Synthesis, absolute configuration and in vitro cytotoxicity of deschloroketamine enantiomers: rediscovered and abused dissociative anaesthetic
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F18%3A43916571" target="_blank" >RIV/60461373:22310/18:43916571 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22330/18:43916571 RIV/60461373:22340/18:43916571 RIV/60461373:22810/18:43916571
Result on the web
<a href="http://dx.doi.org/10.1039/c8nj03107j" target="_blank" >http://dx.doi.org/10.1039/c8nj03107j</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c8nj03107j" target="_blank" >10.1039/c8nj03107j</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis, absolute configuration and in vitro cytotoxicity of deschloroketamine enantiomers: rediscovered and abused dissociative anaesthetic
Original language description
In this study, we aim to determine differences in cytotoxicity of racemic deschloroketamine and its enantiomers. The synthesized racemate of this recently rediscovered and abused dissociative anaesthetic was resolved by chiral HPLC and the absolute configuration of the enantiomers was assigned using a combination of circular dichroism methods and single-crystal X-ray. Not only the absolute configuration, but also the most preferred conformers present in the crystal were successfully determined by electron and vibrational circular dichroism supported by ab initio calculations, and confirmed by X-ray. The in vitro cytotoxicity of racemic deschloroketamine and its enantiomers was determined for nine different types of cell lines. Generally, (S)-deschloroketamine exhibited higher cytotoxicity in the majority of cases. For human embryonic kidney cells (HEK 293T), the (S)-enantiomer reached the IC50 below 1 mM concentration and, in consequence, proved to be twice as potent as the (R)-enantiomer. On the other hand, live-cell fluorescence microscopy imaging at sub-IC50 concentrations provided evidence for only a minor effect of deschloroketamine racemate and enantiomers on endoplasmic reticulum stress and mitochondria morphology in neuroblastoma cells SH-SY5Y. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GJ16-17689Y" target="_blank" >GJ16-17689Y: Novel chiral ion exchange-type stationary phases for enantiomer separation</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
New Journal of Chemistry
ISSN
1144-0546
e-ISSN
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Volume of the periodical
42
Issue of the periodical within the volume
24
Country of publishing house
GB - UNITED KINGDOM
Number of pages
9
Pages from-to
19360-19368
UT code for WoS article
000456501100006
EID of the result in the Scopus database
2-s2.0-85057715599