4 dimethylaminopyridine

Manufactured by Merck Group

Sourced in United States, Germany, United Kingdom, Poland, China, Bulgaria, India

4-dimethylaminopyridine is a chemical compound used as a laboratory reagent. It serves as a nucleophilic catalyst in various organic reactions. The compound is widely utilized in the synthesis of organic compounds and pharmaceutical intermediates.

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Lab products found in correlation

212 protocols using 4 dimethylaminopyridine

Biomimetic Hydrogel for Cell Culture

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All chemicals were used as received unless stated otherwise. Sodium hyaluronate (64 kDa) was purchased from Lifecore Biomedical (Chaska, MN). Dowex™ 500WX8–200 ion-exchange resin (AC335341000) was purchased from Fisher Scientific. GelMA (76292–720) and Seakem® Agarose (12002–102) were purchased from VWR. Lithium phenyl-2,4,6-trimethylbenzoylphosphinate (LAP) was purchased from Colorado Photopolymer Solutions (Boulder, CO). Alexa Fluor™ 647 Phalloidin (A22287), LIVE/DEAD™ Viability/Cytotoxicity kit (L3224), and Hoechst 33342 (H3570) were purchased from Thermo Fisher Scientific. Tetrabutylammonium hydroxide (TBA-OH, 86880–100ML), anhydrous dimethyl sulfoxide (276855), 5-norbornene-2-carboxylic acid (446440), 4-(dimethylamino)pyridine (107700), di-tert-butyl dicarbonate (361941), 4-(dimethylamino)pyridine (107700), tetrabutylammonium hydroxide solution (86880), DL-dithiothreitol (D0632), poly(ethylene oxide) (189456), 2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone (I2959) (410896), fluorescein isothiocyanate-dextran (average molecular weight 2 MDa, FD2000S-1G) and 3-(trimethoxysilyl)propyl methacrylate (TMSPMA) (440159–500ML) were purchased from Sigma-Aldrich (St. Louis, MO).

Prendergast M.E., Davidson M.D, & Burdick J.A. (2021). A Biofabrication Method to Align Cells within Bioprinted Photocrosslinkable and Cell-degradable Hydrogel Constructs via Embedded Fibers. Biofabrication, 13(4), 10.1088/1758-5090/ac25cc.

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Immobilized TRAIL Binding Assay

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6× His-TRAIL was obtained from UBPBio. Mouse Anti-Human TRAIL-UNLB and mouse Anti-Human TRAIL-BIOT (Dallas, TX, USA) were purchased from SouthernBiotech (Birmingham, AL, USA) for ELISA. Dulbecco’s Modified Eagle Medium (DMEM), penicillin–streptomycin, fetal bovine serum (FBS), trypsin, and phosphate-buffered saline (PBS) were purchased from Corning (Corning, NY, USA). Heparin and Bacteroides Heparinase II were received from Selleckchem (Radnor, PA, USA) and New England Biolabs (Beverly, MA, USA), respectively. EZ-Cytox was purchased from DoGenBio (Seoul, Korea). Fmoc-Asp and Fmoc-Arg were obtained from BOC Science (Shirley, NY, US). Monomethoxy polyethylene glycol 750, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), N-hydroxy succinimide (NHS), tetrabutylammonium bromide (TBAB), 4-dimethyl amino pyridine (DMAP), dimethyl formamide (DMF) (anhydrous), 1,4-dioxane, piperidine, 3,3′,5,5′-Tetramethylbenzidine (TMB), and streptavidin-HRP conjugate were obtained from Sigma-Aldrich (St. Louis, MO, USA). Ethylene glycol diglycidyl ether (EGDE) was obtained from TCI (Tokyo, Japan). Protease inhibitor and Live and dead staining kit were obtained from ThermoScientific (Waltham, MA, USA).

Kim S., Jwa Y., Hong J, & Kim K. (2022). Inhibition of Colon Cancer Recurrence via Exogenous TRAIL Delivery Using Gel-like Coacervate Microdroplets. Gels, 8(7), 427.

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Mitochondrial Coating with Dextran-TPP

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The isolated mitochondria were coated with dextran-TPP polymer conjugates as described previously.^{[24 ]} Briefly, N,N′-dicyclohexylcarbodiimide (Sigma-Aldrich, St. Louis, MO, USA), 4-(Dimethylamino) pyridine (Sigma-Aldrich, St. Louis, MO, USA), and (5-Carboxypentyl) TPP bromide (TPP-COOH, Alfa Aesar, Lancashire, UK) were dissolved in anhydrous dimethyl sulfoxide (DMSO, Sigma-Aldrich, St. Louis, MO, USA) and mixed with dextran derived from Leuconostoc mesenteroides (Mw 150 kDa, Sigma-Aldrich, St. Louis, MO, USA) in DMSO. The solution was purified by dialysis in water for 3 days using Slide-A-Lyzer MINI Dialysis Devices (3.5K MWCO, Fisher Scientific, Waltham, MA, USA) and lyophilized to obtain functional dextran-TPP polymer conjugates. The isolated mitochondria were coated with this solution as described previously,^{[24 ]} washed twice with respiration buffer to remove excess dextran-TPP, and resuspended in respiration buffer.^{[21 (link),74 (link)]}

Alexander J.F., Mahalingam R., Seua A.V., Wu S., Arroyo L.D., Hörbelt T., Schedlowski M., Blanco E., Kavelaars A, & Heijnen C.J. (2022). Targeting the Meningeal Compartment to Resolve Chemobrain and Neuropathy via Nasal Delivery of Functionalized Mitochondria. Advanced healthcare materials, 11(8), e2102153.

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Synthesis of Cobaltocenium-Containing Methacrylate Monomer

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Chain transfer agent 2-cyano-2-propyl benzodithioate (97%, CPB) was purchased from Sigma-Aldrich and used directly. Monomer 2-cobaltocenium amidoethyl methacrylate hexafluorophosphate (CoAEMAPF₆) was synthesized by reacting cobaltocenium monocarboxylic acid with 2-aminoethyl methacrylate hydrochloride in the presence of coupling agent N-(3-(dimethylamino)propyl)-N'-ethylcarbodiimide (EDC) according to established methods.^{47 (link)–49 (link)} 2-aminoethyl methacrylate hydrochloride (90%), N-(3-dimethylaminopropyl)-N'-ethylcarbodi imide hydrochloride (EDC-HCl, 98%), 4-(dimethylamino)pyridine and tetrabutylammonium chloride (TBACl) were purchased from Sigma-Aldrich and used as received. HPMA was purchased from Alfa-Aesar, which comprises approximately 75% 2-hydroxypropyl methacrylate and 25% 2-hydroxyisopropyl methacrylate. AIBN and 2,2'-azobis (2-(2-imidazoline-2-yl)propane) dihydrochloride were purchased from VWR. Water was purified using Thermo Scientific Nanopure with ion conductivity at 18.2 MΩ. All other chemicals were from commercial sources and used as received.

Rahman M.A., Cha Y., Yuan L., Pageni P., Zhu T., Jui M.S, & Tang C. (2019). Polymerization-Induced Self-Assembly of Metallo-Polyelectrolyte Block Copolymers. Journal of polymer science (2020), 58(1), 77-83.

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Quantification of Oxysterols by LC-MS/MS

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24S-Hydroxycholesterol [cholest-5-ene-3-beta,24S-diol], 25-hydroxycholesterol [cholest-5-ene-3-beta,25-diol], 27-hydroxycholesterol [cholest-5-ene-3beta,27-diol], 24(R/S)-hydroxycholesterol-d6 [26, 26, 26, 27, 27, 27-hexadeuterocholest-5-ene-3 beta,24-diol], 25-hydroxycholesterol-d6 [26, 26, 26, 27, 27, 27-hexadeuterocholest-5-ene-3 beta,25-diol] and 27-hydroxycholesterol-d6 [25, 26, 26, 26, 27, 27-hexadeuterocholest-5-ene-3 beta,27-diol] were obtained from Avanti Polar Lipids (Alabama, USA). 2-methyl-6-nitrobenzoic anhydride, 4-dimethylamino pyridine, picolinic acid, pyridine and trimethylamine were purchased from Sigma Aldrich Co. (St. Louis, USA). Phosphoric acid and potassium hydroxide were provided by Junsei (Tokyo, Japan). Distilled water was purified using a Milli-Q purification system (Millipore, Massachusetts, USA). High performance liquid chromatography (HPLC)-grade m ethanol, ethanol, hexane and 2-propanol were purchased from Burdick & Jackson (Ulsan, Korea).

Cha E., Lee K.M., Park K.D., Park K.S., Lee K.W., Kim S.M, & Lee J. (2016). Hydroxycholesterol Levels in the Serum and Cerebrospinal Fluid of Patients with Neuromyelitis Optica Revealed by LC-Ag+CIS/MS/MS and LC-ESI/MS/MS with Picolinic Derivatization: Increased Levels and Association with Disability during Acute Attack. PLoS ONE, 11(12), e0167819.

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Organic Synthesis Reagent Procurement

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The different solvents used for the organic syntheses were purchased from Acros Organics (Fisher Scientific SAS, Illkirch, France). The reagents used were purchased from Acros Organics (2,3,4,6‐tetra‐O‐acetyl‐alpha‐D‐glucopyranosyl bromide, 5‐chlorosalicylic acid, copper sulfate pentahydrate, sodium ascorbate, sodium azide), TCI Europe N.V. (Paris, France; 2‐bromoethylamine hydrobromide, 3,5‐dichlorosalicylic acid, (1‐(3‐dimethylaminopropyl)‐3‐ethylcarbodiimide hydrochloride (EDCl), N‐Boc‐L‐glutamic acid 1‐tert‐butyl ester, propargylamine), Alfa Aesar (Thermo Fisher GmbH, Kandel, Germany; 4‐dimethylaminopyridine (DMAP), acetic anhydride, Amberlite IRN 77, sodium acetate), Sigma Aldrich (Merck KGaA, Darmstadt, Germany; salicylic acid, aspirin, 2‐(N‐morpholino)ethanesulfonic acid monohydrate [MES buffer]), Solarbio (Solarbio Science & Technology Co., Ltd., Beijing, China; surfactant Silwet‐L77, Tween‐20).

Guichard B., Wu H., La Camera S., Hu R., Marivingt‐Mounir C, & Chollet J. (2022). Synthesis, phloem mobility and induced plant resistance of synthetic salicylic acid amino acid or glucose conjugates. Pest Management Science, 78(11), 4913-4928.

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Synthesis of N-Phenylmaleimide Derivatives

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The following chemicals were used as received, unless mentioned otherwise. Pentafluorophenol (Carbolution Chemicals GmbH, Saarbrücken, Germany, 99%), 4-pentenoic acid (Sigma-Aldrich, Steinheim, Germany, 95%), (S)-perillic acid (Sigma-Aldrich, Buchs, Switzerland, 95%), N-phenylmaleimide (Sigma-Aldrich, Steinheim, Germany, 97%), N,N′-dicyclohexylcarbodiimide (Sigma-Aldrich, Steinheim, Germany 99%), 4-dimethylaminopyridine (Sigma-Aldrich, Steinheim, Germany, 99%), 1,2-dichloroethan (Alfa Aesar, ThermoFisher (Kandel) GmbH, Karlsruhe, Germany, 99+%), 1,4-dioxane (Acros Organics, Geel, Belgium, 99.5%), N,N-dimethylformamide (Sigma-Aldrich, Steinheim, Germany, 99.8%), 2,2′-azobis (2-methylpropionitrile) (Acros Organics, Geel, Belgium, 98%), n-hexylamine (Sigma-Aldrich, Steinheim, Germany, 99%), benzylamine (MERCK, Kenilworth, NJ, USA, >99%), CDCl₃ (Deutero GmbH, Kastellaun, Germnay, 99.8%), 1,1,1,3,3,3-hexafluoro-2-phenyl-2-propanol (abcr, Karlsruhe, Germany, 99%). 2,2′-azobis (2-methylpropionitrile) (AIBN, Acros Organics, Geel, Belgium, 98%) was recrystallized from methanol.

Kubatzki F., Al-Shok L, & ten Brummelhuis N. (2017). Synthesis and Functionalization of Periodic Copolymers. Polymers, 9(5), 166.

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Synthesis of Resveratrol-Butyrate Esters

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The mixtures of RBEs were synthesized based on our protocol, as described previously [13 (link)]. The butyric acid (ACROS, Morris Plains, NJ, USA) was mixed with resveratrol (TCI Development Co., Ltd., Shanghai, China) in tetrahydrofuran (Echo Chemical Co., Ltd., Miaoli County, Taiwan). Later, N-ethyl-N′-(3-dimethylaminopropyl) carbodiimide (Sigma-Aldrich, Saint Louis, MO, USA) and 4-dimethylaminopyridine (Sigma-Aldrich, Saint Louis, MO, USA) were added. Then, the esterification reaction was conducted by avoiding light for 48 h. Upon completion, the reaction mixture was mixed with distilled water and filtered in order to obtain the precipitated RBEs. The RBEs were kept within a −20 °C freezer.

Tain Y.L., Chang C.I., Hou C.Y., Chang-Chien G.P., Lin S, & Hsu C.N. (2023). Dietary Resveratrol Butyrate Monoester Supplement Improves Hypertension and Kidney Dysfunction in a Young Rat Chronic Kidney Disease Model. Nutrients, 15(3), 635.

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Synthesis and Evaluation of PEGylated Gemcitabine Conjugates

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Gemcitabine hydrochloride was obtained from LC Laboratories (Woburn,
MA). Retinoic acid, imidazole, tert-butyldimethylsilyl chloride (TBDMS-Cl),
dimethyl sulfoxide, triethylamine, pyrene,
N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl),
4-Dimethylaminopyridine (DMAP), tetrabutylammonium fluoride solution 1.0 M in
THF, cytidine deaminase, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium
bromide (MTT), N,N′-Diisopropylcarbodiimide,
N,N-Diisopropylethylamine (DIPEA) and Cathepsin B was
purchased from Sigma (St. Louis, MO). Methoxy polyethyleneglycol 750 was
obtained from Fisher Scientific (Santa Clara, CA). Methoxy-PEG2k-cholesterol
(CholPEG) was purchased from Nano CS (Boston, MA). Anhydrous dimethylformamide
was obtained from Acros Organics (Fair Law, NJ). The Cell Meter ™ TUNEL
Apoptosis Assay kit was purchased from AAT Bioquest (Sunnyvale, CA).

Kakwere H., Ingham E.S., Tumbale S.K, & Ferrara K.W. (2020). Gemcitabine-retinoid prodrug loaded nanoparticles display in vitro antitumor efficacy towards drug-resilient human PANC-1 pancreatic cancer cells. Materials science & engineering. C, Materials for biological applications, 117, 111251.

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Synthesis of Conjugated Polymer Precursor

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3-hexylthiophene ≥
98.0% (3HT) and hydroxymethyl EDOT ≥ 97.0% were supplied by
TCI; iron(III) chloride, sodium hydroxide, and methanol ≥ 99.9%
were purchased from Fluka; methanesulfonic acid ≥ 99.0% ≥
99.0% (MSA) and 4-(dimethylamino)pyridine ≥ 98.0% (DMAP) were
provided by Sigma-Aldrich and used as received. l-Lactide
≥ 85.0% (LA) was purchased from Sigma-Aldrich and purified
by solving the lactic acid in toluene at 60 °C, followed by the
precipitation and crystallization at room temperature twice. Then,
the toluene was removed by rotary evaporation, and the final product
was dried under vacuum.

Criado-Gonzalez M., Bondi L., Marzuoli C., Gutierrez-Fernandez E., Tullii G., Ronchi C., Gabirondo E., Sardon H., Rapino S., Malferrari M., Cramer T., Antognazza M.R, & Mecerreyes D. (2023). Semiconducting Polymer Nanoporous Thin Films as a Tool to Regulate Intracellular ROS Balance in Endothelial Cells. ACS Applied Materials & Interfaces, 15(30), 35973-35985.

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