Dye-functionalized phosphate-binding macrocycles: from nucleotide to G-quadruplex recognition and “turn-on” fluorescence sensing

Abstract

A novel strategy to design “turn-on” fluorescent receptors for G-quadruplexes of DNA is presented, which relies on the connection of phosphate binding macrocycles (PBM) with naphthalimide dyes. A new PBM-dye...

Fluorescent Chemosensors Based on Polyamine Ligands: A Review

“…This was ascribed to a hindering of the PET process by the proton exchange produced upon binding to the nucleotide. When interacting with G4 structures, the fluorescence of 60 increased four to nine-fold [82].…”

“…Citrate [80] In the case of [Zn2L] 4+ : H2PO4 − , PhP 2− , HPPi, HAMP − , HADP 2− , HATP 3− [81] ATP, GTP, CTP, UTP, G-quadruplex [82] Cu 2+ , Zn 2+ , Cd 2+ , Pb 2+ , Hg 2+ [87] In the case of [Zn 2 L] 4+ : H 2 PO 4 − , PhP 2− , HPPi, HAMP − , HADP 2− , HATP 3− [81] Citrate [80] In the case of [Zn2L] 4+ : H2PO4 − , PhP 2− , HPPi, HAMP − , HADP 2− , HATP 3− [81] ATP, GTP, CTP, UTP, G-quadruplex [82] Cu 2+ , Zn 2+ , Cd 2+ , Pb 2+ , Hg 2+ [87] ATP, GTP, CTP, UTP, G-quadruplex [82] Citrate [80] In the case of [Zn2L] 4+ : H2PO4 − , PhP 2− , HPPi, HAMP − , HADP 2− , HATP Phosphate, pyrophosphoric acid, 1-hydroxyethane 1,1-diphosphonic acid, aminotris(methylenephosphonicacid) [95]…”

Converting pH probes into “turn-on” fluorescent receptors for anions

“…In order to increase the solubility of the receptor and increase the efficiency of PET, we prepared a new family of receptors 30-32 bearing protonable dimethylamino group. 48 We investigated the properties of 29-32 in terms of their interaction with simple nucleotides and DNA G-quadruplexes of different topologies.…”

Macrocyclic Conformational Switch Coupled with Pyridinium-Induced PET for Fluorescence Detection of Adenosine Triphosphate

“…The first generation of our systems demonstrated an excellent ability to fold and unfold depending on the protonation and complexation states. The principle of binding event visualization is based on the supramolecular p K a shift induced by the complexation. , For instance, receptor 1 binds sulfate in a diprotonated state (at pH 3.6), leading to fluorescence quenching. The quenching results from the folding of the receptor, producing a naphthalimide–pyridine–naphthalimide stack (Figure a).…”

“…(a) Binding of sulfate induces folding of pyridine-2,6-dicarboxamide-based receptor 1 . (b) A PET mechanism was realized to generate a turn-on response for 2,6-bis­(aminomethyl)­pyridine-based receptor 2 via nucleotide recognition . (c) Structures of the receptors and sensing mechanism studied in this work.…”