Flavylium Dye as pH-Tunable Fluorescent and CD Probe for Double-Stranded DNA and RNA

Crnolatac, Ivo; Giestas, Letícia; Horvat, Gordan; Parola, A. Jorge; Piantanida, Ivo

doi:10.3390/chemosensors8040129

Cited by 5 publications

(3 citation statements)

References 43 publications

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“…Interestingly, at higher concentrations (10–20 μM), the detected signal of Flav-NH 2 was found to be localized in the cell nuclei (Hoechst 33342 signal in blue, DAPI channel). This is in good agreement with previous literature reports regarding the observed interaction of flavylium cations with double-stranded DNA and RNA [ 39 , 40 ]. Moreover, at lower concentrations (≤10 μM), the reduction product was found to be localized in some organelles such as lysosomes, Golgi apparatus, and mitochondria with Pearson’s coefficients of 0.60, 0.62, and 0.55, respectively ( Figure S7 ).…”

Section: Resultssupporting

confidence: 93%

Flavylium-Based Hypoxia-Responsive Probe for Cancer Cell Imaging

et al. 2021

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A hypoxia-responsive probe based on a flavylium dye containing an azo group (AZO-Flav) was synthesized to detect hypoxic conditions via a reductase-catalyzed reaction in cancer cells. In in vitro enzymatic investigation, the azo group of AZO-Flav was reduced by a reductase in the presence of reduced nicotinamide adenine dinucleotide phosphate (NADPH) followed by fragmentation to generate a fluorescent molecule, Flav-NH2. The response of AZO-Flav to the reductase was as fast as 2 min with a limit of detection (LOD) of 0.4 μM. Moreover, AZO-Flav displayed high enzyme specificity even in the presence of high concentrations of biological interferences, such as reducing agents and biothiols. Therefore, AZO-Flav was tested to detect hypoxic and normoxic environments in cancer cells (HepG2). Compared to the normal condition, the fluorescence intensity in hypoxic conditions increased about 10-fold after 15 min. Prolonged incubation showed a 26-fold higher fluorescent intensity after 60 min. In addition, the fluorescence signal under hypoxia can be suppressed by an electron transport process inhibitor, diphenyliodonium chloride (DPIC), suggesting that reductases take part in the azo group reduction of AZO-Flav in a hypoxic environment. Therefore, this probe showed great potential application toward in vivo hypoxia detection.

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Section: Resultssupporting

confidence: 93%

Flavylium-Based Hypoxia-Responsive Probe for Cancer Cell Imaging

et al. 2021

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“…The phosphate groups on the ssDNA backbone and the NH 2 groups on the membrane surface are both partially protonated, resulting in a reduced net charge on both molecules. This reduction in charge weakens the electrostatic interactions between ssDNA and the membrane, making it easier for ssDNA to detach or desorb from the membrane surface [ 68 , 69 , 70 , 71 ].…”

Section: Resultsmentioning

confidence: 99%

Solid Phase Oligo-DNA Extraction from Complex Medium Using an Aminated Graphene/Nitrocellulose Membrane Hybrid

Toader,

Grigorean,

Ionita

2024

Biomolecules

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A hybrid material, consisting of commercially available nitrocellulose (NC) membrane non-covalently modified with amino-polyethylene glycol functionalized reduced graphene oxide (NH2-PEG-rGO) nanoparticles, was successfully synthesized for oligonucleotide extraction. Fourier Transform Infrared Spectroscopy (FTIR) confirmed the modification of the NC membrane, revealing characteristic peaks of both compounds, i.e., NC and NH2-PEG-rGO. Scanning Electron Microscopy (SEM) exhibited morphological changes in the NC/NH2-PEG-rGO hybrid membrane, marked by the introduction of NH2-PEG-rGO particles, resulting in a distinctly smothered surface compared to the porous surface of the NC control membrane. Wettability assays revealed hydrophobic behavior for the NC/NH2-PEG-rGO hybrid membrane, with a water contact angle exceeding 90°, contrasting with the hydrophilic behavior characterized by a 16.7° contact angle in the NC membrane. The performance of the NC/NH2-PEG-rGO hybrid membrane was evaluated for the extraction of ssDNA with fewer than 50 nucleotides from solutions containing various ionic species (MnCl2, MgCl2, and MnCl2/MgCl2). The NC/NH2-PEG-rGO hybrid membrane exhibited optimal performance when incubated in MgCl2, presenting the highest fluorescence emission at 525 relative fluorescence units (r.f.u.). This corresponds to the extraction of approximately 610 pg (≈13%) of the total oligo-DNA, underscoring the efficacy of the pristine material, which extracts 286 pg (≈6%) of oligo-DNA in complex solutions.

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“…The fact that in molecular metamorphosis, different molecules are formed implies the appearance of new physical chemical properties caused by external inputs. It is possible to profit from this fact to design molecular sensors, , models for optical memories, , and drug delivery based on host–guest chemistry, , among other applications.…”

Section: Introductionmentioning

confidence: 99%

Achieving Complexity at the Bottom: Molecular Metamorphosis Generated by Anthocyanins and Related Compounds

et al. 2021

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The concept of molecular metamorphosis is described. A molecule (flavylium cation) generates a sequence of other different molecules by means of external stimuli. The reversibility of the system allows for the flavylium cation to be recovered by other external stimuli, completing one cycle. Differently from supramolecular chemistry, molecular metamorphosis is not a bottom-up approach. All events occur at the bottom. The procedures to characterize the kinetics and thermodynamics of the cycles are summarized. They are based on direct pH jumps (addition of a base to the flavylium cation) and reverse pH jumps (addition of an acid to equilibrated solutions at higher pH values). Stopped flow is an indispensable tool to characterize these systems. The following metamorphic cycles will be described to illustrate the concept: (i) introducing the flavanone in the metamorphic system and illustrating the concept of a timer at the molecular level; (ii) response of the flavylium-based metamorphosis to light inputs and the write-lock-read-unlock-erase molecular system; (iii) a one-way cycle of direct–reverse pH jumps; (iv) interconversion of the flavylium cation with 2,2′-spirobis[chromene] derivatives; (v) 6,8 A-ring substituent rearrangements.

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Flavylium Dye as pH-Tunable Fluorescent and CD Probe for Double-Stranded DNA and RNA

Cited by 5 publications

References 43 publications

Flavylium-Based Hypoxia-Responsive Probe for Cancer Cell Imaging

Flavylium-Based Hypoxia-Responsive Probe for Cancer Cell Imaging

Solid Phase Oligo-DNA Extraction from Complex Medium Using an Aminated Graphene/Nitrocellulose Membrane Hybrid

Achieving Complexity at the Bottom: Molecular Metamorphosis Generated by Anthocyanins and Related Compounds

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