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Synthesis and in vitro evaluation of N-substituted aza-trozamicol analogs as vesicular acetylcholine transporter ligands. 2006

Thaer Assaad, and Sylvie Mavel, and Stanley M Parsons, and Shane Kruse, and Laurent Galineau, and Hassan Allouchi, and Michael Kassiou, and Sylvie Chalon, and Denis Guilloteau, and Patrick Emond
Université François-Rabelais de Tours, 37200 Tours, France.

As dysfunction of cerebral cholinergic neurotransmission is one of the main features in patients with Alzheimer's disease, in vivo imaging of the vesicular acetylcholine transporter (VAChT) can be of great value for the early diagnosis of this disease. Two series of positional isomers of m-iodobenzyltrozamicol (MIBT): 3-hydroxy-4-(N-phenylpiperazinyl)piperidine and 4-hydroxy-3-(N-phenylpiperazinyl)piperidine substituted by benzyl, aryl, alkyl or vinyl groups at the nitrogen have been synthesized. These compounds have been evaluated in vitro by competition studies and five compounds (N-benzyl derivatives) showed high affinity for the VAChT (11nM<IC(50)<66nM). These compounds will be soon radiolabeled with [(125)I] for further biological evaluation using single photon emission computed tomography (SPECT).

UI MeSH Term Description Entries
D008024 Ligands A molecule that binds to another molecule, used especially to refer to a small molecule that binds specifically to a larger molecule, e.g., an antigen binding to an antibody, a hormone or neurotransmitter binding to a receptor, or a substrate or allosteric effector binding to an enzyme. Ligands are also molecules that donate or accept a pair of electrons to form a coordinate covalent bond with the central metal atom of a coordination complex. (From Dorland, 27th ed) Ligand
D002352 Carrier Proteins Proteins that bind or transport specific substances in the blood, within the cell, or across cell membranes. Binding Proteins,Carrier Protein,Transport Protein,Transport Proteins,Binding Protein,Protein, Carrier,Proteins, Carrier
D000109 Acetylcholine A neurotransmitter found at neuromuscular junctions, autonomic ganglia, parasympathetic effector junctions, a subset of sympathetic effector junctions, and at many sites in the central nervous system. 2-(Acetyloxy)-N,N,N-trimethylethanaminium,Acetilcolina Cusi,Acetylcholine Bromide,Acetylcholine Chloride,Acetylcholine Fluoride,Acetylcholine Hydroxide,Acetylcholine Iodide,Acetylcholine L-Tartrate,Acetylcholine Perchlorate,Acetylcholine Picrate,Acetylcholine Picrate (1:1),Acetylcholine Sulfate (1:1),Bromoacetylcholine,Chloroacetylcholine,Miochol,Acetylcholine L Tartrate,Bromide, Acetylcholine,Cusi, Acetilcolina,Fluoride, Acetylcholine,Hydroxide, Acetylcholine,Iodide, Acetylcholine,L-Tartrate, Acetylcholine,Perchlorate, Acetylcholine
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

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