Reference - Detail
| RRC ID | 81840 |
|---|---|
| Author | Moritsuka N, Kiya N, Moriyama T, Koshino H, Yoritate M, Matoba H, Hirai G. |
| Title | Linkage-Editing of Melibiosamine: Synthesis and Biological Evaluation of CH2- and CHF-Linked Analogs. |
| Journal | J Org Chem |
| Abstract |
Melibiosamine (Gal-α(1,6)-GlcNH2), consisting of galactose and glucosamine linked by an α(1,6)-glycosidic bond, is an artificial disaccharide derivative that selectively inhibits the proliferation of K562 tumor cells relative to HUC-F2 normal cells. In this study, we employed a linkage-editing strategy to synthesize CH2- and CHF-linked melibiosamine analogs through chemo- and stereoselective hydrogenation of fluorovinyl-C-glycoside. (R)-CHF-Melibiosamine exhibited more potent antiproliferative activity than O-linked melibiosamine, while (S)-CHF-melibiosamine was less potent. |
| Volume | 89(17) |
| Pages | 11909-11920 |
| Published | 2024-9-6 |
| DOI | 10.1021/acs.joc.4c01143 |
| PMID | 39119939 |
| MeSH | Antineoplastic Agents / chemical synthesis Antineoplastic Agents / chemistry Antineoplastic Agents / pharmacology Cell Proliferation* / drug effects Disaccharides / chemical synthesis Disaccharides / chemistry Disaccharides / pharmacology Drug Screening Assays, Antitumor Galactose / chemistry Glucosamine / chemistry Humans K562 Cells Molecular Structure Stereoisomerism Structure-Activity Relationship |
| IF | 4.335 |
| Altmetric score |
オルトメトリクス指標項目
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| The most frequently cited source | X(Twitter) |
| Total number of mentions | 13 |
| Altmetric score changes over past 6months | 0.0 |
| Resource | |
| Human and Animal Cells | K562(RCB0027) |