4 hydroxymethyl phenylboronic acid pinacol ester

Manufactured by Merck Group

Sourced in United States

4-(hydroxymethyl) phenylboronic acid pinacol ester is a chemical compound used as a reagent in organic synthesis and analytical chemistry applications. It contains a boronic acid group and a pinacol ester group, which can be used for various chemical transformations and analyses. The specific details and intended uses of this product are not included in this description.

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6 protocols using 4 hydroxymethyl phenylboronic acid pinacol ester

Synthesis and Characterization of Oxi-αCD Nanocarrier

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α-Cyclodextrin (α-CD) was provided by Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 4-(hydroxymethyl) phenylboronic acid pinacol ester, 4-dimethylaminopyridine (DMAP), 1,1′-carbonyldiimidazole (CDI), tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), acetone and Pluronic F127 were supplied by Sigma–Aldrich Co., Ltd. (Shanghai, China). 1,2-Distearoyl-sn-glycero-3-phosphoethanolamine-N-methoxy (polyethylene glycol)-2000 (DSPE-PEG₂₀₀₀), folic acid-conjugated DSPE-PEG-3400 (DSPE-PEG₃₄₀₀-FA) and cRGD-conjugated DSPE-PEG-2000 (DSPE-PEG₂₀₀₀-cRGD) were acquired from Xi’an Ruixi Biological Technology Co., Ltd. (Xi’an, China). Lecithin (refined) was supplied by Alfa Aesar (Shanghai, China). Cy5 free acid was purchased from Lumiprobe, LLC (Hallandale Beach, FL, United States). 4′,6-Diamidino-2-phenylindole (DAPI) was obtained from Beyotime Biotechnology Co., Ltd. (Shanghai, China). Oxi-αCD and Cy5-conjugated Oxi-αCD were synthesized according to our previously reported strategy (Wang et al., 2019 (link)). All chemicals were of analytical grade and used without further purification. Ultrapure water was used throughout this study.

Hu R., Yang Y., Song G., Zhao F., Chen S., Zhou Z., Zheng J, & Shen W. (2022). In vivo targeting capacities of different nanoparticles to prostate tissues based on a mouse model of chronic bacterial prostatitis. Frontiers in Bioengineering and Biotechnology, 10, 1021385.

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Multifunctional Fluorescent Nanoparticles

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Dextran (9-11 kDa), poly(lactic-co-glycolic acid) (PLGA, ratio: 50:50; Mw: 7-17 kDa; alkyl ester terminated), IR-780 iodide (98%), indocyanine green (ICG, USP reference standard), 2-methoxypropene (97%), pyridinium p-toluenesulfonate (99%), 4-(Hydroxymethyl)phenylboronic acid pinacol ester (97%), sodium sulfate (99%), 4-(dimethylamino)pyridine (DMAP), carbonyldiimidazole (≥97%), magnesium sulfate (≥99.5%), and triethylamine (≥99%), were purchased from Sigma Aldrich. Pluronic® F-127 (poloxamer 407, 13 kDa) was purchased from O-BASF. Ovalbumin Alexa Fluor® 594 conjugate (OVA-AF594) and bovine serum albumin fluorescein conjugate (BSA-FITC) were purchased from Life Technologies. Fetal bovine serum (FBS) was purchased from Omega Scientific. Chloroform (CHCl₃, 99.8%, EMD), acetone (Fisher Scientific), dimethyl sulfoxide (DMSO, 99%, Aldrich), tetrahydrofuran (THF, Aldrich), ethyl acetate (EtOAc, Fisher Scientific), dichloromethane (DCM, Fisher Scientific) and Dulbecco's Phosphate-Buffered Saline (DPBS, 1×, Life Technologies) were used without further purification. De-ionized water (DI H₂O) was purified from a Millipore system (18.2 MΩ).

Viger M.L., Collet G., Lux J., Huu V.A., Guma M., Foucault-Collet A., Olejniczak J., Joshi-Barr S., Firestein G.S, & Almutairi A. (2017). Distinct ON/OFF fluorescence signals from dual-responsive activatable nanoprobes allows detection of inflammation with improved contrast. Biomaterials, 133, 119-131.

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Evaluation of Antioxidant Compounds

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The following materials and chemicals were used as received without further purification.
4-amino-1,8-naphthalic anhydride (95%), 4-(hydroxymethyl)phenylboronic acid pinacol ester (97%), lipopolysaccharides (LPS) from Escherichia coli, D-Penicillamine (DPA, US Pharmacopeia Reference Standard), catalase from bovine liver, and tert-butyl hydroperoxide solution (TBHP, 70 wt. % in H₂O) were purchased from Sigma-Aldrich Co. LLC. (USA), used as received.
Triphosgene (99%), and 4-dimethylaminopyridine (99%) were purchased from Aladdin Industrial Inc. (China), and used as received.
Organic solvents and other chemicals used were provided by Shanghai Chemical Co. (China).
Dulbecco’s Modified Eagle Medium cell culture media, fetal bovine serum and phosphate buffered saline (PBS, pH = 7.4) were purchased from Life Technologies Corporation (USA), and used as recommended.
Trypsin-EDTA solution (0.05%, with phenol red) and Penicillin-Streptomycin solution (10 000 U/ml) were purchased from Biological Industries Israel Beit-Haemek Ltd. (Israel), and used as recommended.

Rong L., Zhang C., Lei Q., Hu M.M., Feng J., Shu H.B., Liu Y, & Zhang X.Z. (2016). Hydrogen peroxide detection with high specificity in living cells and inflamed tissues. Regenerative Biomaterials, 3(4), 217-222.

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Thermoresponsive Polymer Hydrogel Synthesis

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All chemicals were obtained from Sigma-Aldrich unless otherwise described. N-Isopropylacrylamide (NIPAAm, TCI) was recrystallized in hexane 3 times before use. 2-Hydroxyethyl methacrylate (HEMA, Alfa Aesar) was used after passing through a column filled with inhibitor removers. Benzoyl peroxide (BPO, Fisher Scientific) was freeze-dried before polymerization. Acryloyl chloride (Sigma), 4-(hydroxymethyl)-phenylboronic acid pinacol ester (Sigma-Aldrich, HPPE), triethylamine (TEA, VWR), and hydrogen peroxide (H₂O₂) (30%, Sigma-Aldrich) were used as received. rhMG53 protein was purified from E. coli fermentation as described previously [33 ].

Niu H., Li H., Guan Y., Zhou X., Li Z., Zhao S.L., Chen P., Tan T., Zhu H., Bergdall V., Xu X., Ma J, & Guan J. (2022). Sustained delivery of rhMG53 promotes diabetic wound healing and hair follicle development. Bioactive Materials, 18, 104-115.

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Pullulan-Based Theranostic Nanoparticles

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Pullulan (MW 0.2 MDa) was obtained from Hayashibara Biochemical Laboratory (Okayama, Japan). Selenium powder, 4-Bromobenzyl alcohol, hydrazine hydrate, 1-ethyl-3-[3-(dimethylaminopropyl)]carbodiimide hydrochloride (EDCI), 4-Dimethylaminopyridine (DMAP), p-nitrobenzoyl chloride, 4-(hydroxymethyl) phenylboronic acid pinacol ester, fluorescein isothiocyanate (FITC-dextran), and doxorubicin hydrochloride (DOX•HCl) were obtained from Sigma-Aldrich (Milwaukee, USA). β-Lapachone were purchased from Sinopharm Chemical Reagent Co., Ltd (China). Also, 2,7-dichlorodihydroﬂuorescein diacetate (DCFH-DA) was procured from Beyotime Biotechnology Co., Ltd (China). All chemicals were of analytical grade and were used as received without further purification. Solvents were dried and distilled before use.

Li Q., Hou W., Li M., Ye H., Li H, & Wang Z. (2020). Ultrasound Combined with Core Cross-Linked Nanosystem for Enhancing Penetration of Doxorubicin Prodrug/Beta-Lapachone into Tumors. International Journal of Nanomedicine, 15, 4825-4845.

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Multifunctional Nanoparticle-based Cancer Therapy

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Chloroauric acid (HAuCl₄·4H₂O), Sodium Citrate (C₆H₅O₇Na₃.2H₂O), 4-(Hydroxymethyl) phenylboronic acid pinacol ester, acryloyl chloride, n-butylamine, hexadecyltrimethylammonium bromide (CTAB), azobis(isobutyronitrile), triethylamine (TEA), tirapazamine (TPZ), glucose oxidase (GOx), N,N-dimethylformamide (DMF), tetrahydrofuran (THF), dichloromethane(DCM), anisole, methanol, 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide-Thiazolyl Blue Tetrazolium Bromide (MTT) and all other chemical reagents were purchased from Sigma-Aldrich without any other purification process. Dulbecco's modified Eagle's medium (DMEM), Hoechst 33342, Amplex® Red, Image-iT™ Green Hypoxia Reagent and other biological reagents were purchased from Thermo Fisher Scientific.

Tang Y., Ji Y., Yi C., Cheng D., Wang B., Fu Y., Xu Y., Qian X., Choonara Y.E., Pillay V., Zhu W., Liu Y, & Nie Z. (2020). Self-accelerating H2O2-responsive Plasmonic Nanovesicles for Synergistic Chemo/starving therapy of Tumors. Theranostics, 10(19), 8691-8704.

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