Antitumor agents. 271: Total synthesis and evaluation of brazilein and analogs as anti-inflammatory and cytotoxic agents

Chiao Ting Yen; Kyoko Nakagawa-Goto; Tsong Long Hwang; Pei Chi Wu; Susan L. Morris-Natschke; Wan Chun Lai; Kenneth F. Bastow; Fang Rong Chang; Yang Chang Wu; Kuo Hsiung Lee

doi:10.1016/j.bmcl.2009.12.041

Antitumor agents. 271: Total synthesis and evaluation of brazilein and analogs as anti-inflammatory and cytotoxic agents

Chiao Ting Yen, Kyoko Nakagawa-Goto, Tsong Long Hwang, Pei Chi Wu, Susan L. Morris-Natschke, Wan Chun Lai, Kenneth F. Bastow, Fang Rong Chang, Yang Chang Wu^*, Kuo Hsiung Lee

^*Corresponding author for this work

School of Traditional Chinese Medicine

Research output: Contribution to journal › Journal Article › peer-review

48 Scopus citations

Abstract

The first total synthesis of the naturally occurring tetracyclic homoisoflavonoid brazilein (1) and 14 new analogs (1a-n) is reported. Target compounds and intermediates were assayed for anti-inflammatory effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB, and for cytotoxic activity against nasopharyngeal (KB), vincristine-resistant nasopharyngeal (KBvin), lung (A549) and prostate (DU-145) human cancer cell lines. The most active compound 1b showed potent effects on superoxide anion generation and elastase release with IC₅₀ values of 1.2 and 1.9 μM, respectively, and was 65 times more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in the latter assay. Additionally, 1b exhibited broad spectrum in vitro anticancer activity with IC₅₀ values of 6-11 μM against the four tested cancer cell lines.

Original language	English
Pages (from-to)	1037-1039
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	3
DOIs	https://doi.org/10.1016/j.bmcl.2009.12.041
State	Published - 01 02 2010

Keywords

Anti-inflammatory
Brazilein
Cytotoxic
Homoisoflavonoid

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmcl.2009.12.041

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Yen, C. T., Nakagawa-Goto, K., Hwang, T. L., Wu, P. C., Morris-Natschke, S. L., Lai, W. C., Bastow, K. F., Chang, F. R., Wu, Y. C., & Lee, K. H. (2010). Antitumor agents. 271: Total synthesis and evaluation of brazilein and analogs as anti-inflammatory and cytotoxic agents. Bioorganic and Medicinal Chemistry Letters, 20(3), 1037-1039. https://doi.org/10.1016/j.bmcl.2009.12.041

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abstract = "The first total synthesis of the naturally occurring tetracyclic homoisoflavonoid brazilein (1) and 14 new analogs (1a-n) is reported. Target compounds and intermediates were assayed for anti-inflammatory effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB, and for cytotoxic activity against nasopharyngeal (KB), vincristine-resistant nasopharyngeal (KBvin), lung (A549) and prostate (DU-145) human cancer cell lines. The most active compound 1b showed potent effects on superoxide anion generation and elastase release with IC50 values of 1.2 and 1.9 μM, respectively, and was 65 times more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in the latter assay. Additionally, 1b exhibited broad spectrum in vitro anticancer activity with IC50 values of 6-11 μM against the four tested cancer cell lines.",

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AU - Hwang, Tsong Long

AU - Wu, Pei Chi

AU - Morris-Natschke, Susan L.

AU - Lai, Wan Chun

AU - Bastow, Kenneth F.

AU - Chang, Fang Rong

AU - Wu, Yang Chang

AU - Lee, Kuo Hsiung

PY - 2010/2/1

Y1 - 2010/2/1

N2 - The first total synthesis of the naturally occurring tetracyclic homoisoflavonoid brazilein (1) and 14 new analogs (1a-n) is reported. Target compounds and intermediates were assayed for anti-inflammatory effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB, and for cytotoxic activity against nasopharyngeal (KB), vincristine-resistant nasopharyngeal (KBvin), lung (A549) and prostate (DU-145) human cancer cell lines. The most active compound 1b showed potent effects on superoxide anion generation and elastase release with IC50 values of 1.2 and 1.9 μM, respectively, and was 65 times more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in the latter assay. Additionally, 1b exhibited broad spectrum in vitro anticancer activity with IC50 values of 6-11 μM against the four tested cancer cell lines.

AB - The first total synthesis of the naturally occurring tetracyclic homoisoflavonoid brazilein (1) and 14 new analogs (1a-n) is reported. Target compounds and intermediates were assayed for anti-inflammatory effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB, and for cytotoxic activity against nasopharyngeal (KB), vincristine-resistant nasopharyngeal (KBvin), lung (A549) and prostate (DU-145) human cancer cell lines. The most active compound 1b showed potent effects on superoxide anion generation and elastase release with IC50 values of 1.2 and 1.9 μM, respectively, and was 65 times more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in the latter assay. Additionally, 1b exhibited broad spectrum in vitro anticancer activity with IC50 values of 6-11 μM against the four tested cancer cell lines.

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KW - Cytotoxic

KW - Homoisoflavonoid

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

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ER -

Antitumor agents. 271: Total synthesis and evaluation of brazilein and analogs as anti-inflammatory and cytotoxic agents

Abstract

Keywords

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