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Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

“…In these compounds, the distance between the two anchored glycotopes can be modulated by varying the spacer link connecting the external sugars and the CD core (Scheme 7). [68][69][70][71] This feature was exploited by the authors to estimate the separation between two bGal binding sites in peanut agglutinin (PNA) lectin by employing surface plasmon resonance (SPR). They also confirmed that the inclusion properties of bCD remained operative in the bis-conjugates, using doxorubicin as a model guest.…”

“…Ether-linked and aGlc-coated divalent derivatives were also prepared. [68][69][70][71] Driguez and co-workers communicated the preparation of heptavalent CD-centred glycoclusters by S N 2 displacement in per-(C-6)-Br bCD by thiolate-functionalized fully-unprotected galactose derivatives of all bromo groups. 77 The reaction proceeded in dimethylpropyleneurea (DMPU) at 70 1C with moderate to good yields (50-80%) using either glycosyl thiolates (a and bGal) or thiol-terminated spacer-armed derivatives (bGal) as nucleophiles (Fig.…”

Editorial (Thematic Issue: The Role of Reactive Oxygen Species in Organ Pathologies Due to Drugs Abuse: Do We Have the Culprit?)

“…As an alternative to the persubstituted glycoCDs and glycodendrimer-CD conjugates, the synthesis of bis-branched-CDs has been reported [22] (Fig. 8).…”

Syntheses and Doxorubicin-Inclusion Abilities of .BETA.-Cyclodextrin Derivatives with a Hydroquinone .ALPHA.-Glycoside Residue Attached at the Primary Side

“…mp: 57. 6 4-O-(3-Hydroxypropyl)phenyl 2,3,4,6-Tetra-O-benzyl-a a-D-glucopyranoside (10) To a solution of 9 (303 mg, 0.45 mmol) in THF (7 ml) was added in 0.5 M 9-BBN THF solution (2 ml, 1 mmol) at 0°C. After the reaction mixture was stirred for 5 h at room temperature, a 0.5 M NaOH aqueous solution (2.7 ml, 1.4 mmol) and a 30% H 2 O 2 aqueous solution (0.46 ml, 4.5 mmol) were added.…”

“…5) The CyD derivatives attached to saccharide moieties are expected to carry drug molecules to specific cells, because they have both the drug-inclusion ability of CyDs and the cell-recognition of saccharides. 4,[6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22] Then, our next objective was the synthesis of a novel b-CyD conjugate having another hydroquinone glycoside. This paper describes the synthesis of two novel b-CyD derivatives attached to a hydroquinone glycoside containing an a-D-glucopyranosidic or 2-acetamido-2-deoxy-a-D-glucopyranosidic linkage and the evaluation of their DXR-inclusion abilities.…”