Tags

Type your tag names separated by a space and hit enter

Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents.
Eur J Med Chem. 2005 Jan; 40(1):103-12.EJ

Abstract

In an effort to develop potent anti-inflammatory and cancer chemopreventive agents, a series of chalcones were prepared by Claisen-Schmidt condensation of appropriate acetophenones with suitable aromatic aldehyde or prepared with appropriate dihydrochalcone reacted with appropriate alkyl bromide or prepared in one-pot procedure involving acetophenone and convenient aromatic aldehyde using ultrasonic agitation on basic alumina. The synthesized products were tested for their inhibitory effects on the activation of mast cells, neutrophils, macrophages, and microglial cells. The potent inhibitors of NO production in macrophages and microglial cells were further evaluated for their in vitro cytotoxic effects against several human cancer cell lines. 2'-Hydroxychalcones 1-3, and 2',5'-dihydroxychalcone 7 exhibited potent inhibitory effects on the release of beta-glucuronidase or lysozyme from rat neutrophils stimulated with formyl-Met-Leu-Phe (fMLP)/cytochalasin B (CB). Two 2'-hydroxychalcones (1 and 3) showed potent inhibitory effects on superoxide anion generation in rat neutrophils in response to fMLP/CB. The previously reported chalcone, 5, 6, and 12, exhibited potent inhibitory effect on NO production in lipopolysaccharide (LPS)/interferon-gamma (IFN-gamma)-activated N9 microglial cells or in LPS-activated RAW 264.7 macrophage-like cells. The potent inhibitors 5, 6, and 12 of NO production in macrophages or microglial cells revealed significant or marginal cytotoxic effects against several human cancer lines. Compound 12 manifested potent selective cytotoxicity against human MCF-7 cells and caused cell death by apoptosis. The present results demonstrated that 1-3, and 7 have anti-inflammatory effects and 5, 6, and 12 are potential anti-inflammatory and cancer chemopreventive agents.

Authors+Show Affiliations

Won SJ
Department of Microbiology and Immunology, National Cheng Kung University, Tainan 701, Taiwan.
Liu CT
No affiliation info available
Tsao LT
No affiliation info available
Weng JR
No affiliation info available
Ko HH
No affiliation info available
Wang JP
No affiliation info available
Lin CN
No affiliation info available

MeSH

AnimalsAnti-Inflammatory AgentsAnticarcinogenic AgentsApoptosisCell Line, TumorChalconesChemopreventionHumansLipopolysaccharidesMacrophagesMast CellsMiceMicrogliaNeoplasmsNeutrophilsNitric OxideRatsStructure-Activity Relationship

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15642415

Citation

Won, Shen-Jeu, et al. "Synthetic Chalcones as Potential Anti-inflammatory and Cancer Chemopreventive Agents." European Journal of Medicinal Chemistry, vol. 40, no. 1, 2005, pp. 103-12.
Won SJ, Liu CT, Tsao LT, et al. Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. Eur J Med Chem. 2005;40(1):103-12.
Won, S. J., Liu, C. T., Tsao, L. T., Weng, J. R., Ko, H. H., Wang, J. P., & Lin, C. N. (2005). Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. European Journal of Medicinal Chemistry, 40(1), 103-12.
Won SJ, et al. Synthetic Chalcones as Potential Anti-inflammatory and Cancer Chemopreventive Agents. Eur J Med Chem. 2005;40(1):103-12. PubMed PMID: 15642415.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. AU - Won,Shen-Jeu, AU - Liu,Cheng-Tsung, AU - Tsao,Lo-Ti, AU - Weng,Jing-Ru, AU - Ko,Horng-Huey, AU - Wang,Jih-Pyang, AU - Lin,Chun-Nan, PY - 2004/03/01/received PY - 2004/09/01/revised PY - 2004/09/06/accepted PY - 2005/1/12/pubmed PY - 2005/6/3/medline PY - 2005/1/12/entrez SP - 103 EP - 12 JF - European journal of medicinal chemistry JO - Eur J Med Chem VL - 40 IS - 1 N2 - In an effort to develop potent anti-inflammatory and cancer chemopreventive agents, a series of chalcones were prepared by Claisen-Schmidt condensation of appropriate acetophenones with suitable aromatic aldehyde or prepared with appropriate dihydrochalcone reacted with appropriate alkyl bromide or prepared in one-pot procedure involving acetophenone and convenient aromatic aldehyde using ultrasonic agitation on basic alumina. The synthesized products were tested for their inhibitory effects on the activation of mast cells, neutrophils, macrophages, and microglial cells. The potent inhibitors of NO production in macrophages and microglial cells were further evaluated for their in vitro cytotoxic effects against several human cancer cell lines. 2'-Hydroxychalcones 1-3, and 2',5'-dihydroxychalcone 7 exhibited potent inhibitory effects on the release of beta-glucuronidase or lysozyme from rat neutrophils stimulated with formyl-Met-Leu-Phe (fMLP)/cytochalasin B (CB). Two 2'-hydroxychalcones (1 and 3) showed potent inhibitory effects on superoxide anion generation in rat neutrophils in response to fMLP/CB. The previously reported chalcone, 5, 6, and 12, exhibited potent inhibitory effect on NO production in lipopolysaccharide (LPS)/interferon-gamma (IFN-gamma)-activated N9 microglial cells or in LPS-activated RAW 264.7 macrophage-like cells. The potent inhibitors 5, 6, and 12 of NO production in macrophages or microglial cells revealed significant or marginal cytotoxic effects against several human cancer lines. Compound 12 manifested potent selective cytotoxicity against human MCF-7 cells and caused cell death by apoptosis. The present results demonstrated that 1-3, and 7 have anti-inflammatory effects and 5, 6, and 12 are potential anti-inflammatory and cancer chemopreventive agents. SN - 0223-5234 UR - https://www.unboundmedicine.com/medline/citation/15642415/Synthetic_chalcones_as_potential_anti_inflammatory_and_cancer_chemopreventive_agents_ DB - PRIME DP - Unbound Medicine ER -