An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing

Diana, Rosita; Panunzi, Barbara; Tuzi, Angela; Piotto, Stefano; Concilio, Simona; Caruso, Ugo

doi:10.3390/molecules24213833

Cited by 27 publications

(19 citation statements)

References 68 publications

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“…All starting products were commercially available. 5-(4-Formyl-3-hydroxyphenoxy)-N,N,Ntrimethylpentan-1-aminium bromide [24] was obtained as described in the literature. Benzothiazole-2-carboxylic acid hydrazide [25] was obtained by common synthetic route placing ethyl benzothiazole-2-carboxylate under reflux in ethanol with an excess of hydrazine for 1 h.…”

Section: Methodsmentioning

confidence: 99%

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A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

et al. 2020

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A new 5-(4-((2-(benzothiazole-2-carbonyl)hydrazono)methyl)-3-hydroxyphenoxy)-N,N,N-trimethylpentan-1-aminium bromide (BTABr) fluorescent and colorimetric pH probe was easily synthesized by the condensation reaction of benzothiazole-2-carbohydrazide with 5-(4-formyl-3-hydroxyphenoxy)-N,N,N-trimethylpentan-1-aminium bromide. The benzothiazole moiety provided the emissive part of the molecule and the charged trimethyl amino group guaranteed outstanding solubility in water, for an organic molecule. pH titration experiments indicated that the probe is useful for monitoring acidic and alkaline solutions, turning reversibly in color/fluorescence just at a neutral pH value. Naked-eye colorimetric response was observed both in solution and in the solid state. In addition, the probe showed high stability and selectivity and large Stokes shifts. Because of these features, BTABr can potentially work as an on-off real-time pH sensor for intracellular pH imaging. The crystal structure of BTABr examined by single-crystal analysis showed a planar geometry of the molecule and confirmed the presence of a molecular stacking between molecules joined in a complex tridimensional hydrogen bonding pattern.

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Section: Methodsmentioning

confidence: 99%

“…Recently, we designed and synthesized an amphiphilic picolinoyl-hydrazone-based sensor [24] with a charged side chain capable of guaranteeing water solubility. In that study, we checked the effect of the heterocycle on the spectroscopic response involving pH determination.…”

Section: Introductionmentioning

confidence: 99%

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

et al. 2020

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“…The use of optical probes for non-electrochemical pH determination is common in complex biological systems [ 92 ]. Diana et al synthesized and characterized a new pH sensitive fluorescent molecule (5-(4-formyl-3-hydroxyphenoxy)- N , N , N -trimethylpentan-1-aminium bromide, PHABr), which changes from transparent to yellow at pH above 7 with increased fluorescence [ 93 ]. The experimental photophysical characterization was carried out in solution, and no relevant probe-membrane interaction measurements were performed.…”

Section: Charge-transfer-based and Other Solvatochromic Probesmentioning

confidence: 99%

The Secret Lives of Fluorescent Membrane Probes as Revealed by Molecular Dynamics Simulations

2020

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Fluorescent probes have been employed for more than half a century to study the structure and dynamics of model and biological membranes, using spectroscopic and/or microscopic experimental approaches. While their utilization has led to tremendous progress in our knowledge of membrane biophysics and physiology, in some respects the behavior of bilayer-inserted membrane probes has long remained inscrutable. The location, orientation and interaction of fluorophores with lipid and/or water molecules are often not well known, and they are crucial for understanding what the probe is actually reporting. Moreover, because the probe is an extraneous inclusion, it may perturb the properties of the host membrane system, altering the very properties it is supposed to measure. For these reasons, the need for independent methodologies to assess the behavior of bilayer-inserted fluorescence probes has been recognized for a long time. Because of recent improvements in computational tools, molecular dynamics (MD) simulations have become a popular means of obtaining this important information. The present review addresses MD studies of all major classes of fluorescent membrane probes, focusing in the period between 2011 and 2020, during which such work has undergone a dramatic surge in both the number of studies and the variety of probes and properties accessed.

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“…These methods require the use of fluorescent probes, able to penetrate the membranes allowing a precise and immediate analysis [ 2 , 3 ]. The number of probes developed for the study of raft membranes is continuously increasing; those so far reported have restrictions related to the type of membrane and the fluorescence technique used [ 4 , 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

“…The most recently identified class of probes corresponds to the class of environment-sensitive probes, which can directly distinguish the Lo and Ld phases due to differences in their intrinsic properties. These probes can change their fluorescence properties, fluorescence intensity, and even the emission color in response to changes in the environment [ 5 , 7 , 8 , 9 ]. This class includes solvatochromic fluorescent probes that show variations in their fluorescence properties depending on the polarity and hydration of the environment.…”

Section: Introductionmentioning

confidence: 99%

A Flavone-Based Solvatochromic Probe with A Low Expected Perturbation Impact on the Membrane Physical State

et al. 2020

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The study of the cell membrane is an ambitious and arduous objective since its physical state is regulated by a series of processes that guarantee its regular functionality. Among the different methods of analysis, fluorescence spectroscopy is a technique of election, non-invasive, and easy to use. Besides, molecular dynamics analysis (MD) on model membranes provides useful information on the possibility of using a new probe, following its positioning in the membrane, and evaluating the possible perturbation of the double layer. In this work, we report the rational design and the synthesis of a new fluorescent solvatochromic probe and its characterization in model membranes. The probe consists of a fluorescent aromatic nucleus of a 3-hydroxyflavone moiety, provided with a saturated chain of 18 carbon atoms and a zwitterionic head so to facilitate the anchoring to the polar heads of the lipid bilayer and avoid the complete internalization. It was possible to study the behavior of the probe in GUV model membranes by MD analysis and fluorescence microscopy, demonstrating that the new probe can efficiently be incorporated in the lipid bilayer, and give a color response, thanks to is solvatochromic properties. Moreover, MD simulation of the probe in the membrane supports the hypothesis of a reduced perturbation of the membrane physical state.

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An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing

Cited by 27 publications

References 68 publications

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

The Secret Lives of Fluorescent Membrane Probes as Revealed by Molecular Dynamics Simulations

A Flavone-Based Solvatochromic Probe with A Low Expected Perturbation Impact on the Membrane Physical State

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