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Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues
Wang, Yue-Hu1,2; Goto, Masuo1; Wang, Li-Ting1; Hsieh, Kan-Yen1; Morris-Natschke, Susan L.1; Tang, Gui-Hua3; Long, Chun-Lin2,4; Lee, Kuo-Hsiung1,5; Wang,YH (reprint author),Univ N Carolina,Eshelman Sch Pharm,Nat Prod Res Labs,Chapel Hill,NC 27599 USA.; wangyuehu@mail.kib.ac.cn; khlee@unc.edu
2014-10-15
Source PublicationBIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN0960-894X
Volume24Issue:20Pages:4818-4821
AbstractTwenty-five amide alkaloids (1-25) from Piper boehmeriifolium and 10 synthetic amide alkaloid derivatives (39-48) were evaluated for antiproliferative activity against eight human tumor cell lines, including chemosensitive and multidrug-resistant (MDR) cell lines. The results suggested tumor type-selectivity. 1-[7-(3,4,5-Trimethoxyphenyl) heptanoyl] piperidine (46) exhibited the best inhibitory activity (IC50 = 4.94 mu M) against the P-glycoprotein (P-gp)-overexpressing KBvin MDR sub-line, while it and all other tested compounds, except 9, were inactive (IC50 > 40 mu M) against MDA-MB-231 and SK-BR-3. Structure-activity relationships (SARs) indicated that (i) 3,4,5-trimethoxy phenyl substitution is critical for selectivity against KBvin, (ii) the 4-methoxy group in this pattern is crucial for antiproliferative activity, (iii) double bonds in the side chain are not needed for activity, and (iv), in arylalkenylacyl amide alkaloids, replacement of an isobutylamino group with pyrrolidin-1-yl or piperidin-1-yl significantly improved activity. Further study on Piper amides is warranted, particularly whether side chain length affects the ability to overcome the MDR cancer phenotype. (C) 2014 Elsevier Ltd. All rights reserved.
KeywordPiper Piperaceae Amide Alkaloids Cytotoxicity Multidrug Resistance
Subject AreaPharmacology & Pharmacy ; Chemistry
DOI10.1016/j.bmcl.2014.08.063
Indexed BySCI ; IC
Language英语
WOS IDWOS:000342575200009
Citation statistics
Cited Times:14[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/18408
Collection资源植物与生物技术所级重点实验室
Corresponding AuthorWang,YH (reprint author),Univ N Carolina,Eshelman Sch Pharm,Nat Prod Res Labs,Chapel Hill,NC 27599 USA.; wangyuehu@mail.kib.ac.cn; khlee@unc.edu
Affiliation1.Univ N Carolina, Eshelman Sch Pharm, Nat Prod Res Labs, Chapel Hill, NC 27599 USA
2.Chinese Acad Sci, Kunming Inst Bot, Key Lab Econ Plants & Biotechnol, Kunming 650201, Peoples R China
3.Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
4.Minzu Univ China, Coll Life & Environm Sci, Beijing 100081, Peoples R China
5.China Med Univ & Hosp, Chinese Med Res & Dev Ctr, Taichung 40447, Taiwan
Recommended Citation
GB/T 7714
Wang, Yue-Hu,Goto, Masuo,Wang, Li-Ting,et al. Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,2014,24(20):4818-4821.
APA Wang, Yue-Hu.,Goto, Masuo.,Wang, Li-Ting.,Hsieh, Kan-Yen.,Morris-Natschke, Susan L..,...&khlee@unc.edu.(2014).Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,24(20),4818-4821.
MLA Wang, Yue-Hu,et al."Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues".BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 24.20(2014):4818-4821.
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