N n dimethylaminopyridine

Manufactured by Merck Group

Sourced in United States

N,N-dimethylaminopyridine is a heterocyclic organic compound commonly used as a catalyst and reagent in organic synthesis. It serves as a nucleophilic acyl transfer agent and has applications in various chemical reactions.

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Dimethylaminopyridine (23 citations) 4-N,N-dimethylaminopyridine (DMAP) (7 citations) N,N′-Dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP), (5 citations) 4-N,N′-dimethylaminopyridine (3 citations) Anhydrous N,N-dimethylformamide (DMF), 4-dimethylaminopyridine (DMAP), hydrochloric acid (HCl), (2 citations) N,N-dicyclohexylcarbodiimide (DCC), N,N-dimethylaminopyridine (DMAP), trifluoroacetic acid (TFA), (2 citations)

11 protocols using n n dimethylaminopyridine

Synthesis and Characterization of PGG-PTX Nanoconjugate

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PGG-PTX nanoconjugate (Poly-(L-γ-glutamyl-glutamine)-paclitaxel) (PTX, 34.9 wt%) were synthesized by our laboratory^{26 (link)}. p-NH₂-Bn-DTPA (S-2-(4-Aminobenzyl)-diethylenetriamine pentaacetic acid) was purchased from Macrocyclicas (USA). GdCl₃·6H₂O, N-hydroxysuccinimide (NHS) and N,N′-dimethylaminopyridine were supplied from Sigma-Aldrich, Inc. Magnevist (Gd-DTPA) was obtained from Bayer Schering Pharma AG (Berlin, Germany). N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (EDC) was purchased from EMD Chemicals Inc. (Darmstadt, Germany). All other chemicals and reagents were commercially available and directly used.
Human NCI-H460 carcinoma cell line was obtained from ATCC. Cell Counting Kit-8(CCK-8) was purchased from DOJINDO Laboratorise chemical technology (Shanghai) co., LTD. DiO (3,3′-dioctadecyloxacarbocyanine, perchlorate) and DiR (1,1′-dioctadecyl-3,3,3′,3′-tetramethyl indotricarbocyanine Iodide) were purchased from Tianjin Biolite Biotech Co., LTD. Hoechst 33342 was purchased from Beyotime Institute of Biotechnology.

Gao L., Zhou J., Yu J., Li Q., Liu X., Sun L., Peng T., Wang J., Zhu J., Sun J., Lu W., Yu L., Yan Z, & Wang Y. (2017). A Novel Gd-DTPA-conjugated Poly(L-γ-glutamyl-glutamine)-paclitaxel Polymeric Delivery System for Tumor Theranostics. Scientific Reports, 7, 3799.

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Synthesis and Characterization of Multifunctional Nanomedicine

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P1 (M_n (GPC) = 18 800, M_w/M_n = 1.43, M_n (NMR) = 12 100; the molecular weights of RED, PCL, and PEG are 1072, 4200, and 6800 respectively) with α,ω-diamino terminal groups was prepared according to our previous publication.^{42 (link)} 4-Maleimidopropionic acid N-hydroxysuccinimide ester (compound 1) shown in Scheme 1 was prepared according to procedures described in literature.^{44 (link)} 4-(2-Hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES), 3-(4,5-dimethyl thiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), acetic anhydride, and N,N′-dimethylaminopyridine were purchased from Sigma-Aldrich (St. Louis, MO) and used without further purification. Poly(ethylene oxide-b-ε-caprolactone) (P4, M_w/M_n = 1.30, PEO molecular weight is 2000, PCL molecular weight is 5000) was purchased from Polymer Source (Montreal, Canada). Cyclo(Arg-Gly-Asp-D-Phe-Cys) (cRGDfc, catalogue number PCI 3686-PI) was purchased from Peptide International Inc (Louisville, KT). Dialysis membranes (regenerate cellulose, M_w cut off 12 000) were purchased from Pierce (Rockford, IL). Dulbecco's modified Eagle's medium (DMEM) and nuclei staining dye Hoechst 33342 were acquired from Invitrogen (Carlsbad, CA). Human glioblastoma tumor U87MG and cervical cancer HeLa cell lines were purchased from American Type Culture Collection (ATCC, Manassas, VA).

Wu S., Su F., Magee H.Y., Meldrum D.R, & Tian Y. (2019). cRGD functionalized 2,1,3-benzothiadiazole (BTD)-containing two-photon absorbing red-emitter-conjugated amphiphilic poly(ethylene glycol)-block-poly(ε-caprolactone) for targeted bioimaging. RSC Advances, 9(59), 34235-34243.

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Synthesis and Antioxidant Evaluation of Gallic Acid and Phloretin Derivatives

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Acetone, hydrochloric acid, chloroform, diethyl ether, ethanol, isopropanol, methanol, n-hexane, tetrahydrofuran (THF), allyl alcohol, and sodium sulfate were purchased from Carlo Erba Reagents (Milan, Italy). Gallic acid (MW = 170.12), phloretin (MW = 274.27), dicyclohexylcarbodiimide (DCC), N,N-dimethylaminopyridine (DMAP), potassium tert-butoxide, N,N-dimethylacrylamide (DMAA), ammonium persulfate (NH₄)₂S₂O₈, N,N′-methylene-bis-acrylamide, sorbitan trioleate (Span85), polyoxymethylene sorbitan trioleate (Tween85), N,N,N′,N′-tetramethyl-ethylenediamine (TMEDA), tert-butylhydroperoxide (t-BOOH), trichloroacetic acid (TCA), 2-thiobarbituric acid (TBA), and butylated hydroxytoluene (BHT) were Purchased from Sigma-Aldrich (Sigma Chemical Co, St. Louis, MO, USA).

Cassano R., Curcio F., Sole R, & Trombino S. (2023). Transdermal Delivery of Phloretin by Gallic Acid Microparticles. Gels, 9(3), 226.

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Boronic Acid-Functionalized Nanoparticles

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Carboxylatedpoly(vinyl chloride) (>97% GC) (PVCCOOH), bis-(2-ethylhexyl)sebacate (DOS), polycaprolactone (M_n 70,000-90,000) (PCL), tridodecylmethylammonium chloride (TDMAC), alizarin, 4-carboxy-3-fluorophenylboronic acid (1), 3-fluoro-4-methoxycarbonylphenylboronic acid (2a), D-(+)-glucose, tetrahydrofuran (≥ 99.9%) (THF), dicyclohexylcarbodiimide solution (60% w/v in xylene) (DCC), N-hydroxysuccinimide (NHS), aniline(≥ 99.5%), 1-propanol (anhydrous, 99.7%), 1-butanol (HPLC, 99.7%), 1-hexanol (98%), cyclohexanol(99%),sodium sulfate (anhydrous,≥ 99.9%), sodium chloride, ethyl acetate (anhydrous, 99.8%), hexane (anhydrous, 99.5%), N, N’-dimethylformamide (DMF) and N, N’-dimethylaminopyridine (DMAP) were purchased from Sigma Aldrich (St Louis, MO, USA). Octylboronic acid (>97%) and Citroflex A-6 were acquired from Synthonix (Wake Forest, NC, USA) and Vertellus (Indianapolis, IN, USA), respectively. Phosphate Buffered Saline (PBS) (1x, pH = 7.4) was purchased as a solution from Invitrogen (Carlsbad, CA, USA). Hydrochloric acid (1.0 N) and sodium bicarbonate were purchased from Fisher Scientific (Fair Lawn, NJ, USA). 1,2-distearoyl-snglycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-550] (ammonium salt) (DSPE-mPEG550) was purchased from Avanti Polar Lipids, Inc. SKH1-E mice were acquired from Charles River Laboratories International Inc. (Wilmington, MA).

Balaconis M.K., Luo Y, & Clark H.A. (2015). Glucose-Sensitive Nanofiber Scaffolds with Improved Sensing Design for Physiological Conditions. The Analyst, 140(3), 716-723.

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Synthesis of Functional Polymer Materials

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2-Bromoisobutyric acid (98%), 2-bromoethanol (95%), 2-(dimethylamino)ethyl methacrylate (DMAEMA, 98%), poly-(ethylene glycol) methyl ether methacrylate (OEGMA, MW = 500), methacrylic acid (99%), N-(3-(dimethylamino)propyl)-N′-ethylcarbodiimide hydrochloride (EDC, ≥99%), N,N-dimethylamino pyridine (DMAP, ≥99%), copper bromide (≥99.99%), ascorbic acid, (AA, ≥99%) were purchased from Sigma-Aldrich. 2-(Methylthio)-ethanol (≥99%) was purchased from Alfa Aesar. Hydrogen peroxide solution (30%) was purchased from Fisher Scientific. All methacrylate monomers were passed through basic alumina columns before use. Tris(2-pyridylmethyl)amine (TPMA) was synthesized according to previous procedures.⁷⁶ All solvents and other chemicals were of reagent quality and were used as received unless special treatments discussed below were applied.

Li S., Omi M., Cartieri F., Konkolewicz D., Mao G., Gao H., Averick S.E., Mishina Y, & Matyjaszewski K. (2018). Cationic Hyperbranched Polymers with Biocompatible Shells for siRNA Delivery. Biomacromolecules, 19(9), 3754-3765.

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Aminated Glass Beads for Antibiotic Delivery

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Glass beads (Spheriglass-2429, 70–100 μm average particle size, Potters, UK) were aminated as previously reported [22 (link)]. Acrylic acid (AA), 3-(aminopropyl) trimethoxysilane (APTMS), ciprofloxacin (CIP), N,N-dimethylaminopyridine (DMAP), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC), hexamethyldisilazane (HMDS), N-hydroxysuccinimide (NHS), N-isopropylacrylamide (NIPAm), levofloxacin (LEV), N,N′-methylene-bis-acrylamide (BIS), morpholinethanesulfonic acid (sodium salt, MES), succinic anhydride, N-tertbutylacrylamide (TBAm), ammonium persulfate (APS), N,N,N′,N′-tetramethylethylenediamine (TEMED) were obtained from Sigma-Merck (Milan, Italy). Solvents and all other chemicals were purchased from Sigma-Merck (Milan, Italy). All the solvents were of HPLC grade, whereas all chemicals were of analytical grade. The water used was ultrapurified in Purelab Prima System from Elga (Marlow, UK). Antibiotic stock solutions were prepared by dissolving 25 mg of the substance in 25 mL of water/methanol 1 + 1 (v/v) then stored in the dark at −20 °C.

Chiarello M., Anfossi L., Cavalera S., Di Nardo F., Artusio F., Pisano R, & Baggiani C. (2021). Effect of Polymerization Time on the Binding Properties of Ciprofloxacin-Imprinted nanoMIPs Prepared by Solid-Phase Synthesis. Polymers, 13(16), 2656.

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Betulinic Acid Induced Apoptosis

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Betulinic acid (>90% pure), dichloroacetylchloride, N,N-dimethylaminopyridine (DMAP), dimethylsulphoxide (DMSO), paraformaldehyde, Dulbecco's modified eagles medium (DMEM), bovine serum albumin (BSA) and Histopaque-1077 were purchased from Sigma (St. Louis, Missouri, USA). RPMI 1640, PenStrep, MTT (3-[4,5-dimethylthiazol-2-yl]-2,5- diphenyltetrazoliumbromide), Hoechst 33342 (bisbenzamide trihydrochloride), 5,5′,6,6′-tetrachloro-1,1′,3,3′- tetraethyl benzimidazolyl carbocyanine iodide (JC-1), fetal bovine serum (FBS), Calcein-AM was obtained from Life Technologies (Carlsbad, CA, USA). Dichlorofluorescein diacetate (DCFDA) and Protein-A HRP were obtained from Calbiochem/Merck-Millipore (Darmstadt, Germany). The antibodies viz., anti-Bcl-2, anti-Bcl-xl, anti-Bax, anti-Cyt c, anti-cleaved caspase3, anti-β-actin was purchased from Cell Signalling Technologies (Beverly, MA). Other reagents were of analytical grade.

Saha S., Ghosh M, & Dutta S.K. (2015). A potent tumoricidal co-drug ‘Bet-CA' - an ester derivative of betulinic acid and dichloroacetate selectively and synergistically kills cancer cells. Scientific Reports, 5, 7762.

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Antioxidant Capacity Assay Protocol

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Hydrochloric acid, chloroform, diethyl ether, ethanol, isopropanol, methanol, n-hexane, tetrahydrofuran (THF) and sodium sulfate were purchased from Carlo Erba Reagents (Milan, Italy). Gallic acid (MW = 170.12), phloretin (MW = 274.27), acrylic acid (MW = 72.06, d = 1051 g/mL), dicyclohexylcarbodiimide (DCC), N,N-dimethylaminopyridine (DMAP), N, N-dimethylacrylamide (DMAA), tert-butylhydroperoxide (t-BOOH), trichloroacetic acid (TCA) acid, 2-thiobarbituric acid (TBA), and butylated hydroxytoluene (BHT) were purchased from Sigma-Aldrich (SGFma Chemical Co., St Louis, MO, USA). Folin–Ciocolteau and 2,2-difenil-1-picrylidrazyl (DPPH) were purchased from Sigma-Aldrich (SGFma Chemical Co., St Louis, MO, USA), while acid 2,2′-azino-bis (ABTS) was purchased from Alfa Aesar (Ward Hill, MA, USA).

Cassano R., Curcio F., Sole R., Mellace S, & Trombino S. (2024). Gallic Acid-Based Hydrogels for Phloretin Intestinal Release: A Promising Strategy to Reduce Oxidative Stress in Chronic Diabetes. Molecules, 29(5), 929.

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Synthesis of BHA for Biomedical Applications

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2,6-bis(hydroxymethyl)aniline (BHA) was synthesized according to literature report ^{16 (link)}. Anhydrous dimethylformamide (DMF), anhydrous tetrahydrofuran (THF), camptothecin (CPT), mPEG (Mw 5000), 3-chloro-1-propanol, sodium azide, tert-butyldimethylchlorosilane (TBSCl), 2-hydroxyethyl disulfide, N,N-dimethylamino pyridine, dithiothreitol(DTT), copper(I) iodide, propargyl bromide, triphosgene and MTT (3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide) were purchased from Sigma-Aldrich. Phosphate buffered saline (PBS) was purchased from Mediatech, Inc.

He X., Cai K., Zhang Y., Lu Y., Guo Q., Zhang Y., Liu L., Ruan C., Chen Q., Chen X., Li C., Sun T., Cheng J, & Jiang C. (2018). Dimeric Prodrug Self-Delivery Nanoparticles with Enhanced Drug Loading and Bioreduction-Responsiveness for Targeted Cancer Therapy. ACS applied materials & interfaces, 10(46), 39455-39467.

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Synthesis of Functional Polymers via ATRP

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2-(Methylthio)ethanol (≥99%) was purchased from Alfa Aesar. Hydrogen peroxide solution (30%) was purchased from Fisher Scientific. Acrylic acid (≥99%), tin(II) 2-ethylhexanoate (Sn^II(EH)₂, ≥95%), methyl acrylate (≥99%), n-butyl acrylate (≥99%), poly(ethylene glycol) methyl ether acrylate (OEGA, average M_n = 480), N-(3-(dimethylamino)propyl)-N′-ethylcarbodiimide hydrochloride (EDC, ≥99%), N,N-dimethylamino pyridine (DMAP, ≥99%), copper bromide (≥99.99%), ascorbic acid, (AA, ≥99%), divinylbenzene (DVB, technical grade, 80%), and ethyl α-bromoiso-butyrate (EBiB, 98%) were purchased from Sigma-Aldrich. Acrylic acid was distilled under vacuum before use. All acrylate monomers were passed through basic alumina columns before use. Tris(2-pyridylmethyl)amine (TPMA) was synthesized according to previous procedures.^{41 (link)} All solvents and other chemicals are of reagent quality and were used as received unless special treatments discussed below were applied.

Li S., Chung H.S., Simakova A., Wang Z., Park S., Fu L., Cohen-Karni D., Averick S, & Matyjaszewski K. (2017). Biocompatible Polymeric Analogues of DMSO Prepared by Atom Transfer Radical Polymerization. Biomacromolecules, 18(2), 475-482.

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