Photo-uncaging of BODIPY oxime ester for histone deacetylases induced apoptosis in tumor cells

Sambath, Karthik; Zhao, Tinghan; Wan, Zhaoxiong; Zhang, Yuanwei

doi:10.1039/c9cc07199g

Cited by 28 publications

(29 citation statements)

References 29 publications

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“…A different approach to using BODIPY scaffolds for photorelease is to introduce photoreactive functional groups in the 2,6-positions ( 157 ). 836 , 837 This approach is exemplified by the photorelease of amines from sulfonamide groups in the BODIPY 2,6-positions (λ irr = 470 ± 20 nm, chemical yields = 45–50%, Φ r = 0.022–0.11). 836 These photoreactions were insensitive to the presence of oxygen, required a carboxylic functional group in the α-position of the amide chain, and exhibited pH-dependent rates, proceeding less efficiently under acidic conditions.…”

Section: Photorelease From Organic Photoactivatable Compoundsmentioning

confidence: 99%

“… 859 In the case of 159 , back electron transfer was found to be favorable; the 2-cyano BODIPY photoproduct was obtained in 60% chemical yield. 837 The histone deacetylase inhibitor valproic acid (VPA) was caged as a BODIPY oxime ester in this way; in HeLa cells, this compound caused light- and dose-dependent toxicity with an IC 50 100-times lower than that of free VPA. 837 …”

Section: Photorelease From Organic Photoactivatable Compoundsmentioning

confidence: 99%

“… 837 The histone deacetylase inhibitor valproic acid (VPA) was caged as a BODIPY oxime ester in this way; in HeLa cells, this compound caused light- and dose-dependent toxicity with an IC 50 100-times lower than that of free VPA. 837 …”

Section: Photorelease From Organic Photoactivatable Compoundsmentioning

confidence: 99%

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Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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Photoactivatable (alternatively, photoremovable, photoreleasable, or photocleavable) protecting groups (PPGs), also known as caged or photocaged compounds, are used to enable non-invasive spatiotemporal photochemical control over the release of species of interest. Recent years have seen the development of PPGs activatable by biologically and chemically benign visible and near-infrared (NIR) light. These long-wavelength-absorbing moieties expand the applicability of this powerful method and its accessibility to non-specialist users. This review comprehensively covers organic and transition metal-containing photoactivatable compounds (complexes) that absorb in the visible- and NIR-range to release various leaving groups and gasotransmitters (carbon monoxide, nitric oxide, and hydrogen sulfide). The text also covers visible- and NIR-light-induced photosensitized release using molecular sensitizers, quantum dots, and upconversion and second-harmonic nanoparticles, as well as release via photodynamic (photooxygenation by singlet oxygen) and photothermal effects. Release from photoactivatable polymers, micelles, vesicles, and photoswitches, along with the related emerging field of photopharmacology, is discussed at the end of the review.

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Section: Photorelease From Organic Photoactivatable Compoundsmentioning

confidence: 99%

Section: Photorelease From Organic Photoactivatable Compoundsmentioning

confidence: 99%

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Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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“…Another example where the cargo has been introduced at the 2 position was reported in 2019 by Zhang and coworkers. [32] They took advantage of the weak NÀ O bond of oxime esters [33,34] to design a BODIPY photocage 7 that released aliphatic and aromatic carboxylic acids upon green light irradiation (500-520 nm). The photolysis mechanism proceeds at least partially via a triplet excited state, releasing the acid along with the 2-cyano-BODIPY photoproduct.…”

Section: Cargo At the 26-positionsmentioning

confidence: 99%

“…Another example where the cargo has been introduced at the 2 position was reported in 2019 by Zhang and coworkers [32] . They took advantage of the weak N−O bond of oxime esters [33,34] to design a BODIPY photocage 7 that released aliphatic and aromatic carboxylic acids upon green light irradiation (500‐520 nm).…”

Section: Bodipymentioning

confidence: 99%

In the Search for Photocages Cleavable with Visible Light: An Overview of Recent Advances and Chemical Strategies

Josa-Culleré

Llebaría

2020

ChemPhotoChem

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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 the active molecule. Caging groups have long been known and many chemical scaffolds have already been used in different applications. However, most of the initial examples are cleaved with UV light, which suffers from low tissue permeability and cell damage. Recently, caging groups that are released under visible light have been reported, which expand their utility. In this review, we outline the chemical strategies that have been used to increase the absorption wavelengths; we compare their photophysical properties, discuss their synthetic accessibility, and exemplify some of their biological applications.

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Photoresponsive Small Molecule Inhibitors for the Remote Control of Enzyme Activity

Laczi

Johnstone

Fleming

2022

Chemistry An Asian Journal

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The development of new and effective therapeutics is reliant on the ability to study the underlying mechanisms of potential drug targets in live cells and multicellular systems. A persistent challenge in many drug development programmes is poor selectivity, which can obscure the mechanisms involved and lead to poorly understood modes of action. In efforts to improve our understanding of these complex processes, small molecule inhibitors have been developed in which their OFF/ON therapeutic activity can be toggled using light. Photopharmacology is devoted to using light to modulate drugs. Herein, we highlight the recent progress made towards the development of light‐responsive small molecule inhibitors of selected enzymatic targets. Given the size of this field, literature from 2015 onwards has been reviewed.

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Photo-uncaging of BODIPY oxime ester for histone deacetylases induced apoptosis in tumor cells

Abstract: A new photo-uncaging platform to guide drug delivery with enhanced therapeutic effect.

Cited by 28 publications

References 29 publications

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

In the Search for Photocages Cleavable with Visible Light: An Overview of Recent Advances and Chemical Strategies

Photoresponsive Small Molecule Inhibitors for the Remote Control of Enzyme Activity

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