Mannich-type modifications of (−)-cannabidiol and (−)-cannabigerol leading to new, bioactive derivatives

(−)-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 medicina...

Teljes leírás

Elmentve itt :
Bibliográfiai részletek
Szerzők: Lőrincz Eszter Boglárka
Tóth Gergely
Spolárics Júlia
Herczeg Mihály
Hodek Jan
Zupkó István
Minorics Renáta
Ádám Dorottya
Oláh Attila
Zouboulis Christos C.
Weber Jan
Nagy Lajos
Ostorházi Eszter
Bácskay Ildikó
Borbás Anikó
Herczegh Pál
Bakai-Bereczki Ilona
Dokumentumtípus: Cikk
Megjelent: 2023
Sorozat:SCIENTIFIC REPORTS 13 No. 1
Tárgyszavak:
doi:10.1038/s41598-023-45565-7

mtmt:34316518
Online Access:http://publicatio.bibl.u-szeged.hu/29100
Leíró adatok
Tartalmi kivonat:(−)-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.
Terjedelem/Fizikai jellemzők:20
ISSN:2045-2322