A Self‐Quenching System Based on Bis‐Naphthalimide: A Dual Two‐Photon‐Channel GSH Fluorescent Probe

Shen, Wei; Ge, Jingyan; He, Siyang; Zhang, Ruoyu; Zhao, Chengyan; Fan, Yong; Yu, Shian; Liu, Bin; Zhu, Qing

doi:10.1002/asia.201700340

Cited by 14 publications

(10 citation statements)

References 38 publications

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“…Conventional fluorescent dyes for nucleoli or mitochondria (lysosomes) staining have been widely developed. − However, poor permeability, poor selectivity, and tedious synthetic steps of most probes have limited their broad applicability in live cell imaging. Hence, the development of efficient probes for live cell imaging that are easy to synthesize, are nontoxic and provide high sensitivity and selectivity is receiving attention, especially the probes that are capable of multicolor imaging for different organelles in live cells.…”

Section: Resultsmentioning

confidence: 99%

“…Enlarged or aberrant nucleolus and the associated number are often indicative of particular types of cancer and other human disorders. , As for mitochondria and lysosomes, their membrane permeabilization constitutes one of the major checkpoints in inducing apoptotic and necrotic cell death. Both of them play pivotal roles in cell life and death. , Nowadays, a lot of mitochondrial (or lysosomal) probes and nucleolar probes have been reported widely for different purposes. − However, to the best of our knowledge, probes with different color emissions for imaging nucleoli and mitochondria (or lysosomes) simultaneously have rarely been reported so far. , Even though fluorophores with different color emissions for cell imaging have been widely reported, ,,,− they either simply show two different colors from the same target or have no specific targets in cell at all. It would be attractive if a single fluorophore can image two or more organelles with distinct emissions at the same time.…”

Section: Introductionmentioning

confidence: 99%

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Cationic Organochalcogen with Monomer/Excimer Emissions for Dual-Color Live Cell Imaging and Cell Damage Diagnosis

Chao

Wang

Sun

et al. 2018

ACS Appl. Mater. Interfaces

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Studies on the development of fluorescent organic molecules with different emission colors for imaging of organelles and their biomedical application are gaining lots of focus recently. Here, we report two cationic organochalcogens 1 and 2, both of which exhibit very weak green emission (Φ = 0.12%; Φ = 0.09%) in dilute solution as monomers, but remarkably enhanced green emission upon interaction with nucleic acids and large red-shifted emission in aggregate state by the formation of excimers at high concentration. More interestingly, the monomer emission and excimer-like emission can be used for dual color imaging of different organelles. Upon passively diffusing into cells, both probes selectively stain nucleoli with strong green emission upon 488 nm excitation, whereas upon 405 nm excitation, a completely different stain pattern by staining lysosomes (for 1) or mitochondria (for 2) with distinct red emission is observed because of the highly concentrated accumulation in these organelles. Studies on the mechanism of the accumulation in lysosomes (for 1) or mitochondria (for 2) found that the accumulations of the probes are dependent on the membrane permeabilization, which make the probes have great potential in diagnosing cell damage by sensing lysosomal or mitochondrial membrane permeabilization. The study is demonstrative, for the first time, of two cationic molecules for dual-color imaging nucleoli and lysosomes (1)/mitochondria (2) simultaneously in live cell based on monomer and excimer-like emission, respectively, and more importantly, for diagnosing cell damage.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cationic Organochalcogen with Monomer/Excimer Emissions for Dual-Color Live Cell Imaging and Cell Damage Diagnosis

Chao

Wang

Sun

et al. 2018

ACS Appl. Mater. Interfaces

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“…The first generation of reactivity-based organic bioprobes has served as reliable tools for probing living systems through their analytical sensing and optical imaging capabilities. Since their emergence, reactivity-based bioprobes have been designed to detect a plethora of biological analytes (e.g., chymase, gluthathione (GSH), and other intracellular thiols), − radicals and toxins (e.g., hydrazine, 1 O 2 , and H 2 O 2 ), − as well as biomolecular and enzymatic activities (e.g., alkaline phosphatase activity, β-galactosidase activity, lysosomal esterase, and cell-surface proteolytic activity) − in complex biological systems. In one of our initial attempts to construct reactivity-based organic biosensors, we developed a cleavage-based caspase-reactive light-up probe for continuous imaging and monitoring of cell apoptosis in real time (reactivity-based bioprobe type 1) (Figure ).…”

Section: Reactivity-based Organic Biosensing/imaging Probesmentioning

confidence: 99%

Reactivity-Based Organic Theranostic Bioprobes

2019

Self Cite

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Conspectus Reactivity-based organic bioprobes have been increasingly designed and developed in the last couple of years to address important questions in numerous fields, particularly in biology and medicine. Contrary to the conventional lock-and-key bioprobes, which rely on molecular recognition to probe biological systems and impart sensing specificity, reactivity-based bioprobes capitalize on molecular reactivity for selective target detection. In fact, reactivity-based sensing exploits the intrinsic differences in chemical reactivity to differentiate various chemical species possessing similar size and shape in biological systems. This unique sensing mechanism has been effective for the detection of a wide range of chemical analytes in living cells, tissues, and animals, although bioprobes with additional functionalities are increasingly required in the quest to unravel and understand the complex biological systems. This is why the integration of diagnostic and therapeutic functions in one theranostic platform has become a continuous pursuit in the development of bioprobes in recent years. To this end, numerous design and synthetic approaches have been explored, notably that combining different organic materials with distinct functionalities into one integrated system, also known as “all-in-one” strategy. Nevertheless, the “all-in-one” strategy is prone to design complexity and unsatisfactory reproducibility. To minimize these undesirable hurdles, the deliberate design and engineering of simple organic molecules with multiple functionalities have been actively pursued, leading to the emergence of a unique approach known as “one-for-all” strategy. A prominent example of this approach leverages on fluorogens with aggregation-induced emission (AIE) characteristic. Through smart molecular engineering, we and other groups have recently shown that conventional organic AIE fluorogens can be specifically tailored to offer both imaging and therapeutic functionalities, such as photosensitizing ability to facilitate photodynamic therapy. The creation of this new class of versatile organic theranostic bioprobes with simultaneous imaging and therapeutic capabilities has further enabled image-guided chemotherapy and image-guided photodynamic therapy. Essentially, from this endeavor, replacing the fluorophores of conventional reactivity-based bioprobes with multifunctional molecules will yield reactivity-based organic theranostic bioprobes with enhanced capabilities and improved performance. In this Account, we summarize the latest advancement of reactivity-based theranostic bioprobes. To start with, we discuss the fundamental differences between conventional lock-and-key and reactivity-based sensing mechanisms, followed by general design routes of reactivity-based organic theranostic bioprobes. We then describe our efforts in recent years in formulating reactivity-based organic biosensing/imaging probes and multifunctional theranostic probes as well as in utilizing these bioprobes in detecting various chemical species in l...

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“…Among those, however, reduction responsive NI organogels are rarely covered in the reported works to date. Given that reductants such as dithiothreitol (DTT) [31] and glutathione (GSH) [32] widely exist in nature and play significant roles in industry and biological processes, the development of reduction responsive organogels bears huge potential in applications of sensing and detection.…”

Section: Introductionmentioning

confidence: 99%

Gallic‐Acid‐Modified Naphthalimide Containing Disulfide Bond as Reduction‐Responsive Supramolecular Organogelator

et al. 2022

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The development of low molecular‐weight gelators for the construction of stimuli‐responsive gels is increasing attention because of the great application potential. In this work, we report the design and synthesis of two new naphthalimide derivatives, GSSN and GN, as supramolecular organogelators. GSSN contains a disulfide bond in the molecule, while GN contains no disulfide bond. As a result, only GSSN exhibited reduction responsiveness. A series of tests, including UV‐vis, temperature‐dependent 1H NMR, XRD, and SEM, were carried out to characterize the gelation capability and probe into the gelation mechanism. Results showed that GN can gelate more organic solvents than GSSN. Both hydrogen bonding and π stacking contribute to the gelation. Due to the difference in the assembly of the organogelator molecules, the organogels formed by GSSN and GN presented distinct morphologies. Moreover, strong hydrophobicity was found in the organogel films of GSSN and GN, suggesting potential application as hydrophobic coating materials.

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A Self‐Quenching System Based on Bis‐Naphthalimide: A Dual Two‐Photon‐Channel GSH Fluorescent Probe

Cited by 14 publications

References 38 publications

Cationic Organochalcogen with Monomer/Excimer Emissions for Dual-Color Live Cell Imaging and Cell Damage Diagnosis

Cationic Organochalcogen with Monomer/Excimer Emissions for Dual-Color Live Cell Imaging and Cell Damage Diagnosis

Reactivity-Based Organic Theranostic Bioprobes

Gallic‐Acid‐Modified Naphthalimide Containing Disulfide Bond as Reduction‐Responsive Supramolecular Organogelator

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