Synthesis and antitumor activities of glucan derivatives

Du, Yuguo; Gu, Guofeng; Yang, Hua; Wei, Guohua; Ye, Xin‐Shan; Yu, Guangli

doi:10.1016/j.tet.2004.05.086

Cited by 16 publications

(14 citation statements)

References 43 publications

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“…It is interesting to note that certain sulfated oligosaccharides showed antitumor activity in a sarcoma-180 mouse model. 27 This is in contrast to the potent proangiogenesis activity in the CAM and in the 3D-ECS for sulfated oligosaccharides, as shown in this report. The effect on tumor weight based on the study design 27 cannot be explained and is difficult to ascertain because of the lack of details about the model.…”

Section: Discussioncontrasting

confidence: 69%

“…27 This is in contrast to the potent proangiogenesis activity in the CAM and in the 3D-ECS for sulfated oligosaccharides, as shown in this report. The effect on tumor weight based on the study design 27 cannot be explained and is difficult to ascertain because of the lack of details about the model. The study performed by Du et al 27 focused on the chemistry aspects and did not clearly provide a detailed description of the model; the effect on sarcoma tumor weight was marginal at doses ranging from 2.5 to 10 mg/kg.…”

Section: Discussioncontrasting

confidence: 69%

“…The effect on tumor weight based on the study design 27 cannot be explained and is difficult to ascertain because of the lack of details about the model. The study performed by Du et al 27 focused on the chemistry aspects and did not clearly provide a detailed description of the model; the effect on sarcoma tumor weight was marginal at doses ranging from 2.5 to 10 mg/kg. In addition, the study did not provide any data on the effect on tumor angiogenesis.…”

Section: Discussionmentioning

confidence: 99%

“…The branched unsulfated and persulfated β (1→3, 6) glucose trisaccharides (Ch 8 and Ch 9, respectively) were synthesized from methyl 4,6-O-benzylidine-D-glucopyranoside in 5 and 6 steps, respectively. 27 The doubly branched persulfated and unsulfated β (1→3, 6) Dglucose hexasaccharides (Ch 2 and Ch 10) were synthesized from phenyl 2, 4-di-O-acetyl-1-thio-β-D-glucopyranside in 6 and 7 steps, respectively. 27 All oligosaccharides were pure (>90%) by capillary electrophoresis 28 and polyacrylamide gel electrophoresis 29 and showed electrospray ionization-mass spectrometry and nuclear magnetic resonance spectra consistent with structure.…”

Section: Oligosaccharides Tested In Angiogenesis Assaysmentioning

confidence: 99%

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Synthetic Oligosaccharide Stimulates and Stabilizes Angiogenesis: Structure-Function Relationships and Potential Mechanisms

Mousa¹,

Feng²,

Xie³

et al. 2006

Journal of Cardiovascular Pharmacology

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To determine the proangiogenesis effect of series of saccharides and a synthetic oligosaccharide and potential mechanisms, an in vitro 3-dimensional endothelial cell sprouting (3D-ECS) assay and the chick chorioallantoic membrane (CAM) model were used. We demonstrated that a sulfated oligosaccharide significantly promotes the endothelial capillary network initiated by vascular endothelial growth factor (VEGF) and basic fibroblast growth factor (b-FGF). Furthermore, although the capillary network initiated by VEGF and b-FGF lasts no more than 7 days, addition of a sulfated oligosaccharide significantly amplifies angiogenesis and stabilizes the capillary network of new blood vessels. In the CAM model, sulfated oligosaccharide also stimulated angiogenesis. In both the CAM and the 3D-ECS assay, structure-function studies reveal that increased saccharide chain length up to the hexa-to decasaccharide show optimal proangiogenesis efficacy. In addition, the sulfation and molecular shape (branched vs linear) of oligosaccharide are important for sustained proangiogenesis efficacy. Data indicate that chemically defined synthetic oligosaccharides can play an important role in regulation of capillary structure and stability, which may contribute to future advances in therapeutic angiogenesis. The proangiogenesis efficacy of an oligosaccharide is mediated via integrin αvβ3 and involves mitogen-activated protein kinase signaling mechanisms. Keywordsangiogenesis; oligosaccharides; αvβ3 integrin; growth factors; mitogen-activated protein kinase Control of angiogenesis is a complex process involving local release of vascular growth factors, the extracellular matrix, adhesion molecules, and metabolic factors. 1-3 Mechanical

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Section: Discussioncontrasting

confidence: 69%

Section: Discussioncontrasting

confidence: 69%

Section: Discussionmentioning

confidence: 99%

Section: Oligosaccharides Tested In Angiogenesis Assaysmentioning

confidence: 99%

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Synthetic Oligosaccharide Stimulates and Stabilizes Angiogenesis: Structure-Function Relationships and Potential Mechanisms

Mousa¹,

Feng²,

Xie³

et al. 2006

Journal of Cardiovascular Pharmacology

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“…Therefore, molecular modification and structure improvement of polysaccharides are a hot topic in recent years. Many studies have demonstrated that biological activities of polysaccharides are increased by molecular modification [3,7,8,21].…”

Section: Introductionmentioning

confidence: 99%

Sulfated modification and cytotoxicity of Portulaca oleracea L. polysaccharides

Chen

Jin

et al. 2010

Glycoconj J

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A water-soluble polysaccharide (POP1) was isolated from Portulaca oleracea L. Four sulfated derivatives of POP1 (POP1-s1, POP1-s2, POP1-s3 and POP1-s4) were prepared by chlorosulfonic acid method with N,N-Dicyclohexylcarbodiimide (DCC) as a dehydration-condensation agent. FT-IR spectra and 13C NMR spectra indicated the sulfated groups had been introduced at the C-6 and C-2 positions of POP1. Sulfated derivatives had different degree of substitution (DS) ranging from 1.01 to 1.81, and different weight-average molecular mass (Mw) ranging from 41.4 to 48.5 KDa. Sulfated derivatives except POP1-s5 inhibited the growth of HepG2 cells and Hela cells in vitro significantly, which indicated that sulfated modification could enhance cytotoxicity of POP1 on tumor cells. Flow cytometric studies revealed that sulfated derivatives could mediate the cell-cycle arrest of Hela cells in the S phase.

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Synthesis of an oligosaccharide–polylysine dendrimer with reducing sugar terminals leading to acquired immunodeficiency syndrome vaccine preparation

Baigude

Katsuraya

Tokunaga

et al. 2005

J. Polym. Sci. A Polym. Chem.

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A novel cellobiose-polylysine dendrimer with reducing sugar terminals was synthesized in which the reactive reducing end of a disaccharide cellobiose was directing outward. Hexa-O-benzyl-4Ј-(1-carboxyethyl)-cellobioside (HBCEC) was synthesized through the reaction of a 4Ј-hydroxyl group of benzyl hexa-O-benzyl-cellobioside with methyl 2-chloropropionate, followed by the removal of the methyl ester group. HBCEC was reacted with polylysine dendrimer generation 3 (G3) to produce benzylated cellobiose-polylysine dendrimer G3. After debenzylation, a cellobiose-polylysine dendrimer G3 was obtained in which the reducing end of the cellobiose was the terminal group of the dendrimer. For the preparation of a dendrimer-type acquired immunodeficiency syndrome vaccine, the cellobiose-polylysine dendrimer was reacted with a tripeptide (glycyl-prolyl-leucine) and a cyclic oligopeptide from the human immunodeficiency virus by reductive amination; this produced a tripeptide-bound cellobiose-polylysine dendrimer and an insoluble compound, respectively. The structure analysis was carried out with NMR and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. 13 (36 mg, 8.7 mol) and Gly-Pro-Leu (20 mg, 70 mol) were dissolved in a 0.1 M borate buffer (pH 9.0, 5 mL). After BH 3 /pyridine (80 mL, 800 mmol) was added, the solution was stirred at 37°C for 5 days. The resulting compound was purified by dialysis and then freeze-dried from water to produce Gly-Pro-Leu-cellobiose-polylysine dendrimer G3 (14; 32 mg) as a white powder. Preparation of Cyclic V3 Loop-Cellobiose-Polylysine Dendrimer G3The cyclic V3 loop (10 mg, 3 mmol) was suspended in 5 mL of a 0.1 M borate buffer (pH 9.0). After cellobiose-polylysine dendrimer (12 mg, 3 mmol) and BH 3 /pyridine (12 mL, 118 mmol) were added, the suspension was stirred at 37°C for 5 days. OLIGOSACCHARIDE-POLYLYSINE DENDRIMER

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Synthesis and antitumor activities of glucan derivatives

Cited by 16 publications

References 43 publications

Synthetic Oligosaccharide Stimulates and Stabilizes Angiogenesis: Structure-Function Relationships and Potential Mechanisms

Synthetic Oligosaccharide Stimulates and Stabilizes Angiogenesis: Structure-Function Relationships and Potential Mechanisms

Sulfated modification and cytotoxicity of Portulaca oleracea L. polysaccharides

Synthesis of an oligosaccharide–polylysine dendrimer with reducing sugar terminals leading to acquired immunodeficiency syndrome vaccine preparation

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