In the Search for Photocages Cleavable with Visible Light: An Overview of Recent Advances and Chemical Strategies DOI
Laia Josa‐Culleré, Amadeu Llebaria

ChemPhotoChem, Journal Year: 2020, Volume and Issue: 5(4), P. 296 - 314

Published: Dec. 4, 2020

Abstract Photopharmacological tools enable the precise spatiotemporal control of small molecule drugs. Amongst them, caged compounds incorporate a photolabile moiety which is released under illumination, thus liberating active molecule. Caging groups have long been known and many chemical scaffolds already used in different applications. However, most initial examples are cleaved with UV light, suffers from low tissue permeability cell damage. Recently, caging that visible light reported, expand their utility. In this review, we outline strategies to increase absorption wavelengths; compare photophysical properties, discuss synthetic accessibility, exemplify some biological

Language: Английский

Molecular photoswitches in aqueous environments DOI Creative Commons
Jana Volarić, Wiktor Szymański, Nadja A. Simeth

et al.

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(22), P. 12377 - 12449

Published: Jan. 1, 2021

Molecular photoswitches are inherently lipophilic and do not spontaneously dissolve in water. We describe the effect of water on photochemical properties strategies to solubilize organic apply them aqueous media.

Language: Английский

Citations

278

Designing light-driven rotary molecular motors DOI Creative Commons
Daisy R. S. Pooler, Anouk S. Lubbe, Stefano Crespi

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 12(45), P. 14964 - 14986

Published: Jan. 1, 2021

Various families of light-driven rotary molecular motors and the key aspects motor design are discussed. Comparisons made between strengths weaknesses each motor. Challenges, applications, future prospects explored.

Language: Английский

Citations

152

Taking phototherapeutics from concept to clinical launch DOI Open Access
Brianna M. Vickerman, Emilia M. Zywot, Teresa K. Tarrant

et al.

Nature Reviews Chemistry, Journal Year: 2021, Volume and Issue: 5(11), P. 816 - 834

Published: Oct. 6, 2021

Language: Английский

Citations

129

Stepping Out of the Blue: From Visible to Near‐IR Triggered Photoswitches DOI
Zhiwei Zhang, Wenhui Wang, Michael O’Hagan

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(31)

Published: May 7, 2022

Abstract Light offers unique opportunities for controlling the activity of materials and biosystems with high spatiotemporal resolution. Molecular photoswitches are chromophores that undergo reversible isomerization between different states upon irradiation light, allowing a convenient means to control their influence over system interest. However, significant limitation classical is requirement initiate switching in one or both directions using deleterious UV light poor tissue penetration. Red‐shifted hence demand have attracted keen recent research In this Review, we highlight progress towards development visible‐ NIR‐activated characterized by distinct photochromic reaction mechanisms. We hope inspire further endeavors field, full potential these tools biotechnology chemistry applications be realized.

Language: Английский

Citations

106

Rational Design in Photopharmacology with Molecular Photoswitches DOI Creative Commons
Piermichele Kobauri, Frank J. Dekker, Wiktor Szymański

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(30)

Published: April 7, 2023

Photopharmacology is an attractive approach for achieving targeted drug action with the use of light. In photopharmacology, molecular photoswitches are introduced into structure biologically active small molecules to allow optical control their potency. Going beyond trial and error, photopharmacology has progressively applied rational design methodologies devise light-controlled bioactive ligands. this review, we categorize photopharmacological efforts from standpoint medicinal chemistry strategies, focusing on diffusible photochromic ligands modified that operate through E-Z bond isomerization. vast majority cases, photoswitchable designed as analogs existing compounds, a variety approaches. By analyzing in detail comprehensive list instructive examples, describe state art discuss future opportunities photopharmacology.

Language: Английский

Citations

106

Smart Photochromic Materials Triggered with Visible Light DOI
Anna‐Lena Leistner, Zbigniew Pianowski

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(19)

Published: Feb. 26, 2022

Abstract Molecular photoswitches reversibly convert the energy of light into a variety structural changes at molecular level. They can be integrated smart materials with broad range applicability. While most photochromic systems require UV for activation, application operational entirely within visible or NIR brings considerable benefits, such as biocompatibility, better penetration through material, propelling sunlight, possibility to design dual that are mutually activated frequencies two distinct functions. In this Review, we discuss relevant classes photoswitches, and demonstrate selection polymers, gels, porous materials, surfaces, energy‐storing other triggered light.

Language: Английский

Citations

91

Triggered azobenzene-based prodrugs and drug delivery systems DOI
Jundong Zhu, Tao Guo, Zheng Wang

et al.

Journal of Controlled Release, Journal Year: 2022, Volume and Issue: 345, P. 475 - 493

Published: March 23, 2022

Language: Английский

Citations

85

Photoswitchable diarylethenes: From molecular structures to biological applications DOI
Ziyong Li,

Xiaoyan Zeng,

Caimin Gao

et al.

Coordination Chemistry Reviews, Journal Year: 2023, Volume and Issue: 497, P. 215451 - 215451

Published: Sept. 18, 2023

Language: Английский

Citations

73

Visible light-responsive materials: the (photo)chemistry and applications of donor–acceptor Stenhouse adducts in polymer science DOI Creative Commons
Michèle Clerc, Sara Sandlass, Omar Rifaie‐Graham

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(23), P. 8245 - 8294

Published: Jan. 1, 2023

Donor-acceptor Stenhouse adduct (DASA) photoswitches have gained a lot of attention since their discovery in 2014. Their negative photochromism, visible light absorbance, synthetic tunability, and the large property changes between photoisomers make them attractive candidates over other commonly used for use materials with responsive or adaptive properties. The development such translation into advanced technologies continues to widely impact forefront research, DASAs thus attracted considerable interest field visible-light molecular switches dynamic materials. Despite this interest, there been challenges understanding complex behavior context both small molecule studies Moreover, incorporation polymers can be challenging due incompatibility conditions most common polymerization techniques. In review, therefore, we examine critically discuss recent developments DASA-containing polymers, aiming at providing better interplay properties constituents (matrix photoswitch). first part summarizes current DASA design switching second section discusses strategies materials, methods studying We also emerging applications polymeric ranging from light-responsive drug delivery systems, photothermal actuators, sensors photoswitchable surfaces. Last, summarize venture on steps required explore novel systems expand functional application opportunities polymers.

Language: Английский

Citations

54

Phenylazothiazoles as Visible-Light Photoswitches DOI
Runze Lin, P. K. Hashim, Saugata Sahu

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(16), P. 9072 - 9080

Published: April 12, 2023

A novel class of photoswitches based on a phenylazothiazole scaffold that undergoes reversible isomerization under visible-light irradiation is reported. The photoswitch, which comprises thiazole heteroaryl segment directly connected to phenyl azo chromophore, has very different spectral characteristics, such as redshifted absorption maximum wavelength and well-separated bands the trans cis isomers, than conventional azobenzene other compounds. Substituents at ortho para positions ring photoswitch resulted in further shift longer wavelengths up 525 nm with small thermal stability compensation. These showed excellent photostationary distributions half-lives 7.2 h, reductant stability. X-ray crystal structure analysis revealed isomers exhibited planar geometry T-shaped orthogonal geometry. Detailed ab initio calculations demonstrated plausible electronic transitions energy barriers, were consistent experimental observations. fundamental design principles elucidated this study will aid development wide variety for photopharmacological applications.

Language: Английский

Citations

50