Search results for: CF350, aminooxy
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Synthesis of O-Amino Sugars and Nucleosides.Nucleic acids and carbohydrates are essential biomolecules involved in numerous biological and pathological processes. Development of multifunctional building blocks based on nucleosides and sugars is in high demand for the generation of novel oligonucleotide mimics and glycoconjugates for biomedical applications. Recently, aminooxyl-functionalized compounds have attracted increasing research interest because of their easy derivatization through oxime ligation or-oxyamide formation reactions. Various biological applications have been reported for-amino carbohydrate- and nucleoside-derived compounds. Here, we report our efforts in the design and synthesis of glyco-, glycosyl, nucleoside- and nucleo-aminooxy acid derivatives from readily available sugars and amino acids, and their use for the generation of-oxyamide-linked oligosaccharides, glycopeptides, glycolipids, oligonucleosides and nucleopeptides as novel glycoconjugates or oligonucleotide mimics. Delicate and key points in the synthesis will be emphasized.
2-Amino Benzimidazole Su 2-Amino Benzimidazole Su Cellufine Amino , 50 ml Cellufine Amino Media Cellufine Amino , 500 ml Cellufine Amino Media Cellufine Amino Media Fibroblast Growth Factor Fibroblast Growth Factor AFC (7-amino-4-trifluorom AFC (7 amino 4 trifluorom AFC (7 amino 4 trifluorom
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Preparation and functional analysis of gossypols having two carbohydrate appendages with enaminooxy linkages.We developed new gossypol (Gos)-based glycoconjugates through dehydration condensation of native Gos and chemically modified glycosides having aminooxy groups. The resultant glycoconjugates (glycoGos) were resistant to hydrolysis, although they were light-sensitive and slowly decomposed even under indoor lighting. The glycoGos also exhibited improved water solubility compared with native Gos, but their saturated concentrations in water were still low (6.4-17 μM), due to their hydrophobic naphthyl rings. We also carried out WST-8 assays to assess the anticancer activity of the glycoGos on DLD-1 and HepG2 cells and found that the glycoGos having β-lactosides and having β-galactosides (specific ligands for asialoglycoprotein receptors) showed enhanced anticancer activity on HepG2 cells.
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Glycoconjugate Oxime Formation Catalyzed at Neutral pH: Mechanistic Insights and Applications of 1,4-Diaminobenzene as a Superior Catalyst for Complex Carbohydrates.The reaction of unprotected carbohydrates with aminooxy reagents to provide oximes is a key method for the construction of glycoconjugates. Aniline and derivatives serve as organocatalysts for the formation of oximes from simple aldehydes, and we have previously reported that aniline also catalyzes the formation of oximes from the more complex aldehydes, carbohydrates. Here, we present a comprehensive study of the effect of aniline analogues on the formation of carbohydrate oximes and related glycoconjugates depending on organocatalyst structure, pH, nucleophile, and carbohydrate, covering more than 150 different reaction conditions. The observed superiority of the 1,4-diaminobenzene (PDA) catalyst at neutral pH is rationalized by NMR analyses and DFT studies of reaction intermediates. Carbohydrate oxime formation at pH 7 is demonstrated by the formation of a bioactive glycoconjugate from a labile, decorated octasaccharide originating from exopolysaccharides of the soil bacterium Mesorhizobium loti. This study of glycoconjugate formation includes the first direct comparison of aniline-catalyzed reaction rates and equilibrium constants for different classes of nucleophiles, including primary oxyamines, secondary N-alkyl oxyamines, as well as aryl and arylsulfonyl hydrazides. We identified 1,4-diaminobenzene as a superior catalyst for the construction of oxime-linked glycoconjugates under mild conditions.
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Delivery of Amonafide from Fructose-Coated Nanodiamonds by Oxime Ligation for the Treatment of Human Breast Cancer.The introduction of a strategy toward polymer/nanodiamond hybrids with high polymer grafting density and accessible polymer structural characterization is of critical importance for nanodiamonds' surface modification and bioagent attachment for their biomedical application. Here, we report a glycopolymer/nanodiamond hybrid drug delivery system, which was prepared by grafting amonafide-conjugated glycopolymers onto the surface of nanodiamonds via oxime ligation. Poly(1-O-methacryloyl-2,3:4,5-di-O-isopropylidene-β-d-fructopyranose)-b-poly(3-vinylbenzaldehyde-co-methyl methacrylate), featuring pendant aldehyde groups, is prepared via RAFT polymerization. The anticancer drug amonafide is conjugated to the polymer chains via imine chemistry, resulting in acid-degradable imine linkages. The obtained amonafide-conjugated glycopolymers are subsequently grafted onto the surface of aminooxy-functionalized nanodiamonds via oxime ligation. The molecular weight of the conjugated polymers is characterized by size-exclusion chromatography (SEC), while the successful conjugation and corresponding grafting density is assessed by nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FTIR), and thermogravimetric aanalysis (TGA). Our results indicate that the mass percentage of amonafide in the polymer chains is around 17% and the surface density of polymer chains is 0.24 molecules/nm. The prepared drug delivery system has a hydrodynamic size around 380 nm with low PDI (0.3) and can effectively deliver amonafide into breast cancer cell and significantly inhibit the cancer cell viability. In 2D cell culture models, the ICvalues of ND-Polymer-AMF delivery system (7.19 μM for MCF-7; 4.92 μM for MDA-MB-231) are lower than those of free amonafide (11.23 μM for MCF-7; 13.98 μM for MDA-MB-231). An inhibited cell viability of nanodiamonds/polymer delivery system is also observed in 3D spheroids' models, suggesting that polymer-diamonds hybrid materials can be promising platforms for breast cancer therapy.
1957 related Products with: Delivery of Amonafide from Fructose-Coated Nanodiamonds by Oxime Ligation for the Treatment of Human Breast Cancer.Breast cancer membrane pr Human breast invasive duc Human Breast Cancer Antig Bone Morphogenetic Protei Growth Differentiation Fa Mouse Anti-Human CA19-9 ( succinate-CoA ligase, GDP TCP-1 theta antibody Sour formin-like 1 antibody So Recombinant Human PKC the Recombinant Human PKC the Recombinant Human PKC the
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Quantitative profiling of carbonyl metabolites directly in crude biological extracts using chemoselective tagging and nanoESI-FTMS.The extensive range of chemical structures, wide range of abundances, and chemical instability of metabolites present in the metabolome pose major analytical challenges that are difficult to address with existing technologies. To address these issues, one approach is to target a subset of metabolites that share a functional group, such as ketones and aldehydes, using chemoselective tagging. Here we report a greatly improved chemoselective method for the quantitative analysis of hydrophilic and hydrophobic carbonyl-containing metabolites directly in biological samples. This method is based on direct tissue or cells extraction with simultaneous derivatization of stable and labile carbonylated metabolites using N-[2-(aminooxy)ethyl]-N,N-dimethyl-1-dodecylammonium (QDA) andCDlabeled QDA. We combined innovations of direct quenching of biological sample with frozen derivatization conditions under the catalyst N,N-dimethyl-p-phenylenediamine, which facilitated the formation of oxime stable-isotope ion pairs differing by m/z 4.02188 while minimizing metabolite degradation. The resulting oximes were extracted by HyperSep C8 tips to remove interfering compounds, and the products were detected using nano-electrospray ionization interfaced with a Thermo Fusion mass spectrometer. The quaternary ammonium tagging greatly increased electrospray MS detection sensitivity and the signature ions pairs enabled simple identification of carbonyl compounds. The improved method showed the lower limits of quantification for carbonyl standards to be in the range of 0.20-2 nM, with linearity of R> 0.99 over 4 orders of magnitude. We have applied the method to assign 66 carbonyls in mouse tumor tissues, many of which could not be assigned solely by accurate mass and tandem MS. Fourteen of the metabolites were quantified using authentic standards. We also demonstrated the suitability of this method for determiningC labeled isotopologues of carbonyl metabolites inC-glucose-based stable isotope-resolved metabolomic (SIRM) studies.
1131 related Products with: Quantitative profiling of carbonyl metabolites directly in crude biological extracts using chemoselective tagging and nanoESI-FTMS.Inflammation (Human) Quan Inflammation (Human) Quan Inflammation (Human) Quan Inflammation (Mouse) Quan Inflammation (Rat) Quanti Rat Inflammation ELISA St Cortisol Enzyme Immunoass Alamar Blue™, REDOX ind Alamar Blue™, REDOX ind Interleukin-34 IL34 (N-t Interleukin-34 IL34 anti Sterile filtered goat se
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Reductive oxyamination: a method for the qualitative and quantitative analysis of monosaccharides with a new aminooxy reagent using high-performance liquid chromatography with fluorescence detection.Derivatization of carbohydrates with aminooxy agents to form oximes can be used for qualitative and quantitative analysis of carbohydrates; however, the formation of isomeric products limits its application. A new reductive oxyamination procedure developed for the analysis of monosaccharides with a novel fluorescent O-substituted aminooxy reagent, 4-((aminooxy)methyl)-6-chloro-7-hydroxycoumarin (AOCC), is reported. In this procedure, monosaccharides undergo an oxime formation reaction with AOCC and are then readily reduced with 2-picoline-borane, followed by analysis with high-performance liquid chromatography with fluorescence detection. Good separation of five monosaccharide derivatives was achieved within 40 min with acetonitrile-water-tetrahydrofuran as the mobile phase. The detection limits were on the order of femtomoles. The linear range was 0.2-4000 nM, with a good correlation coefficient (R ≥ 0.9985). Furthermore, the method was applied for analysis of real samples, such as bovine milk powder, without complicated and tedious sample treatment. This reductive oxyamination method circumvents the problem caused by oxime isomers and can be used for the highly sensitive and selective analysis of monosaccharides with high accuracy, providing an effective and promising method for the analysis of carbonyls with aminooxy agents.
2683 related Products with: Reductive oxyamination: a method for the qualitative and quantitative analysis of monosaccharides with a new aminooxy reagent using high-performance liquid chromatography with fluorescence detection.QuantiChrom™ Acetylchol QuantiChrom™ Formaldehy QuantiChrom™ BCP Albumi EnzyChrom™ Acetylcholin EnzyChrom™ Ascorbic Aci EnzyChrom™ Catalase Ass EnzyChrom™ D-Lactate As EnzyChrom™ Free Fatty A EnzyChrom™ Fructose Ass EnzyChrom™ Lactose Assa EnzyChrom™ Pyruvate Ass Amplite™ Fluorimetric F
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Oriented, molecularly imprinted cavities with dual binding sites for highly sensitive and selective recognition of cortisol.Novel, molecularly imprinted polymers (MIPs) were developed for the highly sensitive and selective recognition of the stress marker cortisol. Oriented, homogeneous cavities with two binding sites for cortisol were fabricated by surface-initiated atom transfer radical polymerization, using a cortisol motif template molecule (TM1) which consists of a polymerizable moiety attached at the 3-carbonyl group of cortisol via an oxime linkage and an adamantane carboxylate moiety coupled with the 21-hydroxyl group. TM1 was orientationally immobilized on a βcyclodextrin (β-CD)-grafted gold-coated sensor chip by inclusion of the adamantane moiety of TM1, followed by copolymerization of a hydrophilic comonomer, 2-methacryloyloxyethyl phosphorylcholine, with or without a cross-linker,-methylenebisacrylamide. Subsequent cleavage of the oxime linkage leaves the imprinted cavities that contain dual binding sites-namely, the aminooxy group and β-CD-capable of oxime formation and hydrophobic interaction, respectively. As an application, MIP-based picomolar level detection of cortisol was demonstrated by a competitive binding assay using a fluorescent competitor. Cross-linking of the MIP imparts rigidity to the binding cavities, and improves the selectivity and sensitivity significantly, reducing the limit of detection to 4.8 pM. In addition, detection of cortisol in saliva samples was demonstrated as a feasibility study.
1846 related Products with: Oriented, molecularly imprinted cavities with dual binding sites for highly sensitive and selective recognition of cortisol.Cortisol Binding Globulin Beta Amyloid (1 42) High Sheep Anti-Human Cortisol Rabbit Anti-Rat Androgen Highly Sensitive 8 OHdG C 8 Octadecyloxypyrene 1,3, 4 Methylumbelliferyl sulf Cellufine Formyl , 50 ml Cellufine Formyl Media Cellufine Formyl , 500 ml Cellufine Formyl Media Cellufine Formyl Media
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Cross-Linked Collagen Triple Helices by Oxime Ligation.Covalent cross-links are crucial for the folding and stability of triple-helical collagen, the most abundant protein in nature. Cross-linking is also an attractive strategy for the development of synthetic collagen-based biocompatible materials. Nature uses interchain disulfide bridges to stabilize collagen trimers. However, their implementation into synthetic collagen is difficult and requires the replacement of the canonical amino acids (4R)-hydroxyproline and proline by cysteine or homocysteine, which reduces the preorganization and thereby stability of collagen triple helices. We therefore explored alternative covalent cross-links that allow for connecting triple-helical collagen via proline residues. Here, we present collagen model peptides that are cross-linked by oxime bonds between 4-aminooxyproline (Aop) and 4-oxoacetamidoproline placed in coplanar Xaa and Yaa positions of neighboring strands. The covalently connected strands folded into hyperstable collagen triple helices (T≈ 80 °C). The design of the cross-links was guided by an analysis of the conformational properties of Aop, studies on the stability and functionalization of Aop-containing collagen triple helices, and molecular dynamics simulations. The studies also show that the aminooxy group exerts a stereoelectronic effect comparable to fluorine and introduce oxime ligation as a tool for the functionalization of synthetic collagen.
CL APC (Cross linked Phyc Polystyrene Particle Size Picro-Sirius Red Stain K ELCI ELISA grade chick ty ELCI ELISA grade chick ty ELISA grade chick type I ELBI ELISA grade bovine t ELBI ELISA grade bovine t ELISA grade bovine type I ELISA grade porcine type ELPI ELISA grade porcine ELPI ELISA grade porcine
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New method for estimating clustering of DNA lesions induced by physical/chemical mutagens using fluorescence anisotropy.We have developed a new method for estimating the localization of DNA damage such as apurinic/apyrimidinic sites (APs) on DNA using fluorescence anisotropy. This method is aimed at characterizing clustered DNA damage produced by DNA-damaging agents such as ionizing radiation and genotoxic chemicals. A fluorescent probe with an aminooxy group (AlexaFluor488) was used to label APs. We prepared a pUC19 plasmid with APs by heating under acidic conditions as a model for damaged DNA, and subsequently labeled the APs. We found that the observed fluorescence anisotropy (r) decreases as averaged AP density (λ: number of APs per base pair) increases due to homo-FRET, and that the APs were randomly distributed. We applied this method to three DNA-damaging agents,Co γ-rays, methyl methanesulfonate (MMS), and neocarzinostatin (NCS). We found that r-λrelationships differed significantly between MMS and NCS. At low AP density (λ < 0.001), the APs induced by MMS seemed to not be closely distributed, whereas those induced by NCS were remarkably clustered. In contrast, the AP clustering induced byCo γ-rays was similar to, but potentially more likely to occur than, random distribution. This simple method can be used to estimate mutagenicity of ionizing radiation and genotoxic chemicals.
2912 related Products with: New method for estimating clustering of DNA lesions induced by physical/chemical mutagens using fluorescence anisotropy.Amplite™ Fluorimetric F QuantiChrom™ Formaldehy QuantiChrom™ Urea Assay 5 Carboxy X Rhodamine, NH OxiSelect™ Cellular UV- MOUSE ANTI APAAP COMPLEX, Cellufine Formyl , 50 ml Cellufine Formyl Media Cellufine Formyl , 500 ml Cellufine Formyl Media Cellufine Formyl Media Protease, DNASE free hea
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Metabolic control of T17 and induced Tcell balance by an epigenetic mechanism.Metabolism has been shown to integrate with epigenetics and transcription to modulate cell fate and function. Beyond meeting the bioenergetic and biosynthetic demands of T-cell differentiation, whether metabolism might control T-cell fate by an epigenetic mechanism is unclear. Here, through the discovery and mechanistic characterization of a small molecule, (aminooxy)acetic acid, that reprograms the differentiation of T helper 17 (T17) cells towards induced regulatory T (iT) cells, we show that increased transamination, mainly catalysed by GOT1, leads to increased levels of 2-hydroxyglutarate in differentiating T17 cells. The accumulation of 2-hydroxyglutarate resulted in hypermethylation of the Foxp3 gene locus and inhibited Foxp3 transcription, which is essential for fate determination towards T17 cells. Inhibition of the conversion of glutamate to α-ketoglutaric acid prevented the production of 2-hydroxyglutarate, reduced methylation of the Foxp3 gene locus, and increased Foxp3 expression. This consequently blocked the differentiation of T17 cells by antagonizing the function of transcription factor RORγt and promoted polarization into iTcells. Selective inhibition of GOT1 with (aminooxy)acetic acid ameliorated experimental autoimmune encephalomyelitis in a therapeutic mouse model by regulating the balance between T17 and iTcells. Targeting a glutamate-dependent metabolic pathway thus represents a new strategy for developing therapeutic agents against T17-mediated autoimmune diseases.
1671 related Products with: Metabolic control of T17 and induced Tcell balance by an epigenetic mechanism.Brain cancer test tissue Brain tumor tissue array Brain tumor tissue array EZH2 KMT6 Control Peptid GFP control peptide anti Anti AGO2 Human, Monoclon Anti AGO2 Mouse, Monoclon Anti AGO2 Human, Monoclon Anti AGO2 Mouse, Monoclon Androgen Receptor (Phosph Androgen Receptor (Phosph Rabbit Anti-Human Androge
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