- Double conjugation strategy to incorporate lipid adjuvants into multiantigenic vaccines
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Conjugation of multiple peptides by their N-termini is a promising technique to produce branched multiantigenic vaccines. We established a double conjugation strategy that combines a mercapto-acryloyl Michael addition and a copper-catalysed alkyne-azide 1,3-dipolar cycloaddition (CuAAC) reaction to synthesise self-adjuvanting branched multiantigenic vaccine candidates. These vaccine candidates aim to treat cervical cancer and include two HPV-16 derived epitopes and a novel self-adjuvanting moiety. This is the first report of mercapto-acryloyl conjugation applied to the hetero conjugation of two unprotected peptides by their N-termini followed by a CuAAC reaction to conjugate a novel synthetic lipoalkyne self-adjuvanting moiety. In vivo experiments showed that the most promising vaccine candidate completely eradicated tumours in 46% of the mice (6 out of 13 mice).
- Hussein, Waleed M.,Liu, Tzu-Yu,Maruthayanar, Pirashanthini,Mukaida, Saori,Moyle, Peter M.,Wells, James W.,Toth, Istvan,Skwarczynski, Mariusz
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Read Online
- Double-hydrophobic group surfactant and preparation method thereof
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The invention relates to a surfactant, in particular to a double-hydrophobic group surfactant and a preparation method thereof. The molecular structural formula of the double-hydrophobic group surfactant is shown in the description. The preparation method for the double-hydrophobic group surfactant comprises the steps that the reaction formula of the method is shown in the description, ethanol (ROH) and epoxy chloropropane are taken as raw materials, a phase transfer catalyst is added, under the stirring and reflux condensing conditions, the reaction is conducted for 2 h-8 h at the temperatureof 45 DEG C-65 DEG C, and the molar ratio of the ethanol (ROH) to the epoxy chloropropane to the phase transfer catalyst is 1:2.2-3.5:0.03-0.15; after reaction, the product is subjected to pressure reduction and suction filtration, the generated salt is removed, a saturated sodium chloride aqueous solution is washed to be neutral, and after drying, pressure reduction and distillation, the transparent and slightly viscous liquid is taken as the surfactant and obtained.
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Paragraph 0067-0068
(2019/01/23)
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- Clickosomes - Using triazole-linked phospholipid connectors to fuse vesicles
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Two complementary artificial diether phospholipids were synthesized that can undergo a Cu(i)-catalyzed Huisgen-Sharpless click reaction. The resulting lipid can bridge the membranes of large unilamellar vesicles and cause their aggregation and ultimately their fusion.
- Loosli, Frederic,Doval, David Alonso,Grassi, David,Zaffalon, Pierre-Leonard,Favarger, France,Zumbuehl, Andreas
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supporting information; experimental part
p. 1604 - 1606
(2012/03/11)
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- BODP - A versatile reagent for phospholipid synthesis
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Benzyloxydichlorophosphine (BODP) has been found to be a convenient reagent for the synthesis of phospholipids. A series of artificial ether and ester phospholipids have been prepared in good to high yields. Georg Thieme Verlag Stuttgart New York.
- Zaffalon, Pierre-Leonard,Zumbuehl, Andreas
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experimental part
p. 778 - 782
(2011/04/22)
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- Complex hydrophobe-containing oligomers
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This invention relates to polymers, especially emulsion polymers, and their use for the thickening of a variety of aqueous systems, to methods of thickening utilizing the polymers, to enhancement of such thickening by the addition of surfactants, solvents or non-solvents, and to other aspects including coating compositions and other aqueous systems thickened with the polymers. This invention also relates to new complex hydrophobe-containing oligomers and their use in producing the polymers of this invention.
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- Synthesis and interfacial behavior of three homologous glycero neoglycolipids with various chain lengths
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Three neoglycolipids 1a-c derived from glycerol were synthezised and their molecular arrangements were studied at the air/water interface through Langmuir-Blodgett technique. The common structural features of these neoglycolipids are: a triethyleneglycol spacer at C-2 of glycerol, a GlcNAc hydrophilic head group at the end of the spacer, two saturated aliphatic chains at C-1 and C-3 of glycerol, linked by ether bonds. Compounds 1a-c differ only by the length of their lipid moieties. By increasing the hydrocarbon chain length from C11 to C16, a densely packed state was reached in the monolayer. The compression isotherms displayed an expanded state during the whole compression for compounds 1a and 1c bearing two C11 or one C11 and one C16 chains. Compound 1b bearing two C16 chains displayed a quite different interfacial behavior. The transfer of these monolayers onto a solid substrate can be obtained only with a trigger molecule, a phosphatidic acid.
- Boullanger,Sancho-Camborieux,Bouchu,Marron-Brignone,Morelis,Coulet
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- Complex hydrophobe compounds
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This invention relates to complex hydrophobe compounds and to alkoxylation products, i.e., condensation reaction products of alkylene oxides and complex hydrophobe compounds having at least one active hydrogen. This invention also relates to alkoxylation products that have beneficial, narrow molecular weight ranges.
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- Polysaccharides containing complex hydrophobic groups
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Polysaccharides, including hydroxyethyl cellulose, having complex hydrophobic group substitution, provide latex compositions, such as paints, with improved rheology and stability. Improved processes for producing such polysaccharides are also provided.
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- Synthesis of 1,3-di-O-alkyl-2-O-(β-glycosyl)glycerols bearing oligosaccharides as hydrophilic groups
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A novel series of synthetic glycolipids, 1,3-di-O-alkyl-2-O-(β-glycosyl)glycerols, and their efficient synthetic route were proposed.These glyceroglycolipids were synthesized in good overall yields and stereoselectivity in five steps via trichloroacetimidate glycosylation with 1,3-di-O-alkylglycerols.This route was applied to prepare the glycolipids bearing a cello- or malto-oligosaccharide with a definite number of sugar residues from one to six.Thin-layer chromatography, elemental analysis, nuclear magnetic resonance spectroscopy and infrared absorption spectroscopy confirmed that these glycolipids were chemically pure compounds.Keywords: Glyceroglycolipids; Oligosaccharide headgroups; Synthesis
- Minamikawa, Hiroyuki,Murakami, Teiichi,Hato, Masakatsu
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p. 111 - 118
(2007/10/02)
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- Hypocholesterolemic activity of 1,3 bis(substituted phenoxy) 2 propanones
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A series of 1,3 bis (substituted phenoxy) 2 propanones was found to be active hypocholesterolemic agents at 10 mg/kg/day. The p chloro and p methyl substituted phenoxy compounds possess the highest activity. These compounds did not possess the estrogenic and antifertility activities of the related previously reported derivatives of the bis (β phenylethyl) ketone series. The 1,3 bis (p methylphenoxy) 2 propanone (7) also lowered serum triglycerides and glycerol which appeared to be due to increased levels of serum lipase and reduced activity of liver lipase. There was reduced incorporation of free fatty acids into complex lipids by the liver. Cholesterol was excreted faster in the treated animals.
- Piantadosi,Hall,Wyrick,Ishaq
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p. 222 - 229
(2007/10/12)
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- Synthesis of glycerol 1,3-dihexadecyl ether.
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The synthesis of 1,3-dihexadecyloxy-2-propanol (glycerol 1,3-dihexadecyl ether) is reported. The method is applicable to the preparation of other 1,3-disubstituted glycerols where the substituents are not affected by acid or by catalytic hydrogenolysis conditions.
- Damico,Callahan,Mattson
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