World Library  
My Account |  Register |  Help  
  
Flag as Inappropriate
Email this Article

Desformylflustrabromine

Article Id: WHEBN0012761009
Reproduction Date:

Title: Desformylflustrabromine  
Author: World Heritage Encyclopedia
Language: English
Subject: Alpha-4 beta-2 nicotinic receptor, 5-Bromo-DMT, Aeruginascin, Alkenes, 5-MeO-2-TMT
Collection: Alkenes, Metabolism, Nicotinic Agonists, Organobromides, Tryptamines
Publisher: World Heritage Encyclopedia
Publication
Date:
 

Desformylflustrabromine

Desformylflustrabromine
Systematic (IUPAC) name
2-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine
Clinical data
Legal status
?
Identifiers
CAS number  YesY
ATC code None
PubChem
ChemSpider  N
Chemical data
Formula C16H21BrN2 
Mol. mass 321.254 g/mol
 N   

Desformylflustrabromine (dFBr) is a tryptamine derivative which was first isolated as an active metabolite of the marine bryozoan Flustra foliacea.[1]

Bioactivity

dFBr has been identified as a novel positive allosteric modulator of neuronal nicotinic acetylcholine receptor with sub-type specificity for heteromeric receptor with no effect on homomeric sub-type.[2] A recent study has been published which describes the synthesis of water-soluble salts of dFBr and its action has been confirmed as selective potentiator of α4β2 nicotinic acetylcholine receptor responses by using two-electrode voltage clamp whole cell recordings.[3] In the year 2002 it was reported that dFBr was cytotoxic on human colon cancer cell line HCT-116.[4] Desformylflustrabromine has also been found to be a positive allosteric modulator for the α2β2 subtype of neuronal nicotinic acetylcholine receptor. Additionally it relieves the inhibition of both α2β2 and α4β2 Nicotinic Acetylcholine Receptors by β-Amyloid (1–42) Peptide.[5] Thus Desformylflustrabromine can potentially be used in the treatment of Alzheimer’s disease. Many of the deconstructed analogs of dFBr are reported to have a potentiating effect on the α4β2 receptors.[6]

References

  1. ^ Peters, Lars; Wright, Anthony D.; Kehraus, Stefan; Gündisch, Daniela; Tilotta, M. C.; König, Gabriele M. (October 2004). "Prenylated indole alkaloids from Flustra foliacea with subtype specific binding on NAChRs". Planta Med. 70 (10): 883–6.  
  2. ^ Sala, Francisco; Mulet, José; Reddy, Krishna P.; Bernal, José Antonio; Wikman, Philip; Valor, Luis Miguel; Peters, Lars; König, Gabriele M.; Criado, Manuel (January 2005). "Potentiation of human alpha4beta2 neuronal nicotinic receptors by a Flustra foliacea metabolite". Neurosci. Lett. 373 (2): 144–9.  
  3. ^ Kim, Jin-Sung; Padnya, Anshul; Weltzin, Maegan; Edmonds, Brian W.; Schulte, Marvin K.; Glennon, Richard A. (Sep 2007). "Synthesis of desformylflustrabromine and its evaluation as an alpha4beta2 and alpha7 nACh receptor modulator". Bioorganic and Medicinal Chemistry Letters 17 (17): 4855–60.  
  4. ^ Lysek, N; Rachor, E; Lindel, T (2002). "Isolation and structure elucidation of deformylflustrabromine from the North Sea bryozoan Flustra foliacea". Z. Naturforsch., C, J. Biosci. 57 (11–12): 1056–61.  
  5. ^ Pandya, Anshul; Yakel, Jerrel L. (September 2011). "Allosteric modulator Desformylflustrabromine relieves the inhibition of α2β2 and α4β2 nicotinic acetylcholine receptors by β-amyloid(1-42) peptide". J. Mol. Neurosci. 45 (1): 42–7.  
  6. ^ German, Nadezhda; Kim, Jin-Sung; Jain, Atul; Dukat, Malgorzata; Pandya, Anshul; Ma, Yilong; Weltzin, Maegan; Schulte, Marvin K.; Glennon, Richard A. (October 2011). "Deconstruction of the α4β2 nicotinic acetylcholine receptor positive allosteric modulator desformylflustrabromine". J. Med. Chem. 54 (20): 7259–67.  


This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.
 


Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.