Succinyl-Beta-Cyclodextrin

Ye L, et al. Analytica Chimica Acta, 2017, 953, 48-56.

Succinyl-beta-cyclodextrin (succinyl-β-CD) was employed to modify gold biochips for enhanced seroimmunological detection of Lyme disease. The chemical modification process began with the activation of succinyl-β-CD by carbodiimide chemistry using EDC (50 mM) and NHS (430 mM) in aqueous solution at 4 °C for 2 hours. Simultaneously, gold slides were functionalized with 16-amino-1-hexadecanethiol (0.8 mM in ethanol) to generate an aminated surface. These aminated slides were subsequently immersed in the activated succinyl-β-CD solution at room temperature under dark conditions for 24 hours to achieve covalent immobilization via amide bond formation. Post-reaction, slides were washed and dried under nitrogen stream.

The resulting succinyl-β-CD modified gold surface provided a host-guest interaction platform with enhanced affinity towards the VlsE antigen, enabling highly sensitive detection (LOD: 0.39 μg/mL) of anti-VlsE IgG antibodies via fluorescence assays. Specificity was validated using immunological blocking, and strong correlation with ELISA (R² = 0.904) confirmed the platform's analytical reliability.

Shinde V. V, et al. Tetrahedron, 2019, 75(6), 778-783.

Succinyl-beta-cyclodextrin (Suc-β-CD) was utilized as a supramolecular organic acid catalyst in the Groebke–Blackburn–Bienaymé (GBB) multicomponent reaction to synthesize the nitrogen-fused heterocycle indazolo[3',2':2,3]imidazo[1,5-c]quinazolin-6(5H)-one (IIQ). This method showcases the efficacy of Suc-β-CD in promoting [4 + 1] cycloaddition via host–guest interactions, offering an atom-economical and environmentally benign protocol. In a typical procedure, a mixture of isatin (1 mmol), 1H-indazol-3-amine (1 mmol), and isocyanide (1 mmol) was reacted in 5 mL of water containing 1 mol% Suc-β-CD. The reaction mixture was stirred at 100 °C, and the progress was monitored using TLC with DCM/methanol (95:5) as the mobile phase. Upon completion, the precipitated IIQ product was isolated by filtration and washed with water. The catalyst was effectively recovered from the aqueous filtrate through acetone-induced precipitation, followed by washing and vacuum drying at 60 °C. The recyclability of Suc-β-CD was confirmed through repeated catalytic cycles with consistent performance.

Tedeschi T, et al. Journal of Biochemical and Biophysical Methods, 2007, 70(5), 735-741.

Succinyl-β-cyclodextrin (Succ-β-CyD) was employed to improve the specificity of a visual DNA mismatch detection system based on the 3,3'-diethylthiacarbocyanine iodide (DiSC2(5)) dye. While DiSC2(5) typically aggregates on fully matched PNA–DNA duplexes, producing a visible color shift from blue to purple, its nonspecific aggregation on mismatched duplexes and even free PNA strands has limited its analytical precision. The introduction of Succ-β-CyD effectively suppressed these nonspecific interactions.

Experimental protocols involved preparing 5 μM solutions of single-stranded PNA or PNA–DNA duplexes in phosphate buffer (10 mM, 100 mM NaCl, pH 7). Duplexes were annealed by heating to 90 °C for 5 minutes followed by slow cooling to room temperature. DiSC2(5) was then added at 15 μM concentration to the prepared solutions, either in the presence or absence of Succ-β-CyD. Absorption spectra were recorded immediately post-addition at controlled temperatures (15–25 °C). Circular dichroism (CD) spectra and melting temperature (Tm) measurements were also conducted to assess dye binding behavior and duplex stability.

Shin G-S, et al. Journal of Molecular Catalysis B: Enzymatic, 2005, 33(3-6), 93-98.

Succinyl-beta-cyclodextrin (suβ-CD) was employed as a chiral selector and phase dispersion agent to facilitate the enantioselective hydrolysis of (R,S)-flurbiprofen ethyl ester ((R,S)-FEE) in an aqueous reaction system catalyzed by Candida rugosa lipase. The process exploited the ability of suβ-CD to form selective inclusion complexes with the enantiomers of FEE, enhancing the substrate's aqueous solubility and enabling effective chiral discrimination.

In the optimized procedure, 50 mM (R,S)-FEE was first dissolved in sodium phosphate buffer (pH 7.0) and mixed with 100 mM suβ-CD. Ultrasonication for 1 minute facilitated the formation of the inclusion complex. Subsequently, 600 units of C. rugosa lipase per mmol of FEE were introduced, and the reaction was maintained at 37 °C with shaking at 300 rpm for 72 hours. A separate set of reactions at higher concentrations—500 mM (R,S)-FEE and 1000 mM suβ-CD—was also evaluated, yielding a remarkable enantiomeric excess (ee) of 0.98 and conversion yield of 0.48.