Hydrophile Fette

Heimann, Ulrich; Vögtle, Fritz

doi:10.1002/jlac.198019800605

Cited by 11 publications

(2 citation statements)

References 13 publications

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“…The resultant was extracted with AcOEt (3Â5 mL) to remove 3a. To the aqueous layer was added cation exchange resin (Amberlite IR 120, 10 mL), and the whole mixture was stirred for 0.5 h. The resin was filtered off, and the filtrate was concentrated under reduced pressure to give the desired 2-(2-methoxyethoxy)acetic acid (2b, 64 mg, 0.48 mmol, 96%) as a colorless liquid: 23 In a similar manner, electrooxidations of amphiphilic alcohols 1b-1e, water-soluble alcohols 1g-1m, and water-insoluble alcohols 1n-1r were carried out. 2877, 1959, 1744, 1644, 1457, 1351, 1292, 1248, 1201, 1106 …”

Section: Tempo-mediated Electrooxidation Of Diethylene Glycol Monometmentioning

confidence: 99%

Electroorganic synthesis in oil-in-water (O/W) nanoemulsion: TEMPO-mediated electrooxidation of amphiphilic alcohols in water

et al. 2009

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Section: Tempo-mediated Electrooxidation Of Diethylene Glycol Monometmentioning

confidence: 99%

Electroorganic synthesis in oil-in-water (O/W) nanoemulsion: TEMPO-mediated electrooxidation of amphiphilic alcohols in water

et al. 2009

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“…Such variations at the interfacial region should in turn influence the association of such assemblies with various biomolecules. Ethyleneoxy units were chosen to be the appropriate hydrophilic linkage functionality in these lipid molecules by considering its literature precedence ( , ). Incorporation of oxyethylene units in lipid molecules have been attempted before, also for achieving some specific biological functions ( , ).…”

Section: Introductionmentioning

confidence: 99%

Cationic Oxyethylene Lipids. Synthesis, Aggregation, and Transfection Properties

Bhattacharya

Dileep

2004

Bioconjugate Chem.

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Four cationic lipids (1-4) with oligo-oxyethylene units at the linkage region between the pseudoglyceryl backbone and the hydrocarbon chains have been synthesized. Two of these lipids (1 and 2) have an equal number of (CH(2)CH(2)O)(n)() units attached to both C-1 and C-2 positions of the pseudoglyceryl backbone, making their linkage regions similar, while the other two (3 and 4) are unsymmetrical in terms of the number of oxyethylene units in the linkage. Synthesis of lipids 1 and 2 involved the coupling of benzyl glycerol with the corresponding tosylates as a key step. Each of these lipids formed membranous aggregates when dispersed in water and exhibited clear thermotropic phase transitions typical of vesicular assemblies. The lipids 1-4 exhibited enhanced biological activities as gene transfer agents compared to their non-oxyethylene diether analogue, DHTMA. Transfection experiments using aqueous suspensions of these lipids and also their mixtures with cholesterol or dioleoyl phosphatidyl ethanolamine (DOPE) were performed on HeLa cells. The best transfection activity was demonstrated by unsymmetrical lipid 3, which had two oxyethylene units only at the C-1 position of the pseudoglycerylbackbone.

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Iron Chelators and Therapeutic Uses

Bergeron

McManis

Weimar

et al. 2003

Burger's Medicinal Chemistry and Drug Discovery

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Iron is an essential cofactor in a variety of biological redox reactions; life without this metal is virtually unknown. Because of its exceptionally poor solubility in the biosphere, bacteria produce relatively low molecular weight, virtually iron(III)‐specific, ligands, siderophores, for the purpose of acquiring this transition metal. On the other hand, higher eukaryotes generate proteins to acquire and store iron. In humans, the process of iron absorption and processing is very tightly controlled. However, the lack of an efficient means of elimination can, under certain conditions, result in iron overload, which can elicit oxidative tissue damage through the Fenton reaction. Accordingly, chelating agents have been tested over the last several decades for the purpose of rendering excess iron excretable. The currently accepted therapy for global iron overload, as occurs after repeated blood transfusions, is a siderophore, desferrioxamine B (DFO), which is administered subcutaneously as its mesylate salt (Desferal). Two synthetic agents, diethylenetriamine pentaacetic acid (DTPA) and 1,2‐dimethyl‐3‐hydroxypyridin‐4‐one (Ferriprox, deferiprone, L1), have been used for the treatment of iron overload as well. Unfortunately, all three of these ligands have drawbacks. The kinetics and lack of oral bioavailability of DFO require that this compound be administered subcutaneously 12 h/day, up to 6 days/week, a regimen with which many patients find it difficult to comply. The lack of chelating specificity of DTPA restricts its use to those who cannot tolerate therapy with DFO; questions remain unanswered regarding the efficacy and toxicity profile of L1. The ongoing efforts to find a worthy successor to DFO include the use of a synthetic agent, N,N ′‐bis(2‐hydroxybenzyl)ethylenediamine‐ N,N ′‐diacetic acid (HBED), which, although it would require subcutaneous administration, is significantly more efficient than DFO. Another avenue is using siderophores (e.g., desferrithiocin, parabactin) as platforms from which to design either orally or parenterally active iron chelators. Because of the necessity of striking a balance between efficacy (i.e., sufficient iron chelation) and toxicity (i.e., excessive iron removal), drug development in the arena of iron chelation therapy presents unique challenges. However, the application of sensible drug design principles predicated on our understanding of iron metabolism, modern synthetic techniques, and the use of appropriate animal models should bring about improved therapeutic agents for the treatment of both global and focal iron overload in the years to come.

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Hydrophile Fette

Cited by 11 publications

References 13 publications

Electroorganic synthesis in oil-in-water (O/W) nanoemulsion: TEMPO-mediated electrooxidation of amphiphilic alcohols in water

Electroorganic synthesis in oil-in-water (O/W) nanoemulsion: TEMPO-mediated electrooxidation of amphiphilic alcohols in water

Cationic Oxyethylene Lipids. Synthesis, Aggregation, and Transfection Properties

Iron Chelators and Therapeutic Uses

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