Click chemistry assembly of G-quadruplex ligands incorporating a diarylurea scaffold and triazole linkers

被引:32
作者
Drewe, William C. [1 ]
Neidle, Stephen [1 ]
机构
[1] Univ London, Sch Pharm, CRUK Biomol Struct Grp, London WC1N 1AX, England
关键词
D O I
10.1039/b814576h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of diarylurea ligands were designed to interact selectively with G-quadruplexes and were synthesised using copper( I) catalysed 'click' chemistry to incorporate the 1,4-substituted 1,2,3-triazole ring into the core of the ligands; the optimal ligands demonstrate a high degree of selective telomeric G-quadruplex stabilisation and are not cytotoxic in several cancer cell lines.
引用
收藏
页码:5295 / 5297
页数:3
相关论文
共 28 条
[1]   Trisubstituted isoalloxazines as a new class of G-quadruplex binding ligands: Small molecule regulation of c-kit oncogene expression [J].
Bejugam, Mallesham ;
Sewitz, Sven ;
Shirude, Pravin S. ;
Rodriguez, Raphael ;
Shahid, Ramla ;
Balasubramanian, Shankar .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (43) :12926-+
[2]   Quadruplex DNA: sequence, topology and structure [J].
Burge, Sarah ;
Parkinson, Gary N. ;
Hazel, Pascale ;
Todd, Alan K. ;
Neidle, Stephen .
NUCLEIC ACIDS RESEARCH, 2006, 34 (19) :5402-5415
[3]   Antitumor polycyclic acridines. 20. search for DNA quadruplex binding selectivity in a series of 8,13-dimethylquino[4,3,2-kl]acridinium salts: Telomere-targeted agents [J].
Cheng, Mai-Kim ;
Modi, Chetna ;
Cookson, Jennifer C. ;
Hutchinson, Ian ;
Heald, Robert A. ;
McCarroll, Andrew J. ;
Missailidis, Sotiris ;
Tanious, Farial ;
Wilson, W. David ;
Mergny, Jean-Louis ;
Laughton, Charles A. ;
Stevens, Malcolm F. G. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (04) :963-975
[4]   Tri- and tetra-substituted naphthalene diimides as potent G-quadruplex ligands [J].
Cuenca, Francisco ;
Greciano, Olga ;
Gunaratnam, Mekala ;
Haider, Shozeb ;
Munnur, Deeksha ;
Nanjunda, Rupesh ;
Wilson, W. David ;
Neidle, Stephen .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (05) :1668-1673
[5]   Targeting telomeres and telomerase [J].
De Cian, Anne ;
Lacroix, Laurent ;
Douarre, Celine ;
Temime-Smaali, Nassima ;
Trentesaux, Chantal ;
Riou, Jean-Francois ;
Mergny, Jean-Louis .
BIOCHIMIE, 2008, 90 (01) :131-155
[6]   Fluorescence-based melting assays for studying quadruplex ligands [J].
De Cian, Anne ;
Guittat, Lionel ;
Kaiser, Markus ;
Sacca, Barbara ;
Amrane, Samir ;
Bourdoncle, Anne ;
Alberti, Patrizia ;
Teulade-Fichou, Marie-Paule ;
Lacroix, Laurent ;
Mergny, Jean-Louis .
METHODS, 2007, 42 (02) :183-195
[7]   A conserved quadruplex motif located in a transcription activation site of the human c-kit oncogene [J].
Fernando, Himesh ;
Reszka, Anthony P. ;
Huppert, Julian ;
Ladame, Sylvain ;
Rankin, Sarah ;
Venkitaraman, Ashok R. ;
Neidle, Stephen ;
Balasubramanian, Shankar .
BIOCHEMISTRY, 2006, 45 (25) :7854-7860
[8]   Mechanism of acridine-based telomerase inhibition and telomere shortening [J].
Gunaratnam, Mekala ;
Greciano, Olga ;
Martins, Cristina ;
Reszka, Anthony P. ;
Schultes, Christoph M. ;
Morjani, Hamid ;
Riou, Jean-Francois ;
Neidle, Stephen .
BIOCHEMICAL PHARMACOLOGY, 2007, 74 (05) :679-689
[9]   Prevalence of quadruplexes in the human genome [J].
Huppert, JL ;
Balasubramanian, S .
NUCLEIC ACIDS RESEARCH, 2005, 33 (09) :2908-2916
[10]   G-quadruplexes in promoters throughout the human genome [J].
Huppert, Julian L. ;
Balasubramanian, Shankar .
NUCLEIC ACIDS RESEARCH, 2007, 35 (02) :406-413