D9754

Sigma-Aldrich

2-Aminoethyl diphenylborinate

97%

Synonym(s):
2-Aminoethyl diphenyl borate, Diphenylborinic acid, 2-APB, 2-Aminoethoxydiphenyl borate, Diphenylboric acid 2-aminoethyl ester, NSC 17107
Linear Formula:
(C6H5)2BOCH2CH2NH2
CAS Number:
Molecular Weight:
225.09
Beilstein/REAXYS Number:
2942273
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

powder

storage temp.

−20°C

SMILES string

NCCOB(c1ccccc1)c2ccccc2

InChI

1S/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

InChI key

BLZVCIGGICSWIG-UHFFFAOYSA-N

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Application

Reactant for:
  • Preparation of apoptotic inducers

  • Activator of the Orai3 (ORAI calcium release-activated calcium modulator 3) protein
  • Inhibits Ca2+ influx through transient receptor potential 2 channels in rat dorsal root ganglion neurons
  • Membrane-permeable SOCE (store operated calcuym entry) inhibitor

Packaging

1, 5, 10, 25 g in glass bottle

Biochem/physiol Actions

Membrane-permeable modulator of intracellular IP3-induced calcium release.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Akinobu Z Suzuki et al.
Bioorganic & medicinal chemistry letters, 20(4), 1395-1398 (2010-01-26)
Store-operated calcium entry (SOCE) is an important mechanism for replenishing intracellular calcium stores and for sustaining calcium signaling. We developed a method for synthesis of bisboron compounds that have two borinic acids or their esters in one molecule. These compounds...
Mustafa Nazıroğlu et al.
The Journal of membrane biology, 241(2), 69-75 (2011-04-22)
Exposure to oxidative stress causes health problems, including sensory neuron neuropathy and pain. Rotenone is a toxin used to generate intracellular oxidative stress in neurons. However, the mechanism of toxicity in dorsal root ganglion (DRG) neurons has not been characterized....
Velasco-Bejarano, B.; et al.
Synlett, 921-921 (2007)
Hyocheol Bae et al.
Marine drugs, 18(1) (2020-01-16)
Marine organisms are sources of several natural compounds with potential clinical use. However, only a few marine-based pharmaceuticals have been approved for use due to limited knowledge on their biological activities. Here, we identified the functional role of fucoidan extracted...
T Maruyama et al.
Journal of biochemistry, 122(3), 498-505 (1997-11-05)
The effects of a novel membrane-penetrable modulator, 2APB (2-aminoethoxy diphenyl borate), on Ins(1,4,5)P3-induced Ca2+ release were examined. 2APB inhibited Ins(1,4,5)P3-induced Ca2+ release from rat cerebellar microsomal preparations without affecting [3H]Ins(1,4,5)P3 binding to its receptor. The IC50 value (concentration producing 50%...

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