Oegma

Manufactured by Merck Group

Sourced in United States

OEGMA is a monofunctional methacrylate monomer derived from oligoethylene glycol. It is commonly used in the synthesis of polymers and hydrogels for various biomedical and pharmaceutical applications.

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Lab products found in correlation

Degma, by Merck Group (3 mentions) 1 4 dioxane, by Merck Group (2 mentions) Meo2ma, by Merck Group (2 mentions) 4 dimethylaminopyridine dmap, by Merck Group (2 mentions) Tetrahydrofuran, by Merck Group (2 mentions) Copper 1 bromide, by Merck Group (2 mentions) 2 hydroxyethyl methacrylate, by Merck Group (2 mentions) 2 methacryloyloxy ethyl dimethyl 3 sulfopropyl ammoniumhydroxide, by Merck Group (1 mentions) Dmaema, by Merck Group (1 mentions) Oligo ethylene glycol methacrylate oegma, by Merck Group (1 mentions) 4 cyano 4 dodecylsulfanylthiocarbonyl pentanoic acid cdp, by Merck Group (1 mentions) 1 iodododecane, by Merck Group (1 mentions) 2 dimethylamino ethyl methacrylate dmaema, by Merck Group (1 mentions) Deuterated chloroform cdcl3, by Merck Group (1 mentions) Cuprous chloride, by Sinopharm (1 mentions) Chloroauric acid hydrate, by Sinopharm (1 mentions) 4 6 diamidino 2 phenylindole (dapi), by Sinopharm (1 mentions) Tris 2 dimethylamino ethyl amine me6tren, by Thermo Fisher Scientific (1 mentions) Dulbecco modified eagle medium (dmem), by Thermo Fisher Scientific (1 mentions) Rpmi 1640, by Thermo Fisher Scientific (1 mentions)

Close spelling variants of this product

Oligo(ethylene glycol) methyl ether methacrylate (OEGMA; (5 citations) (oligo ethylene glycol)methacrylate (OEGMA) (3 citations) Methacrylate OEGMA (3 citations)

14 protocols using oegma

Purification and Storage of Monomers

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All
chemicals and solvents are commercially
available and were used as received unless otherwise stated. Sulfobetaine
methacrylate monomer (SBM, also named [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium
hydroxide, Sigma-Aldrich) was purified by precipitation of its methanol
solution against diethyl ether twice, followed by drying under reduced
pressure at room temperature. The purified monomer was stored in a
fridge before use. Oligo(ethylene glycol) methyl ether methacrylate
(OEGMA, Sigma-Aldrich, averaged molar mass 300 Da) and di(ethylene
glycol) methyl ether methacrylate (DEGMA, Sigma-Aldrich) were purified
by passing through neutral alumina column chromatography to remove
the inhibitors and were stored in a fridge before use. Copper metal
chips were washed, successively, with dilute sulfuric acid and water
(many times) to remove oxidized copper from surface. The cleaned copper
chips were stored under nitrogen gas.

Jiang T., Aseyev V., Niskanen J., Hietala S., Zhang Q, & Tenhu H. (2020). Polyzwitterions with LCST Side Chains: Tunable Self-Assembly. Macromolecules, 53(19), 8267-8275.

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Synthesis of DMAEMA-OEGMA Copolymers

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The monomers 2-(dimethylamino)ethyl methacrylate (DMAEMA, 98%) and (oligo ethylene glycol)methacrylate (OEGMA) (average Mn = 950 g∙mol⁻¹, 19 ethylene oxide units) were purchased from Sigma Aldrich, Greece. Both DMAEMA and OEGMA were purified using a column filled with inhibitor removers before polymerization. 2,2′-Azobis (isobutyronitrile) (AIBN), the radical initiator utilized, was purified by recrystallization from methanol. 4-Cyano-4-(dodecylsulfanylthiocarbonyl)pentanoic acid (CDP) as the CTA, methyl iodide (CH₃I) 1-iodohexane (C₆H₁₃I, ≥98%), 1-iodododecane (C₁₂H₂₅I, 98%), 1,4-dioxane (≥99.8% pure), and tetrahydrofuran (THF, ≥99.9% pure) were obtained from Sigma Aldrich, Greece and used as received, except 1-4-dioxane, which was first dried over molecular sieves. Deuterated chloroform (CDCl₃) was used as the solvent for the ¹H-NMR experiments and was also obtained from Sigma Aldrich, Greece. Dialysis tubing membranes (MEMBRA-CEL^®) from regenerated cellulose of MWCO 3500 and a diameter of 22 mm were purchased from SERVA, Heidelberg, Germany.

Vardaxi A, & Pispas S. (2023). Stimuli-Responsive Self-Assembly of Poly(2-(Dimethylamino)ethyl Methacrylate-co-(oligo ethylene glycol)methacrylate) Random Copolymers and Their Modified Derivatives. Polymers, 15(6), 1519.

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Dual-Responsive Nanoparticle Synthesis

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MEO₂MA, OEGMA, bis[2-(2′-broMoisobutyryloxy)-ethyl]disulfide (BiBOEDS), silver trifluoroacetate (CF₃COOAg) and poly(vinylpyrrolidone) (PVP, M_w=55kD) were obtained from Sigma-Aldrich Corp (St Louis, MO, USA). Tris(2-dimethyl-aminoethyl)amine (Me₆TREN) and anhydrous sodium hydrosulfide (NaHS) were purchased from Alfa Aesar (Shanghai, China). Ethylene glycol (EG, purity>99.0%), cuprous chloride (CuCl), chloroauric acid hydrate (HAuCl₄·4H₂O, Au content>47.8%) and 4'6-diamidino-2-phenylindole (DAPI) were purchased from Sinopharm Chemical Reagent Co., Ltd (Beijing, China). DMEM, RPMI 1640 and fetal bovine serum (FBS) were obtained from Gibco BRL/Life Technologies (Grand Island, NY, USA). pHLIP (ACEQNPIYWARYADWLFTTPLLLLDLALLVDADEGT) was synthesized by Bankpeptide Inc. (Heifei, China). All other reagents were of analytical grade and used without any further purification.

Huang W., Zhao H., Wan J., Zhou Y., Xu Q., Zhao Y., Yang X, & Gan L. (2019). pH- and photothermal-driven multistage delivery nanoplatform for overcoming cancer drug resistance. Theranostics, 9(13), 3825-3839.

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Synthesis of Thermoresponsive Polymer Brushes

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The solvents petroleum ether (40–60 °C), diethyl ether, dichloromethane, ethyl acetate and acetone, and the reagents cyanomethyl dodecyl trithiocarbonate, 4,4′-azobis(4-cyanovaleric acid) (ACVA) and 4-dimethylaminopyridine (DMAP) were purchased from Sigma Aldrich and used as received. N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC·HCl) was purchased from Alpha Aesar and used as received. 1,4-Dioxane, and the monomers DEGMA, OEGMA (M_n = 300 g mol^–1), nBA and DMA were purchased from Sigma Aldrich and passed through a column of basic alumina prior to use. NIPAM was purchased from Sigma Aldrich and recrystallized from a toluene–hexane mixture prior to use. 2,2′-Azobisisobutyronitrile (AIBN) was purchased from Sigma Aldrich and recrystallized from methanol prior to use. Dialysis membrane (MWCO = 3.5–5 kDa) was purchased from Spectra/Por. The synthesis of N,N-diethylacrylamide,⁶¹ 2-cyano-2-propyl dodecyl trithiocarbonate,⁶² 4-cyano-4-(((ethylthio)carbonothioyl)thio) pentanoic acid⁶³ have been described previously in the literature.

Blackman L.D., Gibson M.I, & O'Reilly R.K. (2016). Probing the causes of thermal hysteresis using tunable N agg micelles with linear and brush-like thermoresponsive coronas †Electronic supplementary information (ESI) available: NMR spectra of small molecules and polymers, SEC chromatograms of the polymers, DLS, SLS and turbidimetry data for the micelles, a discussion of the chain density of micelles 11–15, additional calculations regarding the core composition of polymers 1–5 and definitions and calculations related to the light scattering data. See DOI: 10.1039/c6py01191h Click here for additional data file.. Polymer Chemistry, 8(1), 233-244.

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Purification and Characterization of OEGMA

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OEGMA (with nominal molecular
weights of 188, 300, 950, and 2050 g·mol^–1)
and α-CD were purchased from Sigma-Aldrich. In this work, OEGMA
oligomers were purified by passing them through a basic alumina oxide
column to remove inhibitors and α-CD was used as received. All
solutions were prepared with Milli-Q grade water (18.2 MΩ cm).

Mariano M., Bernardinelli O.D., Pires-Oliveira R., Ferreira G.A, & Loh W. (2020). Inclusion Complexation between α-Cyclodextrin and Oligo(ethylene glycol) Methyl Ether Methacrylate. ACS Omega, 5(16), 9517-9528.

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Synthesis and Characterization of Responsive Polymeric Materials

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Materials CPDTC (abcr, 97%), CDTPA (abcr, 97%), DTP (TCI, 98%), 2,2 0 -(ethylenedioxy)diethanethiol (EDT, Sigma Aldrich, 95%), hexylamine (Sigma Aldrich, 99%). BTPEMA was synthesized according to the literature. 22 All the solvents were used as received. OEGMA (Sigma Aldrich, % M n = 300 Da) was passed through activated basic alumina prior to the polymerizations. NIPAM (TCI, 98%) was recrystallized twice from n-hexane and stored at À30 1C.

Xu J, & Abetz V. (2022). Double thermoresponsive graft copolymers with different chain ends: feasible precursors for covalently crosslinked hydrogels. Soft matter, 18(10).

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Pt(IV)-Containing Difunctional Alkyne Synthesis

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DOX and cisplatin were purchased from Beijing Huafeng United Technology Co., Ltd. OEGMA (M_n =480 g/mol, 99%) purchased from Sigma-Aldrich and Co was passed through a neutral alumina column to remove the inhibitor prior to use. Toluene (99%; Aldrich) was refluxed with sodium beads/benzophenone complex and distilled until the solution turned purple. Copper(I) bromide (99.999%; Aldrich), PMDETA (98%; Aldrich), hydrogen peroxide (30%; J&K CHEMICA), sodium vitamin (VcNa; 99%; Aladdin) and succinic anhydride (99%; Aladdin) were used as received without further purification. AzPMA and the difunctional initiator, HBMP, were synthesized according to literature procedures.44 ,45 A Pt(IV)-containing difunctional alkyne was prepared from cisplatin. The experimental procedure is presented in Supplementary materials.

Zhu C., Xiao J., Tang M., Feng H., Chen W, & Du M. (2017). Platinum covalent shell cross-linked micelles designed to deliver doxorubicin for synergistic combination cancer therapy. International Journal of Nanomedicine, 12, 3697-3710.

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Thermosensitive Hydrogel with Antimicrobial Agent

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Briefly, the hydrogel precursor solution was prepared using di(ethylene glycol) methyl ether methacrylate (MEO₂MA, Sigma Aldrich, Taiwan) and oligo (ethylene glycol) methyl ether methacrylate (OEGMA, Sigma Aldrich, Taiwan) monomers mixed at a 9:1 M ratio to achieve a lower critical solution temperature near to body temperature (37 °C). The polymers were cross-linked with di(ethylene glycol) di methacrylate (DEGDMA, Sigma Aldrich, Taiwan) using water/ethanol (1/1) as the solvent. Then, ammonium persulphate (APS, Wako Pure Chemical Industries, Japan) and tetramethyl ethylenediamine (TEMED, Wako Pure Chemical Industries, Japan) were added to initiate and activate the polymerisation, with all ratios kept at 0.5 wt% of the total polymer amount. Subsequently, 0.1 wt% of gentamicin sulphate (GS, Sigma Aldrich, Taiwan) was added to the solution and the mixture was stirred and sonicated for 3 min to form a homogeneous solution. A similar hydrogel solution without added gentamicin was also prepared by this method.

Mohd Razali N.A, & Lin W.C. (2022). Accelerating the excisional wound closure by using the patterned microstructural nanofibrous mats/gentamicin-loaded hydrogel composite scaffold. Materials Today Bio, 16, 100347.

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ATRP of Functionalized Methacrylates

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Ethyl 2-bromo-2-methylpropionate (EBiB, 98%), 2-hydroxyethyl methacrylate (HEMA, ≥99%), oligo(ethylene glycol) methyl ether methacrylate (OEGMA, M_n = 300 g mol⁻¹), copper(i) bromide (CuBr, 98%), benzyl alcohol (BA, ≥99%) and tris[2-(dimethylamino)ethyl]amine (Me₆TREN, ≥99%) were purchased from Sigma-Aldrich. HEMA and OEGMA were purified by passing over a short column of activated basic alumina (Sigma-Aldrich) to remove the inhibitor and stored at −27 °C. Copper bromide was purified according to methods described in ref. 49 and 50 (link) and stored under argon at 4 °C. Dimethyl sulfoxide (DMSO, ≥99.5%, for HPLC) purchased from POCH S.A. (Gliwice, Poland) and water (HPLC Plus) purchased from Sigma-Aldrich were purged with argon before use. Concentrated phosphate-buffered saline (PBS, BioUltra) from Sigma-Aldrich was used after tenfold dilution with filtered, deionized water.

Kasprów M., Machnik J., Otulakowski Ł., Dworak A, & Trzebicka B. (2019). Thermoresponsive P(HEMA-co-OEGMA) copolymers: synthesis, characteristics and solution behavior. RSC Advances, 9(70), 40966-40974.

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Synthesis and Characterization of Theranostic Nanoparticles

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4-Cyano-4-(phenylcarbonothioylthio) pentanoic acid (CPAD), OEGMA, DEA, DTT, DiI, DiO were purchased from Sigma-Aldrich (USA). PDS was synthesized according to our previous report.³² The synthetic starting materials, and PTX were obtained from J&K (China). Fetal bovine serum (FBS) and RPMI 1640 medium were purchased from Biological Industries (USA). Hoechst 33258 and MTT were obtained from Beyotime (China). Milli-Q water purified via the Milli-Q Plus System (Millipore, USA). All the used dialysis membranes (MWCO: 3500 Da) were obtained from Sangon Biotech (China).
¹H NMR spectra were recorded on a 400 MHz Bruker NMR spectrometer and calibrated against tetramethylsilane (TMS) standard. Dynamic light scattering (DLS) and zeta potential measurements were performed by a Malvern Nanozetasizer. The scattering intensity of nanoparticles were monitored by NanoBrook Omni. Gel permeation chromatography (GPC, Waters Acquity) was used to detect the molecular weight of polymers, using PMMA standard with a refractive index detector and DMF as the elution. Transmission electron microscopy (TEM) images were taken from JEM-2100 at 200 KV. The emission spectra were obtained from a Fluoromax-4 spectrofluorimeter.

Song C., Lin T., Zhang Q., Thayumanavan S, & Ren L. (2018). pH-Sensitive Morphological Transitions in Polymeric Tadpole Assemblies for Programmed Tumor Therapy. Journal of controlled release : official journal of the Controlled Release Society, 293, 1-9.

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