Skip to main content
SpringerLink
Log in

Synthesis of a water-soluble macrocyclic anthracenophane and its size-selective molecular recognition

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

A tetraazacyclophane having two anthracene moieties (3) was synthesized by a reaction of nosyl-protected diaminodiphenylmethane with 9,10-bis(bromomethyl)anthracene, followed by removal of the protecting groups. Water-soluble anthraceophane (1) was prepared by condensation of 3 with Fmoc-β-alanine, followed by removal of the Fmoc groups. Host 1 showed size-selective guest discrimination in aqueous media. Bis-ANS (4,4′-dianilino-1,1′-binaphthyl-5,5′-disulfonate) having a suitable molecular size was incorporated in the internal cavity of 1 with binding constant (K) of 2.6 × 105 M−1, although slightly smaller guests such as 1,8-ANS (8-anilinonaphthalene-1-sulfonate) were not, as confirmed by fluorescence titration experiments.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Scheme 1
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Rebek, J. Jr.: Host–guest chemistry of calixarene capsules. Chem. Commun. 637–643 (2000)

  2. Vögtle, F., Seel, C., Windscheif, P.-M.: Chapter 7. In: Vögtle, F. (ed.) Comprehensive Supramolecular Chemistry, vol. 2, pp. 211–265. Pergamon Press, Oxford (1996)

    Google Scholar 

  3. Seward, E., Hopkins, R.B., Sauerer, W., Tam, S.-W., Diederich, F.: Redox-dependent binding ability of a flavin cyclophane in aqueous solution: hydrophobic stacking versus cavity-inclusion complexation. J. Am. Chem. Soc. 112, 1783–1790 (1990)

    Article  CAS  Google Scholar 

  4. Marra, A., Dondoni, A., Sansone, F.: Calixsugars: preparation of upper rim O-ketopyranosyl calix[4]arene. J. Org. Chem. 61, 5155–5158 (1996)

    Article  CAS  Google Scholar 

  5. Cragg, P.J., Sharma, K.: Pillar[5]arenes: fascinating cyclophanes with a bright future. Chem. Soc. Rev. 41, 597–607 (2012)

    Article  CAS  Google Scholar 

  6. Diederich, F., Schuermann, G.: Chao, I.: Designed water-soluble macrocyclic esterases: from nonproductive to productive binding. J. Org. Chem. 53, 2744–2757 (1988)

    Article  CAS  Google Scholar 

  7. Furuike, T., Aiba, S.: Nishimura, S.-I,: A highly practical synthesis of cyclodextrin-based glycoclusters having enhanced affinity with lectins. Tetrahedron 56, 9909–9915 (2000)

    Article  CAS  Google Scholar 

  8. Odashima, K., Koga, K.: Chapter 5. In: Vögtle, F. (ed.) Comprehensive Supramolecular Chemistry, vol. 2, pp. 143–194. Pergamon Press, Oxford (1996)

    Google Scholar 

  9. Ariga, K., Terasaka, Y., Sakai, D., Tsuji, H., Kikuchi, J.: Piezoluminescence based on molecular recognition by dynamic cavity array of steroid cyclophanes at the air–water interface. J. Am. Chem. Soc. 122, 7835–7836 (2000)

    Article  CAS  Google Scholar 

  10. Odashima, K., Itai, A., Iitaka, Y., Arata, Y., Koga, K.: Inclusion complex formation in a particular geometry by a water-soluble paracyclophane in aqueous solution—NMR Studies. Tetrahedron Lett. 21, 4347–4350 (1980)

    Article  CAS  Google Scholar 

  11. Akine, S., Kusama, D., Nabeshima, T.: Conformational control of electron-rich calix[6]arene skeleton by paraquat recognition. Tetrahedron Lett. 54, 205–209 (2013)

    Article  CAS  Google Scholar 

  12. Hayashida, O., Nakamura, Y.: Synthesis of water-soluble cyclophane pentamers using click chemistry as a multivalent host for daunorubicin and doxorubicin. Bull. Chem. Soc. Jpn 86, 223–229 (2013)

    Article  CAS  Google Scholar 

  13. Slavik, J.: Anilinonaphthalene sulfonate as a probe of membrane composition and function. Biochem. Biophys. Acta 694, 1–25 (1982)

    CAS  Google Scholar 

  14. Lookene, A., Zhang, L., Tougu, V., Olivecrona, G.: 1,1′-Bis(anilino)-4-,4′-bis(naphtalene)-8,8′-disulfonate acts as an inhibitor of lipoprotein lipase and competes for binding with apolipoprotein CII. J. Biol. Chem. 278, 37183–37194 (2003)

    Article  CAS  Google Scholar 

  15. Hayashida, O.: Chapter 18. In: Ariga, K., Nalwa, H.S. (eds.) Bottom-Up Nanofabrication, vol. 2, pp. 423–436. American Scientific Publishers, Stevenson Ranch (2009)

    Google Scholar 

  16. Hayashida, O., Nakashima, T.: Synthesis of peptide-based cyclophane oligomers having multivalently enhanced guest-binding affinity. Bull. Chem. Soc. Jpn 85, 715–723 (2012)

    Article  CAS  Google Scholar 

  17. Kitabayashi, Y., Yokoshima, S., Fukuyama, T.: Total synthesis of (−)-lepistine. Org. Lett. 16, 2862–2864 (2014)

    Article  CAS  Google Scholar 

  18. Aathimanikandan, S.V., Sandanaraj, B.S., Arges, C.G., Bardeen, C.J., Thayumanavan, S.: Effect of guest molecule flexibility in access to dendritic interiors. Org. Lett. 7, 2809–2812 (2005)

    Article  CAS  Google Scholar 

  19. Tong, Y., Mei, Y., Li, Y.L., Ji, C.G., Zhang, Z.H.: Electrostatic polarization makes substantial contribution to free energy of avidin-biotin binding. J. Am. Chem. Soc. 132, 5137–5142 (2010)

    Article  CAS  Google Scholar 

  20. Benesi, H.A., Hildebrand, J.H.: A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71, 2703–2707 (1949)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The present work is supported in part by MEXT (No. 24550166), Japan.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Fukuoka University, Nanakuma 8-19-1, Fukuoka, 814-0180, Japan

    Kazuhiro Nakamura, Shuhei Kusano & Osamu Hayashida

Authors
  1. Kazuhiro Nakamura
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shuhei Kusano
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Osamu Hayashida
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Osamu Hayashida.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 1879 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nakamura, K., Kusano, S. & Hayashida, O. Synthesis of a water-soluble macrocyclic anthracenophane and its size-selective molecular recognition. J Incl Phenom Macrocycl Chem 85, 121–126 (2016). https://doi.org/10.1007/s10847-016-0611-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-016-0611-6

Keywords

Search

Navigation