Homo- and Heterogeneous Glycoconjugates on the Basis of N-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation |
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Authors: | Almira Kurbangalieva Regina Zamalieva Igor Nasibullin Kenshiro Yamada Katsunori Tanaka |
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Institution: | 1.Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia; (R.Z.); (I.N.);2.Biofunctional Synthetic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan;3.Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan; |
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Abstract: | Neoglycoconjugates mimicking natural compounds and possessing a variety of biological functions are very successful tools for researchers to understand the general mechanisms of many biological processes in living organisms. These substances are characterized by high biotolerance and specificity, with low toxicity. Due to the difficult isolation of individual glycoclusters from biological objects, special interest has been directed toward synthetic analogs. This review is mainly focused on the one-pot, double-click methodology (containing alkyne–azide click cycloaddition with the following 6π-azaelectrocyclization reactions) used in the synthesis of N-glycoconjugates. Homogeneous (including one type of biantennary N-glycan fragments) and heterogeneous (containing two to four types of biantennary N-glycan fragments) glycoclusters on albumin were synthesized via this strategy. A series of cell-, tissue- and animal-based experiments proved glycoclusters to be a very promising class of targeted delivery systems. Depending on the oligosaccharide units combined in the cluster, their amount, and arrangement relative to one another, conjugates can recognize various cells, including cancer cells, with high selectivity. These results open new perspectives for affected tissue visualization and treatment. |
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Keywords: | N-glycans albumin glycocluster glycoconjugation biodistribution pattern recognition in vivo molecular imaging tumor targeting drug delivery system chemical biology |
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