606130-90-9

Usage

Uses

Used in Bioconjugation:
13-Azido-2,5,8,11-tetraoxa-tridecane is used as a bioconjugation agent for the covalent attachment of biomolecules, such as peptides, proteins, and nucleic acids, to other molecules or surfaces. The azide group enables selective and efficient ligation through click chemistry, allowing for the precise control of biomolecule orientation and stability.
Used in Drug Delivery Systems:
In the pharmaceutical industry, 13-Azido-2,5,8,11-tetraoxa-tridecane is used as a component in drug delivery systems to improve the solubility, stability, and bioavailability of therapeutic agents. The PEG chain can reduce the immunogenicity and non-specific interactions of drug molecules, while the azide group allows for the attachment of targeting ligands or imaging agents through click chemistry.
Used in Materials Science:
13-Azido-2,5,8,11-tetraoxa-tridecane is utilized as a building block in the synthesis of functional materials, such as hydrogels, micelles, and dendrimers, for various applications in tissue engineering, diagnostics, and therapeutics. The azide group facilitates the formation of stable, well-defined structures through click chemistry, enabling the creation of materials with tailored properties and functions.
Used in Chemical Biology Research:
In chemical biology, 13-Azido-2,5,8,11-tetraoxa-tridecane serves as a valuable tool for the study of biological processes and the development of new probes and sensors. The azide group allows for the selective labeling of biomolecules and the formation of bioorthogonal reporter groups, enabling researchers to investigate molecular interactions, cellular processes, and disease mechanisms with high spatial and temporal resolution.

Upstream product

• 86770-67-4 2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol 
• 74-88-4 methyl iodide 
• 112-60-7 Tetraethylene glycol 
• 23783-42-8 tetraethylene glycol monomethyl ether 
• 62921-76-0 2,5,8,11-tetraoxatridecan-13-ol tosylate 

Downstream Products

• 123852-08-4 N,N-bis(tetraethyleneglycol-monomethylether)amine 
• 1184951-69-6 DOX-mPEG₄-GA₃ 
• 85030-56-4 3,6,9,12-tetraoxa-tridecylamine 

Relevant academic research and scientific papers

Synthesis of branched monodisperse oligoethylene glycols and 19f mri-traceable biomaterials through reductive dimerization of azides

Multifunctionalized and branched M-OEGs represent valuable PEGylation agents, linkers, and scaffolds in biomedicine. However, the tedious synthesis limited their availability and application. We herein present an azide reductive dimerization method for the convenient synthesis of aza-M-OEGs and derivatives, which provides easy access to a variety of multifunctionalized and branched M-OEGs in one step. With this method, hexa-arm M-OEGs with 54 symmetrical fluorines were synthesized in two steps as a water-soluble, self-assemble, 19F MRI sensitive, and biocompatible dendritic biomaterial.

Tuneable Transient Thermogels Mediated by a pH- and Redox-Regulated Supramolecular Polymerization

A multistimuli-responsive transient supramolecular polymerization of β-sheet-encoded dendritic peptide monomers in water is presented. The amphiphiles, which contain glutamic acid and methionine, undergo a glucose oxidase catalyzed, glucose-fueled transient hydrogelation in response to an interplay of pH and oxidation stimuli, promoted by the production of reactive oxygen species (ROS). Adjusting the enzyme and glucose concentration allows tuning of the assembly and the disassembly rates of the supramolecular polymers, which dictate the stiffness and transient stability of the hydrogels. The incorporation of triethylene glycol chains introduces thermoresponsive properties to the materials. We further show that repair enzymes are able to reverse the oxidative damage in the methionine-based thioether side chains. Since ROS play an important role in signal transduction cascades, our strategy offers great potential for applications of these dynamic biomaterials in redox microenvironments.

Stereodivergent synthesis of right- and left-handed iminoxylitol heterodimers and monomers. Study of their impact on β-glucocerebrosidase activity

A library of dimers and heterodimers of both enantiomers of 2-O-alkylated iminoxylitol derivatives has been synthesised and evaluated on β-glucocerebrosidase (GCase), the enzyme responsible for Gaucher disease (GD). Although the objective was to target simultaneously the active site and a secondary binding site of the glucosidase, the (-)-2-iminoxylitol moiety seemed detrimental for imiglucerase inhibition and no significant enhancement was obtained in G202R, N370S and L444P fibroblasts. However, all compounds having at least one (+)-2-O-alkyl iminoxylitol are GCase inhibitors in the nano molar range and are significant GCase activity enhancers in G202R fibroblats, as confirmed by a decrease of glucosylceramide levels and by co-localization studies.

MACROCYCLIC PEPTIDES USEFUL AS IMMUNOMODULATORS

The present disclosure provides compounds which are immunomodulators and thus are useful for the amelioration of various diseases, including cancer and infectious diseases.

N-monosubstituted methoxy-oligo(ethylene glycol) carbamate ester prodrugs of resveratrol

Resveratrol is a natural polyphenol with many interesting biological activities. Its pharmacological exploitation in vivo is, however, hindered by its rapid elimination via phase II conjugative metabolism at the intestinal and, most importantly, hepatic levels. One approach to bypass this problem relies on prodrugs. We report here the synthesis, characterization, hydrolysis, and in vivo pharmacokinetic behavior of resveratrol prodrugs in which the OH groups are engaged in an N-monosubstituted carbamate ester linkage. As promoiety, methoxy-oligo(ethylene glycol) groups (m-OEG) (CH3-[OCH2CH2]n-) of defined chain length (n = 3, 4, 6) were used. These are expected to modulate the chemico-physical properties of the resulting derivatives, much like longer poly(ethylene glycol) (PEG) chains, while retaining a relatively low MW and, thus, a favorable drug loading capacity. Intragastric administration to rats resulted in the appearance in the bloodstream of the prodrug and of the products of its partial hydrolysis, confirming protection from first-pass metabolism during absorption.

Esters Of Glucuronide Prodrugs Of Anthracyclines And Method Of Preparation And Use In Tumor-Selective Chemotherapy

The invention relates to novel esters and in particular to some novel esters of glucuronide prodrugs of anthracyclines having tunable water-solubility, their synthesis and use in tumor-selective chemotherapy. It appeared that in the final step in the synt

Post-modification of helical dipeptido polyisocyanides using the 'click' reaction

Polyisocyanopeptides have been synthesised containing acetylene groups on the side arms as scaffolds for multifunctional derivatisation by the copper-catalysed click reaction with a variety of azides. By using ethylene glycol azide and perylene azide chro

Nanowells on silica particles in water containing long-distance porphyrin heterodimers

Smooth and nonswelling spherical silica particles with a diameter of 100 nm and an aminopropyl coating are soluble in water at pH 11, coagulate quickly at pH 3, and redissolve at pH 9. Electron microscopy as well as visible spectra of covalently attached porphyrins indicate the aggregation state of the particles. Long-chain α,ω-dicarboxylic acids with a terminal oligoethyleneglycol (=OEG)-amide group were attached in a second self-assembly step to the remaining amine groups around the porphyrins. Form-stable 2-nm wells were thus obtained and were characterized by fluorescence quenching experiments using the bottom porphyrin as a target. The one-dimensional diffusion of fitting quencher molecules along the 2-nm pathway took several minutes. Porphyrins with a diameter above 2 nm could not enter the form-stable gaps at all. Added tyrosine stuck irreversibly to the walls of the nanowells and prevented the entrance of quencher molecules, the OEG-headgroups fixated 2,6-diaminoanthraquinone. A ring of methylammonium groups was then fixed at the walls of the wells at a distance of 5 or 10 A with respect to the bottom porphyrin. 2,6-Disulfonatoanthraquinone was attached only loosely to this ring, but the exactly fitting manganese(III) meso-(tetraphenyl-4-sulfonato)porphyrinate (Mn(III) TPPS) was tightly bound. Transient fluorescence experiments showed a fast decay time of 0.2 ns for the bottom porphyrin, when the Mn(III) TPPS was fixated at a distance of 5 A. Two different dyes have thus been immobilized at a defined subnanometer distance in an aqueous medium.

Nonionic Amphiphilic Compounds from Lysine as Molecular Mimics of Lecithins

New monodisperse nonionic surfactant molecules, based on lysine with two fatty acid chains in the hydrophobic part and one or two polyoxoethylene methoxycapped chains (EOn-Me) in the hydrophilic headgroup, are synthesized as mimics of natural lecithins.Their surface-activity properties indicate that these compounds have surfactant behavior whose global hydrophobic contribution is comparable to that of one fatty chain. - Key Words: Amphiphilic compounds; critical micelle concentration; mimics of lecithins; surface tension

Lack of effect of the length of oligoglycine- and oligo(ethylene glycol)-derived para-substituents on the affinity of benzenesulfonamides for carbonic anhydrase II in solution

Using 1H NMR spectroscopy, values of T2 have been determined for the methylene protons of the oligoglycine moieties of para-substituted benzenesulfonamides having structures H2NO2SC6H4CO(Gly)(n)OH (n = 1-6) bound at the active site of bovine carbonic anhydrase II (CA, EC 4.2.1.1). These values have been correlated with measurements of dissociation constants of these complexes, in order to infer motion of these ligands when bound to the enzyme. Motion of glycines 1-3 (those closest to the aryl ring) is hindered by their proximity to the protein; motion of glycines 4-6 is relatively unhindered. Despite the restriction to motion inferred for glycines 1-3, the values of K(d) for the six compounds (n = 1-6, 1-6) are indistinguishable within experimental uncertainty (± 20%): K(d) in μM (n) 0.30 (1); 0.26 (2); 0.33 (3); 0.37 (4); 0.37 (5); 0.34 (6). There is, therefore, an unexpected compensation of the loss in conformational entropy on binding by another contributor to the free energy.