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Chemical Compound Review

IPS8     zinc1,4,8,11- tetrazanidacyclotetradecane

Synonyms: (Cyclam-Zn(II))
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Disease relevance of Cyclam


High impact information on Cyclam

  • Understanding the factors which control the thermodynamics and kinetics of the interconversion of configurational states of metallo-cyclams may be a key factor in designing novel cyclam derivatives for future use in medicine [3].
  • Molecular interactions of cyclam and bicyclam non-peptide antagonists with the CXCR4 chemokine receptor [4].
  • These spectral similarities are shown to arise from the fact that 3 contains an alkyl thiolate tethered to the equatorial cyclam ring, resulting in a thiolate orientation that is very similar to the one adopted by the Cys residue in the SOR(red) active site [5].
  • [structure: see text] Novel phenylazomethine dendrimers having a cyclam core were synthesized by the convergent method [6].
  • Lipophilic derivatives of cyclam as new inhibitors of tumor cell growth [7].

Biological context of Cyclam

  • Energy transfer from the lowest singlet and triplet excited states of the peripheral naphthyl units to the lower lying excited states of Nd3+, Eu3+, Tb3+, Dy3+ coordinated to the cyclam core does not take place [8].
  • Hydrolysis of a coumarin ester substrate was catalysed by the Fab derivatized with a cyclam moiety with a kcat of 0.063 min-1 and Km of 11.7 microM; the presence of metal ions was not required for catalysis [9].

Associations of Cyclam with other chemical compounds


Gene context of Cyclam

  • There was very little variation in the values of the Arrhenius preexponential factor between these three complexes, whereas the value of E(a) is 40.6 kJ/mol for the cyclam complex, 35.5 kJ/mol for the 1,11-C(3)-cyclam complex, and 22.3 kJ/mol for the 1,4-C(2)-cyclam complex [14].
  • A survey of the CSD (crystallographic structural database) shows that the trans-III configuration is the most common in the solid state for complexes of cyclam itself [15].

Analytical, diagnostic and therapeutic context of Cyclam


  1. The synthesis and radiolabeling of 2-nitroimidazole derivatives of cyclam and their preclinical evaluation as positive markers of tumor hypoxia. Engelhardt, E.L., Schneider, R.F., Seeholzer, S.H., Stobbe, C.C., Chapman, J.D. J. Nucl. Med. (2002) [Pubmed]
  2. Synthesis and structure-activity relationships of phenylenebis(methylene)-linked bis-tetraazamacrocycles that inhibit HIV replication. Effects of macrocyclic ring size and substituents on the aromatic linker. Bridger, G.J., Skerlj, R.T., Thornton, D., Padmanabhan, S., Martellucci, S.A., Henson, G.W., Abrams, M.J., Yamamoto, N., De Vreese, K., Pauwels, R. J. Med. Chem. (1995) [Pubmed]
  3. Cyclam complexes and their applications in medicine. Liang, X., Sadler, P.J. Chemical Society reviews. (2004) [Pubmed]
  4. Molecular interactions of cyclam and bicyclam non-peptide antagonists with the CXCR4 chemokine receptor. Gerlach, L.O., Skerlj, R.T., Bridger, G.J., Schwartz, T.W. J. Biol. Chem. (2001) [Pubmed]
  5. Synthesis, structure determination, and spectroscopic/computational characterization of a series of Fe(II)-thiolate model complexes: implications for Fe-S bonding in superoxide reductases. Fiedler, A.T., Halfen, H.L., Halfen, J.A., Brunold, T.C. J. Am. Chem. Soc. (2005) [Pubmed]
  6. Synthesis of novel phenylazomethine dendrimers having a cyclam core and their zinc complex. Enoki, O., Imaoka, T., Yamamoto, K. Org. Lett. (2003) [Pubmed]
  7. Lipophilic derivatives of cyclam as new inhibitors of tumor cell growth. Sibert, J.W., Cory, A.H., Cory, J.G. Chem. Commun. (Camb.) (2002) [Pubmed]
  8. Cyclam-based dendrimers as ligands for lanthanide ions. Saudan, C., Ceroni, P., Vicinelli, V., Maestri, M., Balzani, V., Gorka, M., Lee, S.K., van Heyst, J., Vögtle, F. Dalton transactions (Cambridge, England : 2003) (2004) [Pubmed]
  9. Approaches to the design of semisynthetic metal-dependent catalytic antibodies. Nakayama, G.R., Schultz, P.G. Ciba Found. Symp. (1991) [Pubmed]
  10. Dendrimers as ligands: an investigation into the stability and kinetics of Zn2+ complexation by dendrimers with 1,4,8,11-tetraazacyclotetradecane (cyclam) cores. Saudan, C., Balzani, V., Gorka, M., Lee, S.K., Van Heyst, J., Maestri, M., Ceroni, P., Vicinelli, V., Vögtle, F. Chemistry (Weinheim an der Bergstrasse, Germany) (2004) [Pubmed]
  11. Selective recognition of configurational substates of zinc cyclam by carboxylates: implications for the design and mechanism of action of anti-HIV agents. Liang, X., Weishäupl, M., Parkinson, J.A., Parsons, S., McGregor, P.A., Sadler, P.J. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  12. Synthesis, characterization, and x-ray crystal structures of cyclam derivatives. 8. Thermodynamic and kinetic appraisal of lead(II) chelation by octadentate carbamoyl-armed macrocycles. Cuenot, F., Meyer, M., Espinosa, E., Guilard, R. Inorganic chemistry. (2005) [Pubmed]
  13. Remarks on catalytic reduction of CO2, H+ and H2 by monovalent Ni. Grochala, W. Physical chemistry chemical physics : PCCP. (2006) [Pubmed]
  14. Effects of Steric Constraint on Chromium(III) Complexes of Tetraazamacrocycles. 3. Insights into the Temperature-Dependent Radiationless Deactivation of the (2)E(g) (O(h)()) Excited State of trans-[Cr(N(4))(CN)(2)](+) Complexes. Vagnini, M.T., Kane-Maguire, N.A., Wagenknecht, P.S. Inorganic chemistry. (2006) [Pubmed]
  15. Configurations of metallocyclams and relevance to anti-HIV activity. Hunter, T.M., Paisey, S.J., Park, H.S., Cleghorn, L., Parkin, A., Parsons, S., Sadler, P.J. J. Inorg. Biochem. (2004) [Pubmed]
  16. Coated-wire silver ion-selective electrode based on silver complex of cyclam. Sil, A., Ijeri, V.S., Srivastava, A.K. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. (2001) [Pubmed]
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