Biocompatible non -ionic surfactants for biomedical utilization: double- tailed hydrocarbon and/or fluorocarbon synthetic glycolipids

Pucci, Bernard; Guedj, Camille; Pavia, A. A.

doi:10.1016/s0960-894x(00)80276-0

Cited by 9 publications

(5 citation statements)

References 7 publications

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“…Although the coupling reaction to 3a has already been performed with dicyclohexylcarbodiimide (DCC), [18] in our hands, the best results were obtained by using TBTU/HOBt [19] and diisopropylethylamine (DIPEA) in CH 2 Cl 2 at 40°C. Subsequent Boc deprotection with trifluoroacetic acid (TFA) and anisole [20] then set the stage for further attachment of the perfluoroalkylated fatty acid.…”

Section: Synthesis Of Lysine-based Fluorinated Amphiphilesmentioning

confidence: 91%

Synthesis and Antibody Binding of Highly Fluorinated Amphiphilic MUC1 Glycopeptide Antigens

et al. 2011

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The analysis of humoral immune responses is of great importance for basic and clinical research. Mapping the structural requirements of epitope recognition with modified tumor-associated carbohydrate antigens allows both the development of biomarkers and the design of synthetic anticancer vaccines. For this purpose, double-tailed hydrocarbon/fluorocarbon membrane anchors have been prepared and conjugated to a T N dipeptide. Furthermore, a novel hydrophobized MUC1 tandem repeat glycopeptide antigen was fully assembled on a solid support and its specific binding to dif-

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Section: Synthesis Of Lysine-based Fluorinated Amphiphilesmentioning

confidence: 91%

Synthesis and Antibody Binding of Highly Fluorinated Amphiphilic MUC1 Glycopeptide Antigens

et al. 2011

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“…3-Aminopropyl dioctadecylamine (DODAAM, Scheme 1) was prepared by the Michael addition of dioctadecylamine (DODA, Fluka, Switzerland) to acrylonitrile at 80 °C and subsequent reduction with LiAlH 4 in dry tetrahydrofuran (16). Maltose lactone was prepared by the oxidation of maltose with iodine, and subsequent lactonization with cation-exchange resins (Amberlite IR-120 B, H + -form) and silver carbonate as previously reported (11,17,18). Concanavalin A (Con A) from C. ensiformis, L-R-dimyristoyl phosphatidylcholine (DMPC), and N,N′-R, -dicarbobenzoxy-L-lysine (di-Z-L-Lys) were from Sigma.…”

Section: Methodsmentioning

confidence: 99%

Recognition of Novel Lipopolypeptides with Many Pendent Sugar Residues by Lectin

2000

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A lipid-polypeptide conjugate (lipo-polypeptide) was obtained by the ring-opening polycondensation of N-epsilon-Z-L-lysine N-carboxyanhydride (NCA) using 3-aminopropyl dioctadecylamine as initiator and subsequent deprotection. Maltose lactone was coupled with the lipo-polypeptide to give novel amphiphiles which carried many maltoamide residues as pendent groups. The sugar group-carrying amphiphiles incorporated in phospholipid liposomes were recognized by a lectin from Canavalia ensiformis (Con A), which was proven by the increase in turbidity of the liposome suspension after mixing with the lectin. The recognition was largely affected by the degree of polymerization of lysine residues and the surface density of the amphiphile in the liposomes. The association constant (K(ass)) of Con A with maltoamide residues on the liposome was much larger than those for small molecular weight sugars due to the "cluster effect".

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“…The investigation of carbohydrate derived fluorinated amphiphiles has been expending in the recent years [61]. Several works describing the preparation of fluorinated alkyl amides [66][67][68][69][70][71][72][73], ureas [74,75] or carbamates [76][77][78][79][80] derived from carbohydrates have been published. Several works describing the preparation of fluorinated alkyl amides [66][67][68][69][70][71][72][73], ureas [74,75] or carbamates [76][77][78][79][80] derived from carbohydrates have been published.…”

Section: N-(fluorinated Alkyl)-surfactantsmentioning

confidence: 99%

“…Treatment of 1-amino-1-deoxy-lactitol derivative 56 with the fluorinated acylating reagent 57 gave compound 58 (yield 20%) [72].F-alkyl-D-gluconamides 59[68,72] and F-alkyl-Dlactobionamides 61 and 63[65,[68][69][70][71][72][73] were obtained from Treatment of 1-amino-1-deoxy-lactitol derivative 56 with the fluorinated acylating reagent 57 gave compound 58 (yield 20%) [72].F-alkyl-D-gluconamides 59[68,72] and F-alkyl-Dlactobionamides 61 and 63[65,[68][69][70][71][72][73] were obtained from…”

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confidence: 99%

Carbohydrate-Derived Surfactants

Hyaric¹

2005

MROC

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The constant need for products obtained from natural raw materials instead of non-renewable petroleum feedstocks has led to a lot of effort on developing new "natural" surfactants. Most important among these are surfactants derived from carbohydrates and plant oils such as coconut or palm kernel. These compounds find applications in cosmetics, food manufacture, biology, etc, and some of them are studied for their liquid crystalline properties.

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Biocompatible non -ionic surfactants for biomedical utilization: double- tailed hydrocarbon and/or fluorocarbon synthetic glycolipids

Cited by 9 publications

References 7 publications

Synthesis and Antibody Binding of Highly Fluorinated Amphiphilic MUC1 Glycopeptide Antigens

Synthesis and Antibody Binding of Highly Fluorinated Amphiphilic MUC1 Glycopeptide Antigens

Recognition of Novel Lipopolypeptides with Many Pendent Sugar Residues by Lectin

Carbohydrate-Derived Surfactants

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