Stereocontrolled Synthesis of Plasmalogen-Type Lipids from Glyceryl Ester Precursors

Rui, Yuanjin; Thompson, David H.

doi:10.1021/jo00098a040

Cited by 15 publications

(10 citation statements)

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“…Significant efforts were put forward by Thompson and colleagues to design and synthesize plasmenylcholine molecules [56,57]. Photo-oxidation was initiated by several light-responsive molecules such as Zn-phthalocyanine, octabutoxyphthalocyanine, and bacterio-chlorophyll-a.…”

Section: Light-sensitive Liposomes-backgroundmentioning

confidence: 99%

Light-sensitive lipid-based nanoparticles for drug delivery: design principles and future considerations for biological applications

Yavlovich

Smith

Gupta

et al. 2010

Molecular Membrane Biology

155

113

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Radiation-based therapies aided by nanoparticles have been developed since decades, and can be primarily categorized into two main platforms. First, delivery of payload of photo-reactive drugs (photosensitizers) using the conventional nanoparticles, and second, design and development of photo-triggerable nanoparticles (primarily liposomes) to attain light-assisted on-demand drug delivery. The main focus of this review is to provide an update of the history, current status and future applications of photo-triggerable lipid-based nanoparticles (light-sensitive liposomes). We will begin with a brief overview on the applications of liposomes for delivery of photosensitizers, including the choice of photosensitizers for photodynamic therapy, as well as the currently available light sources (lasers) used for these applications. The main segment of this review will encompass the details on the strategies to develop photo-triggerable designer liposomes for their drug delivery function. The principles underlying the assembly of photoreactive lipids into nanoparticles (liposomes) and photo-triggering mechanisms will be presented. We will also discuss factors that limit the applications of these liposomes for in vivo triggered drug delivery and emerging concepts that may lead to the biologically viable photo-activation strategies. We will conclude with our view point on the future perspectives of light-sensitive liposomes in the clinic.

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Section: Light-sensitive Liposomes-backgroundmentioning

confidence: 99%

Light-sensitive lipid-based nanoparticles for drug delivery: design principles and future considerations for biological applications

Yavlovich

Smith

Gupta

et al. 2010

Molecular Membrane Biology

155

113

View full text Add to dashboard Cite

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“…What is clear is that Takai alkylidenation is more reliable and generally higher yielding than the corresponding methylenation. Pivaloate esters 105 and formate esters are poor substrates for Takai alkylidenation, 106 and lactones produce mixtures of enol ethers and ketones (Scheme 70). Takai reagents are prepared by addition of 4 eq.…”

Section: Takai Reagentsmentioning

confidence: 99%

Titanium reagents for the alkylidenation of carboxylic acid and carbonic acid derivatives

Hartley

McKiernan

2002

J. Chem. Soc., Perkin Trans. 1

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“…Rev., 2011, 40, 5170-5180 5173 of plasmalogen-type lipids from glycerol ester precursors, Thompson showed that the combination of hexane as the solvent with slow addition of triethylaluminium to maintain the reaction temperature at 0 1C significantly enhanced the stereoselectivity of the reaction (Scheme 7b). 33 This methodology has been exploited in a number of total syntheses for example that of colneleic acid reported by Corey (Scheme 7c). 34 Other hydride sources are also viable and may offer advantages.…”

Section: Synthesis Involving P-activated Enols 31 C-h Bond Formation-...mentioning

confidence: 99%

“…As with all cross-coupling strategies the Scheme 7 Palladium catalysed reduction of enol phosphates with Et 3 Al. 31,33,34 Scheme 8 Palladium catalysed transfer hydrogenation of enol phosphates. 35,36 most common processes are those combining two sp 2 carbon atoms.…”

Section: C-c Bond Formation-alkylationmentioning

confidence: 99%

Transition metal-catalysed cross-coupling reactions of P-activated enols

2011

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Transition metal catalysed cross-coupling reactions are ubiquitous in organic chemistry providing an impressive technique for C-C bond formation. Whilst many electrophilic partners have been described for these reactions, aryl and vinyl phosphates, phosphonates and phosphonites can offer advantages in terms of preparation, stability and reactivity profile. This critical review summarises the advances made to date utilising P-activated enols in metal-catalysed cross-coupling reactions (97 references).

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Stereocontrolled Synthesis of Plasmalogen-Type Lipids from Glyceryl Ester Precursors

Cited by 15 publications

References 0 publications

Light-sensitive lipid-based nanoparticles for drug delivery: design principles and future considerations for biological applications

Light-sensitive lipid-based nanoparticles for drug delivery: design principles and future considerations for biological applications

Titanium reagents for the alkylidenation of carboxylic acid and carbonic acid derivatives

Transition metal-catalysed cross-coupling reactions of P-activated enols

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