134874-49-0

Usage

Uses

Used in Bioconjugation:
MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER is used as a bioconjugation agent for the formation of stable covalent bonds with maleimide, OPSS, vinylsulfone, and transition metal surfaces. The thiol group in m-PEG12-thiol allows for the attachment of biomolecules, such as proteins or peptides, to various surfaces or other molecules, facilitating the development of novel bioconjugates and biomaterials.
Used in Drug Delivery Systems:
In the pharmaceutical industry, MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER is used as a component in drug delivery systems. The hydrophilic PEG spacer improves the solubility and bioavailability of drugs, while the thiol group enables the formation of stable bonds with drug molecules or carriers, enhancing the overall performance of the drug delivery system.
Used in Surface Modification:
In materials science, MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER is used as a surface modification agent for transition metal surfaces, such as gold and silver. The thiol group can form strong bonds with these surfaces, allowing for the creation of functionalized surfaces with tailored properties, such as improved biocompatibility, enhanced catalytic activity, or targeted drug release.
Used in Diagnostics:
In the diagnostics industry, MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER is used as a component in the development of diagnostic tools and assays. The thiol group can be utilized to attach specific recognition elements, such as antibodies or oligonucleotides, to diagnostic platforms, enabling the detection and quantification of target molecules in biological samples.

Upstream product

• 62921-74-8 2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate 
• 50586-80-6 toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester 
• 62921-76-0 2,5,8,11-tetraoxatridecan-13-ol tosylate 
• 23783-42-8 tetraethylene glycol monomethyl ether 
• 4437-01-8 3,6,9,12,15,18,21-heptaoxadocosan-1-ol 
• 79622-11-0 2,5,8,11,14,17,20-heptaoxadocosan-22-yl 4-methylbenzene-1-sulfonate 
• 1379649-86-1 2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethanethiol 
• 111-77-3 2-(2-methoxyethoxy)ethyl alcohol 
• 112-60-7 Tetraethylene glycol 
• 1347750-79-1 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethanethiol 
• 1310827-26-9 S-2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl ethanethioate 
• 37860-51-8 tetraethylene glycol di(p-toluenesulfonate) 
• 168640-82-2 11-azido-3,6,9-trioxa-undecanyl p-toluenesulfonate 
• 857284-78-7 S-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)ethanethioate 

Downstream Products

• 1229649-33-5 N-(4-((4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)methyl)pyridin-2-yl)-2-(2-(2-methoxyethoxy)ethylthio)acetamide 
• 1643575-07-8 [meso-5,10,15,20-tetrakis(4-[2-(2-methoxyethoxy)ethane]thioxytetra-2,3,5,6-fluorophenyl)porpholactonato]platinum(II) 
• 1266328-47-5 4,5-[2-(2-methoxyethoxy)ethylsulfanyl]phthalonitrile 
• 885476-31-3 C₁₃H₁₄N₂O₂S 
• 1452877-36-9 C₆₀H₁₀₂O₂₁S₃ 

Relevant academic research and scientific papers

Adsorbed surfactants for affinity chromatography: End-group modification of ethylene glycol polymers

The hydroxyl end-groups of PluronicF108 {a tri-block copolymer surfactant of poly(ethylene glycol) and poly(propylene glycol) [PEG-PPG-PEG]} were converted into primary amine and quaternary ammonium equivalents for use in a new approach to affinity chromatography. The preparation of sulphonic acid end-groups was also attempted.

Homoallylglycine residues are superior precursors to orthogonally modified thioether containing polypeptides

Homoallylglycine N-carboxyanhydride, Hag NCA, monomers were synthesized and used to prepare polypeptides containing Hag segments with controllable lengths of up to 245 repeats. Poly(l-homoallylglycine), GHA, was found to adopt an α-helical conf

Biofunctional silicon nanoparticles by means of thiol-ene click chemistry

The preparation and characterization of butylene-terminated silicon nanoparticles (SiNPs) and their functionalization using thiol-ene chemistry is described, as well as the coupling of DNA strands. Bromide-terminated SiNPs were prepared by means of the oxidation of magnesium silicide and functionalized with butylene chains through treatment with the corresponding Grignard reagent. The successful coupling was confirmed by NMR and FTIR spectroscopy. TEM measurements revealed a silicon-core diameter of (2.4±0.5)nm. The fluorescence emission maximum is at λmax=525nm when excited at λexc=430nm. The conjugation of these alkene-terminated SiNPs by means of thiol-ene chemistry is described for a variety of functional thiols. Efficient coupling was evidenced by NMR and FTIR spectroscopy. Moreover, the characteristic fluorescence properties of the SiNPs remained unaltered, thus demonstrating the value of this approach towards functional oxide-free SiNPs. Activation of the attached carboxylic acid moieties allowed for conjugation of NH2-terminated oligo-ssDNA (ss=single strand) to the SiNPs. Successful coupling was confirmed by a characteristic new UV absorption band at 260nm, and by the still-present distinctive fluorescence of the SiNPs at 525nm. Gel electrophoresis confirmed coupling of 2 to 3 DNA strands onto the SiNPs, whereas no uncoupled DNA was observed.

A Modular Synthetic Route Involving N-Aryl-2-nitrosoaniline Intermediates Leads to a New Series of 3-Substituted Halogenated Phenazine Antibacterial Agents

Pathogenic bacteria demonstrate incredible abilities to evade conventional antibiotics through the development of resistance and formation of dormant, surface-attached biofilms. Therefore, agents that target and eradicate planktonic and biofilm bacteria are of significant interest. We explored a new series of halogenated phenazines (HP) through the use of N-aryl-2-nitrosoaniline synthetic intermediates that enabled functionalization of the 3-position of this scaffold. Several HPs demonstrated potent antibacterial and biofilm-killing activities (e.g., HP 29, against methicillin-resistant Staphylococcus aureus: MIC = 0.075 μM; MBEC = 2.35 μM), and transcriptional analysis revealed that HPs 3, 28, and 29 induce rapid iron starvation in MRSA biofilms. Several HPs demonstrated excellent activities against Mycobacterium tuberculosis (HP 34, MIC = 0.80 μM against CDC1551). This work established new SAR insights, and HP 29 demonstrated efficacy in dorsal wound infection models in mice. Encouraged by these findings, we believe that HPs could lead to significant advances in the treatment of challenging infections.

Lithium-Conducting Self-Assembled Organic Nanotubes

Supramolecular polymers are compelling platforms for the design of stimuli-responsive materials with emergent functions. Here, we report the assembly of an amphiphilic nanotube for Li-ion conduction that exhibits high ionic conductivity, mechanical integrity, electrochemical stability, and solution processability. Imine condensation of a pyridine-containing diamine with a triethylene glycol functionalized isophthalaldehyde yields pore-functionalized macrocycles. Atomic force microscopy, scanning electron microscopy, and in solvo X-ray diffraction reveal that macrocycle protonation during their mild synthesis drives assembly into high-aspect ratio (>103) nanotubes with three interior triethylene glycol groups. Electrochemical impedance spectroscopy demonstrates that lithiated nanotubes are efficient Li+ conductors, with an activation energy of 0.42 eV and a peak room temperature conductivity of 3.91 ± 0.38 × 10-5 S cm-1. 7Li NMR and Raman spectroscopy show that lithiation occurs exclusively within the nanotube interior and implicates the glycol groups in facilitating efficient Li+ transduction. Linear sweep voltammetry and galvanostatic lithium plating-stripping tests reveal that this nanotube-based electrolyte is stable over a wide potential range and supports long-term cyclability. These findings demonstrate how the coupling of synthetic design and supramolecular structural control can yield high-performance ionic transporters that are amenable to device-relevant fabrication, as well as the technological potential of chemically designed self-assembled nanotubes.

Thermoresponsive Corannulene

We demonstrate herein that corannulene, a bowl-shaped polycyclic aromatic hydrocarbon, can assemble into larger supramolecular structures in water through a change in the solution temperature. This property is invoked through a simple five-fold symmetric

Solid phase synthesis of oligoethylene glycol-functionalized quinolinecarboxamide foldamers with enhanced solubility properties

A series of octameric quinoline oligoamide foldamers has been synthesized consisting exclusively of monomers which display mono-, di-, tri- or tetra-ethylene glycol side-chains. These oligomers adopt stable helical conformations. New Fmoc-acid monomer precursors were first developed. The microwave assisted solid-phase synthesis (SPS) methodology for oligomer preparation is described, and it is demonstrated that small adjustments in side-chain length translate into large differences in the solubility profile of the oligomers. The impact of such modifications on foldamer preparation, handedness inversion kinetics and potential applications is also discussed.

Tailor-made N-heterocyclic carbenes for nanoparticle stabilization

N-heterocyclic carbenes (NHCs) represent a leading class of ligands in organometallic chemistry, but have been rarely exploited as stabilizers for metal nanoparticles (NPs). We report the first example of NHC stabilized Pd-NPs that demonstrate long term stability. These NHC Pd-NPs were synthesized by a facile ligand exchange protocol using rationally designed long chained NHCs (LC-NHCs). Furthermore, we demonstrate that the surface modification of Pd-NPs results in significant chemoselectivity in a model reaction. The Royal Society of Chemistry 2014.

Interfacial strain-promoted alkyne-azide cycloaddition (I-SPAAC) for the synthesis of nanomaterial hybrids

An interfacial strain promoted azide-alkyne cycloaddition (I-SPACC) is introduced as a method to prepare robust nanomaterial hybrids. This is demonstrated with a reaction between a novel dibenzocyclooctyne-modified single walled carbon nanotubes (DBCO-SWC

Rapid preparation of multifunctional surfaces for orthogonal ligation by microcontact chemistry

Microcontact chemistry has been applied to patterned glass and silicon substrates by successive reaction of unprotected and monoprotected heterobifunctional linkers with alkene-terminated self-assembled monolayers (SAMs) to produce bi-, tri-, and tetrafunctional surfaces. Photochemical microcontact printing of an azide thiol linker followed by immobilization of an acid thiol linker on an undecenyl-terminated SAM results in a well-defined, micropatterned surface with terminal azide, acid, and alkene groups. Biologically relevant molecules (biotin, carbohydrates) have been selectively attached to the surface by means of orthogonal ligation chemistry, and the resulting microarrays display selective binding to fluorescently labeled proteins. An orthogonally addressable, tetrafunctional surface (azide, acid, alkene, and amine) can be prepared by an additional printing step of a tert-butyloxycarbonyl (Boc)-protected alkyne amine linker on the azide structures by using the copper(I)-catalyzed azide-alkyne Huisgen cycloaddition and subsequent removal of the protective group. Copyright