Evaluation of Nicotine and Cotinine Analogs As Potential Neuroprotective Agents for Alzheimer's Disease

Overview

Journal Bioorg Med Chem Lett

Specialty Biochemistry

Date 2014 Mar 4

PMID 24581918

Citations 26

Authors

Jie Gao

Bao-Ling Adam

Alvin V Terry Jr

Affiliations

Soon will be listed here.

Abstract

The currently available therapies for Alzheimer's disease (AD) and related forms of dementia are limited by modest efficacy, adverse side effects, and the fact that they do not prevent the relentless progression of the illness. The purpose of the studies described here was to investigate the neuroprotective effects of the nicotine metabolite cotinine as well as a small series of cotinine and nicotine analogs (including stereoisomers) and to compare their effects to the four clinically prescribed AD therapies.

Citing Articles

Former smoking, but not active smoking, is associated with delirium in postoperative ICU patients: a matched case-control study.

Komninou M, Egli S, Rossi A, Ernst J, Krauthammer M, Schuepbach R Front Psychiatry. 2024; 15:1347071.

PMID: 38559401 PMC: 10979642. DOI: 10.3389/fpsyt.2024.1347071.

Insights into Pharmacological Activities of Nicotine and 6-Hydroxy-L-nicotine, a Bacterial Nicotine Derivative: A Systematic Review.

Boiangiu R, Brinza I, Honceriu I, Mihasan M, Hritcu L Biomolecules. 2024; 14(1).

PMID: 38254623 PMC: 10813004. DOI: 10.3390/biom14010023.

The Recycling of Substandard Rocket Fuel N,N-Dimethylhydrazine via the Involvement of Its Hydrazones Derived from Glyoxal, Acrolein, Metacrolein, Crotonaldehyde, and Formaldehyde in Organic Synthesis.

Ivanova E, Osipova M, Vasilieva T, Eremkin A, Markova S, Zazhivihina E Int J Mol Sci. 2023; 24(24).

PMID: 38139025 PMC: 10742919. DOI: 10.3390/ijms242417196.

Cotinine: Pharmacologically Active Metabolite of Nicotine and Neural Mechanisms for Its Actions.

Tan X, Vrana K, Ding Z Front Behav Neurosci. 2021; 15:758252.

PMID: 34744656 PMC: 8568040. DOI: 10.3389/fnbeh.2021.758252.

Cholinergic Receptor Modulation as a Target for Preventing Dementia in Parkinson's Disease.

Iarkov A, Mendoza C, Echeverria V Front Neurosci. 2021; 15:665820.

PMID: 34616271 PMC: 8488354. DOI: 10.3389/fnins.2021.665820.

References

Anderson D, Arneric S . Nicotinic receptor binding of [3H]cytisine, [3H]nicotine and [3H]methylcarbamylcholine in rat brain. Eur J Pharmacol. 1994; 253(3):261-7. DOI: 10.1016/0014-2999(94)90200-3. View

Riveles K, Huang L, Quik M . Cigarette smoke, nicotine and cotinine protect against 6-hydroxydopamine-induced toxicity in SH-SY5Y cells. Neurotoxicology. 2008; 29(3):421-7. PMC: 2486261. DOI: 10.1016/j.neuro.2008.02.001. View

Abood L, Reynolds D, Booth H, Bidlack J . Sites and mechanisms for nicotine's action in the brain. Neurosci Biobehav Rev. 1981; 5(4):479-86. DOI: 10.1016/0149-7634(81)90018-x. View

Youdim M, Buccafusco J . CNS Targets for multi-functional drugs in the treatment of Alzheimer's and Parkinson's diseases. J Neural Transm (Vienna). 2005; 112(4):519-37. DOI: 10.1007/s00702-004-0214-z. View

Bredesen D . Neurodegeneration in Alzheimer's disease: caspases and synaptic element interdependence. Mol Neurodegener. 2009; 4:27. PMC: 2709109. DOI: 10.1186/1750-1326-4-27. View

Echeverria V, Zeitlin R, Burgess S, Patel S, Barman A, Thakur G . Cotinine reduces amyloid-β aggregation and improves memory in Alzheimer's disease mice. J Alzheimers Dis. 2011; 24(4):817-35. DOI: 10.3233/JAD-2011-102136. View

Terry Jr A, Buccafusco J, Schade R, Vandenhuerk L, Callahan P, Beck W . The nicotine metabolite, cotinine, attenuates glutamate (NMDA) antagonist-related effects on the performance of the five choice serial reaction time task (5C-SRTT) in rats. Biochem Pharmacol. 2012; 83(7):941-51. PMC: 3288613. DOI: 10.1016/j.bcp.2011.12.043. View

Hynd M, Scott H, Dodd P . Glutamate-mediated excitotoxicity and neurodegeneration in Alzheimer's disease. Neurochem Int. 2004; 45(5):583-95. DOI: 10.1016/j.neuint.2004.03.007. View

Buccafusco J . Multifunctional receptor-directed drugs for disorders of the central nervous system. Neurotherapeutics. 2008; 6(1):4-13. PMC: 5084252. DOI: 10.1016/j.nurt.2008.10.031. View

10.

Serres F, Carney S . Nicotine regulates SH-SY5Y neuroblastoma cell proliferation through the release of brain-derived neurotrophic factor. Brain Res. 2006; 1101(1):36-42. DOI: 10.1016/j.brainres.2006.05.023. View

11.

Palmer A . Neuroprotective therapeutics for Alzheimer's disease: progress and prospects. Trends Pharmacol Sci. 2011; 32(3):141-7. DOI: 10.1016/j.tips.2010.12.007. View

12.

Hatsukami D, Grillo M, Pentel P, Oncken C, Bliss R . Safety of cotinine in humans: physiologic, subjective, and cognitive effects. Pharmacol Biochem Behav. 1997; 57(4):643-50. DOI: 10.1016/s0091-3057(97)80001-9. View

13.

Terry Jr A, Hernandez C, Hohnadel E, Bouchard K, Buccafusco J . Cotinine, a neuroactive metabolite of nicotine: potential for treating disorders of impaired cognition. CNS Drug Rev. 2006; 11(3):229-52. PMC: 6741756. DOI: 10.1111/j.1527-3458.2005.tb00045.x. View

14.

Formaggio E, Fazzini F, Dalfini A, Di Chio M, Cantu C, Decimo I . Nicotine increases the expression of neurotrophin receptor tyrosine kinase receptor A in basal forebrain cholinergic neurons. Neuroscience. 2010; 166(2):580-9. DOI: 10.1016/j.neuroscience.2009.12.073. View

15.

Cavalli A, Bolognesi M, Minarini A, Rosini M, Tumiatti V, Recanatini M . Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem. 2008; 51(3):347-72. DOI: 10.1021/jm7009364. View

16.

Picciotto M, Zoli M . Neuroprotection via nAChRs: the role of nAChRs in neurodegenerative disorders such as Alzheimer's and Parkinson's disease. Front Biosci. 2007; 13:492-504. DOI: 10.2741/2695. View

17.

Vainio P, Tuominen R . Cotinine binding to nicotinic acetylcholine receptors in bovine chromaffin cell and rat brain membranes. Nicotine Tob Res. 2001; 3(2):177-82. DOI: 10.1080/14622200110043095. View

18.

Martin L, Freedman R . Schizophrenia and the alpha7 nicotinic acetylcholine receptor. Int Rev Neurobiol. 2007; 78:225-46. DOI: 10.1016/S0074-7742(06)78008-4. View

19.

Rezvani A, Levin E . Cognitive effects of nicotine. Biol Psychiatry. 2001; 49(3):258-67. DOI: 10.1016/s0006-3223(00)01094-5. View

20.

Taguchi R, Shirakawa H, Yamaguchi T, Kume T, Katsuki H, Akaike A . Nitric oxide-mediated effect of nipradilol, an alpha- and beta-adrenergic blocker, on glutamate neurotoxicity in rat cortical cultures. Eur J Pharmacol. 2006; 535(1-3):86-94. DOI: 10.1016/j.ejphar.2006.01.036. View