Selectively O-acylated glycosaminoglycan derivatives

Petitou, Maurice; Coudert, Catherine; Level, Michel; Lormeau, J C; Zuber, Martin; Simenel, Catherine; Fournier, Jean-Paul; Choay, J

doi:10.1016/0008-6215(92)85010-w

Cited by 29 publications

(20 citation statements)

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“…The result indicated that most of total OH groups were introduced into propionoyl groups, since the percentage of degree of substitution was ~95% after 48 h at 60 °C (Table 1). Under similar reaction conditions, Petitou et al [12] successfully introduced acyl groups into other glycosaminoglycans, such as heparin, dermatan sulfate, and chondroitin sulfate.…”

Section: Resultsmentioning

confidence: 99%

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Preparation and Characterization of O-Acylated Fucosylated Chondroitin Sulfate from Sea Cucumber

Gao

Shao

et al. 2012

Marine Drugs

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Fucosylated chondroitin sulfate (FuCS), a kind of complex glycosaminoglycan from sea cucumber, has potent anticoagulant activity. In order to understand the relationship between structures and activity, the depolymerized FuCS (dFuCS) was chosen to prepare its derivates by selective substitution at OH groups. Its O-acylation was carried out in a homogeneous way using carboxylic acid anhydrides. The structures of O-acylated derivatives were characterized by NMR. The results indicated that the 4-O-sulfated fucose residues may be easier to be acylated than the other ones in the sulfated fucose branches. But the O-acylation was always accompanied by the β-elimination, and the degree of elimination was higher as that of acylation was higher. The results of clotting assay indicated that the effect of partial O-acylation of the dFuCS on their anticoagulant potency was not significant and the O-acylation of 2-OH groups of 4-O-sulfated fucose units did not affect the anticoagulant activity.

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Section: Resultsmentioning

confidence: 99%

“…For example, Petitou et al [12] selectively introduced acyl groups into heparin and its fragments. The measurements of anticoagulant and anti-HIV activities of these compounds indicated that their anti-HIV activities did not differ markedly from that of heparin, although their anticoagulant activities were much lower [13].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterization of O-Acylated Fucosylated Chondroitin Sulfate from Sea Cucumber

Gao

Shao

et al. 2012

Marine Drugs

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“…As the key step in glucosinolate synthesis, as originally developed by Benn,17 is the coupling of a protected thioglucose (4) with a suitable oximyl chloride (5) (Scheme 2), the initial synthetic target was 2,3,4,6- was used to make methyl-2,3,4-tri-O-benzyl-a-d-glucopyranoside which was oxidized to 7 in two steps using Swern conditions 19 followed by pyridinium dichromate (PDC) in methanol/dichloromethane, to afford the methyl ester (7) in 58% yield. This oxidation is also reported in the literature in one step using either chromium trioxide in sulfuric acid/acetone 20,21 or PDC in DMF, 22 followed by methylation with diazomethane in each case. The first two deuterium atoms where then introduced at C-6 by reduction with lithium aluminium deuteride in 91% yield, followed by benzylation to give the methyl 2,3,4-tribenzyl-a-D-[6-2 H 2 ]glucopyranoside (8) (Scheme 3).…”

Section: Resultsmentioning

confidence: 64%

The synthesis of glucosinolates deuterium labelled in the glucose fragment

Robertson

Botting

2006

J Label Compd Radiopharm

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Section: Methodsmentioning

confidence: 99%

“…Standard heparin from pig intestinal mucosa (sodium salt, average molecular weight of 12 kDa, specific activity of 168 USP/mg) was from Sanofi Pharma Industrie (France). Periodate depolymerized heparin was prepared as previously described (European patent A-0287477) and selectively O-hexanoylated as described by Petitou et al (1992) to obtain compound SR 80037. [3H]-stauros~orine (160 Ci/ mmol), [3H]-phorbol-12,13-dibutyrate 80 Ci/mmol), (eth~len-[~H])-ketanserin (68 Ci/mmol), and t3H(G)1-labeled sodium heparin (porcine mucosal heparin, prepared by reduction with sodium [3Hl-borohydride, 130 U/mg, specific radioactivity 0.29 mCi/mg) were obtained from New England Nuclear (Dupont, France).…”

Section: Methodsmentioning

confidence: 99%

Characterization of rat aortic smooth muscle cells resistant to the antiproliferative activity of heparin following long‐term heparin treatment

Bârzu

Pascal

Herbert

et al. 1994

Journal Cellular Physiology

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Vascular smooth muscle cells (SMC) do not represent a homogeneous population (Schwartz et al., 1990, Am. J. Pathol. 136: 1417-1428). Cellular clones resistant to the antiproliferative activity of heparin were isolated from rat aortic SMC cultures (Pukac et al., 1990, Cell Regul., 1:435-443; San Antonio et al., 1993, Arterioscler. Thromb., 13:748-757) and from explant of human arterial restenotic lesions (Chan et al., 1993, Lancet, 341:341-342). We have shown in the present study that long-term treatment (growth medium supplemented with 200 micrograms/ml heparin, from the second to the tenth passage) of rat aortic SMC, without cell cloning, resulted in a significant loss of sensitivity to the growth inhibition by heparin and its derivatives. The heparin resistance was stable after growing cells for two passages in heparin-free medium, suggesting the selection of a particular phenotype. We tried to characterize these cells and to determine the causes of the resistance to the growth inhibition by heparin. Heparin-treated SMC (HT-SMC) were smaller than their control culture at the same passage, expressed less alpha-SM actin, and did not overgrow after reaching confluence. As in the heparin-resistant clones (San Antonio et al., 1993, Cell Regul., 1:435-443) expression of alpha-SM actin could be increased in HT-SMC by heparin addition before Western blotting. Heparin resistance was associated with a tenfold decrease in [3H]-heparin binding capacity (Bmax = 1.9 x 10(6) sites per cell) compared to control cultures (Bmax = 1.7 x 10(7) sites per cell), which was irreversible after growing the cells for two additional passages in heparin-free medium. We also investigated protein kinase C (PKC) in HT-SMC in terms of both enzymatic activity and protein expression (evaluated by [3H]-staurosporine and [3H]-phorbol-12,13-dibutyrate binding). We found that HT-SMC had only half the PKC activity and expression as control SMC. Therefore, long-term treatment of rat aortic SMC with heparin allowed the selection of a less differentiated subpopulation of cells, exhibiting low sensitivity to the growth inhibition by heparin, which could be related to the low capacity of binding heparin and to a lower PKC activity and/or expression.

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Selectively O-acylated glycosaminoglycan derivatives

Cited by 29 publications

References 9 publications

Preparation and Characterization of O-Acylated Fucosylated Chondroitin Sulfate from Sea Cucumber

Preparation and Characterization of O-Acylated Fucosylated Chondroitin Sulfate from Sea Cucumber

The synthesis of glucosinolates deuterium labelled in the glucose fragment

Characterization of rat aortic smooth muscle cells resistant to the antiproliferative activity of heparin following long‐term heparin treatment

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