Phosphorescent Thymidine Triphosphate Sensor Based on a Donor–Acceptor Ensemble System using Intermolecular Energy Transfer

Abstract

An ensemble sensor system that exhibited selective luminescence enhancement upon binding to thymidine 5'-triphosphate (TTP) in HEPES buffer over other nucleotides was developed. The ensemble system consisted of an energy acceptor (FIrpic-bis(Zn2+-dipicolylamine conjugate, FIrpic=bis[(4,6-difluorophenyl)-pyridinato-N,C2+]picolinate) derivative) and an energy donor (mCP-Zn2+-cyclen, mCP=N,N'-dicarbazolyl-3,5-benzene). Among the nucleotides, the selective recognition and luminescence enhancement for TTP was achieved by the strong binding of the thymine unit to Zn2+-cyclen (cyclen=1,4,7,10-tetraazacyclododecane) and intermolecular energy transfer between the mCP and FIrpic moieties.

Interaction of bis-aryl functionalized molecules with nucleosides and nucleic acids

“…As shown in Figure 5(a), Job's plot indicates that the receptor 1b can form 1:1 complex with cytidine. It is well known that the Zinc complex of cyclen is able to recognize some of the nucleosides or similar derivatives [41][42][43][44]. To find out the binding site of this type of compounds, zinc ions were introduced and the stoichiometry of the Zn(II) complex was also measured.…”

A nanoparticle formula for delivering siRNA or miRNAs to tumor cells in cell culture and in vivo

“…This is an alternative RNA delivery system based on the use of Zn-DPA analog, an artificial receptor for phosphate anion derivatives. We and others have reported a series of fluorescent chemosensors for the detection of phosphate-containing molecules based on Zn-DPA analogs owing to the selective Zn-DPA-coordinated interaction associated with phosphate groups 12–15 . Similar Zn-DPA analogs were also used as probes for necrotic and apoptotic cells by targeting anionic phosphatidylserine on cell surfaces 16,17 .…”

Zn2+-cyclen-based complex enable a selective detection of single-stranded thymine-rich DNA in aqueous buffer

“…Some crystal structures of Zn 2 þ -cyclen complexes with thymine or its analogues revealed a strong coordinate interaction of Zn 2 þ -cyclen with the deprotonated "imide" anion of the thymine group (Shionoya et al, 1993(Shionoya et al, , 1994Gasser et al, 2007). Based on this special recognition, some sensors were developed for detection of thymine derivatives, such as thymidine nucleotides (Kwon et al, 2008;Zeng et al, 2010;Schmidt et al, 2010), thymidilyl(3′-5′)thymidine (Zeng et al, 2009), thymine flipping (O'Neil andWiest, 2005), thymine bulges in DNA (Mundo et al, 2012). However, there is little work to utilize these complexes as fluorescent probes for single-stranded nucleic acids.…”