C1, C2-ether derivatives of the Amaryllidaceae alkaloid lycorine: Retention of activity of highly lipophilic analogues against cancer cells

被引:54
作者
Dasari, Ramesh [1 ]
Banuls, Laetitia Moreno Y. [2 ]
Masi, Marco [3 ]
Pelly, Stephen C. [4 ]
Mathieu, Veronique [2 ]
Green, Ivan R. [4 ]
van Otterlo, Willem A. L. [4 ]
Evidente, Antonio [3 ]
Kiss, Robert [2 ]
Kornienko, Alexander [1 ]
机构
[1] Texas State Univ, Dept Chem & Biochem, San Marcos, TX 78666 USA
[2] Univ Libre Bruxelles, Fac Pharm, Lab Cancerol & Toxicol Expt, Brussels, Belgium
[3] Univ Naples Federico II, Dipartimento Sci Chim, I-80126 Naples, Italy
[4] Univ Stellenbosch, Dept Chem & Polymer Sci, Western Cape, South Africa
关键词
Cancer; Apoptosis resistance; Melanoma; Glioblastoma; Alkaloid; LEUKEMIA-CELLS; APOPTOSIS; NARCICLASINE; RESISTANCE; CHEMISTRY; BIOLOGY; MODELS; BULBS; CYCLE; MICE;
D O I
10.1016/j.bmcl.2013.12.073
中图分类号
R914 [药物化学];
学科分类号
100705 [微生物与生化药学];
摘要
As a continuation of the studies aimed at the development of new anticancer agents derived from the Amaryllidaceae alkaloid lycorine, 35 C1, C2-ether analogues of this natural product were synthesized. The compounds were evaluated for antiproliferative activities in vitro in a panel of tumor cell lines with varied levels of apoptosis resistance. A strong correlation between the compound lipophilicity and anticancer activity was observed, indicating that cell permeability properties must be an important determinant in the design of lycorine-based anticancer agents. A theoretical docking model, consistent with the experimental observations, is presented. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:923 / 927
页数:5
相关论文
共 29 条
[1]
Evaluation of the efficiency of chemotherapy in in vivo orthotopic models of human glioma cells with and without 1p19q deletions and in C6 rat orthotopic allografts serving for the evaluation of surgery combined with chemotherapy [J].
Branle, F ;
Lefranc, F ;
Camby, I ;
Jeuken, J ;
Geurts-Moespot, A ;
Sprenger, S ;
Sweep, F ;
Kiss, R ;
Salmon, I .
CANCER, 2002, 95 (03) :641-655
[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]
NARCICLASINE - AN ANTIMITOTIC SUBSTANCE FROM NARCISSUS BULBS [J].
CERIOTTI, G .
NATURE, 1967, 213 (5076) :595-&
[4]
ALKALOIDS OF THE AMARYLLIDACEAE [J].
COOK, JW ;
LOUDON, JD .
ALKALOIDS, 1952, 2 :331-352
[5]
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
[6]
EVIDENTE A, 1984, CHEM IND-LONDON, P348
[7]
Exploring Natural Product Chemistry and Biology with Multicomponent Reactions. 5. Discovery of a Novel Tubulin-Targeting Scaffold Derived from the Rigidin Family of Marine Alkaloids [J].
Frolova, Liliya V. ;
Magedov, Igor V. ;
Romero, Anntherese E. ;
Karki, Menuka ;
Otero, Isaiah ;
Hayden, Kathryn ;
Evdokimov, Nikolai M. ;
Banuls, Laetitia Moreno Y. ;
Rastogi, Shiva K. ;
Smith, W. Ross ;
Lu, Shi-Long ;
Kiss, Robert ;
Shuster, Charles B. ;
Hamel, Ernest ;
Betancourt, Tania ;
Rogelj, Snezna ;
Kornienko, Alexander .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (17) :6886-6900
[8]
Ganesan A., 2008, EXPERT OPIN CHEM BIO, V12, P306
[9]
HARTWELL JL, 1967, LLOYD, V30, P379
[10]
Lycorine sensitizes CD40 ligand-protected chronic lymphocytic leukemia cells to bezafibrate- and medroxyprogesterone acetate- induced apoptosis but dasatanib does not overcome reported CD40-mediated drug resistance [J].
Hayden, Rachel E. ;
Pratt, Guy ;
Drayson, Mark T. ;
Bunce, Chris M. .
HAEMATOLOGICA-THE HEMATOLOGY JOURNAL, 2010, 95 (11) :1889-1896