Photoswitchable Peptides and Proteins

Kirchner, Susanne; Leistner, Anna‐Lena; Pianowski, Zbigniew

doi:10.1002/9783527827626.ch40

Cited by 7 publications

(6 citation statements)

References 81 publications

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“…The reported synthesis of a known cross-linker 1 [46] was optimized and the previously low-yielding step (7 %) [46] was improved (23 %). Bisazobenzene 1 was further modified to introduce the reactive chloroacetyl handles (10) for attachment of the model tetra-peptide 14. Cross-linkers 13a and 13b were synthesized by converting the water-solubilizing sulfonate group into its tetra-butyl-ammonium salt that was soluble in organic solvents, thus enabling the Mills coupling towards the two cross-linker cores of 13a and 13b.…”

Section: Discussionmentioning

confidence: 99%

“…[6] Consequently, it comes as no surprise that various photoswitch designs have been applied to manipulate the activity of biological systems, including proteins and peptides. [7][8][9][10][11][12][13][14][15][16][17] Usually, the largest effect on the shape and stability of the target protein structure can be achieved by covalently attaching a photoswitch-based cross-linker via two connection sites at the protein structure. [18][19][20][21][22] While azobenzene-based cross-linkers largely dominate the field, [8,13,18,19,23,24] there are several reports of applying stilbenes, [25][26][27][28] hemithioindigos, [26,[29][30][31] diarylethenes, [32][33][34][35] overcrowded alkenebased molecular motors, [36] spiropyrans [37] and other switches [22,37,39] as cross-linkers.…”

Section: Introductionmentioning

confidence: 99%

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Photoswitchable, Water‐Soluble Bisazobenzene Cross‐Linkers with Enhanced Properties for Biological Applications

et al. 2022

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Photoswitchable cross-linkers are light-responsive molecules that can be attached at two locations to a target biomolecule to modulate its activity. Under irradiation, the cross-linker changes the distance between the residues it spans, affecting the structure and function of the labeled target. Efficient photocontrol is enabled especially by cross-linkers with large end-to-end length change upon switching. The design of water-soluble azobenzene-based cross-linkers for applications in chemical biology remains challenging due to major issues regarding synthesis and purification. Furthermore, the solubility and photochemical properties of the reported systems are frequently not suitable in aqueous media. Herein we report two water-soluble bisazobenzene cross-linkers with extended halflives and high photostationary state isomer distributions that can be achieved upon irradiation. We present molecules that enable cross-linking of biomolecular residues within one target, or are bridging two proteins to allow the study of proteinprotein interactions, which paves the way for light-based manipulation of under-explored biological targets.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photoswitchable, Water‐Soluble Bisazobenzene Cross‐Linkers with Enhanced Properties for Biological Applications

et al. 2022

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“…They have gained a lot of attention in various fields of research because of their ability to reversibly switch between different states. Ongoing research continues to advance the development of new types of photochromic molecules. − Several applications of photoswitches have been reported in the fields of chemical and biological research, including macroscopic bending, fluorescence switching, surface polarity, electrical conductivity, catalytic activity, dynamic holography, and biological function switching. − The simplest types of photochromic compounds are bistable compounds; they can switch between two different isomers by exposure to light. Bistable photochromic compounds are the fundamental building blocks of more complex systems that exhibit multiple states of photochromism.…”

Section: Introductionmentioning

confidence: 99%

Bridged-Imidazole Dimer Exhibiting Three-State Negative Photochromism with a Single Photochromic Unit

2023

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Photochromic molecules that can exhibit multiple states of photochromism in a single photochromic unit are considered more attractive than traditional bistable photochromic molecules because they can offer more versatility and control in photoresponsive systems. We have synthesized a negative photochromic 1-(1-naphthyl)pyrenyl-bridged imidazole dimer (NPy-ImD) that has three different isomers: a colorless isomer, 6MR, a blue-colored isomer, 5MR-B, and a red-colored isomer, 5MR-R. NPy-ImD can interconvert between these isomers via a short-lived transient biradical, BR, upon photoirradiation. 5MR-R is the most stable isomer, and the energy levels of 6MR, 5MR-B, and BR are relatively close to each other. The colored isomers 5MR-R and 5MR-B are photochemically isomerized to 6MR via the short-lived BR upon irradiation with blue light and red light, respectively. The absorption bands of 5MR-R and 5MR-B are well separated by more than 150 nm, with a small overlap, which means they can be selectively excited with different light sources, visible light for 5MR-R and NIR light for 5MR-B. The colorless isomer 6MR is formed from the short-lived BR through a kinetically controlled reaction. 6MR and 5MR-B can then be converted to the more stable isomer 5MR-R through a thermodynamically controlled reaction, which is facilitated by the thermally accessible intermediate, BR. Notably, 5MR-R photoisomerizes to 6MR when irradiated with CW-UV light, whereas it photoisomerizes to 5MR-B by a two-photon process when irradiated with nanosecond UV laser pulses.

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“…Since the structure is often closely linked to the function, a possible solution to such limitation is to control the function of peptides by altering their global conformation (Scheme A). To date, a number of light-mediated conformation-switchable peptides have been designed based on various strategies, including switchable stapling, − backbone amide modification, − β-turn mimicking, , and so on. However, in certain situations, the current strategies for controlling peptides may not offer adequate conformational variation, resulting in insufficient functional differences between the ‘active’ and ‘inactive’ states .…”

Section: Introductionmentioning

confidence: 99%

Rapid Formation of Intramolecular Disulfide Bridges using Light: An Efficient Method to Control the Conformation and Function of Bioactive Peptides

He,

Chai,

Zeng

et al. 2023

J. Am. Chem. Soc.

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Disulfide bonds are widely found in natural peptides and play a pivotal role in stabilizing their secondary structures, which are highly associated with their biological functions. Herein, we introduce a light-mediated strategy to effectively control the formation of disulfides. Our strategy is based on 2-nitroveratryl (oNv), a widely used photolabile motif, which serves both as a photocaging group and an oxidant (after photolysis). We demonstrated that irradiation of oNv-caged thiols with UV light could release free thiols that are rapidly oxidized by locally released byproduct nitrosoarene, leading to a "break-to-bond" fashion. This strategy is highlighted by the in situ restoration of the antimicrobial peptide tachyplesin I (TPI) from its external disulfide-caged analogue TPI-1. TPI-1 exhibits a distorted structure and a diminished function. However, upon irradiation, the β-hairpin structure and membrane activity of TPI were largely restored via rapid intramolecular disulfide formation. Our study proposes a powerful method to regulate the conformation and function of peptides in a spatiotemporal manner, which has significant potential for the design of disulfide-centered light-responsive systems.

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Photoswitchable Peptides and Proteins

Cited by 7 publications

References 81 publications

Photoswitchable, Water‐Soluble Bisazobenzene Cross‐Linkers with Enhanced Properties for Biological Applications

Photoswitchable, Water‐Soluble Bisazobenzene Cross‐Linkers with Enhanced Properties for Biological Applications

Bridged-Imidazole Dimer Exhibiting Three-State Negative Photochromism with a Single Photochromic Unit

Rapid Formation of Intramolecular Disulfide Bridges using Light: An Efficient Method to Control the Conformation and Function of Bioactive Peptides

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