Methacrylate anhydride

Manufactured by Merck Group

Sourced in United States

Methacrylate anhydride is a chemical compound used in various laboratory applications. It is a colorless liquid with a distinctive odor. Methacrylate anhydride is primarily utilized as a reagent or building block in chemical synthesis and research processes.

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11 protocols using methacrylate anhydride

Synthesis of Methacrylated Alginate Biopolymer

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Methacrylated alginate (MeALG) was synthesized as described previously [85 (link),94 (link)]. Briefly, 0.5% (w/v) was prepared by dissolving 5 g of medium viscosity alginate (alginic acid sodium salt from brown algae, Sigma-Aldrich Inc., St. Louis, MO, USA) in 1 L of DI water. The solution was kept under magnetic stirring at 1–4 °C. Once the alginate was fully dissolved, 10 mL of methacrylate anhydride (MA, Sigma-Aldrich Inc., St. Louis, MO, USA) was added dropwise into the solution within a span of 1.5–2 h. 2 M NaOH solution (Sigma-Aldrich Inc., St. Louis, MO, USA) was simultaneously added dropwise to adjust the pH of the solution to 8–9. After the addition of the MA, pH of the mixture was maintained by gradually dripping 2 M NaOH solution for 8 h using an automated pH controller. The solution was kept at 4 °C overnight. The reaction was resumed the following day by adding 5 mL of MA while maintaining the pH at 8–9. The material was then dialyzed (Spectra/Por^®1 dialysis membrane, 6–8 kDa, Fisher Scientific, Pittsburgh, PA, USA) against DI water for 5 days and lyophilized using a benchtop freeze dryer (Labconco FreeZone 4.5 L, Fisher Scientific, Pittsburgh, PA, USA). ¹H NMR (Bruker Advance III HD 500 MHz, Bruker Scientific, Billerica, MA, USA) was used to confirm the methacrylate percentage as described previously [85 (link)].

Gharacheh H, & Guvendiren M. (2022). Cell-Laden Composite Hydrogel Bioinks with Human Bone Allograft Particles to Enhance Stem Cell Osteogenesis. Polymers, 14(18), 3788.

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Photocrosslinkable Gelatin-Hyaluronic Acid Hydrogel

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Hyaluronic acid (molecular weight of 2000 kDa) was purchased from Kikkoman (FCH-200, Tokyo, Japan). Gelatin from porcine skin (type B) and methacrylate anhydride (MA) (molecular weight of 154.16 Da) were purchased from Sigma-Aldrich, St. Louis, MO, USA). The P.I. of lithium phenyl-2,4,6-trimethyl-benzoyl phosphinate (LAP), nano-silica (SiO₂; nSi), 3-acryloxypropyl trimethoxysilane (APMS) were also obtained from Sigma-Aldrich (St. Louis, MO, USA), and the sodium carbonate anhydrous (Na₂CO₃) and sodium bicarbonate (NaHCO₃) were purchased from J.K Baker (Phillipsburg, NJ, USA). The other reagents, such as phosphate-buffered saline (PBS), Dulbecco’s Modified Eagle’s Medium (DMEM), fetal bovine serum (FBS), penicillin, and streptomycin were purchased from Gibco BRL (Grandland, New York, NY, USA). All other solvents were purchased from Merck (Darmstadt, Germany), TEDIA (Fairfield, CT, USA), or J. T. Baker (Phillipsburg, NJ, USA). These chemicals were all analytical/reagent grade and were used without further purification.

Nedunchezian S., Wu C.W., Wu S.C., Chen C.H., Chang J.K, & Wang C.K. (2022). Characteristic and Chondrogenic Differentiation Analysis of Hybrid Hydrogels Comprised of Hyaluronic Acid Methacryloyl (HAMA), Gelatin Methacryloyl (GelMA), and the Acrylate-Functionalized Nano-Silica Crosslinker. Polymers, 14(10), 2003.

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Methacrylated Hyaluronic Acid Synthesis

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MeHA was synthesized as previously described^{18 (link),19 (link)}. In brief, 50 kDa sodium hyaluronate (Lifecore Biomedical, HA40K) was dissolved in deionized water at 1% w/v overnight and reacted with methacrylate anhydride (Sigma-Aldrich, 276685, 6 ml methacrylate anhydride per 1 g sodium hyaluronate) for 8 h on ice at pH 8, followed by overnight incubation at 4 °C, and further reacted with methacrylate anhydride (3 ml methacrylate anhydride per 1 g sodium hyaluronate) at pH 8 on ice for 4 h. The monomer solution was then dialysed (Spectrum Labs, 132655) against deionized water at 4 °C for 3 days followed by lyophilization for another 3 days. The lyophilized MeHA was analysed by ¹H magnetic resonance (NMR) to determine the methacrylate substitution ratio by normalization of the peaks at a chemical shift of 6 ppm, representing the methacrylate group, by peaks between 3 and 4 ppm, which represent native HA. Substitution ratios were computed from triplicate NMR analyses (Fig. 1a).

Kumar A., Thomas S.K., Wong K.C., Lo Sardo V., Cheah D.S., Hou Y.H., Placone J.K., Tenerelli K.P., Ferguson W.C., Torkamani A., Topol E.J., Baldwin K.K, & Engler A.J. (2019). Mechanical activation of noncoding-RNA-mediated regulation of disease-associated phenotypes in human cardiomyocytes. Nature biomedical engineering, 3(2), 137-146.

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Gelatin-Based Photocrosslinkable Hydrogels

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Gelatin (Type A, 300 bloom from porcine skin), methacrylate anhydride (MA), NaOH pellets, NaCl, 3-(trimethoxysilyl)-propyl methacrylate (TMSPMA), and ferritin and apoferritin (both from equine spleen) were purchased from Sigma-Aldrich (St. Louis, Missouri). Irgacure 2959 (2-hydroxy-1-(4-(hydroxyethoxy)-phenyl)-2-methyl-1-propanone), as a photoinitiator (PI), was acquired from Ciba Specialty Chemicals Incorporated (Basel, Switzerland). Dulbecco’s phosphate-buffered saline (DPBS), Dulbecco’s modified Eagle’s medium (DMEM), fetal bovine serum (FBS), and penicillin–streptomycin were bought from Invitrogen (Waltham, Massachusetts). Dialysis membrane tubes, Slide-A-Lyzer Dialysis cassette, glass slides, and coverslips were purchased from Thermo Fisher Scientific (Waltham, Massachusetts). Alexa Fluor 488 Phalloidin, 4′,6-diamidino-2-phenylindole (DAPI), LIVE/DEAD kit, and fluoraldehyde o-phthaldialdehyde (OPA) were acquired from Thermo Fisher Scientific (Waltham, Massachusetts). Omnicure S2000 (EXFO Photonic Solutions Incorporation, Quebec City, Canada) was used for photo-cross-linking. The device for mechanical testing was the 5942 Single Column Tabletop Model testing system from Instron, an ITW company (Illinois Tool Works Incorporation, Glenview, Illinois).

Samanipour R., Wang T., Werb M., Hassannezhad H., Rangel J.M., Hoorfar M., Hasan A., Lee C.K, & Shin S.R. (2019). Ferritin Nanocage Conjugated Hybrid Hydrogel for Tissue Engineering and Drug Delivery Applications. ACS biomaterials science & engineering, 6(1), 277-287.

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Calcium-Gelatin Biomaterial Synthesis

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We obtained calcium chloride (CaCl₂), sodium hydroxide (NaOH), H₂O₂, 30%, ammonium hydroxide solution (50%), gelatin, methacrylate anhydride, and PCL with 80,000 molecular weight from Sigma-Aldrich. Dichloromethane (DCM) was from Merck Millipore. A live/dead cell imaging kit (Invitrogen-Molecular probes) and Alizarin red S was obtained from Thermo Fisher Scientific. Polyethylene glycol 200 (PEG200) was from Fisher Scientific. The following were sourced from Gibco: phosphate-buffered saline (PBS), Dulbecco′s modified Eagle’s medium (DMEM), catalase (H₂O₂:H₂O₂ oxidoreductase, EC 1.11.1.6), penicillin streptomycin solution, trypsin-ethylenediaminetetraacetic acid (EDTA), and fetal bovine serum. The tissue culture flasks and plates used in this research were from GenClone, Genesee Scientific (San Diego, CA, USA).

Augustine R., Nikolopoulos V.K, & Camci-Unal G. (2023). Hydrogel-Impregnated Self-Oxygenating Electrospun Scaffolds for Bone Tissue Engineering. Bioengineering, 10(7), 854.

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Synthesis and Characterization of GelMA

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GelMA was synthesized according to previously reported methods^{76 (link),77 (link)}. In brief, type A gelatin from cold-water fish skin (10 g, M_w = 60 kDa, Sigma-Aldrich, USA) was dissolved in phosphate-buffered saline (100 mL, PBS, ThermoFisher, USA) at the concentration of 10%. Methacrylate anhydride (12 mL, MA, Sigma-Aldrich) was then added dropwise and was reacted with gelatin solution at 50 °C for 2 h. After diluting the solution 1:1 with warm PBS (40 °C) to stop the reaction, dialysis was conducted for 7 days against deionized (DI) water using dialysis membrane (M_w cut off (MWCO): 12–14 kDa, Spectrum Chemical, USA) at 40 °C to remove low-molecular weight impurities. Subsequently, the solution was lyophilized and stored at −20 °C in dark until use. The lyophilized GelMA was further characterized by ¹H NMR spectroscopy (Bruker Avance II 300-MHz NMR, USA). NMR data were processed with the MestreNova (6.2.0) software. The primary amine contents of gelatin and synthesized GelMA were evaluated by TNBSA assay^{78 (link)}.

Wang M., Li W., Hao J., Gonzales A I.I.I., Zhao Z., Flores R.S., Kuang X., Mu X., Ching T., Tang G., Luo Z., Garciamendez-Mijares C.E., Sahoo J.K., Wells M.F., Niu G., Agrawal P., Quiñones-Hinojosa A., Eggan K, & Zhang Y.S. (2022). Molecularly cleavable bioinks facilitate high-performance digital light processing-based bioprinting of functional volumetric soft tissues. Nature Communications, 13, 3317.

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Fabrication of Light-Curable Cornea Hydrogels

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To fabricate light-curable (LC) COMatrix hydrogel from the porcine corneas decellularized with detergent-based or freeze–thaw methods, the already produced thermoresponsive COMatrix hydrogels were reacted with methacrylate anhydride (Sigma, USA) at 4 °C in the dark for 12 h, as previously reported³⁰. Then, the samples were dialyzed against deionized water for 3 days at room temperature using 12–14 kDa MWCO dialysis tubes. The functionalized COMatrix was freeze-dried for 3 days and kept in − 80 °C for further experiments. To prepare the LC-COMatrix solution for experiments, the lyophilized samples were dissolved in a photo-initiating cocktail including Eosin Y, Ethanolamine, and N-Vinylcaprolactam as described before³⁰. Afterward, the LC-COMatrices were cured with green light (520 nm wavelength) to induce photogelation. The light-curable COMatrix hydrogels derived from detergent-based decellularization protocol called, De-LC-COMatrix; and, light-curable hydrogels derived from freeze–thaw decellularization method called, FT-LC-COMatrix.

Yazdanpanah G., Jalilian E., Shen X., Anwar K.N., Jiang Y., Jabbehdari S., Rosenblatt M.I., Pan Y, & Djalilian A.R. (2023). The effect of decellularization protocols on characterizations of thermoresponsive and light-curable corneal extracellular matrix hydrogels. Scientific Reports, 13, 8145.

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Synthesis of Functional Polymeric Materials

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Dopamine hydrochloride (DOPA-HCl, 98%), methacrylate anhydride (MAA, 95%), methoxyethyl acrylate (MEA, 98%), 1-adamantanecarboxylic acid chloride (98%), 2,2′-azobisisobutyronitrile (AIBN, 98%), hexane (99%), tetrahydrofuran (THF), and anhydrous dimethyl formamide (DMF) are purchased from Sigma-Aldrich. Sodium borate, ethyl acetate, sodium bicarbonate, magnesium sulfate, and sodium hydroxide are purchased from Meyer. Before utilization, methacrylate anhydride is passed through a column packed with Al₂O₃ to remove the inhibitor, and AIBN is recrystallized twice from methanol.

Zhao Y., Wu Y., Wang L., Zhang M., Chen X., Liu M., Fan J., Liu J., Zhou F, & Wang Z. (2017). Bio-inspired reversible underwater adhesive. Nature Communications, 8, 2218.

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Hydrogel Synthesis and Characterization

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Iron (II) chloride tetrahydrate (purity > 99.0%, product no. 44939), Iron (III) chloride hexahydrate (purity > 99.0%, product no. 31232), type A gelatin from porcine skin (Gel strength 300, product no. G2500), methacrylate anhydride (MA) (purity ≥ 94.0%, product no. 276685), 2-Hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone (Irgacure 2959) (purity ≥ 97.5%, product no. 410896), and alginic acid salt (low viscosity (4–12 cps), product no. A1112) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Calcium chloride (CaCl₂) (purity = 93.0%, product no. 12316, Alfa Aesar, Haverhill, MA, USA) was purchased from Thermo Fisher Scientific Inc. (Waltham, MA, USA)

Yang H.W., Yeh N.T., Chen T.C., Yeh Y.C., Lee I.C, & Li Y.C. (2023). A Printable Magnetic-Responsive Iron Oxide Nanoparticle (ION)-Gelatin Methacryloyl (GelMA) Ink for Soft Bioactuator/Robot Applications. Polymers, 16(1), 25.

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Synthesis of Isosorbide Dimethacrylate and Urethane Acrylate

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All chemicals used in this study were as follows: isosorbide (1,4:3,6-dianhydro-D-sorbitol, 98%), methacrylate anhydride (94%), ethyl 4-N,N-dimethylaminobenzoate (EDMAB), tetrahydrofuran (THF, anhydrous, 99.9%), and magnesium sulfate (MgSO4, 99.5%) were purchased from Sigma-Aldrich. Triethylamine (TEA) and 4,4-dimethylaminopyridine (DMAP) were purchased from Daejung for isosobide dimethacrylate (ISDM). Poly(tetramethylene ether)glycol (PTMG, average Mn 1000 g/mol), isophorone diisocyanate (IPDI, 98%), and diphenyl (2,4,6-trimethylbenzoyl)phosphine oxide (TPO, Shinyoun Rad Chem Ltd.) were also purchased from Aldrich, Korea, for the synthesis of PTMG-based urethane acrylate. ISDM (Fig. 1f) was synthesized as shown in Fig. S4^{33 (link)}.

Choi J.W., Kim G.J., Hong S., An J.H., Kim B.J, & Ha C.W. (2022). Sequential process optimization for a digital light processing system to minimize trial and error. Scientific Reports, 12, 13553.

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