Abstract
A synthetic series of heptakis-galactose-branched cyclodextrins (termed CDs) having a longer spacer arm using two amino-caproic acids as an enlarging unit were prepared. Starting with heptakis-amino-β-CD or heptakis-amino-caproic-amide-β-CD, treated with galactosyl-glucono-amide-caproic acid, the new compounds heptakis (Gal-cap1)-CD (4) or heptakis (Gal-cap2)-CD (5) were obtained. The longer galactose spacer arm extremely favors the PNA association. The effect of branch length on K with PNA was enhanced up to 138-fold 3 as well as with DXR enhanced up to 81-fold. Hexakis (Gal-cap2)-CD (6) was prepared and the association constants with rat liver cells were observed to be 2.5 × 1010 M−1. A multi-high mannose type oligosaccharide branched CD (7) showed a large association constant with DXR up to 1.1 × 109 M−1. The two-dimensional map for the association constants of newly synthesized oligosaccharide-branched CDs toward lectin or liver cells versus the association constants toward a drug (doxorubicin) suggested a method of finding a better targeting drug carrier. The structural effect of the oligosaccharide-CDs showed that the number and length of the branch were dominant factors in designing for enhanced dual recognition.
Similar content being viewed by others
References
Abe H., Kenmoku A., Yamaguchi N., Hattori K., J. Inclusion Phenom. Macrocyclic. Chem. 52, 39 (2002)
N. Yasuda, N. Aoki, H. Abe, and K. Hattori: Chem. Lett. 2000, 706 (2000)
K. Hattori: European Conference on Drug Delivery and Pharmaceutical Technology, Sevilla May 10–12, Abstract p 47 (2004)
D.E. Koshland Jr.: Proc. Natl. Acad. Sci. US 44, 98 (1958)
Lee Y.C., Lee R.C., Acc. Chem. Res. 28, 321 (1995)
Seglen P.O., Methods Cell Biol. 13, 29 (1976)
Tanaka K., Ichikawa A., Tanpaku Kakusan Kouso 23, 1259 (1978)
Matsuda K., Inazu T., Hanaeda K., Mizuno M., Yamanoi T., Hattori K., Yamamoto K., Kumagai H., Bio. Med. Chem. Lett. 7, 2353 (1977)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Hattori, K., Kenmoku, A., Mizuguchi, T. et al. Saccharide-branched Cyclodextrins as Targeting Drug Carriers. J Incl Phenom Macrocycl Chem 56, 9–16 (2006). https://doi.org/10.1007/s10847-006-9053-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-006-9053-x