Isothiocyanates and cyclic thiocarbamates of α, α′-trehalose, sucrose, and cyclomaltooligosaccharides

García-Fernández, José Manuel; Mellet, Carmen Ortiz; Blanco, José L. Jiménez; Mota, J. Fuentes; Gadelle, A.; Coste-Sarguet, Annie; Defaye, J

doi:10.1016/0008-6215(94)00312-4

Cited by 88 publications

(37 citation statements)

References 31 publications

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“…2. We first exchanged both primary hydroxyls with iodo groups by triphenylphosphine-mediated substitution as described in a previously-published procedure [35] and all secondary hydroxyl groups were acetylated with acetic anhydride in pyridine to yield compound 2 , which was purified by recrystallization from ethanol. (In the case of incomplete iodine substitution, monoiodotrehalose, along with the peracetylated trehalose as side products, can be removed from the product mixture with column chromatography using a mixture of 5% diethyl ether in dichloromethane as eluent.)…”

Section: Resultsmentioning

confidence: 99%

Cationic glycopolymers for the delivery of pDNA to human dermal fibroblasts and rat mesenchymal stem cells

et al. 2012

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Progenitor and pluripotent cell types offer promise as regenerative therapies but transfecting these sensitive cells has proven difficult. Herein, a series of linear trehalose-oligoethyleneamine “click” copolymers were synthesized and examined for their ability to deliver plasmid DNA (pDNA) to two progenitor cell types, human dermal fibroblasts (HDFn) and rat mesenchymal stem cells (RMSC). Seven polymer vehicle analogs were synthesized in which three parameters were systematically varied: the number of secondary amines (4–6) within the polymer repeat unit (Tr433, Tr530, and Tr632), the end group functionalities [PEG (Tr4128PEG-a, Tr4118PEG-b), triphenyl (Tr4107-c), or azido (Tr499-d)], and the molecular weight (degree of polymerization of about 30 or about 100) and the biological efficacy of these vehicles was compared to three controls: Lipofectamine 2000, JetPEI, and Glycofect. The trehalose polymers were all able to bind and compact pDNA polyplexs, and promote pDNA uptake and gene expression [luciferase and enhanced green fluorescent protein (EGFP)] with these primary cell types and the results varied significantly depending on the polymer structure. Interestingly, in both cell types, Tr433 and Tr530 yielded the highest luciferase gene expression. However, when comparing the number of cells transfected with a reporter plasmid encoding enhanced green fluorescent protein, Tr433 and Tr4107-c yielded the highest number of HDFn cells positive for EGFP. Interestingly, with RMSC, all of the higher molecular weight analogs (Tr4128PEG-a, Tr4118PEG-b, Tr4107-c, Tr499-d) yielded high percentages of cells positive for EGFP (30–40%).

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Section: Resultsmentioning

confidence: 99%

Cationic glycopolymers for the delivery of pDNA to human dermal fibroblasts and rat mesenchymal stem cells

et al. 2012

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“…[72][73][74][75][76] The reproducibility and high yield of these transformations have provided an excellent model system to test the suitability of different methodologies towards glycocluster synthesis, which are itemized hereinafter. Moreover, in the resulting ''jellyfish-type'' arrangement the wider secondary rim of the CD platform remains open for the entrance of suitable guests to the internal cavity, potentially retaining the capacity for drug encapsulation and delivery.…”

Section: Primary Face-anchored ''Jellyfish-type'' Glycoclustersmentioning

confidence: 99%

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

2013

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“…1 mmol of 1a, 1b or 1g [12] was suspended in a 1:1:1 (v/v) solution of 25% aqueous NH 3 , water and ethanol (60 ml) and 6, 7 or 8 equivalents, respectively, of freshly distilled CS 2 were added. The reaction mixture was vigorously stirred for 6 h at room temperature (the solid dissolves slowly), then precipitated with acetone (250 ml).…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…The cyclodextrin receptors were prepared by reaction of the readily available per-6-amino-6-deoxycyclodextrins 1a -g [12] with stoichiometric amounts of CS 2 in ammonia solution (Fig. 1).…”

Section: Syntheses and Characterization Of The Cyclodextrin Hostsmentioning

confidence: 99%

Molecular Recognition of Aromatic Nitro Compounds at Cyclodextrin Dithiocarbamate-modified Electrodes

Almirall

Fragoso

Cao

et al. 2003

Supramolecular Chemistry

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Silver electrodes were modified by the adsorption of a-, b-, and g-cyclodextrin dithiocarbamates (2a -g) and characterized by reductive desorption experiments. Their molecular recognition properties were studied by cyclic voltammetry using three families of positional isomers of aromatic nitro compounds. Electrodes modified with 2a and 2b were selective for meta and para isomers while 2g showed little selectivity. These observations are explained in terms of cavity sizes and guest structure. Computational studies suggest that the main reason for the observed selectivity is the different position of the NO 2 group in ortho and para isomers with respect to the CD cavity.

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Isothiocyanates and cyclic thiocarbamates of α, α′-trehalose, sucrose, and cyclomaltooligosaccharides

Cited by 88 publications

References 31 publications

Cationic glycopolymers for the delivery of pDNA to human dermal fibroblasts and rat mesenchymal stem cells

Cationic glycopolymers for the delivery of pDNA to human dermal fibroblasts and rat mesenchymal stem cells

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

Molecular Recognition of Aromatic Nitro Compounds at Cyclodextrin Dithiocarbamate-modified Electrodes

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