Mannich-type modifications of (−)-cannabidiol and (−)-cannabigerol leading to new, bioactive derivatives
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F23%3A00578610" target="_blank" >RIV/61388963:_____/23:00578610 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1038/s41598-023-45565-7" target="_blank" >https://doi.org/10.1038/s41598-023-45565-7</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1038/s41598-023-45565-7" target="_blank" >10.1038/s41598-023-45565-7</a>
Alternative languages
Result language
angličtina
Original language name
Mannich-type modifications of (−)-cannabidiol and (−)-cannabigerol leading to new, bioactive derivatives
Original language description
(−)-Cannabidiol (CBD) and (−)-cannabigerol (CBG) are two major non-psychotropic phytocannabinoids that have many beneficial biological properties. However, due to their low water solubility and prominent first-pass metabolism, their oral bioavailability is moderate, which is unfavorable for medicinal use. Therefore, there is a great need for appropriate chemical modifications to improve their physicochemical and biological properties. In this study, Mannich-type reaction was used for the synthetic modification of CBD and CBG for the first time, and thus fifteen new cannabinoid derivatives containing one or two tertiary amino groups were prepared. Thereafter the antiviral, antiproliferative and antibacterial properties of the derivatives and their effects on certain skin cells were investigated. Some modified CBD derivatives showed remarkable antiviral activity against SARS-CoV-2 without cytotoxic effect, while synthetic modifications on CBG resulted in a significant increase in antiproliferative activity in some cases compared to the parent compound.
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
10607 - Virology
Result continuities
Project
<a href="/en/project/LX22NPO5103" target="_blank" >LX22NPO5103: National Institute of Virology and Bacteriology</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Scientific Reports
ISSN
2045-2322
e-ISSN
2045-2322
Volume of the periodical
13
Issue of the periodical within the volume
November
Country of publishing house
US - UNITED STATES
Number of pages
20
Pages from-to
19618
UT code for WoS article
001136497000014
EID of the result in the Scopus database
2-s2.0-85176264342