Novel Lycorine Derivatives as Anticancer Agents: Synthesis and In Vitro Biological Evaluation

被引：38
作者：
Wang, Peng [1 ,2 ,3 ]
Yuan, Hui-Hui [4 ]
Zhang, Xue [1 ,2 ]
Li, Yun-Ping [4 ]
Shang, Lu-Qing [1 ,2 ]
Yin, Zheng [1 ,2 ]
机构：
[1] Nankai Univ, Coll Pharm, Tianjin 300071, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[3] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China
[4] Nankai Univ, Coll Life Sci, Tianjin 300071, Peoples R China
来源：
MOLECULES | 2014年 / 19卷 / 02期
基金：
中国国家自然科学基金;
关键词：
lycorine derivatives; anticancer; synthesis; HUMAN LEUKEMIA-CELLS; CYCLE ARREST; APOPTOSIS; AMARYLLIDACEAE;
D O I：
10.3390/molecules19022469
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Lycorine, which is the most abundant alkaloid isolated from the Amaryllidaceae family of plants, reportedly exhibits promising anticancer activities. Herein, a series of novel lycorine derivatives were synthesized and evaluated for their in vitro inhibitory activities against seven different cancer cell lines, including A549, HCT116, SK-OV-3, NCI-H460, K562, MCF-7 and HL-60. The results indicated that compounds bearing diverse amine substituents at the C-2 position demonstrated good anticancer activities. The selectivity towards different cancer cell lines of the synthesized derivatives is discussed.
引用
收藏
页码：2469 / 2480
页数：12
相关论文
共 20 条
[1]   Alkaloids from South African Amaryllidaceae -: Part 7 -: Bioactive alkaloids from Brunsvigia radulosa [J].
Campbell, WE ;
Nair, JJ ;
Gammon, DW ;
Codina, C ;
Bastida, J ;
Viladomat, F ;
Smith, PJ ;
Albrecht, CF .
PHYTOCHEMISTRY, 2000, 53 (05) :587-591
[2]   Lycorine hydrochloride selectively inhibits human ovarian cancer cell proliferation and tumor neovascularization with very low toxicity [J].
Cao, Zhifei ;
Yu, Di ;
Fu, Shilong ;
Zhang, Gaochuan ;
Pan, Yanyan ;
Bao, Meimei ;
Tu, Jian ;
Shang, Bingxue ;
Guo, Pengda ;
Yang, Ping ;
Zhou, Quansheng .
TOXICOLOGY LETTERS, 2013, 218 (02) :174-185
[3]   C1, C2-ether derivatives of the Amaryllidaceae alkaloid lycorine: Retention of activity of highly lipophilic analogues against cancer cells [J].
Dasari, Ramesh ;
Banuls, Laetitia Moreno Y. ;
Masi, Marco ;
Pelly, Stephen C. ;
Mathieu, Veronique ;
Green, Ivan R. ;
van Otterlo, Willem A. L. ;
Evidente, Antonio ;
Kiss, Robert ;
Kornienko, Alexander .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (03) :923-927
[4]   In search of a cytostatic agent derived from the alkaloid lycorine: Synthesis and growth inhibitory properties of lycorine derivatives [J].
Evdokimov, Nikolai M. ;
Lamoral-Theys, Delphine ;
Mathieu, Veronique ;
Andolfi, Anna ;
Frolova, Liliya V. ;
Pelly, Stephen C. ;
van Otterlo, Willem A. L. ;
Magedov, Igor V. ;
Kiss, Robert ;
Evidente, Antonio ;
Kornienko, Alexander .
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (23) :7252-7261
[5]   Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives [J].
Evidente, Antonio ;
Kornienko, Alexander .
PHYTOCHEMISTRY REVIEWS, 2009, 8 (02) :449-459
[6]   In vitro cytotoxicity of some medicinal plants from Georgian amaryllidaceae [J].
Jokhadze, Malkhaz ;
Eristavi, Lina ;
Kutchukhidze, Jumber ;
Chariot, Alain ;
Angenot, Luc ;
Tits, Monique ;
Jansen, Olivia ;
Frederich, Michel .
PHYTOTHERAPY RESEARCH, 2007, 21 (07) :622-624
[7]   Chemistry, biology, and medicinal potential of narciclasine and its congeners [J].
Kornienko, Alexander ;
Evidente, Antonio .
CHEMICAL REVIEWS, 2008, 108 (06) :1982-2014
[8]   Lycorine, the Main Phenanthridine Amaryllidaceae Alkaloid, Exhibits Significant Antitumor Activity in Cancer Cells That Display Resistance to Proapoptotic Stimuli: An Investigation of Structure-Activity Relationship and Mechanistic Insight [J].
Lamoral-Theys, Delphine ;
Andolfi, Anna ;
Van Goietsenoven, Gwendoline ;
Cimmino, Alessio ;
Le Calve, Benjamin ;
Wauthoz, Nathalie ;
Megalizzi, Veronique ;
Gras, Thierry ;
Bruyere, Celine ;
Dubois, Jacques ;
Mathieu, Veronique ;
Kornienko, Alexander ;
Kiss, Robert ;
Evidente, Antonio .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (20) :6244-6256
[9]   Lycorine induces cell-cycle arrest in the G0/G1 phase in K562 cells via HDAC inhibition [J].
Li, Lv ;
Dai, Hong-Juan ;
Ye, Mao ;
Wang, Shu-Ling ;
Xiao, Xiao-Juan ;
Zheng, Jie ;
Chen, Hui-Yong ;
Luo, Yu-hao ;
Liu, Jing .
CANCER CELL INTERNATIONAL, 2012, 12
[10]  
Li Y, 2007, ONCOL REP, V17, P377
12