Synthesis and in vitro cytotoxicity of andrographolide-19-oic acid analogues as anti-cancer agents

被引：36

作者：

Chen, Dongsheng ^{[1
]}

Song, Yaping ^{[1
]}

Lu, Yunlong ^{[1
]}

Xue, Xiaowen ^{[1
]}

机构：

[1] China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Jiangsu, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 11期

关键词：

Andrographolide; Structure modification; Andrographolide-19-oic acid derivatives; Cytotoxicity; ANDROGRAPHIS; ARREST; CELLS;

D O I：

10.1016/j.bmcl.2013.04.010

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis of a series of andrographolide-19-oic acid derivatives was described and their in vitro antitumor activity against two human cell lines was evaluated. Most compounds were found to exhibit significant cytotoxicity, better than andrographolide, and compounds 9d and 9b were identified as the most potent with IC50 values of 1.18 and 6.28 mu m against HCT-116 and MCF-7 cell lines, respectively. The preliminary results indicated that the oxidation of C-19-hydroxyl group of andrographolide to corresponding carboxyl group and the subsequent esterification of the formed carboxylic acid led to considerable improvement in cytotoxicity against the cancer cells. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：3166 / 3169

页数：4

共 24 条

[1] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].

BAL, BS ;

CHILDERS, WE ;

PINNICK, HW .

TETRAHEDRON, 1981, 37 (11) :2091-2096

[2] Andrographolide reduces IL-2 production in T-cells by interfering with NFAT and MAPK activation [J].

Carretta, Maria D. ;

Alarcon, Pablo ;

Jara, Evelyn ;

Solis, Loreto ;

Hancke, Juan L. ;

Concha, Ilona I. ;

Hidalgo, Maria A. ;

Burgos, Rafael A. .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2009, 602 (2-3) :413-421

[3] Synthesis, cytotoxicity, and structure-activity relationship (SAR) studies of andrographolide analogues as anti-cancer agent [J].

Das, Bimolendu ;

Chowdhury, Chinmay ;

Kumar, Deepak ;

Sen, Rupashree ;

Roy, Rajneeta ;

Das, Padma ;

Chatterjee, Mitali .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (23) :6947-6950

[4] Efficient and highly selective oxidation of primary alcohols to aldehydes by N-chlorosuccinimide mediated by oxoammonium salts [J].

Einhorn, J ;

Einhorn, C ;

Ratajczak, F ;

Pierre, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7452-7454

[5] Cytotoxic Constituents from Andrographis paniculata Induce Cell Cycle Arrest in Jurkat Cells [J].

Geethangilil, Madamanchi ;

Rao, Yerra Koteswara ;

Fang, Shih-Hua ;

Tzeng, Yew-Min .

PHYTOTHERAPY RESEARCH, 2008, 22 (10) :1336-1341

[6]

Gorter K, 1911, RECL TRAV CH PAYS-BA, V30, P151

[7]

GUPTA S, 1990, International Journal of Crude Drug Research, V28, P273

[8] Novel bioconversion products of andrographolide by Aspergillus ochraceus and their cytotoxic activities against human tumor cell lines [J].

He, Xiangjiu ;

Wang, Yihai ;

Hu, Hui ;

Wu, Yixuan ;

Zeng, Xiaobin .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2011, 68 (01) :89-93

[9] Cytotoxic biotransformed products from andrographolide by Rhizopus stolonifer ATCC 12939 [J].

He, Xiangjiu ;

Zeng, Xiaobin ;

Hu, Hui ;

Wu, Yixuan .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2010, 62 (3-4) :242-247

[10] Benzylidene derivatives of andrographolide inhibit growth of breast and colon cancer cells in vitro by inducing G1 arrest and apoptosis [J].

Jada, S. R. ;

Matthews, C. ;

Saad, M. S. ;

Hamzah, A. S. ;

Lajis, N. H. ;

Stevens, M. F. G. ;

Stanslas, J. .

BRITISH JOURNAL OF PHARMACOLOGY, 2008, 155 (05) :641-654

← 1 2 3 →