Synthesis and in vitro Anti‐Inflammatory Activity of Novel Dendrobine Amide/Sulfonamide Derivatives

• Published in: Chemistry & biodiversity 2024-05, Vol.21 (5), p.e202400030-n/a
• Main Authors: Jiao, Zi‐Wei, Liu, Han‐Fei, Lin, Kai‐Qin, Xie, Guang‐Tong, Lou, Hua‐Yong, Pan, Wei‐Dong, Zhang, Mao‐Sheng
• Format: Article
• Language: English
• Subjects: Amide/sulfonamide; Amides - chemical synthesis; Amides - chemistry; Amides - pharmacology; Animals; Anti-inflammatory; Anti-inflammatory agents; Anti-Inflammatory Agents - chemical synthesis; Anti-Inflammatory Agents - chemistry; Anti-Inflammatory Agents - pharmacology; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis; Anti-Inflammatory Agents, Non-Steroidal - chemistry; Anti-Inflammatory Agents, Non-Steroidal - pharmacology; Cyclooxygenase 2 - metabolism; Dendrobine; Dose-Response Relationship, Drug; Herbal medicine; Inflammation; Lipopolysaccharides; Lipopolysaccharides - antagonists & inhibitors; Lipopolysaccharides - pharmacology; Mice; Molecular docking; Molecular Docking Simulation; Molecular Structure; Natural products; Nitric oxide; Nitric Oxide - antagonists & inhibitors; Nitric Oxide - biosynthesis; Nitric Oxide - metabolism; Nitric Oxide Synthase Type II - antagonists & inhibitors; Nitric Oxide Synthase Type II - metabolism; Nitric-oxide synthase; Prostaglandin endoperoxide synthase; RAW 264.7 Cells; Structural modification; Structure-Activity Relationship; Sulfonamides; Sulfonamides - chemical synthesis; Sulfonamides - chemistry; Sulfonamides - pharmacology; Traditional Chinese medicine
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.202400030

A traditional Chinese medicine ingredient, dendrobine, has been demonstrated to have anti‐inflammatory properties. However, due to its poor anti‐inflammatory properties, its clinical use is limited. Consequently, we have designed and synthesized 32 new amide/sulfonamide dendrobine derivatives and screened their anti‐inflammatory activities in vitro. Experiments showed that nitric oxide (NO) generation in lipopolysaccharide (LPS)‐induced RAW264.7 cells was strongly reduced by derivative 14, with an IC50 of 2.96 μM. Western blot research revealed that 14 decreased the concentration‐dependent expression of cyclooxygenase‐2 (COX‐2) and inducible nitric oxide synthase (INOS). Molecular docking was used to predict the binding of the inflammation‐associated proteins COX‐2 and INOS to compound 14.