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2-Aminoethoxydiphenyl borate

From Wikipedia, the free encyclopedia
2-Aminoethoxydiphenyl borate
2-APB molecule
Names
Preferred IUPAC name
2-[(Diphenylboranyl)oxy]ethan-1-amine
Other names
2-Aminoethyl diphenyl borate
Diphenylborinic acid 2-aminoethyl ester
2-Aminoethyl diphenylborinate
Identifiers
3D model (JSmol)
Abbreviations2-APB
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.007.607Edit this at Wikidata
EC Number
  • 208-366-5
KEGG
UNII
  • 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 checkY
    Key: BLZVCIGGICSWIG-UHFFFAOYSA-N checkY
  • 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 mass225.10 g·mol−1
Appearancewhite
Density1.04g/cm3
Melting point192 to 194 °C (378 to 381 °F; 465 to 467 K)
Boiling point325.3 °C (617.5 °F; 598.5 K) at 760mmHg
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302,H315,H319,H335
P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P312,P321,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
Flash point150.6 °C (303.1 °F; 423.8 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

2-Aminoethoxydiphenyl borate (2-APB) is a chemical that acts to inhibit bothIP3 receptors[1] andTRP channels (although it activatesTRPV1,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 the lack of specific effects make it less than ideal under some circumstances. Additionally, there is evidence that 2-APB acts directly to inhibitgap junctions made of connexin.[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

[edit]
  1. ^Diver, J. M.; Sage, S. O.; Rosado, J. A. (2001-11-01). "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.doi:10.1054/ceca.2001.0239.ISSN 0143-4160.PMID 11733938.
  2. ^Xu, Shang-Zhong; Zeng, Fanning; Boulay, Guylain; Grimm, Christian; Harteneck, Christian; Beech, David J. (2005-06-01)."Block of TRPC5 channels by 2-aminoethoxydiphenyl borate: a differential, extracellular and voltage-dependent effect".British Journal of Pharmacology.145 (4):405–414.doi:10.1038/sj.bjp.0706197.ISSN 0007-1188.PMC 1576154.PMID 15806115.
  3. ^Bootman, Martin D.; Collins, Tony J.; Mackenzie, Lauren; Roderick, H. Llewelyn; Berridge, Michael J.; Peppiatt, Claire M. (2002-08-01)."2-aminoethoxydiphenyl borate (2-APB) is a reliable blocker of store-operated Ca2+ entry but an inconsistent inhibitor of InsP3-induced Ca2+ release".FASEB Journal.16 (10):1145–1150.doi:10.1096/fj.02-0037rev.ISSN 1530-6860.PMID 12153982.S2CID 43766251.
  4. ^Bai, Donglin; del Corsso, Cristiane; Srinivas, Miduturu; Spray, David C. (2006-12-01). "Block of specific gap junction channel subtypes by 2-aminoethoxydiphenyl borate (2-APB)".The Journal of Pharmacology and Experimental Therapeutics.319 (3):1452–1458.doi:10.1124/jpet.106.112045.ISSN 0022-3565.PMID 16985167.S2CID 2375567.
  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.
TRPA
Activators
Blockers
TRPC
Activators
Blockers
TRPM
Activators
Blockers
TRPML
Activators
Blockers
TRPP
Activators
Blockers
TRPV
Activators
Blockers
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