Radical‐Mediated Thiol‐Ene Strategy: Photoactivation of Thiol‐Containing Drugs in Cancer Cells

Sun, Shuang; Oliveira, Bruno L.; Jiménez‐Osés, Gonzalo; Bernardes, Gonçalo J. L.

doi:10.1002/anie.201811338

Cited by 27 publications

(18 citation statements)

References 48 publications

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“…Thus, modifications can be made for a better membrane permeability and thiol liberation inside the cell. In this sense, controlled release of largazole thiol from an isobutylene-caged largazole thiol derivative, which possesses a high permeability, has been achieved by UV light photoactivation of a thiol-ene triggering reaction [90].…”

Section: Cyclic Peptidesmentioning

confidence: 99%

Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds

Ramos-Inza¹,

Aydillo²,

Sanmartín³

et al. 2020

Heterocycles - Synthesis and Biological Activities

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Currently, cancer is one of the major health problems of the human population and prominent cause of death. Thiazole ring has demonstrated many pharmacological activities including anticancer. This scaffold has been found alone or incorporated into the diversity of therapeutic active agents such as tiazofurin, dasatinib, and bleomycin, which are well-known antineoplastic drugs. Recently, most of the compounds isolated from natural sources containing thiazole moiety exhibit notable cytotoxicities and present antitumor potential. In this context, several structural changes have been made in the original structure, such as the incorporation of different substituents or the fusion with other carbo-and heterocycles, in order to increase the antitumoral potency. Related to mechanism of action of these derivatives, some of them act through kinase modulation, polymerization inhibition of microtubule, pro-matrix metalloproteinase activation, signal transducer activation of transcription 3, histone deacetylase inhibition, etc.

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Section: Cyclic Peptidesmentioning

confidence: 99%

Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds

Ramos-Inza¹,

Aydillo²,

Sanmartín³

et al. 2020

Heterocycles - Synthesis and Biological Activities

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“…Furthermore, all the tested GSH contents of Gd-TCPP-NC became much lower than that in Gd-TCPP at the same level. This demonstrates that the NC group in Gd-TCPP-NC underwent thiol-ene click reactions and consumed large amounts of GSH under US [59,60]. Fig.…”

Section: Resultsmentioning

confidence: 83%

Employing the thiol-ene click reaction via metal-organic frameworks for integrated sonodynamic-starvation therapy as an oncology treatment

Jiang

et al. 2021

Sci. China Mater.

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Hypoxia in the tumor microenvironment (TME) greatly limits the tumor-killing therapeutic efficacy of sonodynamic therapy (SDT); this phenomenon is further exacerbated by increased glutathione (GSH) levels in cancer cells. Simultaneously, cancer starvation therapy is increasingly recognized nowadays as a promising clinical translation, but the efficacy of glucose oxidase (GOx)-based starvation therapy is also limited by the lack of oxygen in the tumor. Glyceraldehyde-3-phosphate dehydrogenase (GAPDH) is a key glycolytic enzyme and can therefore be a target for starvation therapy in the absence of oxygen engagement. Here, we proposed thiol-ene click reactions based on a two-dimensional metal-organic framework (MOF) modification for tumor treatments to enable the combination of SDT and starvation therapy. Experimental studies demonstrated that the prepared material could consume GSH and GAPDH free from oxygen in TME, which benefited from the thiol-ene click reactions between the MOFs and thiol substances in cancer cells. Further experiments in vitro and in vivo indicated the prepared MOF materials could kill cancer cells efficiently. This study is expected to create a promising avenue for thiol-ene click reactions in SDT and starvation therapy for cancer.

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“…This elegant strategy does not require the probe to undergo any structural changes which may affect its target binding and represents a translatable strategy for targeting other cysteine containing enzymes. The thiol–ene reaction initiated with DPAP and UV irradiation has been applied as a method for photoactivation of small molecules in human colon cancer cells, resulting in only slightly diminished cell viability, 76 while a visible light initiated thiol–ene has also been demonstrated on purified recombinant DUBs. 77 Further studies could help to elucidate the extent of toxicity implications of this radical initiator strategy in living systems.…”

Section: Exogenous Inductionmentioning

confidence: 99%

Flipping the Switch: Innovations in Inducible Probes for Protein Profiling

2021

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Over the past two decades, activity-based probes have enabled a range of discoveries, including the characterization of new enzymes and drug targets. However, their suitability in some labeling experiments can be limited by nonspecific reactivity, poor membrane permeability, or high toxicity. One method for overcoming these issues is through the development of “inducible” activity-based probes. These probes are added to samples in an unreactive state and require in situ transformation to their active form before labeling can occur. In this Review, we discuss a variety of approaches to inducible activity-based probe design, different means of probe activation, and the advancements that have resulted from these applications. Additionally, we highlight recent developments which may provide opportunities for future inducible activity-based probe innovations.

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Radical‐Mediated Thiol‐Ene Strategy: Photoactivation of Thiol‐Containing Drugs in Cancer Cells

Cited by 27 publications

References 48 publications

Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds

Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds

Employing the thiol-ene click reaction via metal-organic frameworks for integrated sonodynamic-starvation therapy as an oncology treatment

Flipping the Switch: Innovations in Inducible Probes for Protein Profiling

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