Chemistry:BQ-123

From HandWiki
BQ-123[1]
BQ-123 structure.svg
Names
IUPAC name
2-[(3R,6R,9S,12R,15S)-6-(1H-indol-3-ylmethyl)-9-(2-methylpropyl)-2,5,8,11,14-pentaoxo-12-propan-2-yl-1,4,7,10,13-pentazabicyclo[13.3.0]octadecan-3-yl]acetic acid
Other names
Cyclo(D-trp-D-asp-L-pro-D-val-L-leu)
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
Properties
C31H42N6O7
Molar mass 610.712 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references

BQ-123, also known as cyclo(-D-Trp-D-Asp-Pro-D-Val-Leu-), is a cyclic pentapeptide that was first isolated from a fermentation broth of Streptomyces misakiensis in 1991.[2] NMR studies indicate that the polypeptide backbone consists of a type II beta turn and an inverse gamma turn.[3][4] The side-chains adopt different orientations depending on the solvent used.[5][6] The proline carbonyl oxygen atom located at the onset of a beta turn is a sodium ion binding site.[7] It has a high affinity for sodium ions and can coordinate up to three of them.[8] Studies have shown that BQ123 is effective in reversing Ischemia-induced acute renal failure, and it has been suggested that this might be because BQ123 increases reabsorption of sodium ions in the proximal tubule cells.[9][10][11][12][13]

BQ-123 is a selective ETA endothelin receptor antagonist.[1][14] As such, it is used as a biochemical tool in the study of endothelin receptor function. BQ-123 works as an ET-1 antagonist by reversing already established contractions to ET-1. This indicates that BQ-123 can work as an antagonist to remove ET-1 from its receptor (ETA).[15]

References

  1. ↑ 1.0 1.1 BQ-123 at Sigma-Aldrich
  2. ↑ "An endothelin receptor (ETA) antagonist isolated from Streptomyces misakiensis". Biochemical and Biophysical Research Communications 178 (1): 132–7. July 1991. doi:10.1016/0006-291X(91)91789-F. PMID 1648907. 
  3. ↑ "Conformational study of cyclo[D-Trp-D-Asp-Pro-D-Val-Leu], an endothelin-A receptor-selective antagonist". FEBS Letters 296 (1): 1–6. January 1992. doi:10.1016/0014-5793(92)80390-3. PMID 1309703. 
  4. ↑ "Solution conformation of a cyclic pentapeptide endothelin antagonist. Comparison of structures obtained from constrained dynamics and conformational search". FEBS Letters 299 (3): 255–61. March 1992. doi:10.1016/0014-5793(92)80127-3. PMID 1544503. 
  5. ↑ "Solvent effects on the conformation of cyclo(-D-Trp-D-Asp-Pro-D-Val-Leu-). An NMR spectroscopy and molecular modeling study". International Journal of Peptide and Protein Research 43 (5): 454–62. May 1994. doi:10.1111/j.1399-3011.1994.tb00544.x. PMID 8070969. 
  6. ↑ "Conformations of cyclic pentapeptide endothelin receptor antagonists". International Journal of Peptide and Protein Research 44 (3): 223–32. September 1994. doi:10.1111/j.1399-3011.1994.tb00164.x. PMID 7822098. 
  7. ↑ "Location of alkali metal binding sites in endothelin A selective receptor antagonists, cyclo(D-Trp-D-Asp-Pro-D-Val-Leu) and cyclo(D-Trp-D-Asp-Pro-D-Ile-Leu), from multistep collisionally activated decompositions". Journal of Mass Spectrometry 35 (2): 265–76. February 2000. doi:10.1002/(SICI)1096-9888(200002)35:2<265::AID-JMS946>3.0.CO;2-#. PMID 10679990. Bibcode: 2000JMSp...35..265N. 
  8. ↑ "Novel sodium binding properties of some cyclopentapeptide endothelin A selective receptor antagonists: electrospray and fast-atom-bombardment mass spectrometric studies". Biochemical and Biophysical Research Communications 254 (3): 713–9. January 1999. doi:10.1006/bbrc.1998.9772. PMID 9920807. 
  9. ↑ "BQ-123, a specific endothelin (ETA) receptor antagonist, prevents ischemia-reperfusion injury in kidney transplantation". Transplant International 9 (3): 201–7. 1996. doi:10.1007/BF00335386. PMID 8723187. 
  10. ↑ "BQ-123, a peptidic endothelin ETA receptor antagonist, prevents the early cerebral vasospasm following subarachnoid hemorrhage after intracisternal but not intravenous injection". Life Sciences 52 (9): 825–34. 1993. doi:10.1016/0024-3205(93)90081-d. PMID 8437512. 
  11. ↑ "Role of endothelin receptor subtypes in the in vivo regulation of renal function". The American Journal of Physiology 268 (3 Pt 2): F455-60. March 1995. doi:10.1152/ajprenal.1995.268.3.F455. PMID 7900845. 
  12. ↑ "Reversal of postischemic acute renal failure with a selective endothelinA receptor antagonist in the rat". The Journal of Clinical Investigation 93 (2): 900–6. February 1994. doi:10.1172/JCI117046. PMID 8113422. 
  13. ↑ "Protective effect of a selective endothelin receptor antagonist, BQ-123, in ischemic acute renal failure in rats". European Journal of Pharmacology 221 (1): 77–83. October 1992. doi:10.1016/0014-2999(92)90774-x. PMID 1459192. 
  14. ↑ "Cyclic pentapeptide endothelin antagonists with high ETA selectivity. Potency- and solubility-enhancing modifications". Journal of Medicinal Chemistry 35 (11): 2139–42. May 1992. doi:10.1021/jm00089a028. PMID 1317926. 
  15. ↑ "Dose- and time-dependency of the dilator effects of the endothelin antagonist, BQ-123, in the human forearm". British Journal of Clinical Pharmacology 44 (6): 569–71. December 1997. doi:10.1046/j.1365-2125.1997.t01-1-00631.x. PMID 9431833. 




Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:BQ-123&oldid=2480880"