524-95-8 Usage
Description
(2-AMINOETHOXY)DIPHENYLBORANE, also known as 2-Aminoethyl diphenylborinate (2-APB), is an organoboron compound where the borane hydrogen is replaced by a 2-aminoethoxy group. It is a white crystalline powder that functions as a modulator of intracellular calcium levels and transient receptor potential (TRP) channels. 2-APB inhibits calcium release induced by inositol-1,4,5-triphosphate (IP3) in rat cerebellar microsomes without affecting IP3 binding to its receptor. It also has various applications in different industries due to its unique properties.
Uses
Used in Pharmaceutical Applications:
(2-AMINOETHOXY)DIPHENYLBORANE is used as a Ca release inhibitor and angiogensin II inhibitor for the manipulation of intracellular release of calcium ions and in the preparation of apoptotic inducers. It serves as a reactant for the preparation of apoptotic inducers and acts as a membrane-permeable store-operated calcium entry (SOCE) inhibitor.
Used in Analytical Chemistry:
(2-AMINOETHOXY)DIPHENYLBORANE is used as a TRP activator for the densitometric determination of flavonoids.
Used in Cell Biology:
In the Cell Biology industry, (2-AMINOETHOXY)DIPHENYLBORANE is used as a modulator of Ins(1,4,5)P3-induced Ca2+ release. It inhibits Ins(1,4,5)P3-induced Ca2+ release from rat cerebellar microsomal preparations and store-operated Ca2+ channels in liver cells.
Used in Neuroscience:
(2-AMINOETHOXY)DIPHENYLBORANE is used in the neuroscience field to reduce protein levels of TRP melastatin 2 (TRPM2) in the rat hippocampus, which helps improve learning and memory deficits induced by amyloid-β (25-35) in rats.
Used in Drug Delivery Systems:
Although not explicitly mentioned in the provided materials, due to its ability to modulate intracellular calcium levels and TRP channels, (2-AMINOETHOXY)DIPHENYLBORANE could potentially be used in the development of novel drug delivery systems to enhance the delivery and efficacy of various therapeutic agents.
Synthesis Reference(s)
Journal of the American Chemical Society, 80, p. 5409, 1958 DOI: 10.1021/ja01553a022Journal of the American Chemical Society, 80, p. 5409, 1958 DOI: 10.1021/ja01553a022
Biological Activity
A functional and membrane permeable D-myo-inositol 1,4,5-trisphosphate (IP 3 ) receptor antagonist (IC 50 = 42 μ M). Stimulates store-operated calcium (SOC) release at low concentrations (< 10 μ M) and inhibits it at higher concentrations (up to 50 μ M). Increases STIM-Orai channel conductance and limits ion selectivity. Modulator of TRP channels; blocks TRPC1, TRPC3, TRPC5, TRPC6, TRPV6, TRPM3, TRPM7, TRPM8 and TRPP2 and at higher concentrations stimulates TRPV1, TRPV2 and TRPV3. Also blocks specific gap channel subtypes.
Biochem/physiol Actions
Membrane-permeable modulator of intracellular IP3-induced calcium release.
References
1) Maruyama et al. (1997) 2APB, 2-aminoethoxydiphenyl borate, a membrane-penetrable modulator of Ins(1,4,5)P3-induced Ca2+ release; J. Biochem., 122 498
2) Varnai et al. (2009) STIM and Orai: the long-awaited constituents of store-operated calcium entry; Trends Pharmacol. Sci., 30 118
3) Togashi et al. (2008) Inhibition of the transient receptor potential cation channel TRPM2 by 2-aminoethoxydiphenyl borate (2-APB); Br. J. Pharmacol., 153 1324
4) Xu et al. (2005) Block of TRPC5 channels by 2-aminoethoxydiphenyl borate: a differential, extracellular and voltage-dependent effect; Br. J. Pharmacol., 145 405
5) Bai et al. (2006) Block of specific gap junction channel subtypes by 2-aminoethoxydiphenyl borate (2-APB); J. Pharmacol. Exp. Ther., 319 1452
Check Digit Verification of cas no
The CAS Registry Mumber 524-95-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 4 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 524-95:
(5*5)+(4*2)+(3*4)+(2*9)+(1*5)=68
68 % 10 = 8
So 524-95-8 is a valid CAS Registry Number.
InChI:InChI=1/C14H16BNO/c16-11-12-17-15(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10H,11-12,16H2
524-95-8Relevant articles and documents
Borinic acid catalysed peptide synthesis
El Dine, Tharwat Mohy,Rouden, Jacques,Blanchet, Jér?me
supporting information, p. 16084 - 16087 (2015/11/10)
The catalytic synthesis of peptides is a major challenge in the modern organic chemistry hindered by the well-established use of stoichiometric coupling reagents. Herein, we describe for the first time that borinic acid is able to catalyse this reaction under mild conditions with an improved activity compared to our recently developed thiophene-based boronic acid. This catalyst is particularly efficient for peptide bond synthesis affording dipeptides in good yields without detectable racemization.
2-(N-Alkylamino)-1-(trifluoroacetimidoyl)vinyl ketone derivatives as potential reagents in heterocyclic synthesis
Vasil'Ev,Prezent,Ignatenko,Dorokhov
experimental part, p. 2359 - 2363 (2010/02/16)
A reaction of 3-acetyl-4-amino-5,5,5-trifluoropent-3-en-2-one diphenylboron chelate and ammonia or primary amines affords 4-amino-or 4-alkylamino-3- trifluoroacetimidoylpent-3-en-2-ones, new reagents which can be used for the synthesis of pyrimidines with trifluoromethyl group.
Synthesis and anticoccidial activity of some azacyclo organoborinates
Tabuchi, Hitoshi,Kawaguchi, Harumoto,Taniguchi, Hisashi,Imazaki, Hideyuki,Hayase, Yoshio
, p. 1319 - 1326 (2007/10/03)
A series of azacyclo organoborinates derivatives of piperidinyl and pyridinyl alcohols were prepared and their anticoccidial activity was tested in vitro assay system. Among them, di(4-chlorophenyl)(2-piperidinylmethoxy-O,N)boron, di(3-trifluoromethylphenyl)(2-piperidinylmethoxy-O,N)boron, di(3-trifluoromethylphenyl)(2-pyridinylmethoxy-O,N)boron, and di(3-trifluoromethylphenyl)(2-pyridinylethoxy-O,N)boron, showed moderate anticoccidial activity against Eimeria tenella.