Synthesis, characterization, aggregation-induced enhanced emission and solvatochromic behavior of dimethyl 4′-(diphenylamino)biphenyl-3,5-dicarboxylate: experimental and theoretical studies

Karaman, Merve; Demir, Nuriye; Bilgili, Hakan; Yakalı, Gül; Gokpek, Yenal; Demiç, Şerafettin; Kaya, Nusret; Can, Mustafa

doi:10.1039/d0nj01720e

Cited by 4 publications

(2 citation statements)

References 37 publications

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“…Steady increase in fluorescence intensity (up to ca . 40 % f w ) is characteristic of aggregation‐induced enhanced emission (AIEE) [23] and subsequent decrease in intensity is consistent with polarity‐induced quenching [11g,11,23a–e] . From f w =60 %, the latter effect overcomes the AIEE and suppresses the emission.…”

Section: Resultsmentioning

confidence: 57%

Photophysical Characteristics of Polarity‐Sensitive and Lipid Droplet‐Specific Phenylbenzothiadiazoles

et al. 2021

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In this study, we present a series of solvatochromic phenylbenzothiadiazoles that display dual emission from the locally excited (LE) and intramolecular charge transfer (ICT) excited states. The donor-acceptor derivatives are highly sensitive to polarity changes, which can be monitored by differences in emission efficiency, spectroscopic shifts and variations of the LE/ICT ratio. One of the compounds in the series, containing a thiomethyl substituent, emerged as an excellent blue emitting stain for intracellular lipid droplets, a biomarker for various types of cancer. In addition, a non-emissive nitro derivative becomes fluorescent upon bioreduction in hypoxic cancer cells and accumulates in lipid droplets with a high signal-to-background ratio.

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Section: Resultsmentioning

confidence: 57%

Photophysical Characteristics of Polarity‐Sensitive and Lipid Droplet‐Specific Phenylbenzothiadiazoles

et al. 2021

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“…However, other solvent properties can also play a role. The observed results align with prior studies of solvatochromism in AIE molecules. − …”

Section: Resultsmentioning

confidence: 99%

Detecting Disruption of HER2 Membrane Protein Organization in Cell Membranes with Nanoscale Precision

Moradi,

Lee,

Armani

2023

ACS Sens.

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The spatiotemporal organization of proteins within the cell membrane can affect numerous biological functions, including cell signaling, communication, and transportation. Deviations from normal spatial arrangements have been observed in various diseases, and a better understanding of this process is a key stepping stone to advancing development of clinical interventions. However, given the nanometer length scales involved, detecting these subtle changes has primarily relied on complex super-resolution and single-molecule imaging methods. In this work, we demonstrate an alternative fluorescent imaging strategy for detecting protein organization based on a material that exhibits a unique photophysical behavior known as aggregation-induced emission (AIE). Organic AIE molecules have an increase in emission signal when they are in close proximity, and the molecular motion is restricted. This property simultaneously addresses the high background noise and low detection signal that limit conventional widefield fluorescent imaging. To demonstrate the potential of this approach, the fluorescent molecule sensor is conjugated to a human epidermal growth factor receptor 2 (HER2)-specific antibody and used to investigate the spatiotemporal behavior of HER2 clustering in the membrane of HER2-overexpressing breast cancer cells. Notably, the disruption of HER2 clusters in response to an FDA-approved monoclonal antibody therapeutic (Trastuzumab) is successfully detected using a simple widefield fluorescent microscope. While the sensor demonstrated here is optimized for sensing HER2 clustering, it is an easily adaptable platform. Moreover, given the compatibility with widefield imaging, the system has the potential to be used with high-throughput imaging techniques, accelerating investigations into membrane protein spatiotemporal organization.

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Diacylated 1,10‐diaza‐18‐crown‐6 as an Alternative Template for Fluorescent Sensors of Calcium Ions

Smith,

Anene,

Wheeler

2024

Analytical Science Advances

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The performance of many known fluorescent sensors for Ca2+ is pH‐dependent. We set out to address this by preparing a novel calcium sensor based on diacylated 1,10‐diaza‐18‐crown‐6 and containing no basic centres. The sensor is sensitive to sub‐millimolar levels of Ca2+ and partially tolerant of an aqueous environment. However, it suffers from a lack of selectivity over some other divalent cations, and retained pH sensitivity in the acidic range. The relations between these properties and the sensor's structure are discussed.

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Synthesis, characterization, aggregation-induced enhanced emission and solvatochromic behavior of dimethyl 4′-(diphenylamino)biphenyl-3,5-dicarboxylate: experimental and theoretical studies

Abstract: Red shift in the emission wavelength by 149 nm as a result of increased solvent polarity.

Cited by 4 publications

References 37 publications

Photophysical Characteristics of Polarity‐Sensitive and Lipid Droplet‐Specific Phenylbenzothiadiazoles

Photophysical Characteristics of Polarity‐Sensitive and Lipid Droplet‐Specific Phenylbenzothiadiazoles

Detecting Disruption of HER2 Membrane Protein Organization in Cell Membranes with Nanoscale Precision

Diacylated 1,10‐diaza‐18‐crown‐6 as an Alternative Template for Fluorescent Sensors of Calcium Ions

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