Inhibition of LPS-stimulated ROS production by fluorinated and hydroxylated chalcones in RAW 264.7 macrophages with structure-activity relationship study.
Based on the importance of the previous fluorinated and/or hydroxylated chalcones studies, thirty-six compounds were designed as phenyl or hydroxyphenyl bearing fluoro, trifluoromethyl or trifluoromethoxy phenyl propenones and synthesized by applying modified Claisen-Schmidt condensation reaction as a single step. Inhibitory effects of the synthesized compounds on ROS production stimulated by LPS in RAW 264.7 macrophage were evaluated. Structure-activity relationship (SAR) study revealed that the compounds possessing para-hydroxyphenyl group combined with meta-fluoro or meta-trifluoromethyl phenyl group, and meta/para-hydroxyphenyl group combined with ortho-trifluoromethoxyphenyl group have an essential role in inhibiting the LPS-stimulated ROS production in RAW 264.7 macrophages. The most significant inhibitory effect on LPS-stimulated ROS production in RAW 264.7 macrophages was observed in compound 30 that possessed para-hydroxyphenyl group along with ortho-trifluoromethoxyphenyl group.
College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Republic of Korea.
Ganesh
G
Bist
College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Republic of Korea.
Nirmala Tilija
NT
Pun
College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Republic of Korea.
Til Bahadur Thapa
TB
Magar
College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Republic of Korea.
Aarajana
A
Shrestha
College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Republic of Korea.
Hye Jin
HJ
Oh
College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Republic of Korea.
Amrita
A
Khakurel
College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Republic of Korea. Electronic address: parkp@yu.ac.kr.
Pil-Hoon
PH
Park
College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Republic of Korea. Electronic address: eslee@yu.ac.kr.
Eung-Seok
ES
Lee
D000818:Animals; D002460:Cell Line; D047188:Chalcones / Q000737:chemistry / Q000494:pharmacology*; D005461:Fluorine / Q000737:chemistry; D006900:Hydroxylation; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors* / Q000494:pharmacology; D051379:Mice; D017382:Reactive Oxygen Species / Q000378:metabolism*; D013329:Structure-Activity Relationship
D047188:Chalcones; D008070:Lipopolysaccharides; D017382:Reactive Oxygen Species; D005461:Fluorine
Fluorinated and hydroxylated chalcones; Inhibition of LPS-stimulated ROS production; SAR study