Neuronal nicotinic acetylcholine receptor binding affinities of boron-containing nicotine analogues

Rui Xu, Linda P. Dwoskin, Vladimir P. Grinevich, Gabriela Deaciuc, Peter A. Crooks

Research output: Contribution to journalArticlepeer-review

26 Scopus citations


A series of boron-containing nicotine (NIC) analogues 7-9 was synthesized and evaluated for binding to α4β2 and α7 nicotinic receptors. Compound ACME-B inhibited [3H]methyllycaconitine binding to rat brain membranes with a similar potency compared to NIC (Ki=2.4 and 0.77 μM, respectively), but was markedly less potent in inhibiting [3H]NIC binding when compared to NIC (Ki=0.60 μM and 1.0 nM, respectively). Thus, tethering a two-carbon bridge between the 2-pyridyl and 3′-pyrrolidino carbons of NIC or 7 affords analogues that bind to the α7 receptor in a manner similar to NIC, but with a dramatic loss of affinity for the α4β2 receptor.

Original languageEnglish
Pages (from-to)1245-1248
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Issue number9
StatePublished - May 7 2001

Bibliographical note

Funding Information:
This work was supported by grants from the National Institute on Drug Abuse (DA10394 and DA00399) and Layton Bioscience, Inc.

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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