Fluorinated Azobenzenes Switchable with Red Light

Overview

Journal Chemistry

Specialty Chemistry

Date 2021 Mar 26

PMID 33769596

Citations 10

Authors

Anna-Lena Leistner

Susanne Kirchner

Johannes Karcher

Tobias Bantle

Mariam L Schulte

Peter Godtel

Christian Fengler

Zbigniew L Pianowski

Affiliations

Soon will be listed here.

Abstract

Molecular photoswitches triggered with red or NIR light are optimal for photomodulation of complex biological systems, including efficient penetration of the human body for therapeutic purposes ("therapeutic window"). Yet, they are rarely reported, and even more rarely functional under aqueous conditions. In this work, fluorinated azobenzenes are shown to exhibit efficient E→Z photoisomerization with red light (PSS >75 % Z) upon conjugation with unsaturated substituents. Initially demonstrated for aldehyde groups, this effect was also observed in a more complex structure by incorporating the chromophore into a cyclic dipeptide with propensity for self-assembly. Under physiological conditions, the latter molecule formed a supramolecular material that reversibly changed its viscosity upon irradiation with red light. Our observation can lead to design of new photopharmacology agents or phototriggered materials for in vivo use.

Citing Articles

All-visible-light-driven stiff-stilbene photoswitches.

Xu F, Sheng J, Stindt C, Crespi S, Danowski W, Hilbers M Chem Sci. 2024; 15(18):6763-6769.

PMID: 38725493 PMC: 11077541. DOI: 10.1039/d4sc00983e.

Visible Light Control over the Cytolytic Activity of a Toxic Pore-Forming Protein.

Volaric J, van der Heide N, Mutter N, Samplonius D, Helfrich W, Maglia G ACS Chem Biol. 2024; 19(2):451-461.

PMID: 38318850 PMC: 10877574. DOI: 10.1021/acschembio.3c00640.

Red-light modulated -chloro azobenzene photoswitch for peptide stapling aromatic substitution.

Kapun M, Perez-Areales F, Ashman N, Rowling P, Schober T, Fowler E RSC Chem Biol. 2024; 5(1):49-54.

PMID: 38179193 PMC: 10763561. DOI: 10.1039/d3cb00176h.

Design and Synthesis of Visible-Light-Responsive Azobenzene Building Blocks for Chemical Biology.

Volaric J, Buter J, Schulte A, van den Berg K, Santamaria-Aranda E, Szymanski W J Org Chem. 2022; 87(21):14319-14333.

PMID: 36285612 PMC: 9639001. DOI: 10.1021/acs.joc.2c01777.

Photoresponsive Dissipative Macrocycles Using Visible-Light-Switchable Azobenzenes.

Nieland E, Voss J, Mix A, Schmidt B Angew Chem Int Ed Engl. 2022; 61(48):e202212745.

PMID: 36165240 PMC: 9828355. DOI: 10.1002/anie.202212745.

References

Georgiev V, Grafmuller A, Bleger D, Hecht S, Kunstmann S, Barbirz S . Area Increase and Budding in Giant Vesicles Triggered by Light: Behind the Scene. Adv Sci (Weinh). 2018; 5(8):1800432. PMC: 6096984. DOI: 10.1002/advs.201800432. View

Hammerich M, Schutt C, Stahler C, Lentes P, Rohricht F, Hoppner R . Heterodiazocines: Synthesis and Photochromic Properties, Trans to Cis Switching within the Bio-optical Window. J Am Chem Soc. 2016; 138(40):13111-13114. DOI: 10.1021/jacs.6b05846. View

Dong M, Babalhavaeji A, Samanta S, Beharry A, Woolley G . Red-Shifting Azobenzene Photoswitches for in Vivo Use. Acc Chem Res. 2015; 48(10):2662-70. DOI: 10.1021/acs.accounts.5b00270. View

Ter Schiphorst J, Melpignano G, Eslami Amirabadi H, Houben M, Bakker S, den Toonder J . Photoresponsive Passive Micromixers Based on Spiropyran Size-Tunable Hydrogels. Macromol Rapid Commun. 2017; 39(1). DOI: 10.1002/marc.201700086. View

Wegener M, Hansen M, Driessen A, Szymanski W, Feringa B . Photocontrol of Antibacterial Activity: Shifting from UV to Red Light Activation. J Am Chem Soc. 2017; 139(49):17979-17986. PMC: 5730949. DOI: 10.1021/jacs.7b09281. View

Lerch M, Hansen M, van Dam G, Szymanski W, Feringa B . Emerging Targets in Photopharmacology. Angew Chem Int Ed Engl. 2016; 55(37):10978-99. DOI: 10.1002/anie.201601931. View

Heinrich B, Bouazoune K, Wojcik M, Bakowsky U, Vazquez O . ortho-Fluoroazobenzene derivatives as DNA intercalators for photocontrol of DNA and nucleosome binding by visible light. Org Biomol Chem. 2019; 17(7):1827-1833. DOI: 10.1039/c8ob02343c. View

Manna D, Udayabhaskararao T, Zhao H, Klajn R . Orthogonal light-induced self-assembly of nanoparticles using differently substituted azobenzenes. Angew Chem Int Ed Engl. 2015; 54(42):12394-7. DOI: 10.1002/anie.201502419. View

Beharry A, Woolley G . Azobenzene photoswitches for biomolecules. Chem Soc Rev. 2011; 40(8):4422-37. DOI: 10.1039/c1cs15023e. View

10.

Lubbe A, Szymanski W, Feringa B . Recent developments in reversible photoregulation of oligonucleotide structure and function. Chem Soc Rev. 2017; 46(4):1052-1079. DOI: 10.1039/c6cs00461j. View

11.

Yang Y, Hughes R, Aprahamian I . Near-infrared light activated azo-BF2 switches. J Am Chem Soc. 2014; 136(38):13190-3. DOI: 10.1021/ja508125n. View

12.

Schwarz F, Heinrich T, Kaufmann J, Lippitz A, Puttreddy R, Rissanen K . Photocontrolled On-Surface Pseudorotaxane Formation with Well-Ordered Macrocycle Multilayers. Chemistry. 2016; 22(40):14383-9. DOI: 10.1002/chem.201603156. View

13.

Karcher J, Pianowski Z . Photocontrol of Drug Release from Supramolecular Hydrogels with Green Light. Chemistry. 2018; 24(45):11605-11610. DOI: 10.1002/chem.201802205. View

14.

Szymanski W, Beierle J, Kistemaker H, Velema W, Feringa B . Reversible photocontrol of biological systems by the incorporation of molecular photoswitches. Chem Rev. 2013; 113(8):6114-78. DOI: 10.1021/cr300179f. View

15.

Babii O, Afonin S, Berditsch M, ReiBer S, Mykhailiuk P, Kubyshkin V . Controlling biological activity with light: diarylethene-containing cyclic peptidomimetics. Angew Chem Int Ed Engl. 2014; 53(13):3392-5. DOI: 10.1002/anie.201310019. View

16.

Aemissegger A, Krautler V, van Gunsteren W, Hilvert D . A photoinducible beta-hairpin. J Am Chem Soc. 2005; 127(9):2929-36. DOI: 10.1021/ja0442567. View

17.

Lameijer L, Budzak S, Simeth N, Hansen M, Feringa B, Jacquemin D . General Principles for the Design of Visible-Light-Responsive Photoswitches: Tetra-ortho-Chloro-Azobenzenes. Angew Chem Int Ed Engl. 2021; 59(48):21663-21670. PMC: 7756550. DOI: 10.1002/anie.202008700. View

18.

Zhang L, Linden G, Vazquez O . In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization. Beilstein J Org Chem. 2019; 15:2500-2508. PMC: 6839558. DOI: 10.3762/bjoc.15.243. View

19.

Masutani K, Morikawa M, Kimizuka N . A liquid azobenzene derivative as a solvent-free solar thermal fuel. Chem Commun (Camb). 2014; 50(99):15803-6. DOI: 10.1039/c4cc07713j. View

20.

Mart R, Allemann R . Azobenzene photocontrol of peptides and proteins. Chem Commun (Camb). 2016; 52(83):12262-12277. DOI: 10.1039/c6cc04004g. View