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Divalent Naphthalene Diimide Ligands Display High Selectivity for the Human Telomeric G‐quadruplex in K + Buffer
Author(s) -
Street Steven T. G.,
Chin Donovan N.,
Hollingworth Gregory J.,
Berry Monica,
Morales Juan C.,
Galan M. Carmen
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700140
Subject(s) - g quadruplex , hela , ligand (biochemistry) , chemistry , divalent , selectivity , stereochemistry , cationic polymerization , combinatorial chemistry , conjugate , dna , receptor , in vitro , polymer chemistry , biochemistry , organic chemistry , catalysis , mathematical analysis , mathematics
Selective G‐quadruplex ligands offer great promise for the development of anti‐cancer therapies. A novel series of divalent cationic naphthalene diimide ligands that selectively bind to the hybrid form of the human telomeric G‐quadruplex in K + buffer are described herein. We demonstrate that an imidazolium‐bearing mannoside‐conjugate is the most selective ligand to date for this quadruplex against several other quadruplex and duplex structures. We also show that a similarly selective methylpiperazine‐bearing ligand was more toxic to HeLa cancer cells than doxorubicin, whilst exhibiting three times less toxicity towards fetal lung fibroblasts WI‐38.