Spectroscopic, calorimetric, cyclic voltammetric and molecular modeling studies of new methylene blue-polyadenylic acid interaction and comparison to thionine and toluidine blue O: Understanding self-structure formation by planar dyes

Paul, Puja; Mati, Soumya Sundar; Bhattacharya, Sumanta; Kumar, Gopinatha Suresh

doi:10.1016/j.dyepig.2016.08.027

Cited by 14 publications

(15 citation statements)

References 101 publications

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“…It is known that poly(A) has the unique capability of transforming from ss to ds conformation in a narrow pH range . Previously, many small molecules have been reported to induce such ss to ds conformational change at physiological pH . In this study, the self‐structure of poly(A) was assumed to be an antiparallel duplex on the basis of cooperative CD melting, differential scanning calorimetry, and UV absorbance melting profile results (Figure 6A,B).…”

Section: Resultsmentioning

confidence: 96%

“…60,61 Previously, many small molecules have been reported to induce such ss to ds conformational change at physiological pH. [62][63][64][65][66] In this study, the self-structure of poly(A) was assumed to be an antiparallel duplex on the basis of cooperative CD melting, differential scanning calorimetry, and UV absorbance melting profile results ( Figure 6A,B). The ratio of the calorimetric and van't Hoff enthalpy derived from the differential scanning calorimetry melting profile was near unity, indicating a 2state transition without any intermediate state for the melting of the self-structure of harmaline-induced poly(A) complex.…”

Section: Itc Analysis Of the Harmaline-nucleic Acid Complexmentioning

confidence: 91%

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Binding affinity and in vitro cytotoxicity of harmaline targeting different motifs of nucleic acids: An ultimate drug designing approach

Bhattacharjee

Ghosh

Sarkar

et al. 2017

J of Molecular Recognition

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The work focuses towards interaction of harmaline, with nucleic acids of different motifs by multispectroscopic and calorimetric techniques. Findings of this study suggest that binding constant varied in the order single-stranded (ss) poly(A) > double-stranded calf thymus (CT) DNA > double-stranded poly(G)·poly(C) > clover leaf tRNA . Prominent structural changes of ss poly(A), CT DNA, and poly(G)· poly(C) with concomitant induction of optical activity in the bound achiral alkaloid molecule was observed, while with tRNA , very weak induced circular dichroism perturbation was seen. The interaction was predominantly exothermic, enthalpy driven, and entropy favored with CT DNA and poly(G)·poly(C), while it was entropy driven with poly(A) and tRNA . Intercalated state of harmaline inside poly(A), CT DNA, and poly(G)·poly(C) was shown by viscometry, ferrocyanide quenching, and molecular docking. All these findings unequivocally pointed out preference of harmaline towards ss poly(A) inducing self-structure formation. Furthermore, harmaline administration caused a significant decrease in proliferation of HeLa and HepG cells with GI of 28μM and 11.2μM, respectively. Nucleic acid fragmentation, cellular ultramorphological changes, decreased mitochondrial membrane potential, upregulation of p53 and caspase 3, generation of reactive oxygen species, and a significant increase in the G /M population made HepG more prone to apoptosis than are HeLa cells.

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Section: Resultsmentioning

confidence: 96%

Section: Itc Analysis Of the Harmaline-nucleic Acid Complexmentioning

confidence: 91%

Binding affinity and in vitro cytotoxicity of harmaline targeting different motifs of nucleic acids: An ultimate drug designing approach

Bhattacharjee

Ghosh

Sarkar

et al. 2017

J of Molecular Recognition

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“…The covalent bonding reaction between GO and NMB was successfully confirmed by UV-Vis, fluorescence, and FT-IR spectroscopy. In Figure 1A , NMB displays a strong absorbance at 629 nm corresponding to the π–π* transition of NMB aromatic chromophore (curve a) ( Paul et al, 2017 , 2020 ). After covalently bonding with GO (curve c), this prominent absorption shifts from 629 to 665 nm, which suggest that the plane of NMB is close to the GO plane and causes π–π stacking interaction between the two conjugate planes.…”

Section: Resultsmentioning

confidence: 99%

New Methylene Blue Covalently Functionalized Graphene Oxide Nanocomposite as Interfacial Material for the Electroanalysis of Hydrogen Peroxide

et al. 2021

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New methylene blue (NMB), a phenothiazine dye, was covalently bonded to graphene oxide (GO) using glutaraldehyde as a crosslinking agent, which was characterized by spectroscopic techniques and electrochemistry. The obtained GO–NMB nanocomposite was used as interface material to construct a novel electrochemical sensor for the determination of hydrogen peroxide (H2O2). The electrochemical sensor based on GO–NMB nanocomposite exhibited excellent electrocatalytic activity for the reduction of hydrogen peroxide (H2O2), which was also enhanced by GO within the GO–NMB nanocomposite. With the optimized experimental conditions, the developed sensor showed high sensitivity (79.4 μA mM−1 cm−2) for electrocatalytic determination of H2O2 at the applied potential of −0.50 V in the concentration range of 0.000333 to 2.28 mΜ. The low limit of detection (1.35 μM), good reproducibility, and high stability of the sensor suggests that the electrochemical sensor based on the GO–NMB nanocomposite possesses obvious advantages, which paves a new avenue to functionalize GO for obtaining electrode interface materials.

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“…The crystals were dried in a vacuum desiccator at room temperature to give spectrally pure dye. 71 The purity of the MB solution was checked by measuring the ratio of the absorbance at 665 nm to that at 610 nm, which was always greater than 2.1, indicating the absence of any demethylated dye in the sample. 72 The concentration of lyz, TBO, and MB was calculated by measuring the absorbance using a molar absorption coefficient (ε) values of 37 750 M –1 cm –1 (280 nm), 33 − 35 30 000 M –1 cm –1 (633 nm), 52 and 76 000 M –1 cm –1 (664 nm), 72 respectively.…”

Section: Methodsmentioning

confidence: 99%

“…The fractions were pooled, concentrated under vacuum, and crystallized. The crystals were dried in a vacuum desiccator at room temperature to give spectrally pure dye . The purity of the MB solution was checked by measuring the ratio of the absorbance at 665 nm to that at 610 nm, which was always greater than 2.1, indicating the absence of any demethylated dye in the sample .…”

Section: Methodsmentioning

confidence: 99%

Comparative Study of Toluidine Blue O and Methylene Blue Binding to Lysozyme and Their Inhibitory Effects on Protein Aggregation

et al. 2018

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A comparative binding interaction of toluidine blue O (TBO) and methylene blue (MB) with lysozyme was investigated by multifaceted biophysical approaches as well as from the aspects of in silico biophysics. The bindings were static, and it occurred via ground-state complex formation as confirmed from time-resolved fluorescence experiments. From steady-state fluorescence and anisotropy, binding constants were calculated, and it was found that TBO binds more effectively than MB. Synchronous fluorescence spectra revealed that binding of dyes to lysozyme causes polarity changes around the tryptophan (Trp) moiety, most likely at Trp 62 and 63. Calorimetric titration also depicts the higher binding affinity of TBO over MB, and the interactions were exothermic and entropy-driven. In silico studies revealed the potential binding pockets in lysozyme and the participation of residues Trp 62 and 63 in ligand binding. Furthermore, calculations of thermodynamic parameters from the theoretical docking studies were in compliance with experimental observations. Moreover, an inhibitory effect of these dyes to lysozyme fibrillogenesis was examined, and the morphology of the formed fibril was scanned by atomic force microscopy imaging. TBO was observed to exhibit higher potential in inhibiting the fibrillogenesis than MB, and this phenomenon stands out as a promising antiamyloid therapeutic strategy.

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Spectroscopic, calorimetric, cyclic voltammetric and molecular modeling studies of new methylene blue-polyadenylic acid interaction and comparison to thionine and toluidine blue O: Understanding self-structure formation by planar dyes

Cited by 14 publications

References 101 publications

Binding affinity and in vitro cytotoxicity of harmaline targeting different motifs of nucleic acids: An ultimate drug designing approach

Binding affinity and in vitro cytotoxicity of harmaline targeting different motifs of nucleic acids: An ultimate drug designing approach

New Methylene Blue Covalently Functionalized Graphene Oxide Nanocomposite as Interfacial Material for the Electroanalysis of Hydrogen Peroxide

Comparative Study of Toluidine Blue O and Methylene Blue Binding to Lysozyme and Their Inhibitory Effects on Protein Aggregation

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