Synthesis of structure-defined branched hyaluronan tetrasaccharide glycoclusters

Meng, Sha; Yao, Wang; Zhang, Xiao; Li, Zhongjun

doi:10.1016/j.tetlet.2017.06.032

Cited by 12 publications

(10 citation statements)

References 31 publications

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“…R f = 0.40 (SiO 2 , CH 2 Cl 2 /EtOAc/MeOH = 1.0/1.1/0.20). For the NMR spectra, please see ref . HR-ESI-MS ( m / z ): [M + Na] + : C 50 H 68 N 2 O 33 , calcd for 1247.3597; found 1247.3601.…”

Section: Experimental Sectionsupporting

confidence: 84%

“…As shown in Scheme , HA (MW = 500 kDa, $328/kg) was digested with 2.4% w/w bovine testis (or testicular) hyaluronidase (BTH) ($145/g, 1.2 g for 50 g HA) in acetate saline (pH 5.0) for 14 days. Previously, we developed a continuous esterification method by sequential methylating then acetylating the degradation mixture 9 . This protocol enabled us to afford the protected tetrasaccharide 10 (α/β = 1.7/1) at a quantity of 25 g from 9 in 42% overall yield.…”

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confidence: 99%

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Semisynthesis of Chondroitin Sulfate E Tetrasaccharide from Hyaluronic Acid

et al. 2018

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Chondroitin sulfate (CS) is crucial glycosaminoglycan that regulates key functions of the nervous system. CS-E is one of the key CS subtypes that modulates the biological function of CS. Herein, N-protecting-group-free semisynthesis of CS-E tetrasaccharide is reported using hyaluronic acid as a readily available starting material. The synthetic process utilizes the enzymatic degradation and selective C4 hydroxyl group conversion as key approaches for direct construction of the CS tetrasaccharide precursor, which furnishes the neuroactive CS-E tetrasaccharide in 15 steps.

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Section: Experimental Sectionsupporting

confidence: 84%

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confidence: 99%

Semisynthesis of Chondroitin Sulfate E Tetrasaccharide from Hyaluronic Acid

et al. 2018

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“…The reaction of GATG and G4-PAMAM was performed in two different batches providing two modified dendrimers with different loadings: PAMAM-3GATG and PAMAM-6GATG. The loading of GATG was assessed by the integration of the nuclear magnetic resonance (NMR) signals that were interpreted using previous data describing the conjugation of GATG to lower generation PAMAM derivative [ 29 ]. Synthesis of PAMAM-GATG was confirmed by 1 H-NMR (400 MHz, CD 3 OD).…”

Section: Resultsmentioning

confidence: 99%

“…G4-PAMAM was dissolved in 0.5 mL N , N -dimethylformamide (DMF). Modified gallic acid-triethylene glycol (GATG, MW = 641.6 Da) [ 29 ], 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, MW = 191.7 Da), and 1-Hydroxybenzotriazole (HOBt, MW = 135.1 Da) were dissolved in 0.5 mL DMF and stirred for 1 h at room temperature, and then the G4-PAMAM solution was added and reacted for 24 h under argon protection. After completion of the reaction, the reaction solution was spin-dried and 2 mL of methanol was added for reconstitution.…”

Section: Methodsmentioning

confidence: 99%

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Construction of Hyaluronic Tetrasaccharide Clusters Modified Polyamidoamine siRNA Delivery System

Meng

Cheng

et al. 2018

Nanomaterials

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The CD44 protein, as a predominant receptor for hyaluronan (HA), is highly expressed on the surface of multiple tumor cells. HA, as a targeting molecule for a CD44-contained delivery system, increases intracellular drug concentration in tumor tissue. However, due to the weak binding ability of hyaluronan oligosaccharide to CD44, targeting for tumor drug delivery has been restricted. In this study, we first use a HA tetrasaccharide cluster as the target ligand to enhance the binding ability to CD44. A polyamidoamine (PAMAM) dendrimer was modified by a HA tetrasaccharide cluster as a nonviral vector for small interfering RNA (siRNA) delivery. The dendrimer/siRNA nanocomplexes increased the cellular uptake capacity of siRNA through the CD44 receptor-mediated endocytosis pathway, allowing the siRNA to successfully escape the endosome/lysosome. Compared with the control group, nanocomplexes effectively reduced the expression of GFP protein and mRNA in MDA-MB-231-GFP cells. This delivery system provides a foundation to increase the clinical applications of PAMAM nanomaterials.

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Synthesis of Fucosylated Chondroitin Sulfate Nonasaccharide as a Novel Anticoagulant Targeting Intrinsic Factor Xase Complex

et al. 2018

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Fucosylated chondroitin sulfate (FuCS) is a structurally distinct glycosaminoglycan, and its oligosaccharides exhibit excellent anticoagulant activity with lower risks of adverse effects and bleeding. Herein we report a facile approach to the synthesis of FuCS hexa‐ and nonasaccharides on the basis of the enzymatic degradation of chondroitin over 12 linear steps. As compared with a clinical low‐molecular‐weight heparin drug (enoxaparin), the nonasaccharide synthesized in this study displayed similar APTT activity and selective intrinsic factor Xase complex inhibitory activity ((12.9±0.83) nm) by binding to factor IXa with high affinity, thus offering promise for the development of new anticoagulant agents targeting the intrinsic coagulation pathway.

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Synthesis of structure-defined branched hyaluronan tetrasaccharide glycoclusters

Cited by 12 publications

References 31 publications

Semisynthesis of Chondroitin Sulfate E Tetrasaccharide from Hyaluronic Acid

Semisynthesis of Chondroitin Sulfate E Tetrasaccharide from Hyaluronic Acid

Construction of Hyaluronic Tetrasaccharide Clusters Modified Polyamidoamine siRNA Delivery System

Synthesis of Fucosylated Chondroitin Sulfate Nonasaccharide as a Novel Anticoagulant Targeting Intrinsic Factor Xase Complex

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