84928-99-4Relevant articles and documents
Clickable amino acid derivative tuned self-assembly of antigen and adjuvant for cancer immunotherapy
He, Xiao,Yang, Lan,Su, Hang,Lin, Shan,Qi, Dongmei,Chen, Hui,Qu, Yunfei,Liu, Libing,Feng, Xuli
, p. 306 - 316 (2021)
Amino acid-tuned self-assembly has become an attractive strategy for constructing various functional materials. Here, a series of dibenzocyclooctyne (DIBO) functionalized amphiphilic amino acid derivatives are designed and screened as building blocks of functional supramolecular self-assembly nanoparticles for cancer immunotherapy. One top-performing supramolecular self-assembly material (named DA6C1) is identified through combinatorial screening, and spherical nanoparticles can be easily prepared by this material tuned multicomponent synergistic self-assembly of ovalbumin (OVA) and CpG oligonucleotide. DA6C1 based nanovaccine can significantly enhance the cellular uptake of OVA and CpG into the same bone marrow derived dendritic cells (BMDCs) and greatly improve the activation of DCs. Moreover, after subcutaneous injection, this nanovaccine flows rapidly to the lymph nodes and elicits strong immune responses to achieve effective prophylactic and therapeutic effect. Therefore, our work highlights the great potential of clickable amino acid derivatives as a convenient and powerful tool to construct nanovaccine for effective immunotherapy.
Reactions of unsaturated azides; Part 22:1 The alkyne azide click chemistry as a synthetic tool for the generation of cage-like triazole compounds
Banert, Klaus,Wutke, Jens,Rueffer, Tobias,Lang, Heinrich
, p. 2603 - 2609 (2008)
The applicability of the copper(I)-catalyzed click reaction of terminal trialkynes with triazides to the synthesis of cage-like triazole compounds was determined. A number of starting materials were prepared and several monotriazoles as well as macrocyclic bistriazoles were obtained from the triazide trialkyne reaction. Finally, a tristriazole macrobicyclic compound was synthesized from the previously formed triazole precursors. Georg Thieme Verlag Stuttgart.
Synthesis of Novel Energetic Compounds. 6
Witucki, Edward F.,Wilson, Edgar R.,Flanagan, Joseph E.,Frankel, Milton B.
, p. 285 - 286 (1983)
Reported here are the syntheses and physical properties of five novel energetic aliphatic azido compounds.These include azido nitramines, esters, and amines.The compounds have been characterized in terms of freezing point, refractive index, and impact sensitivity.The properties of these azides indicate that these compounds have a wide liquid range and relatively insensitive to impact.
A general method for selective recognition of monosaccharides and oligosaccharides in water
Gunasekara, Roshan W.,Zhao, Yan
supporting information, p. 829 - 835 (2017/05/17)
Molecular recognition of carbohydrates plays vital roles in biology but has been difficult to achieve with synthetic receptors. Through covalent imprinting of carbohydrates in boroxole-functionalized cross-linked micelles, we prepared nanoparticle receptors for a wide variety of mono- and oligosaccharides. The boroxole functional monomer bound the sugar templates through cis-1,2-diol, cis-3,4-diol, and trans-4,6-diol. The protein-sized nanoparticles showed excellent selectivity for daldohexoses in water with submillimolar binding affinities and completely distinguished the three biologically important hexoses (glucose, mannose, and galactose). Glycosides with nonpolar aglycon showed stronger binding due to enhanced hydrophobic interactions. Oligosaccharides were distinguished on the basis of their monosaccharide building blocks, glycosidic linkages, chain length, as well as additional functional groups that could interact with the nanoparticles.
MULTIVALENT SIALIC ACID DERIVATES
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Page/Page column 33, (2015/03/16)
Disclosed is tri- or tetravalent sialic acid derivatives comprising a core moiety to which 3 or 4 sialic acid residues are connected via a linker. Such derivatives inhibit the binding of adenovirus to human cells, whereby infections, such as epidemic keratoconjunctivitis, may be treated or prevented by administration of the tri- or tetravalent sialic acid derivatives.
Triazole linker-based trivalent sialic acid inhibitors of adenovirus type 37 infection of human corneal epithelial cells
Caraballo, Rémi,Saleeb, Michael,Bauer, Johannes,Liaci, A. Manuel,Chandra, Naresh,Storm, Rickard J.,Fr?ngsmyr, Lars,Qian, Weixing,Stehle, Thilo,Arnberg, Niklas,Elofsson, Mikael
, p. 9194 - 9205 (2015/09/07)
Adenovirus type 37 (Ad37) is one of the principal agents responsible for epidemic keratoconjunctivitis (EKC), a severe ocular infection that remains without any available treatment. Recently, a trivalent sialic acid derivative (ME0322, Angew. Chem. Int. Ed., 2011, 50, 6519) was shown to function as a highly potent inhibitor of Ad37, efficiently preventing the attachment of the virion to the host cells and subsequent infection. Here, new trivalent sialic acid derivatives were designed, synthesized and their inhibitory properties against Ad37 infection of the human corneal epithelial cells were investigated. In comparison to ME0322, the best compound (17a) was found to be over three orders of magnitude more potent in a cell-attachment assay (IC50 = 1.4 nM) and about 140 times more potent in a cell-infection assay (IC50 = 2.9 nM). X-ray crystallographic analysis demonstrated a trivalent binding mode of all compounds to the Ad37 fiber knob. For the most potent compound ophthalmic toxicity in rabbits was investigated and it was concluded that repeated eye administration did not cause any adverse effects.
Synthesis of triazole cages containing C3-symmetric α-cyclic tripeptide scaffold
Chakraborty, Subrata,Tai, Dar-Fu
supporting information, p. 2274 - 2276 (2014/04/17)
Two water-soluble C3-symmetric 1,2,3-triazole cages containing α-cyclic tripeptide were efficiently synthesized. The key steps include a click reaction to incorporate l-glutamic or l-aspartic acids to a tripodal linker and a unique one-pot cyclotrimerization.
High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction
Beckmann, Henning S.G.,Moeller, Heiko M.,Wittmann, Valentin
scheme or table, p. 819 - 826 (2012/08/08)
A series of six mono-, di-, and trivalent N,N'-diacetylchitobiose derivatives was conveniently prepared by employing a one-pot procedure for Cu(II)-catalyzed diazo transfer and Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) starting from commercially available amines. These glycoclusters were probed for their binding potencies to the plant lectin wheat germ agglutinin (WGA) from Triticum vulgaris by an enzyme-linked lectin assay (ELLA) employing covalently immobilized N-acetylglucosamine (GlcNAc) as a reference ligand. IC50 values were in the low micromolar/high nanomolar range, depending on the linker between the two disaccharides. Binding enhancements β up to 1000 for the divalent ligands and 2800 for a trivalent WGA ligand, compared to N,N'-diacetylchitobiose as the corresponding monovalent ligand, were observed. Molecular modeling studies, in which the chitobiose moieties were fitted into crystallographically determined binding sites of WGA, correlate the binding enhancements of the multivalent ligands with their ability to bind to the protein in a chelating mode. The best WGA ligand is a trivalent cluster with an IC50 value of 220 nM. Calculated per mol of contained chitobiose, this is the best WGA ligand known so far.
Ligand-assisted, copper(II) acetate-accelerated azide-alkyne cycloaddition
Michaels, Heather A.,Zhu, Lei
supporting information; experimental part, p. 2825 - 2834 (2012/06/05)
Polytriazole ligands such as the widely used tris[(1-benzyl-1H-1,2,3- triazol-4-yl)methyl]amine (TBTA), are shown to assist copper(II) acetate-mediated azide-alkyne cycloaddition (AAC) reactions that involve nonchelating azides. Tris(2-{4-[(dimethylamino)
