Ligation of polydisperse oligosaccharides is generally very demanding due to their polar character and solubility in polar solvents. For example, low molecular hyaluronans suitable as vectors for the tumor cells are soluble only in water. The aim of this study was to develop methods for ligation of these oligosaccharides by reductive amination through a linker containing an acyl hydrazide group (Figure 1). Hydrazide group will be used for the squaric acid ligation to the transport systems [1] based on self-assembling lipid nanoparticles, or fluorescent diamond nanoparticles as imaging system for real time monitoring of processes in living cells [2].
Figure 1. Proposed synthetic strategy on the solid phase
For this purpose TentaGel S-OH was found as the best solid support which swells well in water and also in other solvents dissolving polyethylene glycol. We worked on NH2-terminated fluorescent nanodiamonds as a suitable imaging system and we prepared self-assembling lipid nanoparticles with anchor presenting polyamine chain as a potential delivery system.
Acknowledgments: This work was partly-financed by the GAČR within grant No.: P304/10/1951 and grant from TAČR No.: TA01011162, Academy of Sciences of Czech Republic No.: RVO 61388963.
References:
1. A. Chernyak; A. Karavanov; Y. Ogawa; P. Kovac; Carbohyd. Res. 2001, 330, 479-486.
2. V. Petrakova; A. Taylor; I. Kratochvilova; F. Fendrych; J. Vack; J. Kucka; J. Stursa; P. Cigler; M. Ledvina; A. Fiserova; P. Knepo; M. Nesladek; Adv. Funct. Mater. 2011, XX, 1-8.
