Reaction #324374

ord-85a0f7713e78471f8f2b54ff219b3f42

Reaction equation

CC(=O)SCC[N+](C)(C)C.[I-]
Acetylthiocholine iodide
C=CC[N+](C)(C)c1ccc(CCC(=O)CCc2ccc([N+](C)(C)CC=C)cc2)cc1
BW284c51
O[C@H](CS)[C@H](O)CS
dithiothreitol
Cl.Nc1c2c(nc3ccccc13)CCCC2.O
tacrine
C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C
decamethonium
CC[N+](C)(C)c1cccc(O)c1
edrophonium
C/C=C1/[C@H]2C=C(C)C[C@]1(N)c1ccc(=O)[nH]c1C2
(−)huperzine A
O=C(O)c1cc(SSc2ccc([N+](=O)[O-])c(C(=O)O)c2)ccc1[N+](=O)[O-]
5,5′-dithiobis(2-nitrobenzoic acid)
C[N+](C)(C)c1cccc(C(=O)CC(F)(F)F)c1
m-(N,N,N-trimethylammonio)trifluoromethylacetophenone
→
C=CC(=O)c1ccc2cc(N(C)C)ccc2c1
Acrylodan

Reactants

CC(=O)SCC[N+](C)(C)C.[I-]
Acetylthiocholine iodide
C=CC[N+](C)(C)c1ccc(CCC(=O)CCc2ccc([N+](C)(C)CC=C)cc2)cc1
BW284c51
O[C@H](CS)[C@H](O)CS
dithiothreitol
Cl.Nc1c2c(nc3ccccc13)CCCC2.O
tacrine
C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C
decamethonium
CC[N+](C)(C)c1cccc(O)c1
edrophonium
C/C=C1/[C@H]2C=C(C)C[C@]1(N)c1ccc(=O)[nH]c1C2
(−)huperzine A
O=C(O)c1cc(SSc2ccc([N+](=O)[O-])c(C(=O)O)c2)ccc1[N+](=O)[O-]
5,5′-dithiobis(2-nitrobenzoic acid)
C[N+](C)(C)c1cccc(C(=O)CC(F)(F)F)c1
m-(N,N,N-trimethylammonio)trifluoromethylacetophenone

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Inhibitors and Substrates-Acetylthiocholine iodide, 5,5′-dithiobis(2-nitrobenzoic acid) (Ellman's reagent), dithiothreitol, tacrine (9-amino-1,2,3,4-tetrahydroacridine hydrochloride hydrate), BW284c51, decamethonium, and edrophonium were purchased from Sigma. m-(N,N,N-trimethylammonio)trifluoromethylacetophenone (TFK+) and (−)huperzine A were purchased from Calbiochem. Acrylodan was obtained from Molecular Probes (Eugene, Oreg.). Fasciculin 2 (purified from the venom of Dendroaspis angusticeps) was a gift of Dr. Pascale Marchot (University of Marseille, France). Drs. Yacov Ashani and Bhupendra P. Doctor (Walter Reed Army Research Center, Washington, D.C.) kindly provided 7-((methylethoxy) phosphinyl)-oxyl)-1-methylquinolinium iodide (MEPQ) and procainamide-linked Sepharose CL-4B resin. m-tert-Butyl trifluoromethylacetophenone (TFK+) was synthesized as described (21) and kindly provided by Dr. Daniel Quinn, University of Iowa, Iowa City, Iowa. All other chemicals were of the highest grade commercially available.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08642273B2uspto-grants-2014_02