Application of nicotine enantiomers, derivatives and analogues in therapy of neurodegenerative disorders

Pogocki, Dariusz; Ruman, Tomasz; Danilczuk, Magdalena; Danilczuk, Marek; Celuch, Monika; Wałajtys-Rode, Elżbieta

doi:10.1016/j.ejphar.2007.02.038

Cited by 68 publications

(68 citation statements)

References 351 publications

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“…(S)-Nicotine is more physiologically potent than the (R)-enantiomer (9), and it has been speculated that from an evolutionary point of view nicotine accumulates in tobacco to deter herbivores (35). Therefore, an evolutionary selection could be operative for plants that produced the more potent form, (S)-nicotine with lower demethylation of the (S) than (R)-enantiomers being favored.…”

Section: Discussionmentioning

confidence: 99%

Enantioselective Demethylation of Nicotine as a Mechanism for Variable Nornicotine Composition in Tobacco Leaf

Cai

Siminszky

Chappell

et al. 2012

Journal of Biological Chemistry

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Background: Nornicotine composition in tobacco leaf has been a puzzle for more than half a century. Results: Three recombinant nicotine demethylases selectively use (R)-nicotine in vitro and in planta. Conclusion: Nornicotine composition in tobacco leaf can be reasonably explained by the combination of three nicotine demethylases. Significance: This knowledge lays the base for the optimization of nornicotine composition in tobacco leaf in the future.

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Section: Discussionmentioning

confidence: 99%

Enantioselective Demethylation of Nicotine as a Mechanism for Variable Nornicotine Composition in Tobacco Leaf

Cai

Siminszky

Chappell

et al. 2012

Journal of Biological Chemistry

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“…Nicotine and other similar compounds can act through both receptor mediated and non-receptor mediated mechanisms [224]. Nicotine treatment has been shown to be effective in attenuating the decline in some cognitive deficits associated with AD [225].…”

Section: Nicotine As a Potential Drugmentioning

confidence: 99%

“…Nicotine receptor stimulation can diminish A toxicity [224]; however, some studies show that nicotine directly interacts with A . It has been shown that nicotine binds to a small-sized soluble -sheet aggregate structure of monomeric A and prevents A senile plaque formation [228].…”

Section: Nicotine As a Potential Drugmentioning

confidence: 99%

Role of Environmental and Inflammatory Toxicity in Neuronal Cell Death

Somayajulu-Nitu¹,

Domazet-Damjanov²,

Matei³

et al. 2008

TOTOXIJ

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“…Many studies have examined the molecular and physiological properties of NC enantiomers [16]. Numerous studies have indicated that the pharmacological effects of (R)-NC are qualitatively similar to but quantitatively less potent than those of (S)-NC [16,17].…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of nicotine alkaloids in cigarettes by CE using sulfated β‐CD as a chiral selector and a capillary coated with amino groups

et al. 2009

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Nicotine (NC) and its related compounds (cotinine (CN), nornicotine (NN), anatabine (AT) and anabasine (AB)) were simultaneously enantioseparated by CE using a capillary with amino groups and sulfated beta-CD as a chiral selector. The optimum running conditions were found to be 30 mM acetate buffer (pH 5.0) containing 8% sulfated beta-CD with an applied voltage of +15 kV at 30 degrees C using direct detection at 260 nm. Using a capillary coated with amino groups, the EOF migrates toward the positive pole. However, when sulfated beta-CD was added to the BGE, it was found that the EOF migrated toward the negative pole due to ionic adsorption of sulfated beta-CD to amino groups on the capillary inner wall. All the cationic analytes migrated as anions, suggesting that they formed stable anionic complexes with sulfated beta-CD. With this system and a simple pretreatment with mini-cartridges, NC alkaloids in five cigarette samples were enantioseparated. As a result, each of the compounds except for CN was detected. In the case of NC, only (S)-NC was detected (more than 99.9%), but in the case of NN, AT and AB, the ratios of (S)-isomer to total isomers were in the ranges 58-70, 81-85 and 59-65%, respectively. On the other hand, only NC was detected in cigarette smoke and the ratio of (S)- and (R)-NCs was 96:4. The amounts of NC alkaloids in cigarettes suggest that the production of (R)-NC resulted from racemization due to the high temperature/burning of the cigarette.

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Application of nicotine enantiomers, derivatives and analogues in therapy of neurodegenerative disorders

Cited by 68 publications

References 351 publications

Enantioselective Demethylation of Nicotine as a Mechanism for Variable Nornicotine Composition in Tobacco Leaf

Enantioselective Demethylation of Nicotine as a Mechanism for Variable Nornicotine Composition in Tobacco Leaf

Role of Environmental and Inflammatory Toxicity in Neuronal Cell Death

Enantioseparation of nicotine alkaloids in cigarettes by CE using sulfated β‐CD as a chiral selector and a capillary coated with amino groups

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