Synthesis of a series of ethylene glycol modified water-soluble tetrameric TPE-amphiphiles with pyridinium polar heads: Towards applications as light-up bioprobes in protein and DNA assay, and wash-free imaging of bacteria

Kumar, Vikash; Naik, Viraj G.; Das, Avijit; Bal, Sourayan Basu; Biswas, Malabika; Kumar, Nupur; Ganguly, Anasuya; Chatterjee, Amrita; Banerjee, Mainak

doi:10.1016/j.tet.2019.05.044

Cited by 12 publications

(13 citation statements)

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“…Formation of the Three-Component Supramolecular Sensing Assembly. As reported earlier, 38 the TPEHP is highly soluble in water and shows minimal fluorescence output from an aqueous solution (Figure 2a). The high aqueous solubility of TPEHP is ensured by the presence of ethylene glycol units and the pyridyl polar head groups.…”

Section: ■ Results and Discussionsupporting

confidence: 80%

“…The water-soluble TPE amphiphile (TPEHP) was synthesized using our previously reported procedures. 38 In brief, TPE-hex-EG with four glycol arms was first synthesized by reacting TPE-tetra-OH with a monoiodide derivative of hexaethylene glycol in good yield (Scheme S1, SI). This compound, on further reaction with mesyl chloride and then with sodium iodide, was converted into the corresponding iodide derivative; finally, the iodide derivative was refluxed with excess pyridine to give the desired tetrameric TPE amphiphile (TPEHP) in overall good yields.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The water-soluble AIE probe, TPEHP, was synthesized by a three-step synthetic procedure from tetrahydroxy-TPE using our previously reported procedures. 38 Cucurbit [6]uril was synthesized adopting a literature known procedure. 65 CB [6] was further converted into CB [6]OH using potassium persulfate.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Solid-Supported Amplification of Aggregation Emission: A Tetraphenylethylene–Cucurbit[6]uril@Hydroxyapatite-Based Supramolecular Sensing Assembly for the Detection of Spermine and Spermidine in Human Urine and Blood

Naik

Kumar

Bhasikuttan

et al. 2021

ACS Appl. Bio Mater.

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The development of sensitive and selective tools for the detection and quantification of biomarkers is important in the diagnosis and treatment of clinical diseases. Spermine (SP) and spermidine (SPD) act as biomarkers for early-stage diagnosis of cancer in humans as their increased levels in urine are indicative of abnormal biological processes associated with this fatal disease. In this study, we introduced a strategy for solid-supported amplification of the effective aggregation-induced-emission (AIE) effect of a water-soluble tetraphenylethylene (TPE)-based probe in developing a supramolecular sensing platform for the rapid, sensitive, and selective detection of SP and SPD in water. The nonemissive TPE derivative (TPEHP) forms a less emissive conjugate with hydroxyl cucurbit[6]uril (CB[6]OH) in water, which undergoes several-fold enhancement of effective emission upon electrostatic interaction with the solid surface of hydroxyapatite nanoparticles (HAp NPs), dispersed in the aqueous media. The corresponding three-component supramolecular assembly disrupts by the intrusion of SP and SPD in the CB[6] portal because of the stronger binding ability with CB[6], resulting in a turn-off fluorescence sensor for SP and SPD with enhanced sensitivity. The assembly–disassembly-based sensing mechanism was thoroughly demonstrated by carrying out isothermal titration calorimetry (ITC), spectroscopic, and microscopic experiments. The sensing system showed low limits of detection (LODs) of 1.4 × 10–8 and 3.6 × 10–8 M for SP and SPD, respectively, which are well below the required range for the early diagnosis of cancer. Besides, a good linear relationship was obtained for both SP and SPD. Nominal interference from various metal ions, anions, common chemicals, amino acids, and other biogenic amines makes this sensing platform suitable for the real-time, low-level measurement of spermine (and spermidine) in human urinary and blood samples.

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Section: ■ Results and Discussionsupporting

confidence: 80%

Section: ■ Results and Discussionmentioning

confidence: 99%

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Solid-Supported Amplification of Aggregation Emission: A Tetraphenylethylene–Cucurbit[6]uril@Hydroxyapatite-Based Supramolecular Sensing Assembly for the Detection of Spermine and Spermidine in Human Urine and Blood

Naik

Kumar

Bhasikuttan

et al. 2021

ACS Appl. Bio Mater.

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“…No significant mammalian cell cytotoxicity and binding by TPETH-2Zn to the mammalian cells was observed, whereas the bacterial killing efficiency was more than 95% at the same concentration. 61 , 78 , 79 This could be due to the selective binding affinities of the AIEgens toward bacteria. Moreover TPETH-2Zn is very selective toward targeted pathogenic bacteria than the nonpathogenic bacteria present in the solution for photoinactivation.…”

Section: Toxicology Aspects Of Aiegensmentioning

confidence: 99%

Advances in aggregation induced emission (AIE) materials in biosensing and imaging of bacteria

Maruthi

Kalangi

2021

Progress in Molecular Biology and Translational Science

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“…A similar dependence of the efficiency of interaction of molecules with DNA on the length of oxyethylated fragments was previously shown in several works. [36,37] Presumably, longer oxyethylated fragments interact more efficiently with DNA base pairs via hydrogen bonding.…”

Section: Interaction Of Egm-tca-cn With Calf Thymus Dnamentioning

confidence: 99%

Amphiphilic N-Oligoethyleneglycol-imidazolium Derivatives of p-tert-Butylthiacalix[4]arene: Synthesis, Aggregation and Interaction with DNA

Gafiatullin¹,

Radaev²,

Osipova³

et al. 2021

MHC

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New water-soluble derivatives of p-tert-butylthiacalix [4]arene have been synthesized in the stereoisomeric form 1,3-alternate with butyl and tetradecyl groups on one side of the macrocyclic platform and tri/tetraethylene glycol substituents on the other. The aggregation characteristics of macrocycles in the aquatic environment (CAC, aggregate size, zeta potential) have been studied. It has been demonstrated that the resulting aggregates have the ability to solubilize the lipophilic azo dye Orange OT, and the solubilizing ability significantly increases on going from butyl to tetradecyl derivatives. Using the methods of dynamic and electrophoretic light scattering and fluorimetry with ethidium bromide as a probe, it was shown that the obtained macrocycles interact with the DNA of the calf thymus. It was found that the efficiency of the interaction is greatly influenced by the length of the oxyethyl fragments: macrocycles containing tetraethylene glycol fragments are more effective than triethylene glycol analogs, causing a 2-fold compaction of DNA.

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Synthesis of a series of ethylene glycol modified water-soluble tetrameric TPE-amphiphiles with pyridinium polar heads: Towards applications as light-up bioprobes in protein and DNA assay, and wash-free imaging of bacteria

Cited by 12 publications

References 70 publications

Solid-Supported Amplification of Aggregation Emission: A Tetraphenylethylene–Cucurbit[6]uril@Hydroxyapatite-Based Supramolecular Sensing Assembly for the Detection of Spermine and Spermidine in Human Urine and Blood

Solid-Supported Amplification of Aggregation Emission: A Tetraphenylethylene–Cucurbit[6]uril@Hydroxyapatite-Based Supramolecular Sensing Assembly for the Detection of Spermine and Spermidine in Human Urine and Blood

Advances in aggregation induced emission (AIE) materials in biosensing and imaging of bacteria

Amphiphilic N-Oligoethyleneglycol-imidazolium Derivatives of p-tert-Butylthiacalix[4]arene: Synthesis, Aggregation and Interaction with DNA

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