23778-52-1

Usage

Uses

Used in Bioconjugation:
PENTAETHYLENE GLYCOL MONOMETHYL ETHER is used as a linker for bioconjugation to facilitate the attachment of biological molecules, such as proteins or antibodies, to other molecules or surfaces. The hydroxyl group enables the formation of stable covalent bonds, improving the stability and functionality of the resulting bioconjugates.
Used in Drug Delivery:
PENTAETHYLENE GLYCOL MONOMETHYL ETHER is used as a component in drug delivery systems to improve the solubility, bioavailability, and targeted delivery of therapeutic agents. The hydrophilic PEG spacer can help reduce the immunogenicity and increase the circulation time of drug carriers, enhancing the overall efficacy of the treatment.
Used in PEG Hydrogels:
PENTAETHYLENE GLYCOL MONOMETHYL ETHER is used as a crosslinker for the formation of PEG hydrogels, which are versatile materials with applications in tissue engineering, drug delivery, and wound healing. The hydroxyl group allows for the formation of stable hydrogel networks with tailored mechanical and swelling properties.
Used in Surface Functionalization:
PENTAETHYLENE GLYCOL MONOMETHYL ETHER is used for surface functionalization to modify the properties of various materials, such as plastics, metals, or glass. The hydroxyl group can be used to attach specific functional groups or biomolecules to the surface, providing improved biocompatibility, antifouling properties, or other desired characteristics.

InChI:InChI=1/C11H24O6/c1-13-4-5-15-8-9-17-11-10-16-7-6-14-3-2-12/h12H,2-11H2,1H3

Upstream product

• 75-21-8 oxirane 
• 109-86-4 2-methoxy-ethanol 
• 52995-76-3 1-chloro-3,6,9-trioxadecane 
• 111-46-6 diethylene glycol 
• 112-60-7 Tetraethylene glycol 
• 6482-24-2 2-Bromoethyl methyl ether 
• 5334-32-7 1⁽²⁾,7-dihydro-pyrazolo[3,4-d]pyrimidine-4,6-dithione 
• 60696-83-5 methanesulfonic acid 2-(2-methoxyethoxy)ethyl ester 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 57671-28-0 2-(2-{2-[2-(2-benzyloxyethoxy)ethoxy]ethoxy}ethoxy)ethanol 
• 4792-15-8 Pentaethylene glycol 
• 112-35-6 triethylene glucol monomethyl ether 
• 62921-74-8 2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate 
• 74-88-4 methyl iodide 

Downstream Products

• 1191-87-3 pentaglyme 
• 870809-06-6 4-vinylbenzyl methoxypentakis(oxyethylene) ether 
• 854601-80-2 1-bromo-2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethane 
• 1451984-48-7 C₄₀H₇₂O₁₉ 
• 1451984-47-6 C₄₃H₇₅N₃O₂₀ 
• 1451984-61-4 C₂₀H₃₂O₉ 

Relevant academic research and scientific papers

Engineering Nanoparticulate Organic Photocatalysts via a Scalable Flash Nanoprecipitation Process for Efficient Hydrogen Production

Directly converting sunlight into hydrogen fuels using particulate photocatalysts represents a sustainable route for clean energy supply. Organic semiconductors have emerged as attractive candidates but always suffer from optical and exciton recombination losses with large exciton “dead zone” inside the bulk material, severely limiting the catalytic performance. Herein, we demonstrate a facile strategy that combines a scalable flash nanoprecipitation (FNP) method with hydrophilic soluble polymers (PC-PEG5 and PS-PEG5) to prepare highly efficient nanosized photocatalysts without using surfactants. Significantly, a 70-fold enhancement of hydrogen evolution rate (HER) is achieved for nanosized PC-PEG5, and the FNP-processed PS-PEG5 shows a peak HER rate of up to 37.2 mmol h?1 g?1 under full-spectrum sunlight irradiation, which is among the highest results for polymer photocatalysts. A scaling-up production of nanocatalyst is demonstrated with the continuously operational FNP.

Hybrids of Small-Molecule CD4 Mimics with Polyethylene Glycol Units as HIV Entry Inhibitors

CD4 mimics are small molecules that inhibit the interaction of gp120 with CD4. We have developed several CD4 mimics. Herein, hybrid molecules consisting of CD4 mimics with a long alkyl chain or a PEG unit attached through a self-cleavable linker were synthesized. In anti-HIV activity, modification with a PEG unit appeared to be more suitable than modification with a long alkyl chain. Thus, hybrid molecules of CD4 mimics, with PEG units attached through an uncleavable linker, were developed and showed high anti-HIV activity and low cytotoxicity. In investigation of pharmacokinetics in a rhesus macaque, a hybrid compound had a more effective PK profile than that of the parent compound, and intramuscular injection was a more useful administration route to maintain the high blood concentration of the CD4 mimic than intravenous injection. The presented hybrid molecules of CD4 mimics with a PEG unit would be practically useful when combined with a neutralizing antibody.

Designing Nonfullerene Acceptors with Oligo(Ethylene Glycol) Side Chains: Unraveling the Origin of Increased Open-Circuit Voltage and Balanced Charge Carrier Mobilities

Despite the recent rapid development of organic solar cells (OSCs), the low dielectric constant (?r=3–4) of organic semiconducting materials limits their performance lower than inorganic and perovskite solar cells. In this work, we introduce oligo(ethylene glycol) (OEG) side chains into the dicyanodistyrylbenzene-based non-fullerene acceptors (NIDCS) to increase its ?r up to 5.4. In particular, a NIDCS acceptor bearing two triethylene glycol chains (NIDCS-EO3) shows VOC as high as 1.12 V in an OSC device with a polymer donor PTB7, which is attributed to reduced exciton binding energy of the blend film. Also, the larger size grain formation with well-ordered stacking structure of the NIDCS-EO3 blend film leads to the increased charge mobility and thus to the improved charge mobility balance, resulting in higher JSC, FF, and PCE in the OSC device compared to those of a device using the hexyl chain-based NIDCS acceptor (NIDCS-HO). Finally, we fabricate NIDCS-EO3 devices with various commercial donors including P3HT, DTS-F, and PCE11 to show higher photovoltaic performance than the NIDCS-HO devices, suggesting versatility of NIDCS-EO3.

Enzyme-Mediated Directional Transport of a Small-Molecule Walker with Chemically Identical Feet

We describe a small-molecule "walker" that uses enzyme catalysis to discriminate between the relative positions of its "feet" on a track and thereby move with net directionality. The bipedal walker has identical carboxylic acid feet, and "steps" along an isotactic hydroxyl-group-derivatized polyether track by the formation/breakage of ester linkages. Lipase AS catalyzes the selective hydrolysis of the rear foot of macrocyclized walkers (an information ratchet mechanism), the rear foot producing an (R)-stereocenter at its point of attachment to the track. If the hydrolyzed foot reattaches to the track in front of the bound foot it forms an (S)-stereocenter, which is resistant to enzymatic hydrolysis. Only macrocyclic walker-track conjugates are efficiently hydrolyzed by the enzyme, leading to high processivity of the walker movement along the track. Conventional chemical reagents promote formation of the ester bonds between the walker and the track. Iterative macrocyclization and hydrolysis reactions lead to 68% of walkers taking two steps directionally along a three-foothold track.

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.

Doubly activated supramolecular reaction: Transesterification of acyclic oligoether esters with metal alkoxides

Transesterification reactions of acyclic oligoether esters E3-E10 with metal alkoxides were accelerated upon noncovalent complexation of the esters with metal ions. In the reaction of monovalent alkaline metal alkoxides, CH3ONa and CH3OK, plots of the observed rate constants kobs with respect to the chain length of E3-E10 showed selective acceleration of the transesterification. Compared with the shortest E3, which can hardly bind metal ion, 4.3- and 6.6-fold accelerations in the maxima were achieved in the combinations of E5/CH3ONa and E6/CH3OK, respectively. Supramolecular intermediate complex could be spectrometrically visualized by ESI-FT-ICR-MS in the course of reaction. Kinetic experiments, together with structural analyses by means of NMR, mass spectrometry, and DFT calculations of the intermediate complexes, indicate that a size-fit complex of host substitute with alkali metal ion allows strong electron withdrawing due to the close contact of the carbonyl oxygen to the metal ion, resulting in the selective rate enhancement of the reaction, while in the reaction of E3-E10 with a divalent alkaline earth metal alkoxide, (CH3- CH2O)2Ba, the kobs values increased stepwise with elongation of the side arm to attain an dramatic large acceleration. In comparison with the kobs of E3, 4610-fold acceleration was achieved in the reaction of E10. The double activation of the host substrate and guest counter nucleophile at once brings about this extraordinary rate acceleration. The strong wrapping complexation of long oligoether ester with barium ethoxide allows for the effective electron withdrawal from the ester carbonyl group (host activation) as well as separation of the accompanying guest alkoxide anions (guest activation).

Polyethylene glycol-based homologated ligands for nicotinic acetylcholine receptors

A homologous series of polyethylene glycol (PEG) monomethyl ethers were conjugated with three ligand series for nicotinic acetylcholine receptors. Conjugates of acetylaminocholine, the cyclic analog 1-acetyl-4,4-dimethylpiperazinium, and pyridyl ether A-84543 were prepared. Each series was found to retain significant affinity at nicotinic receptors in rat cerebral cortex with tethers of up to six PEG units. Such compounds are hydrophilic ligands which may serve as models for fluorescent/affinity probes and multivalent ligands for nAChR.

Effects of hydration on the thermodynamic properties of aqueous ethylene glycol ether solutions

The densities and isobaric specific heat capacities of binary mixtures of water with various open-chain and cyclic ethylene glycol ethers have been measured at 298.15 K using vibrating tube densimetry, and flow or differential scanning calorimetry, respectively. Excess molar volumes were derived over the whole composition range. Molar isobaric heat capacities and the relative apparent thermodynamic quantities were determined in the water-rich region. The data reflect the changes in the structure and hydrogen-bond dynamics of water caused by these non-ionic solutes. The observed effects are discussed in terms of the influence of hydrophobic hydration on the thermodynamic properties of aqueous solutions. Correlations are given that enable the prediction of the thermodynamic properties of open-chain and cyclic oligo(ethylene oxide) ethers in their pure liquid state and at infinite dilution in water.

Chemically modified small molecules

The invention provides small molecule drugs that are chemically modified by covalent attachment of a water-soluble oligomer obtained from a monodisperse or bimodal water-soluble oligomer composition. A conjugate of the invention, when administered by any of a number of administration routes, exhibits a reduced biological membrane crossing rate as compared to the biological membrane crossing rate of the small molecule drug not attached to the water-soluble oligomer.

Synthesis of thermosensitive water-soluble polystyrenics with pendant methoxyoligo(ethylene glycol) groups by nitroxide-mediated radical polymerization

Nitroxide-mediated radical polymerizations of 4-vinylbenzyl methoxytris(oxyethylene) ether (TEGSt), 4-vinylbenzyl methoxytetrakis(oxyethylene) ether (TrEGSt), and 4-vinylbenzyl methoxypentakis-(oxyethylene) ether (PEGSt) were carried out at 120°C using 2,2,5-trimethyl-3-(1-phenylethoxy)-4-phenyl-3-azahexane as initiator. Kinetics study and gel permeation chromatography analysis showed that the polymerizations were living processes yielding polymers with controlled molecular weights and narrow molecular weight distributions. The polymers can be dissolved in water forming transparent solutions and undergo phase transitions when the temperature is above a critical point. The cloud points of the homopolymers of TEGSt, TrEGSt, and PEGSt were around 13, 39, and 55°C, respectively, which were also supported by variable temperature 1H NMR spectroscopy analysis. The high level of alkoxyamine chain end retention allowed the synthesis of diblock copolymers with low polydispersities (1H NMR studies indicated that the diblock copolymers undergo phase transition in water at a temperature between the cloud points of the two corresponding homopolymers.