Cysteine specific bioconjugation with benzyl isothiocyanates

Petri, László; Szijj, Péter A.; Kelemen, Ádám Andor; Imre, Tı́mea; Gömöry, Ágnes; Lee, Maximillian T. W.; Hegedüs, Katalin; Ábrányi‐Balogh, Péter; Chudasama, Vijay; Keserü, György M.

doi:10.1039/d0ra02934c

Cited by 24 publications

(33 citation statements)

References 30 publications

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“…Among others, silver engineered nanomaterials are used in biosensing and imaging when conjugated with dyes [50][51][52]. Specially fluorescein isothiocyanate (FITC) and rhodamine B isothiocyanate (RITC) are widely used in sensing and as labeling systems [53][54][55][56]. To fully exploit the potential of AgNPs conjugated with fluorescent molecules, it is necessary to have a complete understanding of the details of the structures and the interaction between the fluorophore blocked in a position very close to the NP.…”

Section: Introductionmentioning

confidence: 99%

Silver Nanoparticles Functionalized by Fluorescein Isothiocyanate or Rhodamine B Isothiocyanate: Fluorescent and Plasmonic Materials

et al. 2021

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This paper presents the synthesis of silver nanoparticles (AgNPs) functionalized with fluorescent molecules, in particular with xanthene-based dyes, i.e., fluorescein isothiocyanate (FITC, λmax = 485 nm) and rhodamine B isothiocyanate (RITC, λmax = 555 nm). An in-depth characterization of the particle–dye systems, i.e., AgNPs–RITC and AgNPs–FITC, is presented to evaluate their chemical structure and optical properties due to the interaction between their plasmonic and absorption properties. UV–Vis spectroscopy and the dynamic light scattering (DLS) measurements confirmed the nanosize of the AgNPs–RITC and AgNPs–FITC. Synchrotron radiation X-ray photoelectron spectroscopy (SR-XPS) was used to study the chemical surface functionalization by structural characterization, confirming/examining the isothiocyanate–metal interaction. For AgNPs–RITC, in which the plasmonic and fluorescence peak are not superimposed, the transient dynamics of the dye fluorescence were also studied. Transient absorption measurements showed that by exciting the AgNPs–RITC sample at a wavelength corresponding to the AgNP plasmon resonance, it was possible to preferentially excite the RITC dye molecules attached to the surface of the NPs with respect to the free dye molecules in the solution. These results demonstrate how, by combining plasmonics and fluorescence, these AgNPs can be used as promising systems in biosensing and imaging applications.

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Section: Introductionmentioning

confidence: 99%

Silver Nanoparticles Functionalized by Fluorescein Isothiocyanate or Rhodamine B Isothiocyanate: Fluorescent and Plasmonic Materials

et al. 2021

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“…Isothiocyanate (R-C=N=S) can be reactive to both thiol and amine residues of proteins under specific conditions (Figure 11). Under pH 6-8, an isothiocyanate can react with a thiol group to form a dithiocarbamate, while in a more alkaline condition (pH = 9-11), an isothiocyanate preferably reacts with an amine group to form a thiourea [108]. Isothiocyanate chemistry has been widely used for labelling proteins with fluorescent moieties such as fluorescein-5-isothiocyanate (FITC) [109][110][111].…”

Section: Isothiocyanate Chemistrymentioning

confidence: 99%

Chemical Conjugation Strategies for the Development of Protein-Based Subunit Nanovaccines

Duong

Shalash

et al. 2021

Vaccines

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The production of subunit nanovaccines relies heavily on the development of a vaccine delivery system that is safe and efficient at delivering antigens to the target site. Nanoparticles have been extensively investigated for vaccine delivery over the years, as they often possess self-adjuvanting properties. The conjugation of antigens to nanoparticles by covalent bonds ensures co-delivery of these components to the same subset of immune cells in order to trigger the desired immune responses. Herein, we review covalent conjugation strategies for grafting protein or peptide antigens onto other molecules or nanoparticles to obtain subunit nanovaccines. We also discuss the advantages of chemical conjugation in developing these vaccines.

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“…Using such derivatives offers a unique opportunity to create specific pH sensors, and particularly, for biological systems where all proteins are bearing a terminal amine. Even if FITC 2 is still the most prolific derivative in literature ( Figure 6), new fluorescein reactive derivatives are still described with optimized properties [35]. When fluorescein was used for intracellular pH (pH in ) monitoring, a high leakage rate appeared from the cells, which made accurate pH determination difficult.…”

Section: % 84% 2%mentioning

confidence: 99%

Fluorescein Derivatives as Fluorescent Probes for pH Monitoring along Recent Biological Applications

Guern

Mussard

Gaucher

et al. 2020

IJMS

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Potential of hydrogen (pH) is one of the most relevant parameters characterizing aqueous solutions. In biology, pH is intrinsically linked to cellular life since all metabolic pathways are implicated into ionic flows. In that way, determination of local pH offers a unique and major opportunity to increase our understanding of biological systems. Whereas the most common technique to obtain these data in analytical chemistry is to directly measure potential between two electrodes, in biological systems, this information has to be recovered in-situ without any physical interaction. Based on their non-invasive optical properties, fluorescent pH-sensitive probe are pertinent tools to develop. One of the most notorious pH-sensitive probes is fluorescein. In addition to excellent photophysical properties, this fluorophore presents a pH-sensitivity around neutral and physiologic domains. This review intends to shed new light on the recent use of fluorescein as pH-sensitive probes for biological applications, including targeted probes for specific imaging, flexible monitoring of bacterial growth, and biomedical applications.

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Cysteine specific bioconjugation with benzyl isothiocyanates

Abstract: We present herein the development of a new fluorescent dye equipped with a benzyl isothiocyanate warhead, which resulted improved photophysical properties and enhanced labelling efficiency on the Fab antibody subunit and the trastuzumab antibody.

Cited by 24 publications

References 30 publications

Silver Nanoparticles Functionalized by Fluorescein Isothiocyanate or Rhodamine B Isothiocyanate: Fluorescent and Plasmonic Materials

Silver Nanoparticles Functionalized by Fluorescein Isothiocyanate or Rhodamine B Isothiocyanate: Fluorescent and Plasmonic Materials

Chemical Conjugation Strategies for the Development of Protein-Based Subunit Nanovaccines

Fluorescein Derivatives as Fluorescent Probes for pH Monitoring along Recent Biological Applications

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