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Modulating Protein-Protein Interactions with Visible-Light-Responsive Peptide Backbone Photoswitches

Authorized Users Only
2019
Authors
Albert, Lea
Penalver, Alberto
Đoković, Nemanja
Werel, Laura
Hoffarth, Malte
Ružić, Dušan
Xu, Jing
Essen, Lars-Oliver
Nikolić, Katarina
Dou, Yali
Vazquez, Olalla
Article (Published version)
Metadata
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Abstract
Life relies on a myriad of carefully orchestrated processes, in which proteins and their direct interplay ultimately determine cellular function and disease. Modulation of this complex crosstalk has recently attracted attention, even as a novel therapeutic strategy. Herein, we describe the synthesis and characterization of two visible-light-responsive peptide backbone photoswitches based on azobenzene derivatives, to exert optical control over protein-protein interactions (PPI). The novel peptidomimetics undergo fast and reversible isomerization with low photochemical fatigue under alternatively blue-/green-light irradiation cycles. Both bind in the nanomolar range to the protein of interest. Importantly, the best peptidomimetic displays a clear difference between isomers in its protein-binding capacity and, in turn, in its potential to inhibit enzymatic activity through PPI disruption. In addition, crystal structure determination, docking and molecular dynamics calculations allow a mo...lecular interpretation and open up new avenues in the design and synthesis of future photoswitchable PPI modulators.

Keywords:
azobenzenes / isomerization / peptidomimetics / photochemistry / protein-protein interactions
Source:
Chembiochem, 2019, 20, 11, 1417-1429
Publisher:
  • Wiley-VCH Verlag GMBH, Weinheim
Funding / projects:
  • Modeling and Numerical Simulations of Complex Many-Body Systems (RS-171017)

DOI: 10.1002/cbic.201800737

ISSN: 1439-4227

PubMed: 30675988

WoS: 000474071700012

Scopus: 2-s2.0-85065047737
[ Google Scholar ]
22
17
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/3258
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Albert, Lea
AU  - Penalver, Alberto
AU  - Đoković, Nemanja
AU  - Werel, Laura
AU  - Hoffarth, Malte
AU  - Ružić, Dušan
AU  - Xu, Jing
AU  - Essen, Lars-Oliver
AU  - Nikolić, Katarina
AU  - Dou, Yali
AU  - Vazquez, Olalla
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3258
AB  - Life relies on a myriad of carefully orchestrated processes, in which proteins and their direct interplay ultimately determine cellular function and disease. Modulation of this complex crosstalk has recently attracted attention, even as a novel therapeutic strategy. Herein, we describe the synthesis and characterization of two visible-light-responsive peptide backbone photoswitches based on azobenzene derivatives, to exert optical control over protein-protein interactions (PPI). The novel peptidomimetics undergo fast and reversible isomerization with low photochemical fatigue under alternatively blue-/green-light irradiation cycles. Both bind in the nanomolar range to the protein of interest. Importantly, the best peptidomimetic displays a clear difference between isomers in its protein-binding capacity and, in turn, in its potential to inhibit enzymatic activity through PPI disruption. In addition, crystal structure determination, docking and molecular dynamics calculations allow a molecular interpretation and open up new avenues in the design and synthesis of future photoswitchable PPI modulators.
PB  - Wiley-VCH Verlag GMBH, Weinheim
T2  - Chembiochem
T1  - Modulating Protein-Protein Interactions with Visible-Light-Responsive Peptide Backbone Photoswitches
VL  - 20
IS  - 11
SP  - 1417
EP  - 1429
DO  - 10.1002/cbic.201800737
ER  - 
@article{
author = "Albert, Lea and Penalver, Alberto and Đoković, Nemanja and Werel, Laura and Hoffarth, Malte and Ružić, Dušan and Xu, Jing and Essen, Lars-Oliver and Nikolić, Katarina and Dou, Yali and Vazquez, Olalla",
year = "2019",
abstract = "Life relies on a myriad of carefully orchestrated processes, in which proteins and their direct interplay ultimately determine cellular function and disease. Modulation of this complex crosstalk has recently attracted attention, even as a novel therapeutic strategy. Herein, we describe the synthesis and characterization of two visible-light-responsive peptide backbone photoswitches based on azobenzene derivatives, to exert optical control over protein-protein interactions (PPI). The novel peptidomimetics undergo fast and reversible isomerization with low photochemical fatigue under alternatively blue-/green-light irradiation cycles. Both bind in the nanomolar range to the protein of interest. Importantly, the best peptidomimetic displays a clear difference between isomers in its protein-binding capacity and, in turn, in its potential to inhibit enzymatic activity through PPI disruption. In addition, crystal structure determination, docking and molecular dynamics calculations allow a molecular interpretation and open up new avenues in the design and synthesis of future photoswitchable PPI modulators.",
publisher = "Wiley-VCH Verlag GMBH, Weinheim",
journal = "Chembiochem",
title = "Modulating Protein-Protein Interactions with Visible-Light-Responsive Peptide Backbone Photoswitches",
volume = "20",
number = "11",
pages = "1417-1429",
doi = "10.1002/cbic.201800737"
}
Albert, L., Penalver, A., Đoković, N., Werel, L., Hoffarth, M., Ružić, D., Xu, J., Essen, L., Nikolić, K., Dou, Y.,& Vazquez, O.. (2019). Modulating Protein-Protein Interactions with Visible-Light-Responsive Peptide Backbone Photoswitches. in Chembiochem
Wiley-VCH Verlag GMBH, Weinheim., 20(11), 1417-1429.
https://doi.org/10.1002/cbic.201800737
Albert L, Penalver A, Đoković N, Werel L, Hoffarth M, Ružić D, Xu J, Essen L, Nikolić K, Dou Y, Vazquez O. Modulating Protein-Protein Interactions with Visible-Light-Responsive Peptide Backbone Photoswitches. in Chembiochem. 2019;20(11):1417-1429.
doi:10.1002/cbic.201800737 .
Albert, Lea, Penalver, Alberto, Đoković, Nemanja, Werel, Laura, Hoffarth, Malte, Ružić, Dušan, Xu, Jing, Essen, Lars-Oliver, Nikolić, Katarina, Dou, Yali, Vazquez, Olalla, "Modulating Protein-Protein Interactions with Visible-Light-Responsive Peptide Backbone Photoswitches" in Chembiochem, 20, no. 11 (2019):1417-1429,
https://doi.org/10.1002/cbic.201800737 . .

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