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Desformylflustrabromine

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Title: Desformylflustrabromine  
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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
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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.  


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