Supramolecular effect of curcurbit[7]uril on the binding mode of 2-(4-(dimethylamino) styryl)-1-methylpyridinium iodide with Calf Thymus DNA: From minor groove to intercalative

Manna, A. La; Chakravorti, S.

doi:10.1016/j.saa.2015.05.035

Cited by 11 publications

(10 citation statements)

References 39 publications

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“…The dissolution time of both PAAS and HPAM was evaluated at different concentrations [Figure (c)]. As expected, the dissolution time of PAAS was much shorter than HPAM within the entire concentration range, which might be ascribed to the ionization of styryl‐pyridinium structure facilitated the water solubility of PAAS …”

Section: Resultsmentioning

confidence: 99%

“…Following our interest, herein we further explored a series of water‐soluble fluorescent polymers based on styryl‐pyridinium salt monomers (SP‐ n , n = 2, 4, 6, 8, 10) with different substituted alkyl, which displayed extremely adjustable water solubility and distinctive fluorescent property. The styryl derivatives have been widely studied in organic nonlinear optical materials, molecular electronics, Langmuir film, and DNA binders because of their excellent optical properties. Usually, the pyridinium or ammonium salts are introduced into structures to improve the water solubility for biological applications owing to their salt effect, such as DNA and RNA probes .…”

Section: Introductionmentioning

confidence: 99%

“…The styryl derivatives have been widely studied in organic nonlinear optical materials, molecular electronics, Langmuir film, and DNA binders because of their excellent optical properties. Usually, the pyridinium or ammonium salts are introduced into structures to improve the water solubility for biological applications owing to their salt effect, such as DNA and RNA probes . However, it is the first time that the styryl‐pyridinium salt was introduced into the water‐soluble fluorescent polymer for detecting polymer concentration.…”

Section: Introductionmentioning

confidence: 99%

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The design and properties study of a novel styryl‐pyridinium‐based water‐soluble fluorescent copolymer as tracing agent

Yan

Shen

et al. 2018

J of Applied Polymer Sci

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A water-soluble fluorescent copolymer poly(acrylamide-acrylic acid-styrene pyridinium) (PAAS) for detecting polymer concentration in real time was synthesized via micellar free-radical polymerization by acrylamide, acrylic acid, and styryl-pyridinium salt derivative (SP-4). The special Donor-π-Acceptor unit and ionic structure of SP-4 endued the copolymer with excellent fluorescent properties and remarkable water solubility. The fluorescent copolymer was fully characterized by Fourier transform infrared, 1 H nuclear magnetic resonance, thermogravimetry, Ubbelohde viscosity, ultraviolet-visible spectroscopy, and fluorescence measurements. Furthermore, the fluorescence intensity and the concentration of PAAS were verified to have ideal linear relationship with a correlation coefficient up to 0.9993, indicating that the copolymer's concentration can be easily measured by detecting its fluorescence intensity. Most importantly, the introduction of water-soluble fluorescent monomer SP-4 endowed the PAAS with good fluorescent stability in a wide range of temperature, pH, and brine concentrations. This study demonstrated that the fluorescent copolymer PAAS exhibits great potential application in detecting polymer concentration in various environments. Trans-4-[p-(N,N-diethyl) amino-styryl]-N-allyl pyridinium bromide (SP-2). Yield 50%. 1 H NMR (400 MHz, CDCl 3 ) δ: 8.74 (d, J = 6.4 Hz, 2H), 7.84 (d, J = 5.1 Hz, 2H), 7.63 (d, J = 15.8 Hz, 1H), 7.49 (d, J = 7.2 Hz, 2H), 6.80 (d, J = 15.7 Hz, 1H), 6.62 (d, J = 7.2 Hz, 2H), 6.01(m, 1H), 5.46 (d, J = 17.6 Hz, 1H), 5.42 (d, J = 10.8 Hz, 1H), 5.28 (d, J = 5.4 Hz, 2H), 3.38 (t, 4H), 1.16 (q, J = 5.2 Hz, 6H). MS [ESI-time of flight (TOF)] calcd for [C 20 H 25 N 2 ] + [M-Br] + 293.2012, found 293.2009. Trans-4-[p-(N,N-dibutyl) amino-styryl]-N-allyl pyridinium bromide (SP-4). Yield 55%. 1 H NMR (400 MHz, CDCl 3 ) δ: 8.85 (d, J = 6.4 Hz, 2H), 7.79 (d, J = 6.5 Hz, 2H), 7.56 (d, J = 15.9 Hz, 1H), 7.47 (d, J = 8.4 Hz, 2H), 6.78 (d, J = 15.8 Hz, 1H), 6.59 (d, J = 8.5 Hz, 2H), 6.00 (m, J = 16.6, 11.3, 6.5 Hz, 1H), 5.48 (d, J = 17.0 Hz, 1H), 5.41 (d, J = 10.1 Hz, 1H), 5.30 (d, J = 6.4 Hz, 2H), 3.28 (t, J = 7.8 Hz, 4H), 1.53 (m, J = 7.6 Hz, 4H), 1.30 (m, J = 7.4 Hz, 4H), 0.92 (q, 6H). MS (ESI-TOF) calcd for [C 24 H 33 N 2 ] + [M-Br] + 349.2638, found 349.2616. Trans-4-[p-(N,N-dihexyl) amino-styryl]-N-allyl pyridinium bromide (SP-6). Yield 39%. 1 H NMR (400 MHz, CDCl 3 ) δ: 8.85 (d, J = 6.5 Hz, 2H), 7.76 (d, J = 6.5 Hz, 2H), 7.55 (d, J = 15.8 Hz, 1H), 7.47 (d, J = 8.5 Hz, 2H), 6.78 (d, J = 15.8 Hz, 1H), 6.60 (d, J = 8.6 Hz, 2H), 6.02 (m, J = 16.5, 10.6, 5.7 Hz, 1H), 5.49 (d, Scheme 2. The synthesis of fluorescent monomers SP-n. ARTICLEWILEYONLINELIBRARY.COM/APP

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The design and properties study of a novel styryl‐pyridinium‐based water‐soluble fluorescent copolymer as tracing agent

Yan

Shen

et al. 2018

J of Applied Polymer Sci

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“…1). 44 However, no unambiguous evidence for the change of the binding mode in this case was provided.…”

Section: Cb-induced Changing Of the Ligand-dna Binding Modementioning

confidence: 86%

Cucurbiturils in nucleic acids research

Chernikova

Berdnikova

2020

Chem. Commun.

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“…This macrocycle has been used in different studies due to its structural dimensions and its high affinity for electron-poor sites ( Assaf and Nau, 2015 ; Macartney, 2018 ). In this context, dialkylamino substituted coumarins or other dialkylamino substituted chromophores have played a leading role in several studies in the presence of CB7, forming stable inclusion complexes on the side of the dialkylamino group in its protonated or deprotonated form ( Barooah et al, 2012 , 2014 ; Manna and Chakravorti, 2015 ; Aliaga et al, 2017 ; Basílio et al, 2017 ; Jana et al, 2019 ; Paudics et al, 2020 ; Alcázar et al, 2021 ). On the other hand, the pyridinium group has also shown a remarkable affinity for CB7 ( Manna and Chakravorti, 2015 ; Jana et al, 2019 ; Paudics et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

Changes in Protonation Sites of 3-Styryl Derivatives of 7-(dialkylamino)-aza-coumarin Dyes Induced by Cucurbit[7]uril

et al. 2022

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The incorporation of a guest, with different basic sites, into an organized system (host), such as macrocycles, could stabilize, detect, or promote the formation of a certain protomer. In this context, this work aimed to study the influence of cucurbit[7]uril (CB7) on dyes such as 7-(dimethylamino)-aza-coumarins, which have more than one basic site along their molecular structure. For this, three 3-styryl derivatives of 7-(dialkylamino)-aza-coumarin dyes (SAC1-3) were synthesized and characterized by NMR, ESI-HRMS and IR. The spectral behaviour of the SACs in the absence and presence of CB7 was studied. The results showed large shifts in the UV-vis spectrum in acid medium: a hypsochromic shift of ≈5400 cm−1 (SAC1-2) and ≈3500 cm−1 (SAC3) in the absence of CB7 and a bathochromic shift of ≈4500 cm−1 (SAC1-3) in the presence of CB7. The new absorptions at long and short wavelengths were assigned to the corresponding protomers by computational calculations at the density functional theory (DFT) level. Additionally, the binding mode was corroborated by molecular dynamics simulations. Findings revealed that in the presence of CB7 the heterocyclic nitrogen was preferably protonated instead of the dialkylamino group. Namely, CB7 induces a change in the protonation preference at the basic sites of the SACs, as consequence of the molecular recognition by the macrocycle.

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Supramolecular effect of curcurbit[7]uril on the binding mode of 2-(4-(dimethylamino) styryl)-1-methylpyridinium iodide with Calf Thymus DNA: From minor groove to intercalative

Cited by 11 publications

References 39 publications

The design and properties study of a novel styryl‐pyridinium‐based water‐soluble fluorescent copolymer as tracing agent

The design and properties study of a novel styryl‐pyridinium‐based water‐soluble fluorescent copolymer as tracing agent

Cucurbiturils in nucleic acids research

Changes in Protonation Sites of 3-Styryl Derivatives of 7-(dialkylamino)-aza-coumarin Dyes Induced by Cucurbit[7]uril

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