Unravelling the correlation between metal induced aggregation and cellular uptake/subcellular localization of Znsalen: an overlooked rule for design of luminescent metal probes

Tang, Juan; Cai, Yi; Jing, Jing; Zhang, Junlong

doi:10.1039/c4sc03824j

Cited by 54 publications

(29 citation statements)

References 66 publications

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“…Interestingly, when adding a coordinating N, O donor ligand (e. g. Pyridine, DMSO, epoxide…) the dimeric Zn‐sal(ph)en species usually display a structural change forming monomeric species in which the fifth site of the metal is completed by the donor ligand. As this process always gives rise to an important change of optical properties, it leads to interesting sensing applications …”

Section: Introductionmentioning

confidence: 99%

Unexpected Structure of a Helical N₄‐Schiff‐Base Zn(II) Complex and Its Demetallation: Experimental and Theoretical Studies

et al. 2018

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A new Zn‐N4‐Schiff base L=((±)‐trans‐N,N’‐Bis(2‐aminobenzylidene)‐1,2‐diaminocyclohexane) complex was synthesized and fully characterized, showing an unexpected self‐assembled double‐stranded helicate structure. The X‐ray crystal analysis of the Zn2L2 complex ((C40H44N8Zn2,CH2Cl2, a=14.2375(3) Å, b=16.7976(4) Å, c=16.1613(4) Å, monoclinic, P21/n, Z=4) shows a centrosymmetrical structure in which zinc atoms are in distorted tetrahedral environments, revealing an M‐ (R, R) left‐handed helicity in its asymmetric unit. However, it was observed that this dinuclear complex is thermodynamically unstable in the presence of small water amounts and undergoes demetallation into free N4‐Schiff base ligand and ZnO nanoparticles. This hydrolysis process was thoroughly identified and monitored through detailed 1H NMR, DOSY NMR analysis. The reaction mechanism of this demetallation event was elucidated by using the DFT method, involving an activation energy smaller than 13 kcal/mol. Besides, a theoretical mechanism of the demetallation process is given for the first time.

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Section: Introductionmentioning

confidence: 99%

Unexpected Structure of a Helical N₄‐Schiff‐Base Zn(II) Complex and Its Demetallation: Experimental and Theoretical Studies

et al. 2018

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“…Due to the specific charge condition of the membrane of mitochondria, positively charged groups including P‐/N‐containing groups have been widely employed for mitochondria . Herein, triphenylphosphonio was used as mitochondrion‐directing group with a commercially available mitochondrial tracker as control, and excellent results were obtained.…”

Section: Resultsmentioning

confidence: 99%

Rational Design of Fluorescent Phthalazinone Derivatives for One‐ and Two‐Photon Imaging

Yang

Zhu

Shui

et al. 2016

Chemistry A European J

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Phthalazinone derivatives were designed as optical probes for one- and two-photon fluorescence microscopy imaging. The design strategy involves stepwise extension and modification of pyridazinone by 1) expansion of pyridazinone to phthalazinone, a larger conjugated system, as the electron acceptor, 2) coupling of electron-donating aromatic groups such as N,N-diethylaminophenyl, thienyl, naphthyl, and quinolyl to the phthalazinone, and 3) anchoring of an alkyl chain to the phthalazinone with various terminal substituents such as triphenylphosphonio, morpholino, triethylammonio, N-methylimidazolio, pyrrolidino, and piperidino. Theoretical calculations were utilized to verify the initial design. The desired fluorescent probes were synthesized by two different routes in considerable yields. Twenty-two phthalazinone derivatives were synthesized and their photophysical properties were measured. Selected compounds were applied in cell imaging, and valuable information was obtained. Furthermore, the designed compounds showed excellent performance in two-photon microscopic imaging of mouse brain slices.

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“…Thus, directing a probe to LDs through a particular endocytosis trafficking pathway would be a desirable approach. Previously, we reported the importance of intermolecular metal–ligand interaction of ZnSalen on the aggregation and even cellular uptake pathway of ZnSalen . In this work, we performed dynamic light scattering (DLS) to assess the hydrodynamic diameter (ca.…”

Section: Methodsmentioning

confidence: 99%

Precise Labeling and Tracking of Lipid Droplets in Adipocytes Using a Luminescent ZnSalen Complex

Tang

Zhang

Yin

et al. 2017

Chemistry An Asian Journal

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Designing two-photon probes for precise labeling of lipid droplets (LDs) and monitoring LD dynamics in adipocytes is of great significance to understand LD homeostasis. We herein report that a luminescent metal complex LD-TPZn can specifically image LDs in adipose cells and tissue using one- or two-photon fluorescence microscopy. Importantly, LD-TPZn exhibited higher specificity to LDs than the commercial dyes Nile Red and Bodipy 493/503, probably due to different cellular uptake pathways, that is, clathrin-mediated endocytosis and non-selectively passive diffusion, respectively. More importantly, LD-TPZn can be applied as a two-photon LD probe to image adipose tissue, one of the most challengeable tissues for traditional one-photon fluorescence microscope imaging due to the strong light scattering. Most importantly, LD-TPZn can be used to monitor LD growth during adipogenesis of preadipocytes, which is highly desirable to unravel the relationship between LD homeostasis and metabolic diseases.

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Unravelling the correlation between metal induced aggregation and cellular uptake/subcellular localization of Znsalen: an overlooked rule for design of luminescent metal probes

Abstract: We demonstrate the importance of speciation of luminescent metal complexes in water on biological behaviours such as cellular uptake and subcellular localization.

Cited by 54 publications

References 66 publications

Unexpected Structure of a Helical N₄‐Schiff‐Base Zn(II) Complex and Its Demetallation: Experimental and Theoretical Studies

Unexpected Structure of a Helical N₄‐Schiff‐Base Zn(II) Complex and Its Demetallation: Experimental and Theoretical Studies

Rational Design of Fluorescent Phthalazinone Derivatives for One‐ and Two‐Photon Imaging

Precise Labeling and Tracking of Lipid Droplets in Adipocytes Using a Luminescent ZnSalen Complex

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Unravelling the correlation between metal induced aggregation and cellular uptake/subcellular localization of Znsalen: an overlooked rule for design of luminescent metal probes

Abstract: We demonstrate the importance of speciation of luminescent metal complexes in water on biological behaviours such as cellular uptake and subcellular localization.

Cited by 54 publications

References 66 publications

Unexpected Structure of a Helical N4‐Schiff‐Base Zn(II) Complex and Its Demetallation: Experimental and Theoretical Studies

Unexpected Structure of a Helical N4‐Schiff‐Base Zn(II) Complex and Its Demetallation: Experimental and Theoretical Studies

Rational Design of Fluorescent Phthalazinone Derivatives for One‐ and Two‐Photon Imaging

Precise Labeling and Tracking of Lipid Droplets in Adipocytes Using a Luminescent ZnSalen Complex

Contact Info

Product

Resources

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Unexpected Structure of a Helical N₄‐Schiff‐Base Zn(II) Complex and Its Demetallation: Experimental and Theoretical Studies

Unexpected Structure of a Helical N₄‐Schiff‐Base Zn(II) Complex and Its Demetallation: Experimental and Theoretical Studies