PEG‐BZA was synthesized as previously described.[30 ] Briefly, 4‐formyl benzoic acid (0.528 g, 3.52 mmol, 2.1 eq. per amine; Sigma) was dissolved in 5 mL anhydrous DMF (Sigma) and activated with HATU (1.216 g, 3.2 mmol, 2 eq.; Sigma) and 4‐methylmorpholine (0.792 mL, 7.2 mmol, 4.5 eq.; Sigma). The reaction was allowed to stir for 5 min before the addition of 4‐arm 10 kDa PEG‐amine (4 g, 0.2 mmol; Creative PEGworks) dissolved in 5 mL DMF for a total reaction volume of 10 mL. The reaction was allowed stir at RT overnight. The final polymer was precipitated in ethyl ether (Thermo Fisher), pelleted by centrifugation at 22 000 rcf for 20 min, and re‐dissolved in Milli‐Q water. PEG‐BZA was dialyzed (MWCO: 3500 Da; Spectrum) against Milli‐Q water for 3 days at 4 °C, and dialysis water was changed two to three times per day. PEG‐BZA was lyophilized and stored at −20 °C. Modification of PEG‐BZA was estimated using 1H NMR (500 MHz). PEG‐BZA was dissolved in deuterated water (D2O; Sigma) at 10 mg mL−1. δ = 9.9 ppm (1H, s, aldehyde); δ = 7.93 and 7.82 ppm (2H each; d; benzene ring); δ = 3.56 (217H per arm; s; PEG).
4 formylbenzoic acid
Manufactured by Merck Group
Sourced in United States, Germany
4-formylbenzoic acid is a chemical compound used in various laboratory applications. It is a colorless crystalline solid with the molecular formula C₆H₅CO₂H. The compound serves as a precursor and building block for the synthesis of other organic molecules, but a detailed description of its specific applications is not available.
Automatically generated - may contain errors
Lab products found in correlation
Potassium persulfate, by Merck Group (2 mentions)
Acrylamide, by Thermo Fisher Scientific (2 mentions)
Bovine serum albumin (bsa), by Merck Group (2 mentions)
Ethyl ether, by Thermo Fisher Scientific (1 mentions)
4 methylmorpholine, by Merck Group (1 mentions)
Anhydrous dmf, by Merck Group (1 mentions)
N n dicyclohexylcarbodiimide dcc, by Merck Group (1 mentions)
Polyethylene glycol peg, by Thermo Fisher Scientific (1 mentions)
4 dimethylaminopyridine dmap, by Merck Group (1 mentions)
Thiophene, by Thermo Fisher Scientific (1 mentions)
Iron 3 chloride anhydrous fecl3, by Thermo Fisher Scientific (1 mentions)
Polyethylene glycol, by Thermo Fisher Scientific (1 mentions)
Methacrylic anhydride, by Merck Group (1 mentions)
N n dicyclohexylcarbodiimide, by Thermo Fisher Scientific (1 mentions)
Propionic acid, by Sinopharm (1 mentions)
Hydrogen chloride, by Sinopharm (1 mentions)
Pyrrole, by Merck Group (1 mentions)
Trimesoyl chloride, by Merck Group (1 mentions)
Tetrahydrofuran, by Sinopharm (1 mentions)
Sodium hydroxide (naoh), by Sinopharm (1 mentions)
15 protocols using 4 formylbenzoic acid
1
Synthesis and Characterization of PEG-BZA
2
Synthesis of Dialdehyde-Functionalized PEG
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Acrylamide, polyAcrylamide average MW 10 000 and poly(ethylene glycol) (PEG) average MW 2000 were purchased from Acros Organics. Potassium persulfate, 4-formylbenzoic acid, 4-(dimethylamino)pyridine (DMAP) and N,N′-dicyclohexylcarbodiimide (DCC) were obtained from Sigma-Aldrich. Food dyes and conductive carbon black graphite KS-6 were from LorAnn Oils and TIMCAL TIMREX®, respectively. The particle size of KS-6 is 5.8–7.1 μm (d90, laser Malvern), crystallinity hight is 60 nm, specific surface area (BET) is 26 m2 g−1 and bulk density is 0.00253 lb/in3. Dialdehyde-functionalized PEG (DF-PEG) was synthesized according to literature protocol.39 (link) PEG (2.0 g), 4-formylbenzoic acid (0.6 g), DMAP (0.03 g) and DCC (1.13 g) were reaction at room temperature for overnight. The precipitate was filtered and re-dissolved in THF, followed by precipitation with diethyl ether to obtain the DF-PEG polymer.
3
Synthesis of Dialdehyde-Functionalized PEG and PEDOT-co-Thiophene Copolymers
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Acrylamide (AAm) and MBAA
were obtained from
Acros Organics. Thiophene and iron (III) chloride anhydrous (FeCl3) were purchased from Alfa Aesar. 4-Formylbenzoic acid, 4-(dimethylamino)pyridine
(DMAP), N,N′-dicyclohexylcarbodiimide (DCC),
and KPS were obtained from Sigma-Aldrich. 3,4-EthylenedioxyThiophene
(EDOT) was obtained from Tokyo Chemical Industry. Dialdehyde-functionalized
poly(ethylene glycol) (DF-PEG) and the P(EDOT-co-Th)
copolymers were synthesized according to literature procedures.7 (link),51 (link),52 (link) Briefly, DF-PEG was synthesized
by the reaction of 4-Formylbenzoic acid (1.33 g, 8.83 mmol), PEG (3.00
g, 1.5 mmol), DMAP (0.11 g, 0.90 mmol), and DCC (1.86 g, 9.00 mmol)
at room temperature and precipitated with diethyl ether. P(EDOT-co-Th) copolymers, for example, the molar ratio of EDOT/Th
= 9:1, was prepared by the reaction mixtures of EDOT (0.95 mL, 9.00
mmol), Th (0.08 mL, 1.00 mmol), and FeCl3 (8.11 g, 50.0
mmol in 12.5 mL of dried CH3CN) in CH2Cl2 (25 mL) under a nitrogen atmosphere and reaction for 24 h.
P(EDOT-co-Th) copolymers (EDOT: Th = 7:3, 5:5, 3:7
and 1:9) with different molar ratios were synthesized accordingly.
were obtained from
Acros Organics. Thiophene and iron (III) chloride anhydrous (FeCl3) were purchased from Alfa Aesar. 4-Formylbenzoic acid, 4-(dimethylamino)pyridine
(DMAP), N,N′-dicyclohexylcarbodiimide (DCC),
and KPS were obtained from Sigma-Aldrich. 3,4-EthylenedioxyThiophene
(EDOT) was obtained from Tokyo Chemical Industry. Dialdehyde-functionalized
poly(ethylene glycol) (DF-PEG) and the P(EDOT-co-Th)
copolymers were synthesized according to literature procedures.7 (link),51 (link),52 (link) Briefly, DF-PEG was synthesized
by the reaction of 4-Formylbenzoic acid (1.33 g, 8.83 mmol), PEG (3.00
g, 1.5 mmol), DMAP (0.11 g, 0.90 mmol), and DCC (1.86 g, 9.00 mmol)
at room temperature and precipitated with diethyl ether. P(EDOT-co-Th) copolymers, for example, the molar ratio of EDOT/Th
= 9:1, was prepared by the reaction mixtures of EDOT (0.95 mL, 9.00
mmol), Th (0.08 mL, 1.00 mmol), and FeCl3 (8.11 g, 50.0
mmol in 12.5 mL of dried CH3CN) in CH2Cl2 (25 mL) under a nitrogen atmosphere and reaction for 24 h.
P(EDOT-co-Th) copolymers (EDOT: Th = 7:3, 5:5, 3:7
and 1:9) with different molar ratios were synthesized accordingly.
4
Synthesis and Characterization of Functional Polymers
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Acrylamide (AAM) and polyAcrylamide (PAAM, average MW 10000) were obtained from Acros Organics (Geel, Antwerp, Belgium), while polyethylene glycol (PEG, average MW 2000), N-N’-Dicyclohexylcarbodiimide (DCC) were sourced from Alfa Aesar (Ward Hill, MA, USA). Methacrylic anhydride, 4-formylbenzoic acid, and potassium persulfate (PPS) were acquired from Sigma-Aldrich (St. Louis, MO, USA). The compound N-Boc-L-Lysine was purchased from Carbosynth Ltd. (Compton, UK).; 4-dimethylaminopyridine (DMAP) was obtained from Matrix Scientific (Elgin, SC, USA). Deionized water was utilized in all experiments.
5
Polysulfone Membrane Fabrication and Characterization
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Polysulfone base membrane B1 and B2 were supplied by SEAPS Science and Technology Co., Tangshan, China, and the specific parameters are shown in Table 1 . The main difference of the above two membranes is that the BSA (bovine serum albumin) rejection of the B1 membrane is 98.67%, and that of the B2 membrane is 81%, corresponding to a low water flux (112.36 Lm−2h−1bar−1) and a high-water flux (677.52 Lm−2h−1bar−1), respectively. Polysulfone (Ultrason S 6010, Mw = 60,000 g/mol and glass transition temperature Tg = 187 °C) was supplied by BASF China (Mainland) (Shanghai, China). N-N-dimethylacetamide (DMAc ≥99.5%), and polyethylene glycol (average Mn 600) were obtained from Sinopharm (Shanghai, China). 4-formylbenzoic acid (98%), trimesoyl chloride (98%) and pyrrole (99%) were purchased from SIGMA-ALDRICH (Shanghai, China). Propionic acid, sodium hydroxide, hydrogen chloride, tetrahydrofuran, sodium bicarbonate and hexane were obtained from Sinopharm. Bovine serum albumin (BSA, pI = 4.8, Mw = 67,000 g mol−1) was obtained from Shanghai LanJi (Shanghai, China). All chemicals were used as received. Deionized (DI) water (18.2 MΩ cm) was used throughout the experiment.
6
PVA-Chitosan Hydrogel Synthesis and Characterization
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Polyvinyl alcohol (PVA, Mw = 46.8 kDa, 86–89% hydrolyzed) was purchased from Nagart Kft., Győrújbarát, Hungary. Low-molecular-weight (50–190 kDa) chitosan (CHIT, C12H24N2O9, ≥75% deacetylation) was purchased from Merck Ltd. (Darmstadt, Germany). The polydispersity of the PVA and chitosan was shown in Table S1 . 1-(3-Dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDC, C8H17N3·HCl, Mw 191.70, 98+%) was obtained from Thermo Fisher GmbH (Kandel, Germany), while 3-mercaptopropionic acid was purchased from Fluka Analytical (Munich, Germany). Moreover, 4-formylbenzoic acid (FBA, C8H6O3, 97%), N, N’-dicyclohexylcarbodiimide (DCC, C13H22N2, 99%), and 4-(dimethylamino)pyridine (DMAP, C7H10N2, ≥99%) were acquired from Sigma–Aldrich Chemie GmbH, Steinheim, Germany. Phosphate-buffered saline (PBS; pH~7.4) solution was prepared using sodium dihydrogen phosphate monohydrate (NaH2PO4·H2O) from Sigma–Aldrich as well as di-sodium hydrogen phosphate dodecahydrate (Na2HPO4·12H2O) and sodium chloride (NaCl) acquired from Molar Chemicals Kft., Hungary. Tilorone dihydrochloride (C25H34N2O3·2HCl) as an antimusclular atrophy drug was acquired from Merck KGaA, Darmstadt, Germany. All chemicals were used exactly as supplied, with no additional purification.
7
Synthesis of Benzoxazepine Derivatives
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Reagents for synthesis: 2′-aminoacetophenone, 3′-aminoacetophenone, 4′-aminoacetophenone, benzaldehyde, 4-ethylbenzaldehyde, 4-formylbenzoic acid, 4-nitrobenzaldehyde, 4-(benzyloxy)- benzaldehyde, 4-(benzyloxy)-3-methoxy-benzaldehyde and sodium hydroxide were purchased from Sigma Aldrich (St. Louis, MO, USA).
8
Boronic Acid Conjugation Synthesis
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4-formylbenzoic acid, 3-(N,N-dimethylamino)phenylboronic acid, acetic acid (glacial), boron trifluoride-diethyl ether complex (BF3·Et2O), and 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES) were obtained from Sigma-Aldrich Japan (Tokyo, Japan); D-fructose (Fru) and D-glucose (Glc) were obtained from FUJIFILM Wako Pure Chemical Corp. (Osaka, Japan); chloranil was obtained from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan); and cresyl violet (fluorescence reference standard) was obtained from Cosmo Bio Co., Ltd. (Tokyo, Japan). All chemicals were used without further purification.
9
Synthesis of Substituted Acetophenone Derivatives
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Acethophenone, diiodine, thiourea, 4-hydroxyacetophenone, 4-formylbenzoic acid, 3-nitroacetophenone and 4′-hydroxyacetophenone were obtained from Sigma-Aldrich Co., Germany. Pyridine (Py, Fluka) and N-methyl-2-pyrrolidone (NMP, Merck) as polymerization solvents were purified by distillation under reduced pressure over calcium hydride (CaH2). Lithium chloride (LiCl), triphenyl phosphite (TPP), N, N-dimethylacetamide (DMAc), and other solvents such as dimethylformamide (DMF), dimethyl sulfoxide (DMSO) and tetrahydrofuran (THF) were used as received from Merck company.
10
Synthesis of PEG-Benzaldehyde Conjugates
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