Solid-state emitting twisted π-conjugate as AIE-active DSE-gen:<i>in vitro</i>anticancer properties against FaDu and 4T1 with biocompatibility and bioimaging

Bhuin, Shouvik; Sharma, Pravesh; Chakraborty, Purbali; Kulkarni, Onkar P.; Chakravarty, Manab

doi:10.1039/d2tb02078e

Cited by 13 publications

(10 citation statements)

References 93 publications

(95 reference statements)

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“…Initially, the cellular uptake of IAT and IAP was investigated by fluorescence-activated cell sorting analysis against the FaDu cell line to understand the nature of the single-cell population. Both displayed commendable cellular uptake . Also, red fluorescent probes are advancing in biomedical research due to their downright capability of deep tissue penetration and different cell organelles’ visualization .…”

Section: Potential Applicationsmentioning

confidence: 99%

“…36 The π-conjugates were synthesized by the Horner− Wadsworth−Emmons reaction (Scheme S1). 17 All these targeted products were well characterized by 1 H/ 13 C NMR and mass spectroscopic studies.…”

Section: Synthetic Pathwaymentioning

confidence: 99%

“…The compound IAT killed FaDu effectively with a GI 50 concentration of 27.21 μM at a 24 h time-point by keeping the normal cells intact (as the GI 50 concentration for the normal cell is more than 100 μM). 17 Now, we attempted to visualize whether this dye could monitor cell deformation as an effect of its anticancer activity. Therefore, after 6 h of staining with IAT, the images of FaDu cells were captured.…”

Section: Wash-free Bioimaging Of Distorting Cancer Cells With Iat In ...mentioning

confidence: 99%

“…15−17 Recently, we reported an analogous DSEgen with a focus on anticancer (FaDu and 4T1) features with biocompatibility and bioimaging applications, resulting in the detection of dead cancer cells and variation with normal cell lines. 17 Molecular rotors with viscosity-sensitive emissions are of advanced priority due to their success in studying protein environments in biological systems, organelle imaging, and even sensing liquid food spoilage. 18−21 Most significantly, earlier reported relevant single molecules failed to display such diverse photophysical properties (see Figure S1 for a few examples and comparison with this report).…”

Section: ■ Introductionmentioning

confidence: 99%

“…Notably, AIE-gens do not typically offer DSE efficacy. Hence, the development of AIE-active DSE-gens is a new thrust area of research with their emission ability in all the phases like solutions, aggregates, and solids and perceives suave applications as optical and biomaterials. − Recently, we reported an analogous DSE-gen with a focus on anticancer (FaDu and 4T1) features with biocompatibility and bioimaging applications, resulting in the detection of dead cancer cells and variation with normal cell lines . Molecular rotors with viscosity-sensitive emissions are of advanced priority due to their success in studying protein environments in biological systems, organelle imaging, and even sensing liquid food spoilage. − Most significantly, earlier reported relevant single molecules failed to display such diverse photophysical properties (see Figure S1 for a few examples and comparison with this report). ,− Although multitasking D-π-A systems with a precise transient dipole moment and charge separation are well recognized by others, , useful donor-π-donor (D-π-D′) systems are merely explored in the literature.…”

Section: Introductionmentioning

confidence: 99%

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Double-Site Twisted D-π-D′ Conjugates with Versatile Photophysical Facets for Diverse Optical Applications and Wash-Free Bioimaging of Cancer Cells

Bhuin

Chakraborty

Sivasakthi

et al. 2023

ACS Appl. Opt. Mater.

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It is still a conundrum to design a single but simple organic molecule possessing numerous realistic photophysical properties such as mechanofluorochromism, aggregation-induced emission (AIE) properties, solvatochromic DSE-gens (dual-state emissive fluorogens), and viscofluorochromism. Unlike D-π-A, D-π-D′ systems are seldom explored with various applied features. This work finds how a single D-π-D′ indole-anthracene conjugate displays all these properties with real-world applications. Especially, an indole-anthracene-π-phenothiazine conjugate (IAP) appears as a solvatochromic (91 nm shift) DSE-gen that shows the longest 62 nm blueshifted enhanced emission on aggregation and the longest 45 nm blueshifted viscofluorochromic features. Furthermore, IAP adopts a fingertip-pressure-sensitive 35 nm blueshift, while a triphenylamine-linked analogue IAT demonstrates a 23 nm mechanofluorochromic redshift. Conformationally twisted backbone and π-conjugations are judiciously balanced to exhibit these optical features. Such diverse and contrasting photophysical facets are elucidated through experimental and detailed timedependent density functional theory investigations to meet rational understandings. These fluorophores are utilized as hidden patent fingerprint memory-based platforms and software-assisted comparison studies to identify counterfeiters. Furthermore, highly sensitive fingertip-aided mechanofluorochromic features are useful for inkless security writing. Besides, wash-free bioimaging of robust oral cancer cells (FaDu) could be accomplished satisfactorily in the green (IAT) and orange-red regions (IAP) with a lower probe concentration. The anticancer property of IAT enables visualization of the progressive distortion of the dying cancer cells during wash-free bioimaging.

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Section: Potential Applicationsmentioning

confidence: 99%

Section: Synthetic Pathwaymentioning

confidence: 99%

Section: Wash-free Bioimaging Of Distorting Cancer Cells With Iat In ...mentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Double-Site Twisted D-π-D′ Conjugates with Versatile Photophysical Facets for Diverse Optical Applications and Wash-Free Bioimaging of Cancer Cells

Bhuin

Chakraborty

Sivasakthi

et al. 2023

ACS Appl. Opt. Mater.

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Novel Dual‐Emission Emitters Featuring Phenothiazine‐S‐Oxide and Phenothiazine‐S,S‐Dioxide Motifs

Zhang,

Yang,

Tan

et al. 2024

Chemistry An Asian Journal

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In this study, we have successfully designed and synthesized two novel dual‐emission emitters featuring phenothiazine‐5‐oxide and phenothiazine‐5,5‐dioxide motifs, characterized by highly lopsided and asymmetric conformational states. Through rigorous spectral examinations and DFT calculations, the compounds exhibit distinctive ICT phenomena, coupled with efficient emission in solid states and AIEE characteristics under high water fractions in DMF/H2O mixtures. These non‐planar luminogens exhibit vibrant green and blue solid‐state luminescence, with fluorescence quantum yields of 24.1% and 15.21%, respectively. Additionally, they both emit green fluorescence in THF solution, with notable emission quantum yields 36.4% and 30.4%. Comprehensive theoretical investigations unveil well‐defined electron cloud density separation between the energies of HOMO/LUMO levels within the two luminogens. Notably, the targeted molecule harboring the phenothiazine‐S,S‐dioxide motif also demonstrates remarkable reversible mechanofluorochromic properties. Moreover, we testify their potential in applications such as solid‐state rewritable information storage and live‐cell imaging in solution states. Through theoretical calculations and comparative studies, we have explored the intrinsic relationship between molecular structure and performance, effectively screening and identifying new fluorescent molecules exhibiting outstanding luminescent attributes. These discoveries establish robust theoretical and technical foundation for the synthesis and application of efficient DSE‐based MFC materials, opening new avenues in the realm of advanced luminescent materials

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A Novel Approach to the Structural Design of Dual‐State Emission Luminogens by Combining Tetraphenylethylene with Anthracene via Dihydroisoxazole

Lu,

Zhao,

Sun

2024

ChemPhotoChem

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Dual‐state emission luminescent materials (DSEgens), which exhibit bright emissions in boththe solid state and solution, have been attracting research interest in the design of multifunctional materials.The delicate manipulation of molecular structures remains challenging in the synthesis of DSEgens. In this article, two novel molecules with dual‐state emission were synthesized by combining tetraphenylethylene with anthracene via dihydroisoxazole. Tetraphenylethylene acts as a solid‐state emitter, while the anthracene core functions as an emitter in the solution state to achieve DSE fluorescence properties. The THF/DCM mixture resulted in successfully obtaining the crystal structures of TPE−An−H and TPE−An−Cl. The quantum yields (QYs) of TPE−An−H were 31 % and 42 % in EA and the solid state, respectively, while TPE−An−Cl exhibited QYs of 32 % and 34 %. The novel synthesis method in this paper combines AIE with ACQ via dihydroisoxazole to achieve dual‐state emission, offering a new and concise approach.

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Solid-state emitting twisted π-conjugate as AIE-active DSE-gen:in vitroanticancer properties against FaDu and 4T1 with biocompatibility and bioimaging

Abstract: Solid state organic fluorogens (SSOF-gens) with aggregation-induced (enhanced) emission (AIEE/AIE) property are currently defining their insistence as the transpiring tool in biological and biomedical applications. This work focuses on designing...

Cited by 13 publications

References 93 publications

Double-Site Twisted D-π-D′ Conjugates with Versatile Photophysical Facets for Diverse Optical Applications and Wash-Free Bioimaging of Cancer Cells

Double-Site Twisted D-π-D′ Conjugates with Versatile Photophysical Facets for Diverse Optical Applications and Wash-Free Bioimaging of Cancer Cells

Novel Dual‐Emission Emitters Featuring Phenothiazine‐S‐Oxide and Phenothiazine‐S,S‐Dioxide Motifs

A Novel Approach to the Structural Design of Dual‐State Emission Luminogens by Combining Tetraphenylethylene with Anthracene via Dihydroisoxazole

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