4-Aminophenylboronic acid
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4-Aminophenylboronic acid

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4-Aminophenylboronic Acid is a compound being used in the discovery of multi-target receptor tyrosine kinase inhibitors as novel anti-angiogenesis agents.

Category
Peptide Synthesis Reagents
Catalog number
BAT-006307
CAS number
89415-43-0
Molecular Formula
C6H8BNO2
Molecular Weight
136.94
4-Aminophenylboronic acid
IUPAC Name
(4-aminophenyl)boronic acid
Synonyms
B-(4-Aminophenyl)boronic Acid; (4-Anilino)boronic Acid; 4-Aminobenzeneboronic Acid; p-Aminophenylboronic Acid; BORONIC ACID, (4-AMINOPHENYL)-; 4-Aminobenzeneboronic acid hydrochloride; 4-Boronoaniline
Appearance
White to beige crystalline powder
Purity
> 98 % (HPLC)
Density
1.230 g/cm3 (Predicted)
Melting Point
62-66 °C
Boiling Point
355.0 °C at 760 mmHg
Storage
2-8 °C
InChI
InChI=1S/C6H8BNO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H,8H2
InChI Key
MKPDAJWEBQRQCO-UHFFFAOYSA-N
Canonical SMILES
B(C1=CC=C(C=C1)N)(O)O
1. Sensitive sugar detection using 4-aminophenylboronic acid modified graphene
Qi Wang, Izabela Kaminska, Joanna Niedziolka-Jonsson, Marcin Opallo, Musen Li, Rabah Boukherroub, Sabine Szunerits Biosens Bioelectron. 2013 Dec 15;50:331-7. doi: 10.1016/j.bios.2013.06.015. Epub 2013 Jun 25.
A sensitive electrochemical active interface for sugar sensing based on the specific boronic acid-diol binding was established. The sensing matrix was formed by stirring a suspension of graphene oxide (GO) with 4-aminophenylboronic acid (APBA). The resulting composite consists of a water insoluble precipitate of reduced graphene oxide (rGO) with APBA incorporated into the rGO matrix. Differential pulse voltammetry (DPV) on glassy carbon electrodes modified with rGO/APBA was used for the detection of fructose, mannose and glucose. The fabricated sensor exhibited a wide linear range with detection limits of 100 nM for fructose, and around 800 nM for mannose and glucose.
2. A fluoride-driven ionic gate based on a 4-aminophenylboronic acid-functionalized asymmetric single nanochannel
Qian Liu, Kai Xiao, Liping Wen, Yang Dong, Ganhua Xie, Zhen Zhang, Zhishan Bo, Lei Jiang ACS Nano. 2014 Dec 23;8(12):12292-9. doi: 10.1021/nn506257c. Epub 2014 Dec 11.
Fluorine is one of the human body's required trace elements. Imbalanced fluoride levels severely affect the normal functioning of living organisms. In this article, an anion-regulated synthetic nanochannel is described. A fluoride-driven ionic gate was developed by immobilizing a fluoride-responsive functional molecule, 4-aminophenylboronic acid, onto a single conical polyimide nanochannel. When the ionic gate was in the presence of fluoride, the boron bound F-, and the hybridization of the boron center changed from sp2 to sp3. Thus, negatively charged monofluoride adduct (RB(OH)2F-), difluoride adduct (RB(OH)F2-), and trifluoride adduct (RBF3-) modified surfaces with different wettability would be formed successively by increasing the concentration of F-. On the basis of the variation of surface charge and wettability, the nanochannel can actualize reversible switching between the "off" state and the "on" state in the absence and presence of F-, respectively. As an anion-regulated synthetic nanochannel, this fluoride-driven ionic gate was characterized by measuring ionic current, which possesses high sensitivity, fine selectivity, and strong stability. Thus, this gate may show great promise for use in biosensors, water quality monitoring, and drug delivery.
3. 4-Aminophenyl boronic acid modified gold platforms for influenza diagnosis
Sibel Emir Diltemiz, Arzu Ersöz, Deniz Hür, Rüstem Keçili, Ridvan Say Mater Sci Eng C Mater Biol Appl. 2013 Mar 1;33(2):824-30. doi: 10.1016/j.msec.2012.11.007. Epub 2012 Nov 13.
As a potential pandemic threat to human health, there has been an urgent need for rapid, sensitive, simpler and less expensive detection method for the highly pathogenic influenza A virus. For this purpose, Quartz Crystal Microbalance (QCM) and Surface Plasmon Resonance (SPR) sensors have been developed for the recognition of hemagglutinin (HA) which is a major protein of influenza A virus. 4-Aminophenyl boronic acid (4-APBA) has been synthesized and used as a new ligand for binding of sialic acid (SA) via boronic acid-sugar interaction. SA has an important role in binding of HA. QCM and SPR sensor surfaces have been modified with thiol groups and then 4-APBA and SA have been immobilized on sensor surfaces, respectively. Sensor surfaces have been screened with AFM and used for the determination of HA from aqueous solution. The selective recognition of the QCM and SPR sensors toward Concanavalin A has been reported in this work. Also, the binding capacity and detection limits of QCM and SPR sensors have been calculated and detection limits were found to be 4.7 × 10(-2) μM, (0.26 μg ml(-1)) and 1.28 × 10(-1) μM, (0.72 μg ml(-1)) in the 95% confidence interval, respectively.
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