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Chemical Compound Review

Cyclen     1,4,7,10-tetrazacyclododecane

Synonyms: TPC-M003, PubChem23801, CHEMBL19880, SureCN22003, Cyclen IPS1, ...
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Disease relevance of Cyclen

  • The results demonstrate the feasibility of masking the cytotoxicity of hydroxyquinoline-based cytotoxins as Co(III) complexes and demonstrate the utility of cyclen-based auxiliary ligands for optimizing radiolytic activation of these novel prodrugs under hypoxia [1].
  • The macrocyclic polyamines, cyclen and cyclam, and their derivatives have been tested for inhibitory activity against the cytopathogenic effect (CPE) of human immunodeficiency virus type 1 strain HTLV-IIIB (HIV-1IIIB) on CD4+ human lymphoblastoma MT-4 cells [2].

High impact information on Cyclen


Biological context of Cyclen

  • This was achieved by using same synthetic strategy (regioselective protection/first alkylation/deprotection/second alkylation) to give nine cyclen derivatives [6].
  • The cyclen mustard complex showed 24-fold selectivity as a hypoxia-selective bioreductive prodrug, with an IC50 value of 2 microM against the lung tumor cell line A549 [5].
  • Tuning the properties of cyclen based lanthanide complexes for phosphodiester hydrolysis; the role of basic cofactors [7].
  • As the first protein-cleaving catalyst selective for a protein substrate, a catalyst for myoglobin was designed by attaching Cu(II) or Co(III) complex of cyclen to a binding site searched by a combinatorial method using peptide nucleic acid monomers as building units [8].
  • Reductive amination of various aldehydes with cyclen represents a very convenient method for the synthesis of a wide range of 1,7-difunctionalized cyclens, as well as new cryptands [9].

Anatomical context of Cyclen

  • Two types of water-soluble NMDA receptor antagonist, ACCn (1) and TGCn (2), with a 1,4,7,10-tetraazacyclododecane cyclic polyamine group, were synthesized and the effects of both compounds on NMDA receptors were studied using voltage-clamp recordings of recombinant NMDA receptors expressed in Xenopus oocytes [10].

Associations of Cyclen with other chemical compounds

  • For the 1,4,7,10-tetraazacyclododecane-based surfactant, oblate micelles are observed, which are smaller to the prolate micelles formed by the 1,4,7-triazacyclononane analogue [11].
  • The cationic cyclen based Eu(III)-phen conjugated 1.Eu was synthesised as a chemosensor for Cu(II), where the recognition in water at pH 7.4 gave rise to quenching of the Eu(III) luminescence and the formation of tetranuclear polymetallic Cu(II)-Eu(III) macrocyclic complexes in solution where Cu(II) was bound by three 1.Eu conjugates [12].
  • MM/MD calculations and circular dichroism (CD) studies further suggested that cholesterol-armed cyclen helicates have chiral and hydrophobic cavities upon self-aggregation, in which the dansylamino acid anions were specifically accommodated [13].
  • Delayed lanthanide luminescence sensing of aromatic carboxylates using heptadentate triamide Tb(III) cyclen complexes: the recognition of salicylic acid in water [14].
  • The X-ray crystal structure of ZnH(-1)L(3) (where L(3) = N-(4-nitrophenyl)carbamoylmethyl cyclen, pK(a) = 7.01 for ZnL(3) <==> ZnH(-1)L(3)) proved that the zinc(II) binds to the amidate N(-) (Zn-N(-) distance of 1.974(3) A) along with the four nitrogen atoms of cyclen (average Zn-N distance 2.136 A) [15].

Gene context of Cyclen

  • The synthesis and facile aqueous/organic coupling of a peripheral-type benzodiazepine receptor ligand to a cyclen-based fluorophore is described herein [16].
  • [structure: see text] Novel "cone conformation" calix[4]arene derivatives, carrying either one or two cyclen (1,4,7,10-tetra-azacyclododecane) moieties at the upper rim, have been synthesized [17].
  • Light scattering, fluorescence, and TEM characterizations demonstrated that Na+ complex with cholesterol-armed cyclen gave a particularly stable self-aggregate in aqueous solution and offered supramolecular environments effective for sensing and detection of amino acid anions [13].
  • To elucidate intrinsic recognition of carboxamides by zinc(II) in carbonic anhydrase (CA) (as inhibitors) and carboxypeptidase A (CPA) (as substrates), a new series of Zn(2+)-carboxamide-appended cyclen complexes have been synthesized and characterized (cyclen = 1,4,7,10-tetraazacyclododecane) [15].

Analytical, diagnostic and therapeutic context of Cyclen


  1. Optimization of the auxiliary ligand shell of Cobalt(III)(8-hydroxyquinoline) complexes as model hypoxia-selective radiation-activated prodrugs. Ahn, G.O., Ware, D.C., Denny, W.A., Wilson, W.R. Radiat. Res. (2004) [Pubmed]
  2. Inhibition of human immunodeficiency virus proliferation by macrocyclic polyamines and their metal complexes. Inouye, Y., Kanamori, T., Yoshida, T., Bu, X., Shionoya, M., Koike, T., Kimura, E. Biol. Pharm. Bull. (1994) [Pubmed]
  3. Model studies for molecular recognition of carbonic anhydrase and carboxypeptidase. Kimura, E. Acc. Chem. Res. (2001) [Pubmed]
  4. Receptor for anionic pyrene derivatives provides the basis for new biomembrane assays. Winschel, C.A., Kalidindi, A., Zgani, I., Magruder, J.L., Sidorov, V. J. Am. Chem. Soc. (2005) [Pubmed]
  5. A novel design strategy for stable metal complexes of nitrogen mustards as bioreductive prodrugs. Parker, L.L., Lacy, S.M., Farrugia, L.J., Evans, C., Robins, D.J., O'Hare, C.C., Hartley, J.A., Jaffar, M., Stratford, I.J. J. Med. Chem. (2004) [Pubmed]
  6. Comparative in vivo behavior studies of cyclen-based copper-64 complexes: regioselective synthesis, X-ray structure, radiochemistry, log P, and biodistribution. Yoo, J., Reichert, D.E., Welch, M.J. J. Med. Chem. (2004) [Pubmed]
  7. Tuning the properties of cyclen based lanthanide complexes for phosphodiester hydrolysis; the role of basic cofactors. Fanning, A.M., Plush, S.E., Gunnlaugsson, T. Chem. Commun. (Camb.) (2006) [Pubmed]
  8. Protein-cleaving catalyst selective for protein substrate. Jeon, J.W., Son, S.J., Yoo, C.E., Hong, I.S., Song, J.B., Suh, J. Org. Lett. (2002) [Pubmed]
  9. An easy route towards regioselectively difunctionalized cyclens and new cryptands. Chaux, F., Denat, F., Espinosa, E., Guilard, R. Chem. Commun. (Camb.) (2006) [Pubmed]
  10. Design and synthesis of a novel water-soluble NMDA receptor antagonist with a 1,4,7,10-tetraazacyclododecane group. Masuko, T., Metori, K., Kizawa, Y., Kusama, T., Miyake, M. Chem. Pharm. Bull. (2005) [Pubmed]
  11. The structure of metallomicelles. Griffiths, P.C., Fallis, I.A., Willock, D.J., Paul, A., Barrie, C.L., Griffiths, P.M., Williams, G.M., King, S.M., Heenan, R.K., Görgl, R. Chemistry (Weinheim an der Bergstrasse, Germany) (2004) [Pubmed]
  12. Eu(III)-cyclen-phen conjugate as a luminescent copper sensor: the formation of mixed polymetallic macrocyclic complexes in water. Gunnlaugsson, T., Leonard, J.P., Sénéchal, K., Harte, A.J. Chem. Commun. (Camb.) (2004) [Pubmed]
  13. Cholesterol-armed cyclens for helical metal complexes offering chiral self-aggregation and sensing of amino acid anions in aqueous solutions. Shinoda, S., Okazaki, T., Player, T.N., Misaki, H., Hori, K., Tsukube, H. J. Org. Chem. (2005) [Pubmed]
  14. Delayed lanthanide luminescence sensing of aromatic carboxylates using heptadentate triamide Tb(III) cyclen complexes: the recognition of salicylic acid in water. Gunnlaugsson, T., Harte, A.J., Leonard, J.P., Nieuwenhuyzen, M. Chem. Commun. (Camb.) (2002) [Pubmed]
  15. Study of pH-dependent zinc(II)-carboxamide interactions by zinc(II)-carboxamide-appended cyclen complexes (cyclen = 1,4,7,10-tetraazacyclododecane). Kimura, E., Gotoh, T., Aoki, S., Shiro, M. Inorganic chemistry. (2002) [Pubmed]
  16. Facile, efficient conjugation of a trifunctional lanthanide chelate to a peripheral benzodiazepine receptor ligand. Manning, H.C., Goebel, T., Marx, J.N., Bornhop, D.J. Org. Lett. (2002) [Pubmed]
  17. Differential and substrate-selective reactivity of calix[4]arene derivatives with cyclenyl-Zn(II) modifications at the upper rim. Ozturk, G., Akkaya, E.U. Org. Lett. (2004) [Pubmed]
  18. In vivo sodium chemical shift imaging. Kohler, S.J., Kolodny, N.H., Celi, A.C., Burr, T.A., Weinberg, D., D'Amico, D.J., Gragoudas, E.S. Magnetic resonance in medicine : official journal of the Society of Magnetic Resonance in Medicine / Society of Magnetic Resonance in Medicine. (1992) [Pubmed]
  19. Polymethylated DOTA ligands. 1. Synthesis of rigidified ligands and studies on the effects of alkyl substitution on acid-base properties and conformational mobility. Ranganathan, R.S., Pillai, R.K., Raju, N., Fan, H., Nguyen, H., Tweedle, M.F., Desreux, J.F., Jacques, V. Inorganic chemistry. (2002) [Pubmed]
  20. A novel procedure for simple and efficient genotyping of single nucleotide polymorphisms by using the Zn2+-cyclen complex. Kinoshita-Kikuta, E., Kinoshita, E., Koike, T. Nucleic Acids Res. (2002) [Pubmed]
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