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    Nicotine Inhibits Amyloid Formation by the β-Peptide†
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    Department of Chemistry and Department of Neurology, School of Medicine, Case Western Reserve University, Cleveland, Ohio 44106
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    Biochemistry

    Cite this: Biochemistry 1996, 35, 42, 13568–13578
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    https://doi.org/10.1021/bi9617264
    Published October 22, 1996
    Copyright © 1996 American Chemical Society
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    Abstract

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    The 42-residue β-(1−42) peptide is the major protein component of amyloid plaque cores in Alzheimer's disease. In aqueous solution at physiological pH, the synthetic β-(1−42) peptide readily aggregates and precipitates as oligomeric β-sheet structures, a process that occurs during amyloid formation in Alzheimer's disease. Using circular dichroism (CD) and ultraviolet spectroscopic techniques, we show that nicotine, a major component in cigarette smoke, inhibits amyloid formation by the β-(1−42) peptide. The related compound cotinine, the major metabolite of nicotine in humans, also slows down amyloid formation, but to a lesser extent than nicotine. In contrast, control substances pyridine and N-methylpyrrolidine accelerate the aggregation process. Nuclear magnetic resonance (NMR) studies demonstrate that nicotine binds to the 1−28 peptide region when folded in an α-helical conformation. On the basis of chemical shift data, the binding primarily involves the N-CH3 and 5‘CH2 pyrrolidine moieties of nicotine and the histidine residues of the peptide. The binding is in fast exchange, as shown by single averaged NMR peaks and the lack of nuclear Overhauser enhancement data between nicotine and the peptide in two-dimensional NOESY spectra. A mechanism is proposed, whereby nicotine retards amyloidosis by preventing an α-helix → β-sheet conformational transformation that is important in the pathogenesis of Alzheimer's disease.

    Copyright © 1996 American Chemical Society

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    †

     Supported in part by Philip Morris, U.S.A. (R.P.F.), the American Health Assistance Foundation (M.G.Z.), the Suntory Institute for Bioorganic Research (M.G.Z.), and a Faculty Scholars Award, Alzheimer's Association (M.G.Z.). The 600 MHz NMR spectrometer was purchased with funds provided by the National Science Foundation, the National Institutes of Health, and the State of Ohio.

    ‡

     Department of Chemistry.

    §

     Department of Neurology, School of Medicine.

    *

     Author to whom correspondence should be addressed:  telephone, (216) 368-3706; Fax, (216) 368-3006; E-mail, [email protected].

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     Abstract published in Advance ACS Abstracts, October 1, 1996.

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    Biochemistry

    Cite this: Biochemistry 1996, 35, 42, 13568–13578
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    https://doi.org/10.1021/bi9617264
    Published October 22, 1996
    Copyright © 1996 American Chemical Society
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