23601-40-3

Usage

Uses

Used in Bioconjugation:
HEXAETHYLENE GLYCOL MONOMETHYL ETHER is used as a crosslinker for bioconjugation, allowing the formation of stable and functional bioconjugates due to its ability to react with various functional groups.
Used in Drug Delivery:
HEXAETHYLENE GLYCOL MONOMETHYL ETHER is used as a component in drug delivery systems, enhancing the solubility and bioavailability of drugs in aqueous media, thanks to its hydrophilic PEG spacer.
Used in PEG Hydrogel:
HEXAETHYLENE GLYCOL MONOMETHYL ETHER is used as a crosslinker in the formation of PEG hydrogels, providing a stable and biocompatible matrix for various applications, such as tissue engineering and drug delivery.
Used in Surface Functionalization:
HEXAETHYLENE GLYCOL MONOMETHYL ETHER is used for surface functionalization, allowing the attachment of various functional groups to surfaces, which can be beneficial in applications such as coatings, sensors, and medical devices.

Upstream product

• 112-35-6 triethylene glucol monomethyl ether 
• 75-21-8 oxirane 
• 109-86-4 2-methoxy-ethanol 
• 52995-76-3 1-chloro-3,6,9-trioxadecane 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 2615-15-8 pentaethylene glycol 
• 74-88-4 methyl iodide 
• 112-60-7 Tetraethylene glycol 
• 50586-80-6 toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester 
• 62921-74-8 2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate 
• 111-77-3 2-(2-methoxyethoxy)ethyl alcohol 
• 75-44-5 phosgene 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 155887-96-0 2,5,8,11,14,17-hexaoxanonadecan-19-yl 4-methylbenzenesulfonate 
• 477788-13-9 activated hexaethylene glycol monomethyl oligomer 
• 211859-58-4 1-Phenyl-2,5,8,11,14,17,20,23,26,29-decaoxatriacontane 
• 1338602-91-7 C₅₂H₈₈O₂₄ 
• 1338602-92-8 C₃₉H₆₂O₁₇ 
• 1338602-94-0 C₅₆H₉₀N₂O₂₅ 
• 1338602-95-1 C₄₃H₆₄N₂O₁₈ 
• 1279100-21-8 C₄₇H₈₆O₂₃ 
• 1338602-87-1 C₃₄H₆₀O₁₆ 
• 1338602-88-2 C₄₆H₈₄O₂₃ 
• 1338602-89-3 C₃₃H₅₈O₁₆ 
• 1440529-35-0 3-(2-(2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)benzyl alcohol 
• 1440529-36-1 3-(2-(2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)benzyl bromide 
• 1440529-29-2 3-(2-(2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)benzyl azide 

Relevant academic research and scientific papers

Effect of the length of polyoxyethylene substituents on luminescent bimetallic lanthanide bioprobes

The new homoditopic ligand H2LC2′ self-assembles with lanthanide ions (LnIII) to yield neutral bimetallic helicates of overall composition [Ln2(L C2′)3]; it is fitted with two hexakis(oxyethylene) chains to test their effects on the thermodynamic, photophysical and biochemical properties of these complexes, with particular emphasis on their uptake by living cells. At physiological pH and under stoichiometric conditions, the conditional stability constants log β23 are around 28 resulting in the speciation of the EuIII helicate being >92% for a total ligand concentration of 1 mM. The ligand triplet state features adequate energy (0-phonon transition at ≈800 cm-1) for sensitising the luminescence of EuIII (Q = 19%) and TbIII (Q = 10%) in aerated water at pH 7.4. The Eu(5D0) emission spectrum and lifetime (2.43 ms) are characteristic of a species with pseudo-D3 symmetry and without bound water in the inner coordination sphere. The viability of HeLa cancerous cells is unaffected when incubated with up to 500 μM [Eu2(LC2′)3] during 24 h. The Eu III helicate permeates into the cytoplasm of these cells by endocytosis and remains essentially undissociated, despite a low intracellular concentration of 0.28 μM. In addition, the leakage of the EuIII helicate out of HeLa cells is very minimal over long periods of time. With respect to similar complexes with ligands bearing shorter tris(oxyethylene) chains, no substantial changes are observed, which opens the way for targeting experiments. This study also demonstrates that the [Ln2(L CX)3] helicates are fairly robust entities since their core is unaffected by the substitution in the pyridine 4-position. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

A Water-Soluble m-Phenylene Ethynylene Foldamer

(Equation presented) A water-soluble m-phenylene ethynylene (mPE) foldamer was realized by appending hexaethylene glycol side chains to the backbone repeat unit. UV spectra of the oligomer in aqueous solutions were consistent with a helical conformation. The association constant of the oligomer with (-)-α-pinene increased dramatically with increasing water composition, peaking at 90% water by volume in acetonitrile. The rate of the host/guest system's approach to equilibrium was found to decrease considerably with increasing water content.

Self-Assembly and Molecular Recognition in Water: Tubular Stacking and Guest-Templated Discrete Assembly of Water-Soluble, Shape-Persistent Macrocycles

Supramolecular chemistry in aqueous media is an area with great fundamental and practical significance. To examine the role of multiple noncovalent interactions in controlled assembling and binding behavior in water, the self-association of five water-soluble hexakis(m-phenylene ethynylene) (m-PE) macrocycles, along with the molecular recognition behavior of the resultant assemblies, is investigated with UV-vis, fluorescence, CD, and NMR spectroscopy, mass spectrometry, and computational studies. In contrast to their different extents of self-aggregation in organic solvents, all five macrocycles remain aggregated in water at concentrations down to the micromolar (μM) range. CD spectroscopy reveals that 1-F6 and 1-H6, two macrocycles carrying chiral side chains and capable of H-bonded self-association, assemble into tubular stacks. The tubular stacks serve as supramolecular hosts in water, as exemplified by the interaction of macrocycles 1-H6 and 2-H6 and guests G1 through G4, each having a rod-like oligo(p-phenylene ethynylene) (p-PE) segment flanked by two hydrophilic chains. Fluorescence and 1H NMR spectroscopy revealed the formation of kinetically stable, discrete assemblies upon mixing 2-H6 and a guest. The binding stoichiometry, determined with fluorescence, 1H NMR, and ESI-MS, reveals that the discrete assemblies are novel pseudorotaxanes, each containing a pair of identical guest molecules encased by a tubular stack. The two guest molecules define the number of macrocyclic molecules that comprise the host, which curbs the "infinite" stack growth, resulting in a tubular stack with a cylindrical pore tailoring the length of the p-PE segment of the bound guests. Each complex is stabilized by the action of multiple noncovalent forces including aromatic stacking, side-chain H-bonding, and van der Waals interactions. Thus, the interplay of multiple noncovalent forces aligns the molecules of macrocycles 1 and 2 into tubular stacks with cylindrical inner pores that, upon binding rod-like guests, lead to tight, discrete, and well-ordered tubular assemblies that are unprecedented in water.

Monodisperse oligoethylene glycols modified Camptothecin, 10-Hydroxycamptothecin and SN38 prodrugs

Camptothecin, which represents a class of natural products with high anticancer activity, suffers low water solubility which hampers its clinic application. To address this issue, monodisperse polyethylene glycols were employed to modify this class of natural products, including Camptothecin, 10-Hydroxycamptothecin, and SN38. Through selective modification with a series of monodisperse polyethylene glycols, 31 Camptothecin derivatives, including 9 ethers and 22 carbonates, were prepared using a macrocyclic sulfate-based strategy with high efficacy. Monodisperse polyethylene glycols modification provided the Camptothecin derivatives with high purity and fine-tunable water solubility. Through the physicochemical and biological assays, a few novel prodrugs with good solubility, cytotoxicity, and valuable drug release profile were identified as promising anticancer drug candidates.

AMYLOID TARGETING AGENTS AND METHODS OF USING THE SAME

Provided herein is the design and synthesis of novel molecular rotor fluorophores useful for detection of amyloid or amyloid like proteins. The fluorophores are designed to exhibit enhanced fluorescence emission upon associating with amyloid or amyloid like proteins as compared to unbound compound. Also disclosed herein are methods for treating diseases associated with amyloid or amyloid like proteins.

Facially Amphipathic Glycopolymers Inhibit Ice Recrystallization

Antifreeze glycoproteins (AFGPs) from polar fish are the most potent ice recrystallization (growth) inhibitors known, and synthetic mimics are required for low-temperature applications such as cell cryopreservation. Here we introduce facially amphipathic glycopolymers that mimic the three-dimensional structure of AFGPs. Glycopolymers featuring segregated hydrophilic and hydrophobic faces were prepared by ring-opening metathesis polymerization, and their rigid conformation was confirmed by small-angle neutron scattering. Ice recrystallization inhibition (IRI) activity was reduced when a hydrophilic oxo-ether was installed on the glycan-opposing face, but significant activity was restored by incorporating a hydrophobic dimethylfulvene residue. This biomimetic strategy demonstrates that segregated domains of distinct hydrophilicity/hydrophobicity are a crucial motif to introduce IRI activity, which increases our understanding of the complex ice crystal inhibition processes.

Monodisperse oligoethylene glycols modified Propofol prodrugs

The low water solubility of Propofol resulted in complicated formulation and adverse effects during its clinical application. To improve its water solubility and maintain its anesthetic effects, Propofol prodrugs with monodisperse oligoethylene glycols as solubility enhancer were designed and synthesized. Monodisperse oligoethylene glycols enable the concise manipulation of water solubility, biocompatibility and anesthetic effects. Through the physicochemical and biological assay, a few water soluble prodrugs of Propofol were identified as promising anesthetic to overcome the drawbacks associated with Propofol.

IN VITRO COMPOSITIONS COMPRISING HUMAN SAMPLE AND AMYLOID TARGETING AGENT

Provided herein are compositions and methods useful for detection of amyloid related disorders in samples, such as human tissue, cell or body fluid. Use of the compositions and methods herein allows for the rapid, in vitro detection of amyloid accumulation, often before amyloid disorder symptoms are manifest or without introduction of foreign fluorophore molecules into a subject.

AMYLOID TARGETING AGENTS AND METHODS OF USING THE SAME

Provided herein is the design and synthesis of novel molecular rotor fluorophores useful for detection of amyloid or amyloid like proteins. The fluorophores are designed to exhibit enhanced fluorescence emission upon associating with amyloid or amyloid like proteins as compared to unbound compound. Also disclosed herein are the methods for treating of diseases associated with an amyloid or amyloid like proteins.

Gold nanoparticles generated by thermolysis of "all-in-one" gold(i) carboxylate complexes

Consecutive synthesis methodologies for the preparation of the gold(i) carboxylates [(Ph3P)AuO2CCH2(OCH 2CH2)nOCH3] (n = 0-6) (6a-g) are reported, whereby selective mono-alkylation of diols HO(CH2CH 2O)nH (n = 0-6), Williamson ether synthesis and metal carboxylate (Ag, Au) formation are the key steps. Single crystal X-ray diffraction studies of 6a (n = 0) and 6b (n = 1) were carried out showing that the P-Au-O unit is essentially linear. These compounds were applied in the formation of gold nanoparticles (NP) by a thermally induced decomposition process and hence the addition of any further stabilizing and reducing reagents, respectively, is not required. The ethylene glycol functionalities, providing multiple donating capabilities, are able to stabilise the encapsulated gold colloids. The dependency of concentration, generation time and ethylene glycol chain lengths on the NP size and size distribution is discussed. Characterisation of the gold colloids was performed by TEM, UV/Vis spectroscopy and electron diffraction studies revealing that Au NP are formed with a size of 3.3 (±0.6) to 6.5 (±0.9) nm in p-xylene with a sharp size distribution. Additionally, a decomposition mechanism determined by TG-MS coupling experiments of the gold(i) precursors is reported showing that 1 st decarboxylation occurs followed by the cleavage of the Au-PPh 3 bond and finally release of ethylene glycol fragments to give Au-NP and the appropriate organics. The Royal Society of Chemistry 2012.