DIPHENYLBORINIC ANHYDRIDE - CAS 4426-21-5
Category:
Main Product
Product Name:
DIPHENYLBORINIC ANHYDRIDE
Catalog Number:
4426-21-5
Synonyms:
DIPHENYLBORINIC ANHYDRIDE; TETRAPHENYLDIBOROXANE; OXYBIS(DIPHENYLBORANE); DIPHENYLBORINIC ANHYDRIDE, FOR FLUORESCE NCE; Oxybis(diphenylborane), Tetraphenyldiboroxane
CAS Number:
4426-21-5
Molecular Weight:
346.04
Molecular Formula:
C24H20B2O
Quantity:
Data not available, please inquire.
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
B(C1=CC=CC=C1)(C2=CC=CC=C2)OB(C3=CC=CC=C3)C4=CC=CC=C4
InChI:
InChI=1S/C24H20B2O/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22)27-26(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H
InChIKey:
SNQFEECGHGUHBK-UHFFFAOYSA-N
Chemical Structure
CAS 4426-21-5 DIPHENYLBORINIC ANHYDRIDE

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Reference Reading


1.Activation of transient receptor potential vanilloid 3 channel suppresses adipogenesis.
Cheung SY1, Huang Y, Kwan HY, Chung HY, Yao X. Endocrinology. 2015 Jun;156(6):2074-86. doi: 10.1210/en.2014-1831. Epub 2015 Mar 16.
The present study shows that activation of the transient receptor potential vanilloid 3 channel (TRPV3) suppresses adipocyte differentiation. We also found that a major functional catechin compound in green tea and cocoa, (-)-epicatechin, exerts antiadipogenic effects in the adipocytes through direct activation of TRPV3. TRPV3 was detected in the 3T3-L1 adipocytes using immunohistochemistry and semiquantitative PCR. TRPV3 activation by activators (-)-epicatechin and diphenylborinic anhydride was determined using live cell fluorescent Ca(2+) imaging and patch-clamp electrophysiology. Using RNA interference, immunoblotting, and Oil red O staining, we found that the TRPV3 agonists prevented adipogenesis by inhibiting the phosphorylation of insulin receptor substrate 1, the downstream phosphoinositide 3-kinase/Akt/forkhead box protein O1 axis, and the expression of the adipogenic genes peroxisome proliferator-activated receptor γ and CCAAT/enhancer-binding protein α.
2.2-Aminoethoxydiphenyl borate blocks electrical coupling and inhibits voltage-gated K+ channels in guinea pig arteriole cells.
Ma KT1, Guan BC, Yang YQ, Nuttall AL, Jiang ZG. Am J Physiol Heart Circ Physiol. 2011 Jan;300(1):H335-46. doi: 10.1152/ajpheart.00737.2010. Epub 2010 Oct 29.
2-Aminoethoxydiphenyl borate (2-APB) analogs are potentially better vascular gap junction blockers than others widely used, but they remain to be characterized. Using whole cell and intracellular recording techniques, we studied the actions of 2-APB and its potent analog diphenylborinic anhydride (DPBA) on vascular smooth muscle cells (VSMCs) and endothelial cells in situ of or dissociated from arteriolar segments of the cochlear spiral modiolar artery, brain artery, and mesenteric artery. We found that both 2-APB and DPBA reversibly suppressed the input conductance (G(input)) of in situ VSMCs (IC(50) ≈ 4-8 μM). Complete electrical isolation of the recorded VSMC was achieved at 100 μM. A similar gap junction blockade was observed in endothelial cell tubules of the spiral modiolar artery. Similar to the action of 18β-glycyrrhetinic acid (18β-GA), 2-APB and DPBA depolarized VSMCs. In dissociated VSMCs, 2-APB and DPBA inhibited the delayed rectifier K(+) current (I(K)) with an IC(50) of ∼120 μM in the three vessels but with no significant effect on G(input) or the current-voltage relation between -140 and -40 mV.
3.The effects of 2-aminoethoxydiphenyl borate and diphenylboronic anhydride on gap junctions composed of Connexin43 in TM₄ sertoli cells.
Yang Y1, Cao MH, Wang Q, Yuan DD, Li L, Tao L. Biol Pharm Bull. 2011;34(9):1390-7.
2-Aminoethoxydiphenyl borate (2-APB) has recently been demonstrated to inhibit gap junction (GJ) channels, whereas the underlying mechanisms are still unknown. Using mouse TM₄ Sertoli cell which expresses connexin43 (Cx43), we explored the effects of 2-APB and its analogues on dye-coupling through junctional channels formed by Cx43 and on expression of Cx43. Exposure of the cells to 2-APB (1-50 µM) and one of its analogues diphenylboronic anhydride (DPBA) (1-30 µM) for 4 h leads to a significant decrease in dye coupling of GJ in a concentration-dependent manner. The inhibitory effects of 2-APB and DPBA are reversible since decreased GJ coupling resumes after the two compounds are washed out. The disfunction of GJ induced by 2-APB and DPBA is associated with a decrease in total amount of Cx43 protein and number of GJs on the cell membrane. 2-APB and DPBA do not alter Cx43 phosphorylation state and the level of Cx43 mRNA expression. The loss of Cx43 protein is prevented by either lysosomal or proteasomal inhibitor, suggesting that the decrease in Cx43 results from a 2-APB or DPBA-enhanced degradation of Cx43.
4.Separation and determination of alpha-amino acids by boroxazolidone formation.
Strang CJ1, Henson E, Okamoto Y, Paz MA, Gallop PM. Anal Biochem. 1989 May 1;178(2):276-86.
Reaction of an alpha-amino acid (alpha-AA) with 1,1-diphenylborinic acid (DPBA) leads to the formation of a kinetically stable adduct at pH 2-5 in which both the alpha-amino and the alpha-carboxyl groups are bound to boron forming a cyclic mixed anhydride termed a boroxazolidone. In this adduct, the greater than N:B bond is coordinate, involving the free electron pair of nitrogen, thereby satisfying the octet rule for the second electron shell of boron (Group IIIA). Consequently, the alpha-amino function of the boroxazolidone can be primary, secondary, or tertiary, as demonstrated by boroxazolidone formation with glycine, N-methylglycine, and N,N-dimethylglycine. On reaction with DPBA, the alpha-AA moiety of N-terminal gamma-glutamyl peptides is also derivatized as demonstrated by the formation of a glutathione boroxazolidone. The 1,1-diphenylboroxazolidone adducts of alpha-AA may be separated by reversed-phase (RP)-HPLC (AA-DPBA/RP-HPLC) enabling the derivatization procedure to be used as a precolumn reaction for alpha-AA analysis.