrogen atoms, creating a highly stable ring structure. Its synthetic pathway involves the reaction of diethylenetriamine with formaldehyde and a reducing agent, leading to the formation of the cyclic structure. Cyclen's applications extend to various fields, including:
* **Bioinorganic Chemistry:** Studying metal-ion transport and mimicking metalloenzymes.
* **Medicine:** Developing metal-based anticancer drugs and diagnostic agents.
* **Catalysis:** Serving as a ligand in homogeneous catalysis, influencing reaction rates and selectivity.
* **Materials Science:** Designing metal-organic frameworks with potential for gas storage and separation.
Cyclen's importance lies in its ability to control metal-ion reactivity, creating opportunities for tailored chemical transformations. Researchers continue to investigate its use in various applications, exploring its potential for advancements in medicine, catalysis, and materials science.'
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cyclen: macrocyclic polyamine metal-complexing agent [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1,4,7,10-tetraazacyclododecane : An azacycloalkane that is cyclododecane in which the carbon atoms at positions 1, 4, 7 and 10 are replaced by nitrogen atoms. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID64963
CHEMBL ID19880
CHEBI ID37391
SCHEMBL ID22003
MeSH IDM0114784

Synonyms (59)

Synonym
nsc-629374
smr000059056
NCI60_009514
[12]anen4
294-90-6
CHEBI:37391 ,
1,4,7,10-tetrazacyclododecane
cyclen
nsc629374
1,4,7,10-tetraazacyclododecane
cyclen, 97%
nsc 629374
brn 0606114
MLS000069489
NCGC00018128-01
T1874
1,4,7,10-tetraaza-cyclododecane
1,4,7,10tetraaza-cyclododecane
CHEMBL19880
NCGC00018128-03
NCGC00018128-02
tetraaza-12-crown-4
A819936
BCP9000563
ec 425-450-9
1,4,7,10 tetrazacyclododecane
unii-964584yo2o
5-26-11-00023 (beilstein handbook reference)
ec 608-365-3
964584yo2o ,
BCPP000272
FT-0631904
SC11813
1,4,7,10-tetraazacyclododecane;1,4,7,10-tetracyclododecane;1,4,7,10-tetrazacyclododecane;cyclen;kryptofix 11 aza
AM20090388
AKOS015854526
cyclen [mi]
BP-21078
BP-21532
SCHEMBL22003
J-503960
QBPPRVHXOZRESW-UHFFFAOYSA-N
1,4,7,10 tetraazacyclododecane
1,4,7,10-tetraaza cyclododecane
GS-0907
mfcd00066281
J-802177
CS-W007656
DTXSID60183621
A1-01690
AC-8363
Q63390538
HY-W007656
254444-71-8
BCP01943
CCG-266373
S4927
EN300-136271
Z1255383182

Research Excerpts

Overview

Zn2+-cyclen is a typical state 1(T) inhibitor. It interacts selectively with Ras in a weak effector binding state.

ExcerptReferenceRelevance
"Zn2+-cyclen is a typical state 1(T) inhibitor; i.e., it interacts selectively with Ras in conformational state 1(T), a weak effector binding state."( Elucidating the mode of action of a typical Ras state 1(T) inhibitor.
Filchtinski, D; Herrmann, C; Kalbitzer, HR; Kieninger, B; Lopes, RP; Rosnizeck, IC; Spoerner, M, 2014
)
0.86

Dosage Studied

ExcerptRelevanceReference
" Efficient magnetic resonance signal intensity enhancements and prolonged residence lifetime induced by this small molecular complex in vivo were demonstrated even with one-fifth of the standard dosage used in the clinic."( Fast water-exchange Gd3+-(DO3A-like) complex functionalized with aza-15-crown-5 showing prolonged residence lifetime in vivo.
Law, GL; Lei, H; Li, C; Li, YX; Man, K; Wong, WT,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
saturated organic heteromonocyclic parent
crown amineCrown compounds containing only nitrogen as coordinating atom.
azacycloalkane
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
hypoxia-inducible factor 1, alpha subunit (basic helix-loop-helix transcription factor)Homo sapiens (human)Potency12.58930.00137.762544.6684AID914; AID915
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID197832Binding constant for spermine binding to Ribonuclease S (RNA ase) by saturation curve method1999Bioorganic & medicinal chemistry letters, May-03, Volume: 9, Issue:9
Design and semisynthesis of spermine-sensitive Ribonuclease S'.
AID325972Cytotoxicity against HEK cells2008Bioorganic & medicinal chemistry letters, Apr-01, Volume: 18, Issue:7
Synthesis and anti-protozoal activity of C2-substituted polyazamacrocycles.
AID317102Inhibition of mouse neuroblast cell migration from subventricular zone tissue explants at 224 uM after 48 hrs relative to control2008Bioorganic & medicinal chemistry letters, Jan-01, Volume: 18, Issue:1
Discovery of new small molecules that influence neuroblast cell migration from the subventricular zone.
AID325973Partition coefficient, log P of the compound2008Bioorganic & medicinal chemistry letters, Apr-01, Volume: 18, Issue:7
Synthesis and anti-protozoal activity of C2-substituted polyazamacrocycles.
AID317103Inhibition of mouse neuroblast cell migration from subventricular zone tissue explants at 22 uM after 48 hrs relative to control2008Bioorganic & medicinal chemistry letters, Jan-01, Volume: 18, Issue:1
Discovery of new small molecules that influence neuroblast cell migration from the subventricular zone.
AID621474Induction of Escherichia coli pUC19 DNA cleavage assessed as conversion of supercoiled plasmid DNA to nicked circular DNA at 20 uM after 48 hrs by agarose gel electrophoresis2011Bioorganic & medicinal chemistry letters, Oct-01, Volume: 21, Issue:19
Metal-free cleavage efficiency toward DNA by a novel PNA analog-bridged macrocyclic polyamine.
AID325971Antiprotozoal activity against Plasmodium falciparum2008Bioorganic & medicinal chemistry letters, Apr-01, Volume: 18, Issue:7
Synthesis and anti-protozoal activity of C2-substituted polyazamacrocycles.
AID325970Antiprotozoal activity against Trypanosoma brucei by Alamar blue assay2008Bioorganic & medicinal chemistry letters, Apr-01, Volume: 18, Issue:7
Synthesis and anti-protozoal activity of C2-substituted polyazamacrocycles.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (234)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (0.85)18.7374
1990's6 (2.56)18.2507
2000's84 (35.90)29.6817
2010's130 (55.56)24.3611
2020's12 (5.13)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 73.48

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index73.48 (24.57)
Research Supply Index5.50 (2.92)
Research Growth Index5.84 (4.65)
Search Engine Demand Index127.05 (26.88)
Search Engine Supply Index2.03 (0.95)

This Compound (73.48)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (1.64%)6.00%
Case Studies1 (0.41%)4.05%
Observational0 (0.00%)0.25%
Other239 (97.95%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]