2-Aminoethoxydiphenyl borate

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2-Aminoethoxydiphenyl borate
2-APB.png
2-APB molecule
Names
IUPAC name
2-Diphenylboranyloxyethanamine
Other names
2-Aminoethyl diphenyl borate
Diphenylborinic acid 2-aminoethyl ester
2-Aminoethyl diphenylborinate
Identifiers
524-95-8 N
Abbreviations 2-APB
ChEBI CHEBI:131184 N
ChEMBL ChEMBL169233 YesY
ChemSpider 1540 YesY
2433
Jmol 3D model Interactive image
Interactive image
PubChem 1598
  • 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 YesY
    Key: BLZVCIGGICSWIG-UHFFFAOYSA-N YesY
  • 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
    Key: BLZVCIGGICSWIG-UHFFFAOYAJ
  • B(C1=CC=CC=C1)(C2=CC=CC=C2)OCCN
  • O(B(c1ccccc1)c2ccccc2)CCN
Properties
C14H16BNO
Molar mass 225.10 g·mol−1
Appearance white
Density 1.04g/cm3
Melting point 192 to 194 °C (378 to 381 °F; 465 to 467 K)
Boiling point 325.3 °C (617.5 °F; 598.5 K) at 760mmHg
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

2-Aminoethoxydiphenyl borate (2-APB) is a chemical that acts to inhibit both IP3 receptors[1] and TRP channels (although it activates TRPV1, TRPV2, & TRPV3 at higher concentrations).[2][3] In research it is used to manipulate intracellular release of calcium ions (Ca2+) and modify TRP channel activity, although there its lack of specific effects make it less than ideal under some circumstances. Additionally, there is evidence that 2-APB acts directly to inhibit gap junctions made of connexin26 or connexin32.[4] Increasing evidence showed that 2-APB is a powerful modifier of store-operated calcium channels (SOC) function, low concentration of 2-APB can enhance SOC while high concentration induces a transient increase followed by complete inhibition.[5][6][7]

References

  1. ↑ Diver JM, Sage SO, Rosado JA (2001). The inositol trisphosphate receptor antagonist 2-aminoethoxydiphenylborate (2-APB) blocks Ca2+ entry channels in human platelets: cautions for its use in studying Ca2+ influx. Cell Calcium, 30(5), 323-329.
  2. ↑ Xu SZ, Zeng F, Boulay G, Grimm C, Harteneck C, Beech DJ (2005). Block of TRPC5 channels by 2-aminoethoxydiphenyl borate: a differential, extracellular and voltage-dependent effect. British Journal of Pharmacology, 145(4), 320-328.
  3. ↑ Bootman, MD, Collins, TJ, Makenzie, L, Roderick, HL, Berridge, MJ, & Peppiatt, CM (2002). 2-Aminoethoxydiphenyl borate (2-APB) is a reliable blocker of store-operated Ca2+ entry but an inconsistent inhibitor of InsP3-induced Ca2+ release. The FASEB Journal, 16(10), 1145-1150.
  4. ↑ Tao, L, & Harris, AL (2007). 2-aminoethoxydiphenyl borate directly inhibits channels composed of connexin26 and/or connexin32. Molecular Pharmacology, 71(2), 570-579.
  5. ↑ Ma HT, et al. (2000) Requirement of the inositol trisphosphate receptor for activation of store-operated Ca2+ channels. Science 287:1647–1651.
  6. ↑ Prakriya M, Lewis RS (2001) Potentiation and inhibition of Ca2+ release-activated Ca2+ channels by 2-aminoethyldiphenyl borate (2-APB) occurs independently of IP 3 receptors. J Physiol 536:3–19.
  7. ↑ Ma HT, Venkatachalam K, Parys JB, Gill DL (2002) Modification of store-operated channel coupling and inositol trisphosphate receptor function by 2-aminoethoxydiphenyl borate in DT40 lymphocytes. J Biol Chem 277:6915–6922.
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