Amber Light Control of Peptide Secondary Structure by a Perfluoroaromatic Azobenzene Photoswitch

Cataldi, Eleonora; Raschig, Martina; Gutmann, Marcus; Geppert, Patrick T; Ruopp, Matthias; Schock, Marvin; Gerwe, Hubert; Bertermann, Rüdiger; Meinel, Lorenz; Finze, Maik; Nowak‐Król, Agnieszka; Decker, Michael; Lühmann, Tessa

doi:10.1002/cbic.202200570

Cited by 10 publications

(21 citation statements)

References 64 publications

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“…Cataldi et al took advantage of the change of geometry of azobenzene upon light irradiation to disturb the α-helix structure of an analogue of the cell penetrating peptide LK 1 . [72] Cysteines were introduced in the primary structure of the peptide of interest to perform crosslinking of a perfluorinated azobenzene. The cysteines were separated by 4 residues on the primary structure of the peptide.…”

Section: Secondary Structure Modificationmentioning

confidence: 99%

The Growing Field of Photoswitchable Macrocycles: A Promising Way to Tune Various Properties with Light

Ludwig

Xie

2023

ChemPhotoChem

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Thanks to supramolecular interactions of macrocyclic compounds with their guest ions or molecules, macrocycles have found wide applications in molecular and chiral recognition, separation, transportation, molecular machines, and so on. Photoswitchable macrocycles are especially appealing and attracting more and more interest because the embedded molecular photoswitch enables dynamic control of molecular shape, conformation, and different properties by light, a non‐invasive, remote and highly tunable stimulus. With available photochromic compounds, various photoswitchable macrocycles have been developed. In this review paper, we describe the recently reported photoswitchable macrocyclic compounds, with a focus on the control of the macrocyclic structure, dynamic, photo or thermal isomerization, as well as their applications on encapsulation and release of ionic or aromatic species, on the reversible modulation of chemical, biological, electronic, fluorescent and chiroptical properties by light.

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Section: Secondary Structure Modificationmentioning

confidence: 99%

The Growing Field of Photoswitchable Macrocycles: A Promising Way to Tune Various Properties with Light

Ludwig

Xie

2023

ChemPhotoChem

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“…IL-4 is a small cytokine with a molecular weight of 13.5 kDa. It is mainly known for the stimulation of B cells and T cells and the differentiation of naïve T helper cells into Th2 cells. − Additionally, IL-4 plays a significant role in the alternative polarization of tissue macrophages relevant for inflammatory diseases such as rheumatoid arthritis and wound repair. − …”

Section: Introductionmentioning

confidence: 99%

Bioconjugation of a Fibroblast Activation Protein Targeted Interleukin-4

Ruopp,

Zhu,

Worschech

et al. 2023

ACS Biomater. Sci. Eng.

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) is an immune-modulating therapeutic with growing potential for the treatment of inflammatory diseases. Current challenges of IL-4 therapy include a low serum half-life and pleiotropic activity, suggesting effective targeting of IL-4. To develop an interleukin-4 bioconjugate with rapid targeting to inflammatory disease sites, we report the chemical synthesis, bioconjugation, and in vitro characterization of a murine interleukin-4 (mIL-4) conjugate decorated with a fibroblast activation protein inhibitor (FAPI). The FAPI targeting moiety features 2,2′,2″,2‴-(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetraacetic acid (DOTA) to allow future biodistribution and imaging studies of the FAPI-mIL-4 bioconjugate. We demonstrated site-specific coupling of mIL-4 and FAPI-DOTA deploying chemo-enzyme and enzyme chemistries with a high purity exceeding 95%. The FAPI-DOTA modified mIL-4 was bioactive with polarization of murine macrophages into the M2 state while maintaining specific binding to FAP on fibroblast cells. Together, these results point to future in vivo use of the FAPI-mIL-4 bioconjugate to assess biodistribution and biological effects in animal models of inflammatory joint disease.

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“…In contrast, azobenzene photoswitches are frequently used to reversibly control PPIs by stabilizing or destabilizing the peptide's 3D structure, depending on the configuration of the photoswitch [24,56,59,60] . However, due to the larger structural change, the biological effect of photochemical uncaging is often higher than the one observed after photoswitching [61] …”

Section: Introductionmentioning

confidence: 99%

“…Also, the effect of photoswitching on the secondary structure of the functionalized peptide was studied extensively, [61–67] while photocages are typically used to impair functional groups or PPI sites [68,69] . A structural insight into the influence of photocaged bioactive peptides and photocaged staples on the 3D structure of defined secondary structures is under investigated.…”

Section: Introductionmentioning

confidence: 99%

“…[24,56,59,60] However, due to the larger structural change, the biological effect of photochemical uncaging is often higher than the one observed after photoswitching. [61] Also, the effect of photoswitching on the secondary structure of the functionalized peptide was studied extensively, [61][62][63][64][65][66][67] while photocages are typically used to impair functional groups or PPI sites. [68,69] A structural insight into the influence of photocaged bioactive peptides and photocaged staples on the 3D structure of defined secondary structures is under investigated.…”

Section: Introductionmentioning

confidence: 99%

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Modulating Secondary Structure Motifs Through Photo‐Labile Peptide Staples

et al. 2023

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Peptide‐protein interactions (PPIs) are facilitated by the well‐defined three‐dimensional structure of bioactive peptides, interesting compounds for the development of new therapeutic agents. Their secondary structure and thus their propensity to engage in PPIs can be influenced by the introduction of peptide staples on the side chains. In particular, light‐controlled staples based on azobenzene photoswitches and their structural influence on helical peptides have been studied extensively. In contrast, photolabile staples bearing photocages as a structural key motif, have mainly been used to block supramolecular interactions. Their influence on the secondary structure of the target peptide is under‐investigated. Thus, in this study we use a combination of spectroscopic techniques and in silico simulations to systematically study a series of helical peptides with varying length of the photo‐labile staple to obtain a detailed insight into the structure‐property relationship in such photoresponsive biomolecules.

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Amber Light Control of Peptide Secondary Structure by a Perfluoroaromatic Azobenzene Photoswitch

Cited by 10 publications

References 64 publications

The Growing Field of Photoswitchable Macrocycles: A Promising Way to Tune Various Properties with Light

The Growing Field of Photoswitchable Macrocycles: A Promising Way to Tune Various Properties with Light

Bioconjugation of a Fibroblast Activation Protein Targeted Interleukin-4

Modulating Secondary Structure Motifs Through Photo‐Labile Peptide Staples

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