Extended Naphthalene Diimides with Donor/Acceptor Hydrogen‐Bonding Properties Targeting G‐Quadruplex Nucleic Acids. Issue 28 (6th October 2016)

• Record Type: Journal Article
• Authors: Doria, Filippo; Nadai, Matteo; Costa, Giosuè; Sattin, Giovanna; Gallati, Caroline; Bergamaschi, Greta; Moraca, Federica; Alcaro, Stefano; Freccero, Mauro; Richter, Sara N.
• Is Part Of: European journal of organic chemistry. Issue 28(2016)
• Page Start: 4824
• Page End: 4833
• Publication Date: 2016-10-06
• Subjects: Nucleic acids -- Cross‐coupling -- Hydrogen bonds -- Carboximides -- G‐Quadruplexes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600757
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Naphthalene diimides with one or two centrosymmetric arylethynyl moieties capable of synergic donor and acceptor hydrogen bonding exhibit promising binding properties and selectivity towards parallel G‐quadruplex (G4) nucleic acids (c‐myc, bcl‐2 and parallel hTel22). The hydrogen‐bonding network involving the phosphate backbone and outside rim of the G‐quartet represents an opportunity to exploit G4 selectivity for extended aromatics. Abstract : X‐shaped naphthalene diimides with synergic donor and acceptor hydrogen‐bonding moieties selectively bind parallel G‐quadruplex nucleic acids (c‐myc, bcl‐2 and parallel hTel22). The hydrogen‐bonding network involving the outside rim of the G‐quartet is a key factor controlling the selectivity