Download PDF
Synlett 2009(17): 2875-2879  
DOI: 10.1055/s-0029-1217988
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Potential Supramolecular Cyclodextrin Dimers Using Nucleobase Pairs

Florian Hamona, Bruno Violeaua, Frédéric Turpinb, Mathilde Bellotc, Laurent Bouteillerc, Florence Djedaini-Pilardd, Christophe Len*a
a Université de Poitiers, UMR 6514 CNRS, Synthèse et Réactivité des Substances Naturelles, 40 Avenue du Recteur Pineau, 86022 Poitiers Cedex, France
Fax: +33(5)49453501; e-Mail: christophe.len@univ-poitiers.fr;
b Biocydex, 40 Avenue du Recteur Pineau, 86022 Poitiers Cedex, France
c Université Paris 6, UMR 7610 CNRS, 4 Place Jussieu, 75252 Paris, France
d Université de Picardie Jules Verne, UMR 6219 CNRS, Laboratoire des Glucides, 33 Rue Saint Leu, 80039 Amiens, France
Further Information

Publication History

Received 11 June 2009
Publication Date:
24 September 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

The synthesis of six new cyclodextrin derivatives having nucleobase moiety is described. These two moieties are linked by different spacers, such as aminoethyl and 1,2,3-triazolyl groups. Example of association constants for complexation of adenine and thymine derivatives: K AT = 385 M-¹ using NMR methodology is reported. Study of interaction between four cyclodextrin derivatives and one adamantyl guest is described by ITC.

Key words

click chemistry - nucleobase - cyclodextrin

    References and Notes

  • 1 Klein S. Zoeller T. Pharmazeutische Zeitung  2008,  153:  24 
    Google Scholar
  • 2 Perly B. Moutard S. Djedaini-Pilard F. PharmaChem  2005,  4:  4 
    Google Scholar
  • 3 Li J. Xiao H. Li J. Zhong YP. Int. J. Pharm.  2004,  278:  329 
    CrossrefGoogle Scholar
  • 4 Bhushan R. Kumar R. J. Chromatogr., A  2002,  62:  2667 
    Google Scholar
  • 5 Mauri-Aucejo A. Llobat-Estelles M. Escarti-Carrasco M. Marin-Saez R. Anal. Chem.  2006,  39:  183 
    Google Scholar
  • 6 Yakahisa E. Engel KH. J. Chromatogr., A  2005,  1076:  148 
    CrossrefGoogle Scholar
  • 7 Breslow R. Dong AD. Chem. Rev.  1998,  98:  1997 
    CrossrefGoogle Scholar
  • 8 Kataky R. Mogan E. Biosens. Bioelectron.  2003,  18:  1407 
    CrossrefGoogle Scholar
  • 9 Surpateanu G. Becuwe M. Lungu NC. Dron P. Fourmentin S. Landy D. Surpateanu G. J. Photochem. Photobiol., A.  2007,  185:  312 
    Google Scholar
  • 10 Ueno A. Ikeda H. Mol. Supramol. Photochem.  2001,  8:  461 
    Google Scholar
  • 11 Bjerre J. Fenger TH. Marinescu LG. Bols M. Eur. J. Org. Chem.  2007,  704 
    CrossrefGoogle Scholar
  • 12 Blach P. Landy D. Fourmentin S. Surpateanu G. Bricout H. Ponchel A. Hapiot F. Monflier E. Adv. Synth. Catal.  2005,  347:  1301 
    CrossrefGoogle Scholar
  • 13 Huskens J. Deij MA. Reinhould DN. Angew. Chem. Int. Ed.  2002,  41:  4467 
    CrossrefGoogle Scholar
  • 14 Hamada F. Kondo Y. Ishikawa K. Ittto H. Suzuki I. Osa T. Ueno A. J. Inclusion Phenom. Mol. Recognit. Chem.  1994,  17:  267 
    CrossrefGoogle Scholar
  • 15a Aime S. Gianolio E. Arena F. Barge A. Martina K. Heropoulos G. Cravotto G. Org. Biomol. Chem.  2009,  7:  370 
    Google Scholar
  • 15b Sliwa W. Girek T. Koziol JJ. Curr. Org. Chem.  2004,  8:  1445 
    Google Scholar
  • 15c Liu Y. Chen Y. Acc. Chem. Res.  2006,  39:  681 
    Google Scholar
  • 16a Zhang B. Breslow R. J. Am. Chem. Soc.  1997,  119:  1676 
    Google Scholar
  • 16b Yan J. Breslow R. Tetrahedron Lett.  2000,  41:  2059 
    Google Scholar
  • 16c Nelissen HFM. Schut AFJ. Feiters MC. Nolte RJM. Venema F. Chem. Commun.  2000,  577 
    Google Scholar
  • 16d Liu Y. You CC. Wada T. Inoue Y. Tetrahedron Lett.  2000,  41:  6869 
    Google Scholar
  • 16e Baugh SDP. Yang Z. Leung DK. Wilson DM. Breslow R. J. Am. Chem. Soc.  2001,  123:  12488 
    Google Scholar
  • 16f Bommel KJCV. Jong MRD. Metselaar GA. Verboom W. Huskens J. Hulst R. Kooijman H. Spek AL. Reinhould DN. Chem. Eur. J.  2001,  7:  3603 
    Google Scholar
  • 16g Liu Y. Li L. Zhang HY. Song Y.
    J. Org. Chem.  2003,  68:  527 
    Google Scholar
  • 17 Liu Y. Zhang Q. Chen Y. J. Phys. Chem. B  2007,  111:  12211 
    CrossrefGoogle Scholar
  • 18 Nagai K. Kondo H. Tsuruzoe N. Hayakawa K. Kanematsu K. Heterocycles  1982,  19:  53 
    CrossrefGoogle Scholar
  • 19 Nagai K. Hayakawa K. Kanematsu K. J. Org. Chem.  1984,  49:  1022 
    CrossrefGoogle Scholar
  • 20 Nagai K. Hayakawa K. Ukai S. Kanematsu K. J. Org. Chem.  1986,  51:  3931 
    CrossrefGoogle Scholar
  • 21 Djedaini-Pilard F. Perly B. Dupas S. Miocque M. Galons H. Tetrahedron Lett.  1993,  34:  1145 
    CrossrefGoogle Scholar
  • 22 Kato Y. Nishizawa S. Teramae N. Org. Lett.  2002,  4:  4407 
    CrossrefGoogle Scholar
  • 23 Murray PE. McNally VA. Lockyer SD. Williams KJ. Stratford IJ. Jaffar M. Freeman S. Bioorg. Med. Chem.  2002,  10:  525 
    CrossrefGoogle Scholar
  • 24 Nawrot B. Michalak O. Olejniczak S. Wieczorek MW. Lis T. Stec WJ. Tetrahedron  2001,  57:  3979 
    CrossrefGoogle Scholar
  • 25 Ciapetti P. Taddeai M. Tetrahedron  1998,  54:  11305 
    CrossrefGoogle Scholar
  • 26 Lock L. Pohlsgaard J. Jepsen AS. Hansen LH. Nielsen H. Steffansen SI. Sparving L. Nielsen AB. Vester B. Nielsen P. J. Med. Chem.  2008,  51:  4957 
    CrossrefGoogle Scholar
  • 27 Lindsell WE. Murray C. Preston PN. Woodman TAJ. Tetrahedron  2000,  56:  1233 
    CrossrefGoogle Scholar
  • 32 Sartorius J. Schneider H.-J. Chem. Eur. J.  1996,  2:  1446 
    CrossrefGoogle Scholar
  • 33 Salas M. Gordillo B. Gonzalez FJ. ARKIVOC  2003,  (xi):  72 
    Google Scholar
  • 34 Carrazana J. Jover A. Meijide F. Soto VH. Tato JV. J. Phys. Chem. B.  2005,  109:  9719 ; and references cited therein
    CrossrefGoogle Scholar
  • 35 Tellini VHS. Jover A. Garca JC. Galantini L. Meijide F. Tato JV. J. Am. Chem. Soc.  2006,  128:  5728 
    CrossrefGoogle Scholar
28

Selected Physical Data of Compound 8a
MP 200 ˚C (decomp.). ¹H NMR (500 MHz, D2O): δ = 7.48 (s, 1 H), 5.14-5.08 (m, 7 H), 4.30-4.10 (m, 3 H), 4.03-3.81 (m, 25 H), 3.72-3.50 (m, 15 H), 3.47 (m, 2 H), 3.39 (m, 1 H), 1.91 (s, 3 H) ppm. ¹³C NMR (125 MHz, D2O): δ = 166.8, 153.0, 142.2, 111.5, 102.0-101.0, 83.3-80.8, 71.5-70.5, 67.5, 60.5-59.5, 48.8, 47.6, 45.0, 11.3 ppm. ESI-HRMS: m/z calcd [M + H]+: 1286.4522; found: 1286.4581.

29

Selected Physical Data of Compound 8b
Mp 200 ˚C (decomp.). ¹H NMR (500 MHz, D2O): δ = 7.56 (s, 1 H), 5.36-5.24 (m, 5 H), 4.00 (s, 2 H), 3.89-3.54 (m, 33 H), 3.64-3.62 (m, 21 H), 3.55-3.52 (m, 21 H), 3.43-3.37 (m, 7 H), 3.41-3.40 (m, 21 H), 3.23 (br s, 2 H), 3.18 (br s, 2 H), 1.94 (s, 3 H) ppm. ¹³C NMR (125 MHz, D2O): δ = 166.8, 152.4, 143.1, 110.6, 97.6-96.6, 81.4-75.9, 71.2-69.6, 59.9-58.1, 48.5, 47.4, 47.0, 11.43 ppm. ESI-HRMS: m/z calcd
[M + H]+: 1566.7532; found: 1565.7573.
Selected Physical Data of Compound 9a
Mp 200 ˚C (decomp.). ¹H NMR (500 MHz, D2O): δ = 8.52 (s, 1 H), 8.40 (s, 1 H), 5.17-5.10 (m, 7 H), 4.38 (s, 2 H), 4.00-3.50 (m, 39 H) 3.31 (t, 1 H), 3.11 (m, 2 H), 2.95 (d,
1 H), 2.77 (m, 1 H) ppm. ¹³C NMR (125 MHz, D2O): δ = 155.4, 152.2, 149.5, 142.5, 118.5, 102.0-101.7, 101.0, 83.5, 81.2-80.1, 73.1-70.2, 60.3-59.9, 48.2, 47.0, 43.2 ppm. ESI-HRMS: m/z calcd [M + H]+: 1295,4637; found: 1295.4574.
Selected Physical Data of Compound 9b
Mp 200 ˚C (decomp.). ¹H NMR (500 MHz, D2O): δ = 8.31 (s, 1 H), 8.23 (s, 1 H), 5.29-5.24 (m, 5 H), 5.17 (s, 1 H), 4.98 (s, 1 H), 4.44 (br s, 2 H), 3.88-3.51 (m, 26 H), 3.64-3.62 (m, 21 H), 3.55-3.52 (m, 21 H), 3.41-3.32 (m, 14 H), 3.41-3.40, (m, 21 H), 3.24 (br s, 2 H), 3.05 (br s, 2 H) ppm. ¹³C NMR (125 MHz, D2O): δ = 155.5, 152.4, 149.3, 142.6,118.5, 97.7-96.5, 80.9-76.5, 71.1-70.7, 60.0-58.0, 48.1, 47.5, 43.2 ppm. ESI-HRMS: m/z calcd [M + H]+: 1575.7673; found: 1575.7654.

30

Selected Physical Data of Compound 11
Mp 200 ˚C (decomp.). ¹H NMR (500 MHz, D2O): δ = 8.10 (s, 1 H), 7.66 (s, 1 H), 5.20 (s, 1 H), 5.10-5.03 (m, 9 H), 4.63 (s, 1 H), 4.30 (s, 1 H), 4.08-3.50 (m, 37 H), 3.01 (s, 1 H), 2.70 (s, 1 H), 1.92 (s, 3 H) ppm. ¹³C NMR (125 MHz, D2O): δ = 167.1, 152.2, 142.4, 126.5, 111.2, 101.9-101.4, 83.2-80.5, 73.0-70.4, 60.3, 59.1, 51.4, 42.9, 11.3 ppm. ESI-HRMS: m/z calcd [M + Na+]: 1346.4246; found: 1346.4211.

31

Selected Physical Data of Compound 12
Mp 200 ˚C (decomp.). ¹H NMR (500 MHz, D2O): δ = 8.29 (s, 1 H), 8.26 (s, 1 H), 7.99 (s, 1 H), 5.60 (s, 2 H), 5.15-5.00 (m, 7 H), 4.97 (d, 1 H), 4.59 (dd, 1 H), 4.11 (t, 1 H), 4.00-3.40 (m, 37 H), 2.78 (d, 1 H), 2.60 (d, 1 H) ppm. ¹³C NMR (125 MHz, D2O): δ = 155.6, 152.7, 148.9, 142.6, 142.1, 125.9, 118.6, 101.9, 81.3-80.4, 73.1-70.6, 60.0-58.8, 51.2, 38.4 ppm. ESI-HRMS: m/z calcd [M + Na+]: 1355.4362; found: 1355.4363.