P nitrophenyl chloroformate

Manufactured by Merck Group

Sourced in United States

P-Nitrophenyl chloroformate is a chemical compound used in various laboratory applications. It functions as an activated ester for the synthesis of carbamates and other derivatives. The compound consists of a p-nitrophenyl group attached to a chloroformate group.

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Lab products found in correlation

Horseradish peroxidase hrp, by Merck Group (3 mentions) Tyramine, by Merck Group (3 mentions) Hydrogen peroxide, by Merck Group (3 mentions) Lithium chloride (licl), by Merck Group (3 mentions) N n dimethylformamide (dmf), by Merck Group (3 mentions) Tyramine hcl salt, by Thermo Fisher Scientific (2 mentions) Dmso d6, by Merck Group (2 mentions) Sodium chloride (nacl), by Merck Group (2 mentions) Pyridine, by Merck Group (2 mentions) Ethanol, by Merck Group (2 mentions) Diethyl ether, by Merck Group (2 mentions) 4 4 6 dimethoxy 1 3 5 triazin 2 yl 4 methyl morpholinium chloride dmtmm, by Fluorochem (2 mentions) 4 dimethylaminopyridine, by Merck Group (2 mentions) Dimethyl sulfoxide (dmso), by Merck Group (2 mentions) Dichloromethane, by Avantor (1 mentions) Diethyl ether, by Avantor (1 mentions) Collagenase type 1, by Thermo Fisher Scientific (1 mentions) Ethanol, by Avantor (1 mentions) Dulbecco s pbs dpbs, by Thermo Fisher Scientific (1 mentions) Live dead cell viability kit, by Thermo Fisher Scientific (1 mentions)

7 protocols using p nitrophenyl chloroformate

Photocrosslinkable Hydrogel Fabrication

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GelMA with 90% of free amine groups substituted by methacrylate groups was synthesized as previously reported[20 (link)]. The 8-arm PEG (8PEG, hexaglycerol core, Mw = 20,000 g/mol) was acquired from Jenkem Technology (Allen, Texas, USA), and freeze-dried overnight before use. p-Nitrophenyl chloroformate (PNC), tyramine (TA), lithium phenyl-2,4,6-trimethylbenzoylphosphinate (LAP), hydrogen peroxide (H₂O₂, 30 wt% in H₂O), horseradish peroxidase (HRP) (253 U/mg), hexamethyldisilazane (HMDS), sodium azide, phosphate-buffered saline (PBS), and N, N-dimethylformamide (DMF) were obtained from Sigma-Aldrich. Collagenase (Type I, 260 U/mg) was obtained from Thermo Fisher Scientific. Diethyl ether, dichloromethane, and ethanol were purchased from VWR Chemicals. Dulbecco’s PBS (DPBS, Gibco), α-MEM (A22571, Gibco), fetal bovine serum (FBS, Lonza, Basel, Switzerland), GlutaMAX, trypsin/EDTA, and penicillin/streptomycin (G418) were obtained from Gibco. Live/dead cell viability kit was purchased from Invitrogen Molecular Probes (L3224, Thermo Fisher Scientific, Eugene, USA).

Liang J., Wang Z., Poot A.A., Grijpma D.W., Dijkstra P.J, & Wang R. (2023). Enzymatic post-crosslinking of printed hydrogels of methacrylated gelatin and tyramine-conjugated 8-arm poly(ethylene glycol) to prepare interpenetrating 3D network structures. International Journal of Bioprinting, 9(5), 750.

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Synthesis of Dextran-Hyaluronate Hydrogels

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Dextran (40 kDa, pharmaceutical grade) was purchased from Pharmacosmos, Holbæk, Denmark. Sodium hyaluronate (27 kDa, pharmaceutical grade) was purchased from Contipro Pharma, Dolní Dobrouč, Czech Republic. Tyramine (99%), DMF (anhydrous, 99.8%), LiCl (99.0%), p-nitrophenyl chloroformate (PNC, 96%), pyridine (anhydrous, 99.8%), DMSO-d₆ (99.9%), NaCl (≥99.0%), D₂O (99.9 atom % D), horseradish peroxidase (HRP, 325 U/mg solid), and hydrogen peroxide (30%) were purchased from Sigma-Aldrich, Schnelldorf, Germany. Tyramine∙HCl salt (99%) was obtained from Acros Organics, Fair Lawn, NJ, USA. 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride (DMTMM, 97%) was purchased from Fluorochem Ltd., Hadfield, UK. Ethanol (≥99.9%) and diethyl ether (≥99.7%) were purchased from Merck, Kenilworth, NJ, USA. Milli-Q water was used from the Milli-Q Advantage A10 system (Merck KGaA, Darmstadt, Germany) equipped with a 0.22 μm Millipak^® 40 Express filter.

Fu Y., Both S.K., Plass J.R., Dijkstra P.J., Zoetebier B, & Karperien M. (2022). Injectable Cell-Laden Polysaccharide Hydrogels: In Vivo Evaluation of Cartilage Regeneration. Polymers, 14(20), 4292.

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Functionalization of Polysaccharides for Biomedical Applications

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Dextran (40 kDa, pharmaceutical grade) was purchased from Pharmacosmos, Holbæk. Denmark. Sodium hyaluronate (27 kDa, pharmaceutical grade) was purchased from Contipro Pharma, Dolní Dobrouč, Czech Republic. Tyramine (99%), DMF (anhydrous, 99.8%), LiCl (99.0%), p-nitrophenyl chloroformate (PNC, 96%), pyridine (anhydrous, 99.8%), DMSO-d6 (99.9%), NaCl (≥99.0%), D₂O (99.9 atom % D), horseradish peroxidase (HRP, 325 units/mg solid) and hydrogen peroxide (30%) were purchased from Sigma-Aldrich, St. Louis, MO, USA. Tyramine HCl salt (99%) was obtained from Acros Organics, Fair Lawn, NJ, USA. 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM, 97%) was purchased from Fluorochem Ltd., Hadfield, UK. Ethanol (≥99.9%) and diethyl ether (≥99.7%) were purchased from Merck, Kenilworth, NJ, USA. Milli-Q water was used from the Milli-Q Advantage A10 system equipped with a 0.22 μm Millipak^®-40 Express filter.

Fu Y., Zoetebier B., Both S., Dijkstra P.J, & Karperien M. (2021). Engineering of Optimized Hydrogel Formulations for Cartilage Repair. Polymers, 13(9), 1526.

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Curcumin-Pluronic Nanoparticle Synthesis

Cited 2 times

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Curcumin, pluronic F127 (F127, Mw (Da) = 12,600 and CMC = 2.8 × 10⁻⁶), Pluronic F87 (F87, Mw (Da) = 7700 and CMC = 9.1 × 10⁻⁵) and p-Nitrophenylchloroformate (NPC) were purchased from Sigma Aldrich (St. Louis, MI, USA). THF tetrahydrofuran (THF), Dichloromethane (DCM), Gelatin (Ge; product no. 1040700500) from porcine skin were purchased from Merck (Darmstadt, Germany). Ethanol and diethyl ether were obtained from Scharlau’s Chemicals (Barcelona, Spain). Mono NPC- activated F127-OH and mono NPC-activated F87)-OH were prepared followed protocol in our previous study [27 (link),40 (link)]. Dialysis membranes (molecular weight cut-off/MWCO 14 kDa and MWCO 3.5 kDa cut-off) were supplied from Spectrum Labs (CA, USA).

Nguyen D.T., Dinh V.T., Dang L.H., Nguyen D.N., Giang B.L., Nguyen C.T., Nguyen T.B., Thu L.V, & Tran N.Q. (2019). Dual Interactions of Amphiphilic Gelatin Copolymer and Nanocurcumin Improving the Delivery Efficiency of the Nanogels. Polymers, 11(5), 814.

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Ferulic Acid-Crosslinked Gelatin Hydrogels

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Gelatin (Gtn, type A from porcine skin, <300 bloom), 3-methoxy-4-hydroxycinnamic acid (ferulic acid, FA), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), N-hydroxysuccinimide (NHS), dimethyl sulfoxide (DMSO), Dextran (Dex, MW 70,000), 2–bromoethylamine hydrobromide (BEAHB), triethylamine (TEA), 4–dimethylaminopyridine (DMAP), p–nitro–phenylchloroformate (PNC), poly(ethylene glycol) (PEG, MW 4000), tyramine (TA), laccase (lyophilized powder from mushroom, ≥4.0 units/mg), and deuterium oxide (D₂O) were purchased from Sigma-Aldrich (Saint Louis, MO) and used as obtained without purification. Microbial transglutaminase (mTG) (Activa-TI) was purchased from Ajinomoto, Inc. Dulbecco’s Phosphate-Buffered Saline (DPBS), Dulbecco’s Modified Eagle Medium (DMEM), fetal bovine serum (FBS), and trypsin were all purchased from Gibco, Invitrogen (Life Technologies, CA). Dialysis membranes (molecular cutoff = 3500 Da; molecular cutoff = 6000–8000 Da) were purchased from Spectrum Laboratories (Rancho Dominguez, CA). Endothelial growth media-2 (EGM2) was purchased from Lonza (Walkersville, MD) and used to culture endothelial colony forming cells (ECFCs) (Lonza) on collagen I coated cell culture plates (BD Biosciences, Franklin Lakes, NJ).

Blatchley M., Park K.M, & Gerecht S. (2015). Designer Hydrogels for Precision Control of Oxygen Tension and Mechanical Properties. Journal of materials chemistry. B, Materials for biology and medicine, 3(40), 7939-7949.

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Hyaluronic Acid-PEG Hydrogel Synthesis

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The 8-arm poly(ethylene glycol) (8-arm PEG, hexaglycerol core, Mw = 20,000) was acquired from Jenkem Technology (Allen, Texas, USA) and purified before use by dissolution in dichloromethane and precipitation in cold diethyl ether. Hyaluronic acid sodium salt (Mw = 15–25 kg/mol) was purchased from Contipro. The polymer was dried by lyophilization overnight before use. p-Nitrophenyl chloroformate (PNC, 96%) was purchased from Sigma-Aldrich (Zwijndrecht, the Netherlands) and was sublimated before use. Anhydrous dimethylformamide (DMF, 99.8%), tyramine (99%), anhydrous pyridine (99.8%), hydrogen peroxide (H₂O₂, 30 wt% in H₂O), lithium chloride and HRP (261 U/mg) were obtained from Sigma-Aldrich and used without further purification. dichloromethane (stabilized by Amylene, ≥99.9%), ethanol (99.8%) and diethyl ether (stabilized by BHT, ≥99.5%) were obtained from Biosolve (Valkenswaard, The Netherlands) and used as received. Dialysis membranes (Spectra/Por molecular porous membrane tubing 6, MWCO: 1 kDa) were acquired from Spectrum Laboratories, Inc. (Breda, The Netherlands) and rinsed with distilled water before use. Deuterated solvents were purchased from Aldrich. Phosphate buffered saline (PBS, 150 mM, pH 7.4) was purchased from Gibco Life Technologies Ltd (Paisley, UK).

Wang R., Huang X., Zoetebier B., Dijkstra P.J, & Karperien M. (2022). Enzymatic co-crosslinking of star-shaped poly(ethylene glycol) tyramine and hyaluronic acid tyramine conjugates provides elastic biocompatible and biodegradable hydrogels. Bioactive Materials, 20, 53-63.

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Synthesis of Fluorescent Conjugates

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Bromoethanol, p-nitrophenyl
chloroformate, 3-toluenesulfonyl chloride, triethylamine, 2,4-quinolinediol,
phenylphosphonyl dichloride, p-xylylendiamine, valeroyl
chloride, calcium oxide, di-tert-butyl decarbonate,
deuterated solvents, ethyl acetate, dimethyl sulfoxide (DMSO), sodium
hydroxide (NaOH), hydrochloric acid (HCl), 2,4-dimethoxybenzyl amine,
trifluoroacetic acid (TFA), platinum on carbon (10% Pt/C), benzylamine,
benzyl alcohol, dibenzylamine, 4-dimethylaminopyridine (DMAP), 2,2′-azobis(2-methylpropionitrile)
(AIBN), n-butylamine, N,N-dimethylacrylamide (DMA), sodium bicarbonate (NaHCO₃), cholesterol, acryloxyethyl thiocarbamoyl rhodamine B, 2-mercapto ethanol,
2,2′-dipyridyl disulfide, and N,N′-dicyclohexylcarbodiimide (DCC) were obtained from Sigma-Aldrich.
Potassium sulfite, sulfur, tris(2-carboxyethyl)phosphin (TCEP), and
sodium sulfate were purchased from Acros Organics, Alfa Aesar, TCI
Chemicals, and Carl Roth GmbH+ Co. KG, respectively. N,N-Dimethylformamide (DMF), chloroform, dichloromethane
(DCM), tetrahydrofuran (THF), succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate
(SMCC), and Gibco Dulbecco’s phosphate-buffered saline (DPBS)
were obtained from Thermo Fisher Scientific Inc., and methanol (MeOH),
acetone, and ethanol were obtained from Honeywell International.

Scherger M., Pilger Y.A., Stickdorn J., Komforth P., Schmitt S., Koynov K., Räder H.J, & Nuhn L. (2023). Efficient Self-Immolative RAFT End Group Modification for Macromolecular Immunodrug Delivery. Biomacromolecules, 24(5), 2380-2391.

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