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Hydrophobic Moiety (hydrophobic + moiety)
Selected AbstractsSynthesis and characterization of hydrogels containing biodegradable polymersPOLYMER INTERNATIONAL, Issue 7 2008Adina Cretu Abstract BACKGROUND: Amphiphilic block and graft copolymers constitute a very interesting class of polymers with potential for biomedical applications, due to their special characteristics, which derive from the combination of properties of hydrophilic and hydrophobic moieties. In this work, the synthesis and biodegradation of poly(2-hydroxyethyl methacrylate)- graft -poly(L -lactide) are studied. RESULTS: The graft copolymers were synthesized using the macromonomer technique. In a first step, methacryloyl-terminated poly(L -lactide) macromonomers were synthesized in a wide molecular weight range using different catalysts. Subsequently, these macromonomers were copolymerized with 2-hydroxyethyl methacrylate in order to obtain a graft copolymer. These new materials resemble hydrogel scaffolds with a biodegradable component. The biodegradation was studied in hydrolytic and enzymatic environments. The influence of different parameters (molecular weight, crystallinity, ratio between hydrophilic and hydrophobic components) on the degradation rate was investigated. CONCLUSION: Based on this study it will be possible to tailor the release properties of biodegradable materials. In addition, the materials will show good biocompatibility due to the hydrophilic poly(2-hydroxyethyl methacrylate) hydrogel scaffold. This kind of material has potential for many applications, like controlled drug-delivery systems or biodegradable implants. Copyright © 2008 Society of Chemical Industry [source] Structure,activity relationships for gene activation oestrogenicity: Evaluation of a diverse set of aromatic chemicalsENVIRONMENTAL TOXICOLOGY, Issue 1 2002T. Wayne Schultz Abstract Structure,activity relationships for oestrogenicity were developed based on 120 aromatic chemicals evaluated in the Saccharomyces cerevisiae -based Lac -Z reporter assay. Relative gene activation was compared to 17,-estradiol and varied over eight orders of magnitude. Analysis of the data compared to 17,-estradiol identified three structural criteria that were related to xenoestrogen activity and potency: (1) the hydrogen-bonding ability of the phenolic ring mimicking the A-ring, (2) a hydrophobic centre similar in size and shape to the B- and C-rings, and (3) a hydrogen-bond donor mimicking the 17,-hydroxyl moiety of the D-ring, especially with an oxygen-to-oxygen distance similar to that between the 3- and 17,-hydroxyl groups of 17,-estradiol. Binding data were segregated into activity clusters including strong, moderate, weak, and detectable gene expression, and those compounds that were inactive. The hydrogen-bonding ability of hydroxy group in the 3-position on 17,-estradiol was observed to be essential for gene activation. Compounds with a 4-hydroxyl substituted benzene ring and a hydrophobic moiety of size and shape equivalent to the B-ring of 17,-estradiol were generally observed to be weakly active compounds. Moderately active compounds have a 4-hydroxyl substituted benzene ring with a hydrophobic moiety equivalent in size and shape to the B- and C-ring of 17,-estradiol, or have a high hydrogen-bond donor capacity owing to the presence of halogens on a nonphenolic ring. Strongly active compounds, similar to 4,4,-diethylethylene bisphenol (DES), possess the same hydrophobic ring structure as described for moderately active compounds and an additional hydroxyl group with an oxygen-to-oxygen distance close to that exhibited by the 3- and 17-hydroxyl groups of 17,-estradiol. © 2002 by Wiley Periodicals, Inc. Environ Toxicol 17: 14,23, 2002 [source] Biophysical characterization of synthetic rhamnolipidsFEBS JOURNAL, Issue 22 2006Jörg Howe Synthetic rhamnolipids, derived from a natural diacylated glycolipid, RL-2,214, produced by Burkholderia (Pseudomonas) plantarii, were analyzed biophysically. Changes in the chemical structures comprised variations in the length, the stereochemistry and numbers of the lipid chains, numbers of rhamnoses, and the occurrence of charged or neutral groups. As relevant biophysical parameters, the gel (,) to liquid crystalline (,) phase behavior of the acyl chains of the rhamnoses, their three-dimensional supramolecular aggregate structure, and the ability of the compounds to intercalate into phospholipid liposomes in the absence and presence of lipopolysaccharide-binding protein were monitored. Their biological activities were examined as the ability to induce cytokines in human mononuclear cells and to induce chemiluminescence in monocytes. Depending on the particular chemical structures, the physicochemical parameters as well as the biological test systems show large variations. This relates to the acyl chain fluidity, aggregate structure, and intercalation ability, as well as the bioactivity. Most importantly, the data extend our conformational concept of endotoxicity, based on the intercalation of naturally originating amphiphilic virulence factors into membranes from immune cells. This ,endotoxin conformation', produced by amphiphilic molecules with a hydrophilic charged backbone and apolar hydrophobic moiety, and adopting inverted cubic aggregate structures, causes high mechanical stress in target immune cells on integral proteins, eventually leading to cell activation. Furthermore, biologically inactive rhamnolipids with lamellar aggregate structures antagonize the endotoxin-induced activity in a way similar to lipid A-derived antagonists. [source] Biophysical characterization of the interaction of Limulus polyphemus endotoxin neutralizing protein with lipopolysaccharideFEBS JOURNAL, Issue 10 2004Jörg Andrä Endotoxin-neutralizing protein (ENP) of the horseshoe crab is one of the most potent neutralizers of endotoxins [bacterial lipopolysaccharide (LPS)]. Here, we report on the interaction of LPS with recombinant ENP using a variety of physical and biological techniques. In biological assays (Limulus amebocyte lysate and tumour necrosis factor-, induction in human mononuclear cells), ENP causes a strong reduction of the immunostimulatory ability of LPS in a dose-dependent manner. Concomitantly, the accessible negative surface charges of LPS and lipid A (zeta potential) are neutralized and even converted into positive values. The gel to liquid crystalline phase transitions of LPS and lipid A shift to higher temperatures indicative of a rigidification of the acyl chains, however, the only slight enhancement of the transition enthalpy indicates that the hydrophobic moiety is not strongly disturbed. The aggregate structure of lipid A is converted from a cubic into a multilamellar phase upon ENP binding, whereas the secondary structure of ENP does not change due to the interaction with LPS. ENP contains a hydrophobic binding site to which the dye 1-anilino-8-sulfonic acid binds at a Kd of 19 µm, which is displaced by LPS. Because lipopolysaccharide-binding protein (LBP) is not able to bind to LPS when ENP and LPS are preincubated, tight binding of ENP to LPS can be deduced with a Kd in the low nonomolar range. Importantly, ENP is able to incorporate by itself into target phospholipid liposomes, and is also able to mediate the intercalation of LPS into the liposomes thus acting as a transport protein in a manner similar to LBP. Thus, LPS,ENP complexes might enter target membranes of immunocompetent cells, but are not able to activate due to the ability of ENP to change LPS aggregates from an active into an inactive form. [source] Patterned Polymeric Domes with 3D and 2D Embedded Colloidal Crystals using Photocurable Emulsion DropletsADVANCED MATERIALS, Issue 37 2009Shin-Hyun Kim Hierarchical dome patterns are prepared via a novel single-step patterning process. Photonic domes with isotropic reflection colors are patterned on a prepatterned glass substrate with a hydrophobic moiety using photocurable emulsion droplets of all-equal size, which contain concentrated silica particles. Furthermore, embossed domes are patterned with PS particle-stabilized photocurable emulsion droplets, which can act as a near-field microlens array. [source] Novel Fused Pyrrole Heterocyclic Ring Systems as Structure Analogs of LE 300: Synthesis and Pharmacological Evaluation as Serotonin 5-HT2A, Dopamine and Histamine H1 Receptor LigandsARCHIV DER PHARMAZIE, Issue 2 2010Sherif A. F. Rostom Abstract LE 300 represents a structurally novel type of antagonists acting preferentially at the dopamine D1/D5 receptors and the serotonin 5-HT2A receptor. This compound consists of a ten-membered central azecine ring fused to an indole ring on one side and a benzene moiety on the other side. To estimate the importance of the indole and / or phenyl moieties in this highly active benz-indolo-azecine, both rings were removed and replaced with a 1H -pyrrole counterpart. Accordingly, some new analogs of LE 300 namely, pyrrolo[2,3- g]indolizine, pyrrolo[3,2- a]quinolizine rings and their corresponding dimethylpyrrolo[2,3- d]azonine, and dimethylpyrrolo[2,3- d]azecine were synthesized to be evaluated for their activity at the 5-HT2A and dopamine D1, D2L, D4, D5 receptors in relation to LE 300. In addition, their activity at the H1 -histamine receptors was also determined. The results suggested that the rigid pyrrolo[2,3- g]indolizine 7 and pyrrolo[3,2- a]quinolizine 8 analogs lacked biological activity in the adopted three bioassays. However, their corresponding flexible pyrrolo[2,3- d]azonine 11 and pyrrolo[2,3- d]azecine 12 derivatives revealed weak partial agonistic activity and weak antagonistic potency at the serotonin 5-HT2A and histamine H1 receptors, respectively. Meanwhile, they showed no affinity to any of the four utilized dopamine receptors. Variation in ring size did not contribute to a significant influence on the three tested bioactivities. Removal of the hydrophobic moiety (phenyl ring) and replacement of the indole moiety with a 1H -pyrrole counterpart led to a dramatic alteration in the profile of activity of such azecine-type compounds. [source] Structures of BIR domains from human NAIP and cIAP2ACTA CRYSTALLOGRAPHICA SECTION F (ELECTRONIC), Issue 11 2009Maria Dolores Herman The inhibitor of apoptosis (IAP) family of proteins contains key modulators of apoptosis and inflammation that interact with caspases through baculovirus IAP-repeat (BIR) domains. Overexpression of IAP proteins frequently occurs in cancer cells, thus counteracting the activated apoptotic program. The IAP proteins have therefore emerged as promising targets for cancer therapy. In this work, X-ray crystallography was used to determine the first structures of BIR domains from human NAIP and cIAP2. Both structures harbour an N-terminal tetrapeptide in the conserved peptide-binding groove. The structures reveal that these two proteins bind the tetrapeptides in a similar mode as do other BIR domains. Detailed interactions are described for the P1,,P4, side chains of the peptide, providing a structural basis for peptide-specific recognition. An arginine side chain in the P3, position reveals favourable interactions with its hydrophobic moiety in the binding pocket, while hydrophobic residues in the P2, and P4, pockets make similar interactions to those seen in other BIR domain,peptide complexes. The structures also reveal how a serine in the P1, position is accommodated in the binding pockets of NAIP and cIAP2. In addition to shedding light on the specificity determinants of these two proteins, the structures should now also provide a framework for future structure-based work targeting these proteins. [source] The Structure of MetallomicellesCHEMISTRY - A EUROPEAN JOURNAL, Issue 8 2004P. C. Griffiths Dr. Abstract The morphology of micelles formed by two novel metallosurfactants has been studied by small-angle neutron scattering (SANS) and small-angle-X-ray scattering (SAXS). The two surfactants both contain a dodecyl chain as the hydrophobic moiety, but differ in the structure of the head group. The surfactants are CuII complexes of monopendant alcohol derivatives of a) the face-capping macrocycle 1,4,7-triazacyclanonane (tacn), and b) an analogue based upon the tetraazamacrocycle 1,4,7,10-tetraazacyclododecane. Here, neutron scattering has been used to study the overall size and shape of the surfactant micelles, in conjunction with X-ray scattering to locate the metal ions. For the 1,4,7,10-tetraazacyclododecane-based surfactant, oblate micelles are observed, which are smaller to the prolate micelles formed by the 1,4,7-triazacyclononane analogue. The X-ray scattering analysis shows that the metal ions are distributed throughout the polar head-group region, rather than at a well-defined radius; this is in good agreement with the SANS-derived dimensions of the micelle. Indeed, the same model for micelle morphology can be used to fit both the SANS and SAXS data. [source] Photochemical Key Steps in the Synthesis of Surfactants from Furfural-Derived IntermediatesCHEMSUSCHEM CHEMISTRY AND SUSTAINABILITY, ENERGY & MATERIALS, Issue 12 2009Abdoulaye Gassama Dr. Abstract Furfural is oxidized to 2[5H]-furanone by using hydrogen peroxide or to 5-hydroxy-2[5H]-furanone by using photo-oxygenation. An amine function is introduced by photochemically induced radical addition of tertiairy amines, some of which carry an n -alkyl side chain as hydrophobic moiety. These amines are produced from fatty aldehydes and cyclic secondary amines. The resulting adducts are transformed into amphoteric surfactants possessing an ammonium and a carboxylate function. Amphoteric (pKN and isoelectric point) and surfactant properties such as the critical micelle concentration and the adsorption efficiency are determined. [source] | |||||||||||||