The recognition of 1,5-naphthalenedisulfonate by a protonated azamacrocyclic ligand

Xie, Gaoyi; Jiang, Long; Lu, Tong‐Bu

doi:10.1039/c2ra22423b

Cited by 6 publications

(4 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To confirm that J1 is encapsulated by RNA, the 1 H NMR titration experiments are carried out in D 2 O. As shown in Figure D, the addition of 2 equiv of RNA generated significant upfield shifts of the terpyridine protons H a and H b , which demonstrates the presence of π–π stacking interactions between terpyridine fragments of J1 and RNA …”

Section: Resultsmentioning

confidence: 99%

Highly Hydrophilic, Two-photon Fluorescent Terpyridine Derivatives Containing Quaternary Ammonium for Specific Recognizing Ribosome RNA in Living Cells

Du¹,

Wang²,

Zhu³

et al. 2017

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

A two-photon fluorescent probe (J1) that selectively stains intracellular nucleolar RNA was screened from three water-soluble terpyridine derivatives (J1-J3) with quaternary ammonium groups. The photophysical properties of J1-J3 were systemically investigated both experimentally and theoretically, revealing that J1-J3 possess large Stokes shifts and the two-photon absorption action cross sections range from 38 to 97 GM in the near-infrared region. This indicates that J1 could specifically stain nucleoli by targeting the nucleolar rRNA from the recognition experiments in vitro, the two-photon imaging experiments, and the stimulated emission depletion in vivo. The mechanism of action in which J1 binds to the nucleolar rRNA was researched via both experiments and molecular modeling. The high binding selectivity of J1 to nucleolar RNA over cytosolic RNA made this probe a potential candidate to visualize rRNA probe in the living cells.

show abstract

Section: Resultsmentioning

confidence: 99%

Highly Hydrophilic, Two-photon Fluorescent Terpyridine Derivatives Containing Quaternary Ammonium for Specific Recognizing Ribosome RNA in Living Cells

Du¹,

Wang²,

Zhu³

et al. 2017

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

show abstract

“…Macrocycles 1 – 3 were prepared by the reaction of 9,10‐anthracenedicarboxaldehyde with the corresponding amines in an acetonitrile‐methanol mixture followed by reduction of the produced Schiff base. The preparation methods described earlier for cyclophanes were slightly modified and optimized . Receptors 1 and 2 were synthesized with low yields (ca.…”

Section: Resultsmentioning

confidence: 99%

“…The preparation methods described earlier for cyclophanes were slightly modified and optimized. [11,[33][34][35] Receptors 1 and 2 were synthesized with low yields (ca. 15 %), while macrocycle 3 could be obtained in a 43 %y ield.…”

Section: Synthesismentioning

confidence: 99%

“…We have investigated the effect of ap articular linker on the selectivity of receptors and revealed the presence of different binding modes among five natural nucleoside triphosphates, including the pyrophosphate anion as ar eference. The cyclophanes containing diethylenetriaminea nd 2,2'-oxybis(ethylamine) as linkersh ave already been described, [11,30,[32][33][34] but their host-guest chemistry andsensing properties in particular towards nucleotides have not been studied.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Anthracene‐Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms

Agafontsev

Shumilova

Rüffer

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

Three anthracene‐based cyclophanes were synthesized and their binding properties towards nucleoside triphosphates were studied. A new polycyclic amine derived from dearomatized anthracene was identified as a major side product in the cyclization reaction between 9,10‐anthracenedicarboxaldehyde and diethylenetriamine. Its structure was determined by single‐crystal X‐ray analysis. The cyclophanes were found to form 1:1 complexes with all nucleoside triphosphates as well as with pyrophosphate in a buffered aqueous solution at pH 6.2. A turn‐on fluorescence response was observed for all nucleotides except for GTP, which demonstrated strong fluorescence quenching. The strongest turn‐on fluorescence was observed for the largest receptor 3 in the presence of thymidine triphosphate (TTP). Based on the NMR and fluorescence experiments, two major binding modes for nucleotide complexes were identified.

show abstract

A Highly Selective “On‐Off‐On” Optical Switch for Sequential Detection of Cu²⁺and S²⁻Ions Based on 2, 6‐Diformyl‐4‐methyl Phenol and Catecholase Activity by Its Copper Complex

2018

View full text Add to dashboard Cite

A new highly selective chemosensor for Cu 2 + and S 2 À ions, Ethyl 2-cyano-3-(2-hydroxy-5-methyl-3-(p-tolylimino)methyl) phenyl)acrylate) (HL) based on 2, 6-diformyl-4-methylphenol was designed and synthesized. The ligand exhibited excellent sensitivity towards copper ion by the emission quenching even in the presence of other biologically important metal ions. Once HL combine with Cu 2 + it can display a rapid response and high selectivity toward sulfide anion resulting in off-on sensing via Cu 2 + displacement assay. The signal transduction happen via reversible formation-separation of complex L-Cu and CuS and the complex LÀCu was synthesized by the reaction of HL and Cu 2 + and characterized by single-crystal Xray diffraction and DFT optimization studies. The catecholase like activity for LÀCu complex have been studied by using 3,5di-tertbutylcatechol (3,5-DTBC) as the substrate.[a] Dr.

show abstract

The recognition of 1,5-naphthalenedisulfonate by a protonated azamacrocyclic ligand

Cited by 6 publications

References 35 publications

Highly Hydrophilic, Two-photon Fluorescent Terpyridine Derivatives Containing Quaternary Ammonium for Specific Recognizing Ribosome RNA in Living Cells

Highly Hydrophilic, Two-photon Fluorescent Terpyridine Derivatives Containing Quaternary Ammonium for Specific Recognizing Ribosome RNA in Living Cells

Anthracene‐Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms

A Highly Selective “On‐Off‐On” Optical Switch for Sequential Detection of Cu²⁺and S²⁻Ions Based on 2, 6‐Diformyl‐4‐methyl Phenol and Catecholase Activity by Its Copper Complex

Contact Info

Product

Resources

About

The recognition of 1,5-naphthalenedisulfonate by a protonated azamacrocyclic ligand

Cited by 6 publications

References 35 publications

Highly Hydrophilic, Two-photon Fluorescent Terpyridine Derivatives Containing Quaternary Ammonium for Specific Recognizing Ribosome RNA in Living Cells

Highly Hydrophilic, Two-photon Fluorescent Terpyridine Derivatives Containing Quaternary Ammonium for Specific Recognizing Ribosome RNA in Living Cells

Anthracene‐Based Cyclophanes with Selective Fluorescent Responses for TTP and GTP: Insights into Recognition and Sensing Mechanisms

A Highly Selective “On‐Off‐On” Optical Switch for Sequential Detection of Cu2+and S2−Ions Based on 2, 6‐Diformyl‐4‐methyl Phenol and Catecholase Activity by Its Copper Complex

Contact Info

Product

Resources

About

A Highly Selective “On‐Off‐On” Optical Switch for Sequential Detection of Cu²⁺and S²⁻Ions Based on 2, 6‐Diformyl‐4‐methyl Phenol and Catecholase Activity by Its Copper Complex