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...
Elmentve itt :
| Szerzők: | |
|---|---|
| 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 |
| LEADER | 02444nab a2200409 i 4500 | ||
|---|---|---|---|
| 001 | publ29100 | ||
| 005 | 20231215104052.0 | ||
| 008 | 231215s2023 hu o 0|| Angol d | ||
| 022 | |a 2045-2322 | ||
| 024 | 7 | |a 10.1038/s41598-023-45565-7 |2 doi | |
| 024 | 7 | |a 34316518 |2 mtmt | |
| 040 | |a SZTE Publicatio Repozitórium |b hun | ||
| 041 | |a Angol | ||
| 100 | 1 | |a Lőrincz Eszter Boglárka | |
| 245 | 1 | 0 | |a Mannich-type modifications of (−)-cannabidiol and (−)-cannabigerol leading to new, bioactive derivatives |h [elektronikus dokumentum] / |c Lőrincz Eszter Boglárka |
| 260 | |c 2023 | ||
| 300 | |a 20 | ||
| 490 | 0 | |a SCIENTIFIC REPORTS |v 13 No. 1 | |
| 520 | 3 | |a (−)-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. | |
| 650 | 4 | |a Farmakológia és gyógyszerészet | |
| 700 | 0 | 1 | |a Tóth Gergely |e aut |
| 700 | 0 | 1 | |a Spolárics Júlia |e aut |
| 700 | 0 | 1 | |a Herczeg Mihály |e aut |
| 700 | 0 | 1 | |a Hodek Jan |e aut |
| 700 | 0 | 1 | |a Zupkó István |e aut |
| 700 | 0 | 1 | |a Minorics Renáta |e aut |
| 700 | 0 | 1 | |a Ádám Dorottya |e aut |
| 700 | 0 | 1 | |a Oláh Attila |e aut |
| 700 | 0 | 1 | |a Zouboulis Christos C. |e aut |
| 700 | 0 | 1 | |a Weber Jan |e aut |
| 700 | 0 | 1 | |a Nagy Lajos |e aut |
| 700 | 0 | 1 | |a Ostorházi Eszter |e aut |
| 700 | 0 | 1 | |a Bácskay Ildikó |e aut |
| 700 | 0 | 1 | |a Borbás Anikó |e aut |
| 700 | 0 | 1 | |a Herczegh Pál |e aut |
| 700 | 0 | 2 | |a Bakai-Bereczki Ilona |e aut |
| 856 | 4 | 0 | |u http://publicatio.bibl.u-szeged.hu/29100/1/s41598-023-45565-7.pdf |z Dokumentum-elérés |