Design and synthesis of new N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides as anti-inflammatory agents

Chiao Ting Yen; Tsong Long Hwang; Yang Chang Wu; Pei Wen Hsieh

doi:10.1016/j.ejmech.2008.11.008

Design and synthesis of new N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides as anti-inflammatory agents

Chiao Ting Yen
, Tsong Long Hwang
, Yang Chang Wu^*
, Pei Wen Hsieh

^*Corresponding author for this work

School of Traditional Chinese Medicine

Kaohsiung Medical University

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

23 Scopus citations

Abstract

Twenty-four new dipeptide analogs (1-24) of aurantiamide acetate were designed, synthesized, and assayed for effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, seven N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides (6, 9, 12, 14, 17, 18 and 20) showed potent inhibitory effects. Compounds 9 and 18 showed the most selective effects against human neutrophil elastase release, with IC₅₀ values of 0.8 ± 0.1 and 1.7 ± 0.6 μM, respectively, and were 130-fold more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in this anti-inflammatory assay. These two compounds could be developed as new lead anti-inflammatory agents.

Original language	English
Pages (from-to)	1933-1940
Number of pages	8
Journal	European Journal of Medicinal Chemistry
Volume	44
Issue number	5
DOIs	https://doi.org/10.1016/j.ejmech.2008.11.008
State	Published - 05 2009

Keywords

Anti-inflammatory agents
Aurantiamide derivatives
Fmoc-based dipeptides

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10.1016/j.ejmech.2008.11.008

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title = "Design and synthesis of new N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides as anti-inflammatory agents",

abstract = "Twenty-four new dipeptide analogs (1-24) of aurantiamide acetate were designed, synthesized, and assayed for effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, seven N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides (6, 9, 12, 14, 17, 18 and 20) showed potent inhibitory effects. Compounds 9 and 18 showed the most selective effects against human neutrophil elastase release, with IC50 values of 0.8 ± 0.1 and 1.7 ± 0.6 μM, respectively, and were 130-fold more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in this anti-inflammatory assay. These two compounds could be developed as new lead anti-inflammatory agents.",

keywords = "Anti-inflammatory agents, Aurantiamide derivatives, Fmoc-based dipeptides",

author = "Yen, \{Chiao Ting\} and Hwang, \{Tsong Long\} and Wu, \{Yang Chang\} and Hsieh, \{Pei Wen\}",

year = "2009",

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doi = "10.1016/j.ejmech.2008.11.008",

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T1 - Design and synthesis of new N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides as anti-inflammatory agents

AU - Yen, Chiao Ting

AU - Hwang, Tsong Long

AU - Wu, Yang Chang

AU - Hsieh, Pei Wen

PY - 2009/5

Y1 - 2009/5

N2 - Twenty-four new dipeptide analogs (1-24) of aurantiamide acetate were designed, synthesized, and assayed for effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, seven N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides (6, 9, 12, 14, 17, 18 and 20) showed potent inhibitory effects. Compounds 9 and 18 showed the most selective effects against human neutrophil elastase release, with IC50 values of 0.8 ± 0.1 and 1.7 ± 0.6 μM, respectively, and were 130-fold more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in this anti-inflammatory assay. These two compounds could be developed as new lead anti-inflammatory agents.

AB - Twenty-four new dipeptide analogs (1-24) of aurantiamide acetate were designed, synthesized, and assayed for effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, seven N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides (6, 9, 12, 14, 17, 18 and 20) showed potent inhibitory effects. Compounds 9 and 18 showed the most selective effects against human neutrophil elastase release, with IC50 values of 0.8 ± 0.1 and 1.7 ± 0.6 μM, respectively, and were 130-fold more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in this anti-inflammatory assay. These two compounds could be developed as new lead anti-inflammatory agents.

KW - Anti-inflammatory agents

KW - Aurantiamide derivatives

KW - Fmoc-based dipeptides

UR - https://www.scopus.com/pages/publications/62549132051

U2 - 10.1016/j.ejmech.2008.11.008

DO - 10.1016/j.ejmech.2008.11.008

M3 - 文章

C2 - 19110343

AN - SCOPUS:62549132051

SN - 0223-5234

VL - 44

SP - 1933

EP - 1940

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 5

ER -

Design and synthesis of new N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides as anti-inflammatory agents

Abstract

Keywords

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