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Synthesis and biological evaluation of 3',4',5'-trimethoxychalcone analogues as inhibitors of nitric oxide production and tumor cell proliferation.
Bioorg Med Chem. 2009 Dec 01; 17(23):7909-14.BM

Abstract

A series of 23 3',4',5'-trimethoxychalcone analogues was synthesized and their inhibitory effects on nitric oxide (NO) production in LPS/IFN-gamma-treated macrophages, and tumor cell proliferation has been investigated. 4-Hydroxy-3,3',4',5'-tetramethoxychalcone (7), 3,4-dihydroxy-3',4',5'-trimethoxychalcone (11), 3-hydroxy-3',4,4',5'-tetramethoxychalcone (14), and 3,3',4',5'-tetramethoxychalcone (15) were the most potent growth inhibitory agents on NO production, with an IC(50) value of 0.3, 1.5, 1.3 and 0.3 microM, respectively. The tumor cells proliferation assay results revealed that several compounds exhibited potent inhibition activity against different cancer cell lines. The chalcone 15 was the most potent anti-proliferative compound in the series with IC(50) values of 1.8 and 2.2 microM toward liver cancer Hep G2 and colon cancer Colon 205 cell lines, respectively. 2,3,3',4',5'-Pentamethoxychalcone (1), 3,3',4,4',5,5'-hexamethoxychalcone (3), 2,3',4,4',5,5'-hexamethoxychalcone (5), 2-hydroxy-3,3',4',5'-tetramethoxychalcone (10), 11 and 14 showed significant anti-proliferation actions in Hep G2 and Colon 205 cells with an IC(50) values ranging between 10 and 20 microM. Among the tested agents, compound 7 showed selective NO production inhibition (IC(50)=0.3 microM), while has no effect on tumor cell proliferation (IC(50) >100 microM). 3,3',4,4',5'-Pentamethoxychalcone (2) showed selective anti-proliferation effect in Hep G2 cells, in addition to its potent NO inhibition, however has no such response in Colon 205 cells. In contrast, 3-formyl-3',4',5'-trimethoxychalcone (22) showed moderate growth inhibition in Colon 205 cells, while has no such effect on NO production and Hep G2 cells proliferation. These results provide insight into the correlation between some structural properties of 3',4',5'-trimethoxychalcones and their in vitro anti-inflammatory and anti-cancer differentiation activity.

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Authors+Show Affiliations

Rao YK
Institute of Biochemical Sciences and Technology, Chaoyang University of Technology, Wufeng, Taiwan, ROC.
Fang SH
No affiliation info available
Tzeng YM
No affiliation info available

MeSH

AnimalsAnti-Inflammatory AgentsAntineoplastic AgentsCell ProliferationChalconesHep G2 CellsHumansInhibitory Concentration 50Macrophage ActivationMacrophagesMagnetic Resonance SpectroscopyMiceNitric OxideSpectrometry, Mass, Electrospray Ionization

Pub Type(s)

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

Language

eng

PubMed ID

19875299

Citation

Rao, Yerra Koteswara, et al. "Synthesis and Biological Evaluation of 3',4',5'-trimethoxychalcone Analogues as Inhibitors of Nitric Oxide Production and Tumor Cell Proliferation." Bioorganic & Medicinal Chemistry, vol. 17, no. 23, 2009, pp. 7909-14.
Rao YK, Fang SH, Tzeng YM. Synthesis and biological evaluation of 3',4',5'-trimethoxychalcone analogues as inhibitors of nitric oxide production and tumor cell proliferation. Bioorg Med Chem. 2009;17(23):7909-14.
Rao, Y. K., Fang, S. H., & Tzeng, Y. M. (2009). Synthesis and biological evaluation of 3',4',5'-trimethoxychalcone analogues as inhibitors of nitric oxide production and tumor cell proliferation. Bioorganic & Medicinal Chemistry, 17(23), 7909-14. https://doi.org/10.1016/j.bmc.2009.10.022
Rao YK, Fang SH, Tzeng YM. Synthesis and Biological Evaluation of 3',4',5'-trimethoxychalcone Analogues as Inhibitors of Nitric Oxide Production and Tumor Cell Proliferation. Bioorg Med Chem. 2009 Dec 1;17(23):7909-14. PubMed PMID: 19875299.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and biological evaluation of 3',4',5'-trimethoxychalcone analogues as inhibitors of nitric oxide production and tumor cell proliferation. AU - Rao,Yerra Koteswara, AU - Fang,Shih-Hua, AU - Tzeng,Yew-Min, Y1 - 2009/10/28/ PY - 2009/09/15/received PY - 2009/10/09/revised PY - 2009/10/13/accepted PY - 2009/10/31/entrez PY - 2009/10/31/pubmed PY - 2010/2/13/medline SP - 7909 EP - 14 JF - Bioorganic & medicinal chemistry JO - Bioorg Med Chem VL - 17 IS - 23 N2 - A series of 23 3',4',5'-trimethoxychalcone analogues was synthesized and their inhibitory effects on nitric oxide (NO) production in LPS/IFN-gamma-treated macrophages, and tumor cell proliferation has been investigated. 4-Hydroxy-3,3',4',5'-tetramethoxychalcone (7), 3,4-dihydroxy-3',4',5'-trimethoxychalcone (11), 3-hydroxy-3',4,4',5'-tetramethoxychalcone (14), and 3,3',4',5'-tetramethoxychalcone (15) were the most potent growth inhibitory agents on NO production, with an IC(50) value of 0.3, 1.5, 1.3 and 0.3 microM, respectively. The tumor cells proliferation assay results revealed that several compounds exhibited potent inhibition activity against different cancer cell lines. The chalcone 15 was the most potent anti-proliferative compound in the series with IC(50) values of 1.8 and 2.2 microM toward liver cancer Hep G2 and colon cancer Colon 205 cell lines, respectively. 2,3,3',4',5'-Pentamethoxychalcone (1), 3,3',4,4',5,5'-hexamethoxychalcone (3), 2,3',4,4',5,5'-hexamethoxychalcone (5), 2-hydroxy-3,3',4',5'-tetramethoxychalcone (10), 11 and 14 showed significant anti-proliferation actions in Hep G2 and Colon 205 cells with an IC(50) values ranging between 10 and 20 microM. Among the tested agents, compound 7 showed selective NO production inhibition (IC(50)=0.3 microM), while has no effect on tumor cell proliferation (IC(50) >100 microM). 3,3',4,4',5'-Pentamethoxychalcone (2) showed selective anti-proliferation effect in Hep G2 cells, in addition to its potent NO inhibition, however has no such response in Colon 205 cells. In contrast, 3-formyl-3',4',5'-trimethoxychalcone (22) showed moderate growth inhibition in Colon 205 cells, while has no such effect on NO production and Hep G2 cells proliferation. These results provide insight into the correlation between some structural properties of 3',4',5'-trimethoxychalcones and their in vitro anti-inflammatory and anti-cancer differentiation activity. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/19875299/Synthesis_and_biological_evaluation_of_3'4'5'_trimethoxychalcone_analogues_as_inhibitors_of_nitric_oxide_production_and_tumor_cell_proliferation_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(09)00949-3 DB - PRIME DP - Unbound Medicine ER -