The pyranine-benzalkonium ion pair: A promising fluorescent system for the ratiometric detection of wound pH

Panzarasa, Guido; Osypova, Alina; Toncelli, Claudio; Buhmann, Matthias T.; Rottmar, Markus; Ren, Qun; Maniura‐Weber, Katharina; Rossi, René M.; Boesel, Luciano F.

doi:10.1016/j.snb.2017.04.045

Cited by 42 publications

(38 citation statements)

References 31 publications

(33 reference statements)

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“…Plotting the same data in logarithmic scale allows the linearization of the calibration in the range from pH 5 to 8. This strong response represents a substantial improvement compared to our previous work (sixfold increase from pH 5.5 to 8.5) . The pH‐dependent emission properties of the pyranine‐labeled APCN membranes can also be distinguished by the naked eye, when illuminated with a white light source (Figure d).…”

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confidence: 58%

“…Here, the dye's high water solubility and lack of functional groups besides three sulfonic acids groups can lead to severe limitation in terms of leaching. Recently, we demonstrated that the coupling of pyranine with benzalkonium chloride into a water‐insoluble ion pair can solve this problem for a range of pH values . Loading of the ion pair onto a porous support allowed the fabrication of a sensor for wound pH.…”

mentioning

confidence: 99%

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Pyranine‐Modified Amphiphilic Polymer Conetworks as Fluorescent Ratiometric pH Sensors

Ulrich

Osypova

Panzarasa

et al. 2019

Macromol. Rapid Commun.

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ratiometric pH detection. Typically, ratiometric pH detection requires the combination of one pH-sensitive and one pH-insensitive fluorescent dye. [3] Pyranine, in contrast, allows ratiometric detection of pH from the comparison of one emission intensity at two different excitation wavelengths (406 and 460 nm). [6] This dual excitation-single emission property minimizes the impact of variations in fluorophore concentration, photobleaching, and instrumentation. The pH sensitivity of pyranine arises from its phenol group with a pK a of 7.3 that allows the determination of pH values ranging from ≈5 to ≈9, adequate for biologically or biomedically oriented applications. [7,8] Accordingly, pyranine has been employed to measure intracellular pH, [2,9,10] track protein structural transitions, [9][10][11][12] for metal ion-sensing, [13] and for the development of environmental sensors. [14][15][16] The monitoring of chronic wounds via pH-sensitive wound pads is a relevant application, in particular, due to the similar relevant pH range. [17,18] The low price of pyranine compared to other fluorescent dyes is especially attractive for commercial applications, even allowing its use in fluorescent text markers. However, due to the difficulty of covalent conjugation, with few exceptions, [19][20][21][22] most pyranine sensors are based on non-covalent integration. [15,[23][24][25][26] Here, the dye's high water solubility and lack of functional groups besides three sulfonic acids groups can lead to severe limitation in terms of leaching. Recently, we demonstrated that the coupling of pyranine with benzalkonium chloride into a water-insoluble ion pair can solve this problem for a range of pH values. [27] Loading of the ion pair onto a porous support allowed the fabrication of a sensor for wound pH. Still, at higher pH the ion pair separates and pyranine can leach out. Therefore, a stable covalent conjugation with an adequate host matrix would be preferable.Amphiphilic polymer conetworks (APCNs) represent a class of materials with great potential as matrices for sensor applications. [28][29][30][31] APCNs combine a hydrophilic and a hydrophobic polymer in one network with a nanophase-separated morphology. The synergistic combination of both polymers and the unique structural features of APCNs result in a set of favorable properties that includes, amongst others, optical transparency, mechanical stability, and amphiphilic swelling, resulting in permeability to aqueous solutes and compounds dissolved in organic solvents. Moreover, APCN can be permeable pH SensorsThe authors declare no conflict of interest.

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confidence: 58%

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confidence: 99%

Pyranine‐Modified Amphiphilic Polymer Conetworks as Fluorescent Ratiometric pH Sensors

Ulrich

Osypova

Panzarasa

et al. 2019

Macromol. Rapid Commun.

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“…In the last few years, some temperature and pH sensors have paved the way for a continuous real time wound monitoring by means of wearable devices or materials suitable for integration in commercial dressings [ 120 , 121 , 122 , 126 , 127 ]. Nevertheless, tests on human patients are needed to confirm the reliability of these sensors for practical use.…”

Section: Discussionmentioning

confidence: 99%

“…Panzarasa et al used a pyranine-benzalkonium ion pair incorporated in membranes and wound dressings to detect pH changes in the range 5.5–7.5, however the standard deviation was too high to discriminate pH values that differs for less of about 0.5 pH units [ 127 ].…”

Section: Sensors For Temperature and Phmentioning

confidence: 99%

Sensors and Biosensors for C-Reactive Protein, Temperature and pH, and Their Applications for Monitoring Wound Healing: A Review

Salvo

Dini

Kirchhain

et al. 2017

Sensors

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Wound assessment is usually performed in hospitals or specialized labs. However, since patients spend most of their time at home, a remote real time wound monitoring would help providing a better care and improving the healing rate. This review describes the advances in sensors and biosensors for monitoring the concentration of C-reactive protein (CRP), temperature and pH in wounds. These three parameters can be used as qualitative biomarkers to assess the wound status and the effectiveness of therapy. CRP biosensors can be classified in: (a) field effect transistors, (b) optical immunosensors based on surface plasmon resonance, total internal reflection, fluorescence and chemiluminescence, (c) electrochemical sensors based on potentiometry, amperometry, and electrochemical impedance, and (d) piezoresistive sensors, such as quartz crystal microbalances and microcantilevers. The last section reports the most recent developments for wearable non-invasive temperature and pH sensors suitable for wound monitoring.

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“…Panzaras et al [194] developed "bandages with a voice" using a pyranine-benzalkonium ion pair loaded into wound dressings that are able to detect pH changes in the range of 5.5-7.5, based on the UV-induced fluorescence color change of a dye. The pH of the healing wound is around pH 5-6, while the pH in chronic wounds fluctuates between 7 and 8, indicating bacterial infection (Figure 9).…”

Section: Smart Nanomaterialsmentioning

confidence: 99%

An Update on Antimicrobial Peptides (AMPs) and Their Delivery Strategies for Wound Infections

2020

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Bacterial infections occur when wound healing fails to reach the final stage of healing, which is usually hindered by the presence of different pathogens. Different topical antimicrobial agents are used to inhibit bacterial growth due to antibiotic failure in reaching the infected site, which is accompanied very often by increased drug resistance and other side effects. In this review, we focus on antimicrobial peptides (AMPs), especially those with a high potential of efficacy against multidrug-resistant and biofilm-forming bacteria and fungi present in wound infections. Currently, different AMPs undergo preclinical and clinical phase to combat infection-related diseases. AMP dendrimers (AMPDs) have been mentioned as potent microbial agents. Various AMP delivery strategies that are used to combat infection and modulate the healing rate—such as polymers, scaffolds, films and wound dressings, and organic and inorganic nanoparticles—have been discussed as well. New technologies such as Clustered Regularly Interspaced Short Palindromic Repeat (CRISPR)-associated protein (CRISPR-Cas) are taken into consideration as potential future tools for AMP delivery in skin therapy.

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The pyranine-benzalkonium ion pair: A promising fluorescent system for the ratiometric detection of wound pH

Cited by 42 publications

References 31 publications

Pyranine‐Modified Amphiphilic Polymer Conetworks as Fluorescent Ratiometric pH Sensors

Pyranine‐Modified Amphiphilic Polymer Conetworks as Fluorescent Ratiometric pH Sensors

Sensors and Biosensors for C-Reactive Protein, Temperature and pH, and Their Applications for Monitoring Wound Healing: A Review

An Update on Antimicrobial Peptides (AMPs) and Their Delivery Strategies for Wound Infections

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