Recent progress in the development of organic dye based near-infrared fluorescence probes for metal ions

Wu, Di; Chen, Liyan; Lee, Woolin; Ko, Gyeongju; Yin, Jun; Yoon, Juyoung

doi:10.1016/j.ccr.2017.06.011

Cited by 300 publications

(133 citation statements)

References 214 publications

Supporting

Mentioning

130

Contrasting

Unclassified

Order By: Relevance

“…The aza‐BODIPY dye used in the micelle contrast agent has a similar excitation peak at 683 nm and an emission peak at 717 nm . For deep tissue USF imaging, an NIR contrast agent is desired to increase the photon penetration depth and minimize tissue autofluorescence . Last, current Pluronic micelle based contrast agents are not suitable for an in vivo USF study because they are unstable in biological tissues (such as blood or tissue interstitial fluids) .…”

Section: Introductionmentioning

confidence: 99%

A Biocompatible and Near‐Infrared Liposome for In Vivo Ultrasound‐Switchable Fluorescence Imaging

Liu

Yao

Cai

et al. 2020

Adv Healthcare Materials

View full text Add to dashboard Cite

Fluorescence imaging is a remarkable tool for molecular targeting and multicolor imaging, but it suffers from low resolution in centimeter‐deep tissues. The recently developed ultrasound‐switchable fluorescence (USF) imaging has overcome this challenge and achieved in vivo imaging in a mouse with help from the indocyanine green (ICG) dye encapsulated poly(N‐isopropylacrylamide) (ICG‐PNIPAM) contrast agent. However, the ICG‐PNIPAM has shortcomings, such as concerns about cytotoxicity and blueshifted excitation and emission spectra. This study introduces a newly developed ICG‐encapsulated liposome to broaden the contrast agent selection for USF imaging and resolve the issues mentioned above. The emission peak of the ICG‐liposome is 836 nm with excellent biostability and USF imaging capability. Furthermore, the cell viability test verifies the low cytotoxicity feature. Eventually, both ex vivo and in vivo USF imaging are successfully achieved and 3D USF images are acquired. The ex vivo result confirms that the ICG‐liposome maintains the thermoresponsive characteristic at the right lobe of the liver and is able to conduct the USF imaging. The further in vivo USF imaging demonstrates that although the whole liver emitted fluorescence, only the right lobe of the liver contains the working ICG‐liposome.

show abstract

Section: Introductionmentioning

confidence: 99%

A Biocompatible and Near‐Infrared Liposome for In Vivo Ultrasound‐Switchable Fluorescence Imaging

Liu

Yao

Cai

et al. 2020

Adv Healthcare Materials

View full text Add to dashboard Cite

show abstract

“…In fact, polyamines normally form remarkably stable metal complexes in water solution, in particular with transition metals, and can be easily functionalized at the nitrogen donors, allowing for facile implementation of chemosensors by using the receptor‐spacer‐fluorophore strategy. At the same time, the presence of hydrophilic amine groups generally ensures high solubility in water to the chemosensors and its complexes, a necessary pre‐requisite to obtain metal sensing in aqueous matrices …”

Section: Introductionmentioning

confidence: 99%

Switching on the Fluorescence Emission of Polypyridine Ligands by Simultaneous Zinc(II) Binding and Protonation

et al. 2020

View full text Add to dashboard Cite

The synthesis and characterization of the two new open-chain ligands 1,15-bis-[6-(2,2'-bipyridyl)]-2,5,8,11,14-pentaaza-octadecane (L1) and 1,15-bis-[2-(1,10-phenanthroline)-9-methyl]-2,5,8,11,14-pentaazaoctadecane (L2), both featuring a tetraethylenpentaamine chain linking via methylene bridges the 6 and 2 positions of two identical 2,2'-bipyridyl (bpy) and 9-methyl-1,10phenanthroline (9-methyl-phen) moieties respectively, are reported. Their protonation and binding ability for Cu 2 + , Zn 2 + , Cd 2 + and Pb 2 + have been studied by coupling potentiometric titrations with UV-vis absorption and fluorescence emission measurements in water. L1 and L2 afford stable mono-and dinuclear complexes, in which the metal ion is bound by a single bpy or 9-methyl-phen unit and the amine groups on the aliphatic chain. However, L1 displays a greater binding ability for Cu 2 + and Zn 2 + with respect to L2, the stability constants of the [ML1] 2 + complexes being 21.8 (Cu 2 + ) and 19.4 (Zn 2 + ) log units vs 20.34 and 16.8 log. units for the corresponding L2 species. Among all the metal ions tested, only the Zn 2 + complex with L2 features an enhanced fluorescence emission at neutral pH, thanks to the simultaneous binding of one Zn 2 + ion and H + ion(s), that inhibits any possible photoinduced electron transfer (PET) process from the amine donors to the excited phen moiety. Binding of a second metal switches off the emission again.[a] Dr.by the structural characteristics of the ligand and its Zn 2 + complexes, including the number and disposition of amine donors, the overall rigidity of the molecular backbone, and, in the case of macrocyclic ligands, the dimension of the cavity. In these complexes, the heteroaromatic nitrogens are unequivocally coordinated to the metal cations. However, the stiffening of the macrocyclic structure imposed by the heteroaromatic moieties may not allow the simultaneous coordination to the metal cations of all the nitrogen donors of the binding unit. Interestingly enough, the 'benzylic' amine groups, close to the heteroaromatic unit, are not coordinated, or weakly coordinated, to the metal cation. Therefore, their lone pairs are able to quench the fluorophore excited state thanks to a photoinduced electron transfer (PET) process. As a consequence, normally fluorescent Zn 2 + complexes result to be scarcely emissive. [8a,b,22-24] In this paper, we extend this study to two open-chain ligands, L1 and L2 in Scheme 1, containing a pentaamine aliphatic chain linked at its extremities to two equal 2,2'bipyridyl (bpy) or 9-methyl-1,10-phenanthroline (9-methylphen) moieties, respectively. Our purpose is the analysis of the effects on both metal binding and sensing of the presence of two fluorogenic units linked by a flexible chain.Therefore, complex stability and fluorescence emission in the presence of metal cations will be compared to those of the previously reported ligands L3 [24] and L4 [8a] (Scheme 1), which contain the same aliphatic pentaamine chain linking the 6,6' and 2,9 positions of a single...

show abstract

“…To date, considerable effort has focused on the development of innovative fluorescent dyes for important applications such as labeling reagents, biosensors, and OLEDs . Various highly fluorescent, stable, and/or large Stokes dyes with excellent photophysical and electrochemical properties have been reported .…”

Section: Introductionmentioning

confidence: 99%

“…To date, considerable effort has focused on the development of innovative fluorescentd yes for important applicationss uch as labeling reagents, biosensors,a nd OLEDs. [1] Various highly fluorescent,s table, and/or large Stokesd yes with excellent photophysical and electrochemical properties have been reported. [2] Amongt hese, 4,4'-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)d yes have attracted increasing interesta nd the compounds has been exploited in many fields of science and technology.…”

Section: Introductionmentioning

confidence: 99%

A Simple Central Seven‐Membered BOPYIN: Synthesis, Structural, Spectroscopic Properties, and Cellular Imaging Application

Zhang

Yan

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

A two‐step, one‐flask synthesis of central seven‐membered borondifluoride‐3,3‐dimethyl‐2‐[2‐(2‐pyrrolyl)ethenyl] indole (BOPYIN) ligands has been developed by using the unexplored 3,3‐dimethyl‐2‐[2‐(2‐pyrrolyl)ethenyl] indole. The simple synthetic approach has enabled modification of the electronic structure by changing the substituents on the indole unit. X‐ray analysis indicated that conformations of the seven‐membered BF2 complex including BOPYIN and diazaborepin differ from that of the five‐ and six‐membered organoboron complexes. Interestingly, the bond angle of the N⋅⋅⋅B−N bond increases with the number of atoms in the core ring, based on Baeyer strain theory. These unsymmetric BOPYIN derivatives have excellent photophysical properties, including high fluorescence quantum yields, except for BOPYIN‐4 in the solution state, large Stokes shifts, and good molar absorptivity. The dipole moment of BOPYIN‐3 in the first excited singlet state and ground state was demonstrated by a linear Lippert–Mataga plot. The absorption and emission spectra were not mirror images for BOPYIN‐1–3 and 5, in contradiction to Kasha's rule, as determined by TDDFT. The synthesized BOPYINs have been shown to be biocompatible fluorophores in cell bioimaging.

show abstract

Recent progress in the development of organic dye based near-infrared fluorescence probes for metal ions

Cited by 300 publications

References 214 publications

A Biocompatible and Near‐Infrared Liposome for In Vivo Ultrasound‐Switchable Fluorescence Imaging

A Biocompatible and Near‐Infrared Liposome for In Vivo Ultrasound‐Switchable Fluorescence Imaging

Switching on the Fluorescence Emission of Polypyridine Ligands by Simultaneous Zinc(II) Binding and Protonation

A Simple Central Seven‐Membered BOPYIN: Synthesis, Structural, Spectroscopic Properties, and Cellular Imaging Application

Contact Info

Product

Resources

About