Bay functionalized perylenediimide as a deaggregation based intracellular fluorescent probe for perchlorate

Singh, Prabhpreet; Mittal, Lalit Singh; Vanita, Vanita; Kumar, Rahul; Bhargava, Gaurav; Walia, Amandeep; Kumar, Subodh

doi:10.1039/c4cc06765g

Cited by 55 publications

(22 citation statements)

References 34 publications

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“…In continuation of our interesti nf unctionalized PDIs [12][13][14] and self-assembled supramolecular nanostructures, [32][33][34] herein we employ aw ater-soluble cationic perylenediimide derivative (N 1 -dodecyl-N 3 -(4-phenyl)benzimidazolium-functionalized perylenediimide (DAB-PDI)) to construct as imple,f ast, and sensitive ensemble (DAB-PDI-SDS) for the fluorescencet urn-on detection of spermine in water,u rine, and blood serum. Scheme 1d epictst he rationale for the assay strategy.T he DAB-PDI derivativeiss trongly fluorescent (F = 0.55) and forms nanoaggregates with diameters of 40-80 nm in a1 :1 mixture of H 2 O/CH 3 CN.…”

Section: Introductionmentioning

confidence: 89%

“…All data was further processed by using the instrument software to plot enthalpy change (Δ H in kcal) per mole of injectant against the molar ratio. PDI 1 and 2 were prepared by procedures reported earlier by our group …”

Section: Methodsmentioning

confidence: 99%

“…In continuation of our interest in functionalized PDIs and self‐assembled supramolecular nanostructures, herein we employ a water‐soluble cationic perylenediimide derivative ( N 1 ‐dodecyl‐ N 3 ‐(4‐phenyl)benzimidazolium‐functionalized perylenediimide ( DAB‐PDI )) to construct a simple, fast, and sensitive ensemble ( DAB‐PDI –SDS) for the fluorescence turn‐on detection of spermine in water, urine, and blood serum. Scheme depicts the rationale for the assay strategy.…”

Section: Introductionmentioning

confidence: 99%

“…Perylene diimides( PDIs),w hich form an interesting class of functional organicd yes, have been used as high-performance pigments, [10,11] supramolecularh osts, [12][13][14][15][16][17] and in optoelectronic devices. [18,19] The functionalization of PDIs at bay-, peri-, ortho-, and N-terminal positions is being performed to increaset he solubility of PDIs in organic solvents.…”

Section: Introductionmentioning

confidence: 99%

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Ionic Self‐Assembled Platform of Perylenediimide–Sodium Dodecylsulfate for Detection of Spermine in Clinical Samples

Singh

Mittal

Bhargava

et al. 2017

Chemistry An Asian Journal

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The detection and quantification of spermine in clinical practice is important for early diagnosis of many diseases. Chromatographic and immunoassay-based methods are commonly used. However, a fluorescence-based assay could provide real-time detection. Herein, the synthesis and aggregation properties of a dicationic perylene probe (N -dodecyl-N -(4-phenyl)benzimidazolium-functionalized perylenediimide (DAB-PDI)) used to develop a fluorescent "turn-on" ensemble for the detection of spermine are discussed. The fluorescence of DAB-PDI (10 μm, Φ=0.55) is efficiently quenched by negatively charged sodium dodecylsulfate (SDS) through the formation of ionic self-assembled aggregates (charge ratio of negative (N) in SDS to positive (P) in DAB-PDI (N/P)=9). This negatively charged ionic self-assembly between DAB-PDI and SDS has been characterized by using photophysical, microscopic, dynamic light scattering, isothermal titration calorimetry, and HRMS techniques. The addition of spermine to this ensemble solution results in the breakdown of the DAB-PDI-SDS ensemble owing to strong binding of spermine with SDS and, as a result, the fluorescence of DAB-PDI is recovered. This ensemble exhibits high sensitivity and selectivity for spermine detection in water, urine, and blood serum. The lowest limit of detection is 27.5 nm, which is at least about 36 times lower than that required for early diagnosis of cancer (1 to 10 μm for urinary spermine).

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Section: Introductionmentioning

confidence: 89%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Ionic Self‐Assembled Platform of Perylenediimide–Sodium Dodecylsulfate for Detection of Spermine in Clinical Samples

Singh

Mittal

Bhargava

et al. 2017

Chemistry An Asian Journal

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“…Recently, we reported assembly‐disassembly driven selective and sensitive detection of Cu 2+ , Pd 0 /Pd 2+ , ClO 4 − and picric acid . In continuation of our interest in assembly‐disassembly based chemosensing probes, herein, we report disassembly based AIEgen 1 for the detection of Cu 2+ in water, blood serum and complicated environmental (tap, pond and industrial waste water) samples.…”

Section: Introductionmentioning

confidence: 99%

Nanomolar Cu²⁺Detection in Water Based on Disassembly of AIEgen: Applications in Blood Serum, Cell Imaging and Complex Logic Circuits

Singh

Vanita

et al. 2016

ChemistrySelect

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Here in, we report self‐assembled aggregates of AIEgen 1, which exhibits excited state intramolecular proton transfer (ESIPT) coupled aggregation induced emission (AIE) with intense green fluorescence (λem=526 nm) in aqueous solution as well as in solid state. AIEgen 1 behaves as disassembly based fluorescent probe for selective and sensitive detection of Cu2+ in drinking water with lowest limit of detection of 0.261 ppb (4.13 nM) (much lower than recommended by EPA). AIEgen 1 finds applications for the detection of Cu2+ in blood serum, environmental (tap, pond and industrial waste water) samples. Probably the interaction of Cu2+ ions at Schiff‐base unit of AIEgen 1 via metal chelation disrupts the self‐assembled aggregates and results in disassembly of the nanorods into smaller spherical nanostructures as also evidenced in DLS, SEM and TEM studies. Incubation of HeLa cells with AIEgen 1 results in fluorescence ‘switch‐on’ showing cell internalization of AIEgen 1 with low cytotoxicity and thus establishes the potential of AIEgen 1 in cell imaging. The reversibility influorescence / absorbance of 1‐Cu2+ complex with EDTA helps in elaboration of various reconfigurable and superposed logic gates such as NOT (at F425, A380), INH (at A430), IMP1 (at A380) and IMP2 (at F526). By observing the output switching in absorbance and fluorescence channels on addition of Cu2+ (In1) and EDTA (In2) as inputs, ‘set‐ reset’ flip flop memory element and complementary IMP/INH logic circuits have been elaborated.

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A family of oligo(p‐phenylenevinylene) derivative aggregation‐induced emission probes: Ultrasensitive, rapid, and anti‐interfering fluorescent sensing of perchlorate via precise alkyl chain length modulation

Xiao

et al. 2022

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The precise regulation of interactions provided by aggregation‐induced emission (AIE) probes is of considerable significance for improving the sensing performance in the field of on‐site detection. Here, a highly sensitive perchlorate detection probe was designed by precisely modulating the van der Waals interactions by adjusting the length of the alkyl chain. The optimized AIE probe demonstrated superior perchlorate detection performance owing to its strong van der Waals interactions with perchlorate, including a low detection limit (53.81 nM), rapid response (<5 s), and excellent specificity even in the presence of 16 interfering anions. In addition, a hydrogel‐based device loaded with the probe was constructed to achieve ultrasensitive recognition of perchlorate particles with a detection limit as low as 15 fg under a fluorescence microscope. Moreover, the practicality of the probe was further verified by employing a sensing chip in a portable detector, and thus the probe has been proven to be highly promising for trace perchlorate monitoring in real scenarios. We expect the present study to be of great value for the efficient design of high‐performance fluorescent probes.

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Bay functionalized perylenediimide as a deaggregation based intracellular fluorescent probe for perchlorate

Cited by 55 publications

References 34 publications

Ionic Self‐Assembled Platform of Perylenediimide–Sodium Dodecylsulfate for Detection of Spermine in Clinical Samples

Ionic Self‐Assembled Platform of Perylenediimide–Sodium Dodecylsulfate for Detection of Spermine in Clinical Samples

Nanomolar Cu²⁺Detection in Water Based on Disassembly of AIEgen: Applications in Blood Serum, Cell Imaging and Complex Logic Circuits

A family of oligo(p‐phenylenevinylene) derivative aggregation‐induced emission probes: Ultrasensitive, rapid, and anti‐interfering fluorescent sensing of perchlorate via precise alkyl chain length modulation

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Bay functionalized perylenediimide as a deaggregation based intracellular fluorescent probe for perchlorate

Cited by 55 publications

References 34 publications

Ionic Self‐Assembled Platform of Perylenediimide–Sodium Dodecylsulfate for Detection of Spermine in Clinical Samples

Ionic Self‐Assembled Platform of Perylenediimide–Sodium Dodecylsulfate for Detection of Spermine in Clinical Samples

Nanomolar Cu2+Detection in Water Based on Disassembly of AIEgen: Applications in Blood Serum, Cell Imaging and Complex Logic Circuits

A family of oligo(p‐phenylenevinylene) derivative aggregation‐induced emission probes: Ultrasensitive, rapid, and anti‐interfering fluorescent sensing of perchlorate via precise alkyl chain length modulation

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Nanomolar Cu²⁺Detection in Water Based on Disassembly of AIEgen: Applications in Blood Serum, Cell Imaging and Complex Logic Circuits