4-Isobutylmethcathinone—A Novel Synthetic Cathinone with High In Vitro Cytotoxicity and Strong Receptor Binding Preference of Enantiomers
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F22%3A43925247" target="_blank" >RIV/60461373:22310/22:43925247 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22330/22:43925247 RIV/60461373:22340/22:43925247 RIV/60461373:22810/22:43925247
Result on the web
<a href="https://www.mdpi.com/1424-8247/15/12/1495" target="_blank" >https://www.mdpi.com/1424-8247/15/12/1495</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3390/ph15121495" target="_blank" >10.3390/ph15121495</a>
Alternative languages
Result language
angličtina
Original language name
4-Isobutylmethcathinone—A Novel Synthetic Cathinone with High In Vitro Cytotoxicity and Strong Receptor Binding Preference of Enantiomers
Original language description
New psychoactive substances and among them synthetic cathinones represent a significant threat to human health globally. However, within such a large pool of substances derived from a natural compound ((S)-cathinone), substances with important pharmaceutical uses can be identified, as already documented by bupropione. Therefore, this work aimed to find a synthetic pathway for a novel synthetic cathinone, namely 4-isobutylmethcathinone, and describe its spectroscopic properties and biological activity in vitro. Since cathinones comprise a chiral center in their structure, a method for chiral separation of the substance was elaborated using high-performance liquid chromatography on an analytical and preparative scale. Preparative enantioseparation on a polysaccharide column provided a sufficient amount of the drug for the chiroptical studies leading to the determination of the absolute configuration of enantiomers as well as for their subsequent in vitro cytotoxicity study. The cytotoxicity induced by 4-isobutylmethcathinone was determined in human cells derived from the urinary bladder (5637), neuroblastoma (SH-SY5Y), microglia (HMC-3), and hepatocellular carcinoma (Hep G2), in which the IC50 values after 72 h reached an 18–65 µM concentration. This is significantly higher cytotoxicity in comparison with other synthetic cathinones. In the receptor binding studies, a significant difference in the agonistic effect on dopamine and adrenergic receptors of individual enantiomers was observed. The lack of binding affinity towards the serotonin receptors then relates 4-isobutylmethcathinone to the family of monoamine drugs, such as 3,4-methylenedioxymathamphetamine (ecstasy, MDMA). © 2022 by the authors.
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
10406 - Analytical chemistry
Result continuities
Project
<a href="/en/project/GC21-31139J" target="_blank" >GC21-31139J: Novel chiral ion-exchangers for chromatographic enantioseparations</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Pharmaceuticals
ISSN
1424-8247
e-ISSN
1424-8247
Volume of the periodical
15
Issue of the periodical within the volume
12
Country of publishing house
CH - SWITZERLAND
Number of pages
17
Pages from-to
nestrankovano
UT code for WoS article
000902809200001
EID of the result in the Scopus database
2-s2.0-85144738475