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Chemical Compound Review

PubChem18651     1,4,7,10,13,16- hexaoxacyclooctadecane

Synonyms: CHEMBL155204, CCRIS 3587, ACMC-20c41s, CHEBI:32397, WT603, ...
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Disease relevance of Ethylene oxide cyclic hexamer


High impact information on Ethylene oxide cyclic hexamer

  • The same assay was performed after the exposure of intact mitochondria to NO containing solution (1.25 x 10(-5) M) or 0.1 mM KO2/18-Crown-6 solution, which generated O2.-(6.4 x 10(-5) M) [3].
  • An electrolyte solution consisting of 10.5 mM histidine, 50 mM acetic acid, and 2 mM 18-crown-6 at pH 4.1 was used for the determination of NH(4) (+), K(+), Ca(2+), Na(+), and Mg(2+) [4].
  • The optimized separations were carried out in 10 mmol/L imidazole sulfate, 2 mmol/L 18-crown-6, and 0.02 mmol/L tetradecyltrimethylammonium hydroxide electrolyte (pH 4.0) [5].
  • A background electrolyte composed of 2-[N-Morpholino] ethane-sulfonic acid (MES) (50 mmol/liter) and L-histidine (50 mmol/liter; pH congruent with 6.2), with the additives 18-crown-6 (1 mmol/liter) and methanol (30%) was used for the cation separation combined with conductivity detection [6].
  • The cyclen based aromatic diaza-15-crown-5 and 18-crown-6 ether conjugates 1Tb-4Tb were designed as luminescent switches for sodium and potassium where the delayed Tb(III) emission, occurring as line-like emission bands between 490-622 nm, was 'switched on' upon recognition of these ions in pH 7.4 buffered water solution [7].

Biological context of Ethylene oxide cyclic hexamer

  • The molecular structure of Ba[CN4(NiPr2)]2(18-crown-6) is similar to that of Ba[CN4(NMe2)]2(18-crown-6), except that the tetrazolato ligands exhibit the isomeric 2,3-eta2-coordination mode and the tetrazolato ligand CN4 cores are bent significantly toward the 18-crown-6 ligands [8].
  • We evaluated cytotoxicity effects of 15-crown-5 and 18-crown-6 and the role of oxidative stress in WI38 cells culture [9].
  • The catalytic addition of 18-Crown-6 in some Cs2CO3-promoted amination of triflates and bromides was beneficial to improve sluggish reaction with suppression of the unwanted side products [10].
  • The influence of two experimental parameters, initial 18-crown-6 concentration and temperature, on the adsorption kinetics was evaluated [11].
  • In addition to the 18-crown-6 moiety as a binding site, the host have one thiol and one thio ester with an N-protected alpha-amino acid or a peptide, and have successfully achieved peptide synthesis in an enzyme-mimetic reaction mode [12].

Associations of Ethylene oxide cyclic hexamer with other chemical compounds


Gene context of Ethylene oxide cyclic hexamer

  • When [K(+)] was controlled with 18-crown-6, the observed rate constant k(ex) was a linear function of uncomplexed [K(+)], giving k(K) = (4.3 +/- 0.1) x 10(4) L(2) mol(-2) s(-1) at 25 degrees C and I = 0.26 mol L(-1) for the K(+)-catalyzed pathway [18].
  • Thus, a model hexapeptide was synthesized using Fmoc chemistry containing Lys and Arg residues, which, when complexed with 18-Crown-6, was readily soluble in DCM and coupled quantitatively to a resin-bound tetrapeptide [19].
  • They lowered cell's viability and significantly promoted ROS generation, increased enzyme activities and enhanced oxidative damages in which 18-crown-6 was more effective [9].
  • Structural scaffold of 18-crown-6 tetracarboxylic Acid for optical resolution of chiral amino acid: x-ray crystal analyses of complexes of D- and L-isomers of serine and glutamic acid [20].
  • Another model hexapeptide containing Lys, Tyr, Ser and Asp protected with a TFA-stable adamantyl group was complexed with 18-Crown-6 and coupled to the resin-bound tetrapeptide with near quantitative yield [19].

Analytical, diagnostic and therapeutic context of Ethylene oxide cyclic hexamer

  • Single complexation force of 18-crown-6 with ammonium ion evaluated by atomic force microscopy [21].
  • Stability constants of K, Na, Ca, and Ba with 18-crown-6, K, Na, Li with sulfated beta-cyclodextrin and K, Li, Ca, Mg, Sr, and Ba ions with ([2-hydroxy-1,1-bis(hydroxymethyl) ethyl]-amino)-1-propanesulfonic acid (TAPS) were determined by capillary electrophoresis and computed using a general least squares minimizing program CELET [22].
  • Isothermal calorimetric titration of 18-crown-6 ether with BaCl2 in pure aqueous solution over the temperature range 7-40 degrees C gives precise binding constants and enthalpy changes [23].
  • A much stronger crown ether activation is observed when 18-crown-6 is added prior to lyophilization, and this can be explained by a combination of two effects: the before-mentioned macrocyclic complexation effect, and a less specific, nonmacrocyclic, lyoprotecting effect [24].
  • A method for the determination of N1-Methylnicotinamide (NMNA) was developed by the fluorescence formed by UV irradiation after separation by HPLC with a mobile phase containing hydrogen peroxide and 18-crown-6 [25].


  1. Apparent oral toxicity of 18-crown-6 in dogs. Takayama, K., Hasegawa, S., Sasagawa, S., Nambu, N., Nagai, T. Chem. Pharm. Bull. (1977) [Pubmed]
  2. Behavioral and neuropharmacological toxicology of the macrocyclic ether 18-crown-6. Gad, S.C., Conroy, W.J., McKelvey, J.A., Turney, K.A. Drug and chemical toxicology. (1978) [Pubmed]
  3. Role of nitric oxide and superoxide anion in leukotoxin-, 9,10-epoxy-12-octadecenoate-induced mitochondrial dysfunction. Sakai, T., Ishizaki, T., Nakai, T., Miyabo, S., Matsukawa, S., Hayakawa, M., Ozawa, T. Free Radic. Biol. Med. (1996) [Pubmed]
  4. Application of an external contactless conductivity detector for the analysis of beverages by microchip capillary electrophoresis. Kubán, P., Hauser, P.C. Electrophoresis (2005) [Pubmed]
  5. Single-run capillary electrophoretic determination of inorganic nitrogen species in rainwater. Padarauskas, A., Paliulionyte, V., Pranaityte, B. Anal. Chem. (2001) [Pubmed]
  6. An automated technique for the simultaneous determination of cations in nanoliter volumes. Stocking, C.J., Slater, J.M., Unwin, R., Walter, S., Folkerd, E. Kidney Int. (1999) [Pubmed]
  7. H+, Na+ and K+ modulated lanthanide luminescent switching of Tb(III) based cyclen aromatic diaza-crown ether conjugates in water. Gunnlaugsson, T., Leonard, J.P. Chem. Commun. (Camb.) (2003) [Pubmed]
  8. Weak carbon-hydrogen-nitrogen interactions affect the heterocyclic ligand bonding modes in barium complexes containing eta2-tetrazolato and eta2-pentazolato ligands. Kobrsi, I., Knox, J.E., Heeg, M.J., Schlegel, H.B., Winter, C.H. Inorganic chemistry. (2005) [Pubmed]
  9. Cytotoxicity and the levels of oxidative stress parameters in WI38 cells following 2 macrocyclic crown ethers treatment. Boojar, M.M., Goodarzi, F. Clin. Chim. Acta (2006) [Pubmed]
  10. Modulation of the Cs2CO3-promoted catalytic amination by a crown ether. Torisawa, Y., Nishi, T., Minamikawa, J. Bioorg. Med. Chem. Lett. (2000) [Pubmed]
  11. Adsorption of 18-crown-6 from aqueous solution on granular activated carbon: a kinetic modeling study. Azizian, S., Yahyaei, B. Journal of colloid and interface science. (2006) [Pubmed]
  12. Biomimetic studies using artificial systems. IV. Biomimetic peptide synthesis by using multifunctionalized crown ethers as a novel enzyme model. A new concept in mimicking of enzyme-catalyzed bond-forming reactions. Sasaki, S., Koga, K. Chem. Pharm. Bull. (1989) [Pubmed]
  13. Mechanism of capillary electrophoresis enantioseparations using a combination of an achiral crown ether plus cyclodextrins. Armstrong, D.W., Chang, L.W., Chang, S.S. Journal of chromatography. A. (1998) [Pubmed]
  14. Statistical error in isothermal titration calorimetry: variance function estimation from generalized least squares. Tellinghuisen, J. Anal. Biochem. (2005) [Pubmed]
  15. Separation and determination of cations in beverage products by capillary zone electrophoresis. Fung, Y.S., Lau, K.M. Journal of chromatography. A. (2006) [Pubmed]
  16. Simultaneous separation of anions and cations by capillary electrophoresis with high magnitude, reversed electroosmotic flow. Johns, C., Yang, W., Macka, M., Haddad, P.R. Journal of chromatography. A. (2004) [Pubmed]
  17. Supramolecular complex of cytochrome c with lariat ether: solubilization, redox behavior and catalytic activity of cytochrome c in methanol. Yamada, T., Shinoda, S., Kikawa, K., Ichimura, A., Teraoka, J., Takui, T., Tsukube, H. Inorganic chemistry. (2000) [Pubmed]
  18. Cation-independent electron transfer between ferricyanide and ferrocyanide ions in aqueous solution. Zahl, A., van Eldik, R., Swaddle, T.W. Inorganic chemistry. (2002) [Pubmed]
  19. The use of crown ethers in peptide chemistry-V. Solid-phase synthesis of peptides by the fragment condensation approach using crown ethers as non-covalent protecting groups. Botti, P., Ball, H.L., Lucietto, P., Pinori, M., Rizzi, E., Mascagni, P. J. Pept. Sci. (1996) [Pubmed]
  20. Structural scaffold of 18-crown-6 tetracarboxylic Acid for optical resolution of chiral amino acid: x-ray crystal analyses of complexes of D- and L-isomers of serine and glutamic acid. Nagata, H., Nishi, H., Kamigauchi, M., Ishida, T. Chem. Pharm. Bull. (2006) [Pubmed]
  21. Single complexation force of 18-crown-6 with ammonium ion evaluated by atomic force microscopy. Kado, S., Kimura, K. J. Am. Chem. Soc. (2003) [Pubmed]
  22. Capillary electrophoretic study of interactions of metal ions with crown ethers, a sulfated beta-cyclodextrin, and zwitterionic buffers present as additives in the background electrolyte. Muzikár, M., Havel, J., Macka, M. Electrophoresis (2002) [Pubmed]
  23. Significant discrepancies between van't Hoff and calorimetric enthalpies. II. Liu, Y., Sturtevant, J.M. Protein Sci. (1995) [Pubmed]
  24. Why do crown ethers activate enzymes in organic solvents? van Unen, D.J., Engbersen, J.F., Reinhoudt, D.N. Biotechnol. Bioeng. (2002) [Pubmed]
  25. Determination of N1-methylnicotinamide by HPLC postcolumn photoirradiation. Mawatari, K., Iinuma, F., Watanabe, M. Adv. Exp. Med. Biol. (1999) [Pubmed]
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