PET and FRET utility of an amino acid pair: tryptophan and 4-cyanotryptophan

Ahmed, Ismail A.; Rodgers, Jeffrey M.; Eng, Christina; Troxler, Thomas; Gai, Feng

doi:10.1039/c9cp02126d

Cited by 27 publications

(19 citation statements)

References 33 publications

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“…Bearing this in mind, an original approach for l -Trp@Ti 3 C 2 T x was devised in order to exploit the two molecular properties offered by the aromatic core in l -Trp. In particular, Förster resonance energy transfer (FRET) phenomenon , was considered for the evaluation of the supramolecular interactions and fluorescence all at once (Figure a). Briefly, the process of FRET takes place when a fluorophore in an electronically excited state (donor) transfers its excitation energy to a nearby chromophore (acceptor).…”

Section: Resultsmentioning

confidence: 99%

Multiresponsive 2D Ti₃C₂T_x MXene via Implanting Molecular Properties

et al. 2021

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The design and fabrication of active nanomaterials exhibiting multifunctional properties is a must in the socalled global "Fourth Industrial Revolution". In this sense, molecular engineering is a powerful tool to implant original capabilities on a macroscopic scale. Herein, different bioinspired 2D-MXenes have been developed via a versatile and straightforward synthetic approach. As a proof of concept, Ti 3 C 2 T x MXene has been exploited as a highly sensitive transducing platform for the covalent assembly of active biomolecular architectures (i.e., amino acids). All pivotal properties originated from the anchored targets were proved to be successfully transferred to the resulting bioinspired 2D-MXenes. Appealing applications have been devised for these 2D-MXene prototypes showing (i) chiroptical activity, (ii) fluorescence capabilities, (iii) supramolecular π−π interactions, and (iv) stimuli-responsive molecular switchability. Overall, this work demonstrates the fabrication of programmable 2D-MXenes, taking advantage of the inherent characteristics of the implanted (bio)molecular components. Thus, the current bottleneck in the field of 2D-MXenes can be overcome after the significant findings reported here.

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Section: Resultsmentioning

confidence: 99%

Multiresponsive 2D Ti₃C₂T_x MXene via Implanting Molecular Properties

et al. 2021

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“…RaPID selections for de novo cyclic peptides initiated with ClAc−4CNW or ClAc−AzAla will enable the identification of peptide leads that are inherently fluorescent and can be directly assessed for cell permeability by fluorescence microscopy and flow cytometry. 4CNW and AzAla have also recently been used to probe protein‐protein binding interactions by PET, FRET and VET [9,17,18] . We therefore also envisage that 4CNW/AzAla initiated peptide leads could be used directly in label‐free binding assays.…”

Section: Methodsmentioning

confidence: 99%

“…4CNW and AzAla have also recently been used to probe protein‐protein binding interactions by PET, FRET and VET. [ 9 , 17 , 18 ] We therefore also envisage that 4CNW/AzAla initiated peptide leads could be used directly in label‐free binding assays.…”

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confidence: 99%

Fluorescent Amino Acid Initiated de novo Cyclic Peptides for the Label‐Free Assessment of Cell Permeability**

Bertran

Rowley

et al. 2021

ChemMedChem

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The major obstacle in applying peptides to intracellular targets is their low inherent cell permeability. Standard approaches to attach a fluorophore (e. g. FITC, TAMRA) can change the physicochemical properties of the parent peptide and influence their ability to penetrate and localize in cells. We report a label‐free strategy for evaluating the cell permeability of cyclic peptide leads. Fluorescent tryptophan analogues 4‐cyanotryptophan (4CNW) and β‐(1‐azulenyl)‐L‐alanine (AzAla) were incorporated into in vitro translated macrocyclic peptides by initiator reprogramming. We then demonstrate these efficient blue fluorescent emitters are good tools for monitoring peptide penetration into cells.

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“…Besides its utility in biological microscopy, 4CN-Trp can also be used in various spectroscopic applications. − For example, the study of Ahmed et al demonstrated that Trp can effectively quench the fluorescence of 4CN-Trp via the mechanism of photoinduced electron transfer (PET). Since this quenching process only becomes efficient when the indole and 4CN-indole rings are sufficiently close (i.e., in van der Waals contact), this fluorophore–quencher pair can be used to assess protein conformational dynamics via either ensemble or single-molecule fluorescence techniques.…”

Section: Emerging Visible Fluorescent Amino Acidsmentioning

confidence: 99%

Tryptophan as a Template for Development of Visible Fluorescent Amino Acids

2021

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Most biological systems, at both molecular and cellular levels, are intrinsically complex, diverse, and nonfluorescent. Therefore, studying their structures, dynamics, and interactions via fluorescence-based methods requires incorporation of one or multiple external fluorophores that would not significantly affect any native property of the system in question. This requirement necessitates the development of a diverse set of fluorescence reporters that differ in chemical, physical, and photophysical properties. Herein, we offer our perspective on the need for, recent progress in, and future directions of developing tryptophan-based fluorescent amino acids.

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PET and FRET utility of an amino acid pair: tryptophan and 4-cyanotryptophan

Abstract: The amino acids tryptophan and 4-cyanotryptophan constitute a dual FRET and PET pair, useful for various biological applications.

Cited by 27 publications

References 33 publications

Multiresponsive 2D Ti₃C₂T_x MXene via Implanting Molecular Properties

Multiresponsive 2D Ti₃C₂T_x MXene via Implanting Molecular Properties

Fluorescent Amino Acid Initiated de novo Cyclic Peptides for the Label‐Free Assessment of Cell Permeability**

Tryptophan as a Template for Development of Visible Fluorescent Amino Acids

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PET and FRET utility of an amino acid pair: tryptophan and 4-cyanotryptophan

Abstract: The amino acids tryptophan and 4-cyanotryptophan constitute a dual FRET and PET pair, useful for various biological applications.

Cited by 27 publications

References 33 publications

Multiresponsive 2D Ti3C2Tx MXene via Implanting Molecular Properties

Multiresponsive 2D Ti3C2Tx MXene via Implanting Molecular Properties

Fluorescent Amino Acid Initiated de novo Cyclic Peptides for the Label‐Free Assessment of Cell Permeability**

Tryptophan as a Template for Development of Visible Fluorescent Amino Acids

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Multiresponsive 2D Ti₃C₂T_x MXene via Implanting Molecular Properties

Multiresponsive 2D Ti₃C₂T_x MXene via Implanting Molecular Properties