New β-cyclodextrin derivatives possessing biologically active saccharide antennae

Parrot‐Lopez, Hélène; Leray, E.; Coleman, Anthony W.

doi:10.1080/10610279308029836

Cited by 23 publications

(9 citation statements)

References 13 publications

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“…Therefore, cyclodextrin derivatives bearing small saccharides may be useful as a carrier for transporting active drugs to sugar receptors such as lectins located on the cell surface. In accordance with this concept, several cyclodextrin conjugates with mono- and di-saccharides such as glucose, galactose, mannose, fucose, etc., have been prepared and investigated for binding characteristics to sugar-specific receptors. − The β-cyclodextrin conjugates with galactose showed higher recognition by the galactose specific K. Bulgaricus cell wall lectin (KbCWL); i.e., they inhibited flocculation of K. Bulgaricus cells induced by the isolated KbCWL lectin and their inhibition activity was higher than that of galactose, whereas the glucose derivatives showed no inhibition effect. α-Glucosylgluconoamide-β-cyclodextrin showed a high affinity (association constant 8730 M -1 ) for the glucose-binding protein concanavalin A, a representative of a large family of lectins .…”

Section: Cell Surface Targetingmentioning

confidence: 99%

Cyclodextrin Drug Carrier Systems

1998

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Section: Cell Surface Targetingmentioning

confidence: 99%

Cyclodextrin Drug Carrier Systems

1998

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“…This strategy has been used to connect various sugar units such as β- d -glucose, β- d -galactose, α- d -mannose, and β- d - and l -fructose to cyclodextrins through alkyl chains. These compounds have been used to investigate their antennae effects . Monoamines condense with d- or d- N -dansylleucine in DMF containing DCC and 1-hydroxybenzotriazole at room temperature to form d - or l -mono-6-( N -dansylleucylamino)-6-deoxy-β-cyclodextrin in 50% yield …”

Section: 1 Monosubstitution At the 6-position Of Cyclodextrinsmentioning

confidence: 99%

“…These compounds have been used to investigate their antennae effects. 58 Monoamines condense with D-or D-N-dansylleucine in DMF containing DCC and 1-hydroxybenzotriazole at room temperature to form D-or Monoaldehydic cyclodextrins are an important class of derivatives because they provide a route for further modifications. The monoaldehyde has been synthesized by oxidizing 6-tosyl-β-cyclodextrin using DMSO (VI in Figure 3).…”

Section: Monosubstitution At the 6-position Of Cyclodextrinsmentioning

confidence: 99%

Methods for Selective Modifications of Cyclodextrins

et al. 1998

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be established before the mechanistic information about the artificial enzyme can be reliably derived. Scope of This ReviewIn this review, we present a systematic analysis of methods that are available for modification of cyclodextrins. The focus is on methods for transformation where the number and the exact positions of modifications are ascertained and pure compounds with unambiguous structures are obtained. In cases where the products have unusual and interesting properties, these attributes are mentioned. We have not attempted to cite every cyclodextrin derivative that has been made. This has already been achieved in an excellent and recent review. 12 We have also not included modified cyclodextrins obtained by purely synthetic routes, i.e., strategies to obtain these molecules from appropriately derivatized monosaccharides rather than cyclodextrins. A recent review describes strategies for the preparation of synthetic cyclic oligosacharides. 7 An Overview of Methods for Modification of CyclodextrinsMethods for selective modification of cyclodextrin can be divided into three categories: (1) the "clever"

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“…In accordance with this concept, several CyD derivatives with mono-and di-saccharides, such as glucose, galactose, mannose, fucose, etc., have been prepared and investigated for binding characteristics to sugar-specifi c receptors. [157][158][159] The β -CyD conjugates with galactose exhibited higher recognition by the galactose-specifi c K. bulgaricus cell wall lectin. 160 It is reported that some galactose and fucose conjugates have a signifi cant cytotoxic effect on the human rectal adenocarcinoma cell line, with P-glycoprotein-positive multidrug resistance.…”

Section: B Cell Targetingmentioning

confidence: 98%