53380-10-2Relevant academic research and scientific papers
Dendrimeric-like hexadecahydroxylated zinc phthalocyanine
Alpugan, Serkan,Garcia, Guillaume,Poyer, Florent,Durmu?, Mahmut,Maillard, Philippe,Ahsen, Vefa,Dumoulin, Fabienne
, p. 596 - 603 (2013)
The design of a dendrimeric-like diglycerol-tetrasubstituted Zn(II) phthalocyanine resulted in a remarkably water-soluble compound due to the presence of 16 hydroxyls. Several parameters relevant to evaluate the photodynamic efficiency of a potentiel photosensitizer such as: aggregation behavior, fluorescence properties, singlet oxygen generation, binding to a carrier protein model (Bovine Serum Albumin) and partition coefficient have been measured. Biocompatibility was demonstrated by dark cytotoxicity in in vitro experiments. The absence of phototoxicity can be explained by an elevated hydrophilicity. All the collected data have confirmed that this new substitution pattern is promising to be used on phthalocyanines aiming at being photodynamic therapy agents.
Dendritic Oligoglycerol Regioisomer Mixtures and Their Utility for Membrane Protein Research
Urner, Leonhard H.,Goltsche, Katharina,Selent, Marleen,Liko, Idlir,Schweder, Marc-Philip,Robinson, Carol V.,Pagel, Kevin,Haag, Rainer
supporting information, p. 2537 - 2542 (2020/12/30)
Dendrons are an important class of macromolecules that can be used for a broad range of applications. Recent studies have indicated that mixtures of oligoglycerol detergent (OGD) regioisomers are superior to individual regioisomers for protein extraction. The origin of this phenomenon remains puzzling. Here we discuss the synthesis and characterization of dendritic oligoglycerol regioisomer mixtures and their implementation into detergents. We provide experimental benchmarks to support quality control after synthesis and investigate the unusual utility of OGD regioisomer mixtures for extracting large protein quantities from biological membranes. We anticipate that our findings will enable the development of mixed detergent platforms in the future.
POLYANIONIC DELIVERY OF NUCLEIC ACIDS
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Paragraph 0210; 0211, (2018/09/28)
Disclosed are dendritic anionic lipids which are compounds of Formula (I) : wherein R and R1 are non-polar groups, L is a linking moiety, and Dm is a dendritic moiety of m generations, each as defined herein. These dendritic anionic lipids are useful for delivery and expression of m RNA and encoded protein, e.g., as a component of liposomal delivery vehicle, and accordingly can be useful for treating various diseases, disorders and conditions, such as those associated with deficiency of one or more proteins.
COATED SILICON SURFACES, THEIR MANUFACTURE AND APPLICATION
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Page/Page column 17, (2016/09/26)
Process for coating silicon surfaces comprising the step of treating said silicon surface with at least one (co)polymer A, comprising in copolymerized form (A) at least one comonomer bearing a structural unit according to the general formula (I) wherein R1 is formula (A) m is independently from each other selected from zero to 6, n is independently from each other selected from zero to 200, A1 are different or identical and selected from C2-C10-alkylene, C6-C10-arylene and C7-C10- aralkylene, (B) optionally, at least one ethylenically unsaturated carboxylic acid, (C) optionally, at least one further monomer.
Introducing Chirality into Nonionic Dendritic Amphiphiles and Studying Their Supramolecular Assembly
Kumar, Sumit,Ludwig, Kai,Schade, Boris,Von Berlepsch, Hans,Papp, Ilona,Tyagi, Rahul,Gulia, Monika,Haag, Rainer,B?ttcher, Christoph
supporting information, p. 5629 - 5636 (2016/04/20)
Chiral head groups have been introduced into water-soluble hydroxyl-terminated nonionic amphiphiles and the impact of the head group stereochemistry on the supramolecular ultrastructures has been studied. Enantiomeric isomers were compared with the achiral meso form and the racemic mixture by means of cryogenic transmission electron microscopy and circular dichroism spectroscopy. Structurally, all amphiphiles are composed of the first-generation hydrophilic polyglycerol head group coupled to a single hydrophobic hexadecyl chain through an amide linkage and diaromatic spacer. The enantiomers aggregate to form twisted ribbons with uniform handedness, whereas the meso stereoisomer and racemic mixture produce elongated assemblies, namely, tubules and platelets, but without a chiral ultrastructure. Simulations on the molecular packing geometries of the stereoisomers indicate different preferential assembly routes that explain the individual supramolecular aggregation behavior.
NOVEL ETHER COMPOUND
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Page/Page column 8-9, (2010/04/24)
The present invention provides a novel ether compound represented by formula (1): wherein R represents a hydrocarbon group having 4 to 22 carbon atoms.
Novel chemoenzymatic methodology for the regioselective glycine loading on polyhydroxy compounds
Malhotra, Shashwat,Calderon, Marcelo,Prasad, Ashok K.,Parmar, Virinder S.,Haag, Rainer
scheme or table, p. 2228 - 2237 (2010/07/04)
In the present work, we have developed a highly efficient temperature-dependent chemo-enzymatic methodology for the regioselective synthesis of novel esters of glycerol, G1 tri-glycerol dendrons and related esters for the first time using 4-nitrophenyl 2-(tert-butoxycarbonyl)acetate (Boc-gly-Ph-pNO2) (2) as the acylating agent. This methodology offers efficient and controlled loading of amino acid (glycine) on polyhydroxy compounds.
A convergent approach to biocompatible polyglycerol "click" dendrons for the synthesis of modular core-shell architectures and their transport behavior
Wyszogrodzka, Monika,Haag, Rainer
experimental part, p. 9202 - 9214 (2009/10/01)
Dendrimers are an important class of polymeric materials for a broad range of applications in which monodispersity and multivalency are of interest. Here we report on a highly efficient synthetic route towards bifunctional polyglycerol dendrons on a multigram scale. Commercially available triglycerol (1), which is highly biocompatible, was used as starting material. By applying Williamson ether synthesis followed by an ozonolysis/reduction procedure, glycerol-based dendrons up to the fourth generation were prepared. The obtained products have a reactive core, which was further functionalized to the corresponding monoazido derivatives. By applying cop per(I)-catalyzed 1,3-dipolar cycloaddition, so-called "click" coupling, a library of core-shell architectures was prepared. After removal of the 1,2-diol protecting groups, water-soluble coreshell architectures 24-27 of different generations were obtained in high yields. In the structure-transport relationship with Nile red we observe a clear dependence on core size and generation of the polyglycerol dendrons.
New approaches towards monoamino polyglycerol dendrons and dendritic triblock amphiphiles
Wyszogrodzka, Monika,Moews, Katrin,Kamlage, Stefan,Wodzinska, Joanna,Plietker, Bernd,Haag, Rainer
, p. 53 - 63 (2008/09/17)
In order to improve the water solubility of nonpolar compounds such as drugs or dyes, new amphiphilic molecules are needed. In this paper we describe a new class of triblock amphiphiles that we have synthesized by a straightforward convergent approach. These amphiphiles each consist of a nonpolar biphenyl core and a polar shell based on various generations of monoamino polyglycerol dendrons, coupled to the core through amide linkages (1). For the synthesis of these monoamino dendrons we applied a simple iterative two-step process based on allylation of an alcohol group and catalytic dihydroxylation. As starting materials, D,L-serine/serinol and - in a second, similar pathway - commercially available triglycerol were used. The transport behavior of these defined triblock amphiphiles was then investigated with the nonpolar dye Nile Red in water. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
EMULSION-TYPE EXTERNAL PREPARATIONS FOR SKIN
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Page/Page column 16, (2008/12/05)
The emulsified external skin preparation of the present invention is characterized by comprising a polyglycerol derivative represented by formula (1): wherein, m + 2 represents the average polymerization degree of polyglycerol and 1≦m≦4; R1 is a hydrocarbon group having 1 to 4 carbon atoms or a hydrogen atom; AO is an oxyalkylene group having 3 to 4 carbon atoms; and n is the average addition mole number of the oxyalkylene group and 1≦m×n≦200. In a water-in-oil type external skin preparation, and especially in that containing a polar oil or a silicone oil, emulsion stability is improved. In an oil-in-water type external skin preparation, feeling in use and emulsion stability are improved. Especially, in an oil-in-water type external skin preparation containing hydrophobized powder, powder dispersion stability is improved as well as feeling in use and emulsion stability.
