Molecular‐Recognition and Binding Properties of Cyclodextrin‐Conjugated Polyrotaxanes

Choi, Hak; Takahashi, Akihiro; Ooya, Tooru; Yui, Nobuhiko

doi:10.1002/cphc.200600147

Cited by 5 publications

(2 citation statements)

References 63 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In recent years, molecular recognition has received much attention in chemistry, biology, environmental science, and many other fields. − Cyclodextrins (CDs), a class of macrocyclic oligosaccharides consisting of six, seven, or eight glucose units linked by α-1,4-glucose bonds, have been widely used as receptors in molecular recognition . It has been demonstrated that the formation of inclusion complexes between CDs and guest molecules is cooperatively governed by several weak forces, such as van der Waals, hydrophobic, electrostatic, dipole−dipole, and hydrogen-bonding interactions, and every weak force does its contribution to the complexation.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic Origin of Selective Binding of β-Cyclodextrin Derivatives with Chiral Chromophoric Substituents toward Steroids

Chen

Liu

et al. 2010

J. Phys. Chem. B

View full text Add to dashboard Cite

Two β-cyclodextrin derivatives with chiral chromophoric substituents, that is, L- (1) and D-tyrosine-modified β-cyclodextrin (2), were synthesized and fully characterized. Their inclusion modes, binding abilities, and molecular selectivities with four steroid guests, that is, cholic acid sodium salt (CA), deoxycholic acid sodium salt (DCA), glycochoic acid sodium salt (GCA), and taurocholic acid sodium salt (TCA), were investigated by the circular dichroism, 2D NMR, and isothermal titration microcalorimetry (ITC). The results obtained from the circular dichroism and 2D NMR showed that two hosts adopted the different binding geometry, and these differences subsequently resulted in the significant differences of molecular binding abilities and selectivities. As compared with native β-cyclodextrin and tryptophan-modified β-cyclodextrin, host 2 showed the enhanced binding abilities for CA and DCA but the decreased binding abilities for GCA and TCA; however, host 1 showed the decreased binding abilities for all four bile salts. The best guest selectivity and the best host selectivity were K(S)(2-DCA)/K(S)(2-TCA) = 12.6 and K(S)(2-CA)/K(S)(1-CA) = 10, respectively, both exhibiting great enhancement as compared with the corresponding values of the previously reported L- and D-tryptophan-modified β-cyclodextrins. Thermodynamically, it was the favorable enthalpic gain that led to the high guest selectivity and host selectivity.

show abstract

Section: Introductionmentioning

confidence: 99%

Thermodynamic Origin of Selective Binding of β-Cyclodextrin Derivatives with Chiral Chromophoric Substituents toward Steroids

Chen

Liu

et al. 2010

J. Phys. Chem. B

View full text Add to dashboard Cite

show abstract

“…However, few of the growing class of synthetic supramolecular assemblies [3,[9][10][11] such as pseudorotaxanes (ring around a thread) and pseudopolyrotaxanes (many rings around a thread) and related mechanically-interlocked molecules [11][12][13] such as rotaxanes (ring around a dumbbell-shaped thread), catenanes (ring threaded through another ring), and polyrotaxanes (many rings on a dumbbell-shaped component) have been examined in biochemical contexts [14][15][16][17][18]. Recently, we [19][20][21] and Yui and co-workers [22][23][24][25] have used supramolecular chemistry to develop architectures for multivalent binding that are at the flexible and adaptable end of the ligand-display spectrum.…”

Section: Introductionmentioning

confidence: 99%

Multivalent Interactions between Lectins and Supramolecular Complexes: Galectin-1 and Self-Assembled Pseudopolyrotaxanes

Belitsky

Nelson

Hernandez

et al. 2007

Chemistry & Biology

View full text Add to dashboard Cite

Supramolecular chemistry has been employed to develop flexible and adaptable multivalent neoglycoconjugates for binding galectin-1 (Gal-1). Gal-1, a dimeric lectin with two galactoside-binding sites, regulates cancer progression and immune responses. Self-assembled pseudopolyrotaxanes consisting of lactoside-displaying cyclodextrin (LCD) "beads" threaded onto polyviologen "strings" display mobile ligands as a result of cyclodextrin rotation about, and limited translation along, the polymer chain. The pseudopolyrotaxanes rapidly and efficiently precipitate Gal-1 and provide valency-corrected enhancements of up to 30-fold compared to native lactose and 20-fold over free LCD in a T-cell agglutination assay. A supramolecular statistical effect was observed, wherein the efficacy of Gal-1 inhibition correlates with the number of ligands connected to each other solely through mechanical and noncovalent interactions. Such flexible and adaptable self-assembled pseudopolyrotaxanes show promise for the study of multivalent interactions and targeting of therapeutically relevant lectins.

show abstract

Linear Movements

2008

Molecular Devices and Machines

View full text Add to dashboard Cite

Molecular‐Recognition and Binding Properties of Cyclodextrin‐Conjugated Polyrotaxanes

Cited by 5 publications

References 63 publications

Thermodynamic Origin of Selective Binding of β-Cyclodextrin Derivatives with Chiral Chromophoric Substituents toward Steroids

Thermodynamic Origin of Selective Binding of β-Cyclodextrin Derivatives with Chiral Chromophoric Substituents toward Steroids

Multivalent Interactions between Lectins and Supramolecular Complexes: Galectin-1 and Self-Assembled Pseudopolyrotaxanes

Linear Movements

Contact Info

Product

Resources

About