ACES  Vol.4 No.4 , October 2014
Synthesis and Guest-Binding Behavior of Water-Soluble Cyclophanes Bearing PEG Residues
Abstract: A water-soluble cyclophane (1) having poly(ethylene glycol) (PEG) moieties has been prepared from a tetraazide-functionalized cyclophane derivative and four poly(ethylene glycol) methyl ether acetylenes by Cu(I)-catalyzed 1,3 dipolar cycloadditions (click chemistry). An analogous derivative having a pyrene moiety (2) was also prepared in a similar manner. The guest-binding behavior of 1 and 2 toward anionic guests such as 6-p-toluidinonaphthalene-2-sulfonate was investigated by fluorescence spectroscopy. The binding constants (K) of the host-guest complexes were evaluated.
Cite this paper: Hayashida, O. , Nakamura, Y. and Sato, T. (2014) Synthesis and Guest-Binding Behavior of Water-Soluble Cyclophanes Bearing PEG Residues. Advances in Chemical Engineering and Science, 4, 409-416. doi: 10.4236/aces.2014.44045.

[1]   Ramaiah, D., Neelakandan, P.P., Nair, A.K. and Avirah, R.R. (2010) Functional Cyclophanes: Promising Hosts for Optical Biomolecular Recognition. Chemical Society Reviews, 39, 4158-4168.

[2]   Ariga, K., Ito, H., Hill, J.P. and Tsukube, H. (2012) Molecular Recognition: From Solution Science to Nano/Materials Technology. Chemical Society Reviews, 41, 5800-5835.

[3]   Hayashida, O. and Hamachi, I. (2004) Fluorophore Appended Saccharide Cyclophane: Self-Association, Fluorescent Properties, Heterodimers with Cyclodextrins, And Cross-Linking Behavior with Peanut Agglutinin of Dansyl-Modified Saccharide Cyclophane. The Journal of Organic Chemistry, 69, 3509-3516.

[4]   Hayashida, O. and Kaku, Y. (2013) Synthesis of Dabsyl-Appended Cyclophanes and Their Heterodimer Formation with Pyrene-Appended Cyclophanes. The Journal of Organic Chemistry, 78, 10437-10442.

[5]   Castelletto, V., McKendrick, J.E., Hamley, I.W., Olsson, U. and Cenker, C. (2010) PEGylated Amyloid Peptide Nanocontainer Delivery and Release System. Langmuir, 26, 11624-11627.

[6]   Xin, H., Sha, X., Jiang, X., Zhang, W., Chen, L. and Fang, X. (2012) Anti-Glioblastoma Efficacy and Safety of Paclitaxel-Loading Angiopep-Conjugated Dual Targeting PEG-PCL Nanoparticles. Biomaterials, 33, 8167-8176.

[7]   Odashima, K., Itai, A., Iitaka, Y. and Koga, K. (1985) Biomimetic Studies Using Artificial Systems. 3. Design, Synthesis, and Inclusion Complex Forming Ability of a Novel Water-Soluble Paracyclophane Possessing Diphenylmethane Skeletons. The Journal of Organic Chemistry, 50, 4478-4484.

[8]   Hayashida, O. and Nakamura, Y. (2013) Synthesis of Water-Soluble Cyclophane Pentamers Using Click Chemistry as a Multivalent Host for Daunorubicin and Doxorubicin. Bulletin of the Chemical Society of Japan, 86, 223-229.

[9]   Hayashida, O., Eguchi, C., Kimura, K., Oyama, Y. and Shioji, K. (2010) Guest Binding, Cellular Uptake, and Molecular Delivery of Water-Soluble Cyclophanes Having a Pyrene Moiety. Chemistry Letters, 39, 321-1322.

[10]   Kappe, C.O. and Eycken, E.V. (2010) Click Chemistry Under Non-Classical Reaction Conditions. Chemical Society Reviews, 39, 1280-1290.

[11]   Zhang, K., Lackey, M.A. Wu, Y. and Tew, G.N. (2011) Universal Cyclic Polymer Templates. Journal of the American Chemical Society, 133, 6906-6909.

[12]   Slavik, J. (1982) Anilinonaphthalene Sulfonate as a Probe of Membrane Composition And Function. Biochimica et Biophysica Acta - Reviews on Biomembranes, 694, 1-25.

[13]   Hayashida, O., Ogawa, N. and Uchiyama, M. (2007) Surface Recognition and Fluorescence Sensing of Histone by Dansyl-Appended Cyclophane-Based Resorcinarene Trimer. Journal of the American Chemical Society, 129, 13698-13705.