Next Article in Journal
Previous Article in Journal
Int. J. Mol. Sci. 2013, 14(5), 9873-9882; doi:10.3390/ijms14059873
Article

Caffeine Inhibits Acetylcholinesterase, But Not Butyrylcholinesterase

1,*  and 2
Received: 4 April 2013; in revised form: 29 April 2013 / Accepted: 30 April 2013 / Published: 8 May 2013
(This article belongs to the Section Molecular Toxicology)
View Full-Text   |   Download PDF [327 KB, uploaded 19 June 2014]
Abstract: Caffeine is an alkaloid with a stimulant effect in the body. It can interfere in transmissions based on acetylcholine, epinephrine, norepinephrine, serotonin, dopamine and glutamate. Clinical studies indicate that it can be involved in the slowing of Alzheimer disease pathology and some other effects. The effects are not well understood. In the present work, we focused on the question whether caffeine can inhibit acetylcholinesterase (AChE) and/or, butyrylcholinesterase (BChE), the two enzymes participating in cholinergic neurotransmission. A standard Ellman test with human AChE and BChE was done for altering concentrations of caffeine. The test was supported by an in silico examination as well. Donepezil and tacrine were used as standards. In compliance with Dixon’s plot, caffeine was proved to be a non-competitive inhibitor of AChE and BChE. However, inhibition of BChE was quite weak, as the inhibition constant, Ki, was 13.9 ± 7.4 mol/L. Inhibition of AChE was more relevant, as Ki was found to be 175 ± 9 µmol/L. The predicted free energy of binding was −6.7 kcal/mol. The proposed binding orientation of caffeine can interact with Trp86, and it can be stabilize by Tyr337 in comparison to the smaller Ala328 in the case of human BChE; thus, it can explain the lower binding affinity of caffeine for BChE with reference to AChE. The biological relevance of the findings is discussed.
Keywords: acetylcholinesterase; butyrylcholinesterase; caffeine; Alzheimer disease; myasthenia gravis; acetylcholine; inhibition; coffee; alkaloid; chocolate acetylcholinesterase; butyrylcholinesterase; caffeine; Alzheimer disease; myasthenia gravis; acetylcholine; inhibition; coffee; alkaloid; chocolate
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


MDPI and ACS Style

Pohanka, M.; Dobes, P. Caffeine Inhibits Acetylcholinesterase, But Not Butyrylcholinesterase. Int. J. Mol. Sci. 2013, 14, 9873-9882.

AMA Style

Pohanka M, Dobes P. Caffeine Inhibits Acetylcholinesterase, But Not Butyrylcholinesterase. International Journal of Molecular Sciences. 2013; 14(5):9873-9882.

Chicago/Turabian Style

Pohanka, Miroslav; Dobes, Petr. 2013. "Caffeine Inhibits Acetylcholinesterase, But Not Butyrylcholinesterase." Int. J. Mol. Sci. 14, no. 5: 9873-9882.


Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert