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Similar Safety Profile of the Enantiomeric N-Aminoalkyl Derivatives of Trans-2-Aminocyclohexan-1-ol Demonstrating Anticonvulsant Activity

Department of Pharmaceutical Biochemistry, Faculty of Pharmacy, Jagiellonian University Medical College, 9 Medyczna Street, 30-688 Krakow, Poland
Author to whom correspondence should be addressed.
Molecules 2019, 24(13), 2505;
Received: 25 June 2019 / Revised: 7 July 2019 / Accepted: 9 July 2019 / Published: 9 July 2019
(This article belongs to the Section Medicinal Chemistry)
PDF [2844 KB, uploaded 9 July 2019]


Epilepsy is one of the most common neurological disorder in the world. Many antiepileptic drugs cause multiple adverse effects. Moreover, multidrug resistance is a serious problem in epilepsy treatment. In the present study we evaluated the safety profile of three (13) new chiral N-aminoalkyl derivatives of trans-2-aminocyclohexan-1-ol demonstrating anticonvulsant activity. Our aim was also to determine differences between the enantiomeric compounds with respect to their safety profile. The results of the study indicated that compounds 13 are non-cytotoxic for astrocytes, although they exhibit cytotoxic activity against human glioblastoma cells. Moreover, 13 did not affect the viability of HepG2 cells and did not produce adducts with glutathione. Compounds 13 demonstrated no mutagenic activity either in the Salmonella typhimurium or in Vibrio harveyi tests. Additionally, the compounds displayed a strong or moderate antimutagenic effect. Finally, the P-glycoprotein (P-gp) ATPase assay demonstrated that both enantiomers are potent P-gp inhibitors. To sum up, our results indicate that the newly synthesized derivatives may be considered promising candidates for further research on anticonvulsant drug discovery and development. Our study indicated the similar safety profile of the enantiomeric N-aminoalkyl derivatives of trans-2-aminocyclohexan-1-ol, although in the previous studies both enantiomers differ in their biotransformation pathways and pharmacological activity. View Full-Text
Keywords: aminocyclohexanol; cytotoxicity; enantiomers; epilepsy; mutagenicity; P-glycoprotein aminocyclohexanol; cytotoxicity; enantiomers; epilepsy; mutagenicity; P-glycoprotein

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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 (CC BY 4.0).

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Słoczyńska, K.; Koczurkiewicz, P.; Piska, K.; Powroźnik, B.; Wójcik-Pszczoła, K.; Klaś, K.; Wyszkowska-Kolatko, M.; Pękala, E. Similar Safety Profile of the Enantiomeric N-Aminoalkyl Derivatives of Trans-2-Aminocyclohexan-1-ol Demonstrating Anticonvulsant Activity. Molecules 2019, 24, 2505.

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