Homo- and Heterogeneous Glycoconjugates on the Basis of <i>N</i>-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation
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, wi...
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MDPI AG
2022-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/4/1285 |
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| author | Almira Kurbangalieva Regina Zamalieva Igor Nasibullin Kenshiro Yamada Katsunori Tanaka |
| author_facet | Almira Kurbangalieva Regina Zamalieva Igor Nasibullin Kenshiro Yamada Katsunori Tanaka |
| author_sort | Almira Kurbangalieva |
| collection | DOAJ |
| description | 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 <i>N</i>-glycoconjugates. Homogeneous (including one type of biantennary <i>N</i>-glycan fragments) and heterogeneous (containing two to four types of biantennary <i>N</i>-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. |
| first_indexed | 2024-03-09T21:21:02Z |
| format | Article |
| id | doaj.art-a6b0e65190134bf5b2cc76459049f27b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T21:21:02Z |
| publishDate | 2022-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a6b0e65190134bf5b2cc76459049f27b2023-11-23T21:21:37ZengMDPI AGMolecules1420-30492022-02-01274128510.3390/molecules27041285Homo- and Heterogeneous Glycoconjugates on the Basis of <i>N</i>-Glycans and Human Serum Albumin: Synthesis and Biological EvaluationAlmira Kurbangalieva0Regina Zamalieva1Igor Nasibullin2Kenshiro Yamada3Katsunori Tanaka4Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, RussiaBiofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, RussiaBiofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, RussiaDepartment 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, JapanBiofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, RussiaNeoglycoconjugates 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 <i>N</i>-glycoconjugates. Homogeneous (including one type of biantennary <i>N</i>-glycan fragments) and heterogeneous (containing two to four types of biantennary <i>N</i>-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.https://www.mdpi.com/1420-3049/27/4/1285<i>N</i>-glycansalbuminglycoclusterglycoconjugationbiodistributionpattern recognition |
| spellingShingle | Almira Kurbangalieva Regina Zamalieva Igor Nasibullin Kenshiro Yamada Katsunori Tanaka Homo- and Heterogeneous Glycoconjugates on the Basis of <i>N</i>-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation Molecules <i>N</i>-glycans albumin glycocluster glycoconjugation biodistribution pattern recognition |
| title | Homo- and Heterogeneous Glycoconjugates on the Basis of <i>N</i>-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation |
| title_full | Homo- and Heterogeneous Glycoconjugates on the Basis of <i>N</i>-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation |
| title_fullStr | Homo- and Heterogeneous Glycoconjugates on the Basis of <i>N</i>-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation |
| title_full_unstemmed | Homo- and Heterogeneous Glycoconjugates on the Basis of <i>N</i>-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation |
| title_short | Homo- and Heterogeneous Glycoconjugates on the Basis of <i>N</i>-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation |
| title_sort | homo and heterogeneous glycoconjugates on the basis of i n i glycans and human serum albumin synthesis and biological evaluation |
| topic | <i>N</i>-glycans albumin glycocluster glycoconjugation biodistribution pattern recognition |
| url | https://www.mdpi.com/1420-3049/27/4/1285 |
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