Two-photon uncaging of bioactive thiols in live cells at wavelengths above 800 nm

Hammers, Matthew D.; Hodny, Michael H; Bader, Taysir K.; Mahmoodi, Mohammad; Fang, Sifei; Fenton, Alexander D.; Nurie, Kadiro; Trial, Hallie O.; Xu, Feng; Healy, Andrew T.; Ball, Zachary T.; Blank, David A.; Distefano, Mark D.

doi:10.1039/d0ob01986k

Cited by 7 publications

(3 citation statements)

References 51 publications

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“…In a follow-up study, Distefano and co-workers sought to address this concern, identifying novel caged cysteine 310 in which the methoxy substituent increases the 2PE cross section relative to 306 . A very recent report from the same authors demonstrated the use of a dimethylamine-functionalized NDBF PPG for two-photon uncaging of biologically active thiols in live cells, although this has not yet been applied to cysteine residues …”

Section: Photoactivation Of Biological Functionmentioning

confidence: 99%

“…540 A very recent report from the same authors demonstrated the use of a dimethylamine-functionalized NDBF PPG for twophoton uncaging of biologically active thiols in live cells, although this has not yet been applied to cysteine residues 541. Another class of PPGs that have found widespread use in chemical biology are based on the (coumarin-4-yl)methyl group (311) (Scheme 91).…”

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confidence: 99%

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Visible-Light-Mediated Modification and Manipulation of Biomacromolecules

et al. 2021

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Chemically modified biomacromoleculesi.e., proteins, nucleic acids, glycans, and lipidshave become crucial tools in chemical biology. They are extensively used not only to elucidate cellular processes but also in industrial applications, particularly in the context of biopharmaceuticals. In order to enable maximum scope for optimization, it is pivotal to have a diverse array of biomacromolecule modification methods at one’s disposal. Chemistry has driven many significant advances in this area, and especially recently, numerous novel visible-light-induced photochemical approaches have emerged. In these reactions, light serves as an external source of energy, enabling access to highly reactive intermediates under exceedingly mild conditions and with exquisite spatiotemporal control. While UV-induced transformations on biomacromolecules date back decades, visible light has the unmistakable advantage of being considerably more biocompatible, and a spectrum of visible-light-driven methods is now available, chiefly for proteins and nucleic acids. This review will discuss modifications of native functional groups (FGs), including functionalization, labeling, and cross-linking techniques as well as the utility of oxidative degradation mediated by photochemically generated reactive oxygen species. Furthermore, transformations at non-native, bioorthogonal FGs on biomacromolecules will be addressed, including photoclick chemistry and DNA-encoded library synthesis as well as methods that allow manipulation of the activity of a biomacromolecule.

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Section: Photoactivation Of Biological Functionmentioning

confidence: 99%

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confidence: 99%

Visible-Light-Mediated Modification and Manipulation of Biomacromolecules

et al. 2021

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“…Currently, most PPGs are based on o -nitrobenzyl or coumarinyl scaffolds, ,, which are usually activated by light in the UV region. As UV light may raise risk for DNA damage, particularly with exposure for a prolonged period of time, and have limitations on tissue penetration, PPGs activated by more biologically benign visible and near-infrared (NIR) light are being advanced significantly. , Advantages of photocaged compounds over other pharmacological tools can be recognized in their spatiotemporal confinement, tunability, and reagentless deprotection. − In drug discovery, photocaged compounds are highly desirable to reduce the side effects of drugs by precise optical control over the treatment in the targeted disease area . Of particular note, the cascade photocaging concept has emerged in recent years, in which the first PPG is removed upon light irradiation to in turn trigger the release of the second PPG.…”

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Discovery of a Novel Photocaged PI3K Inhibitor Capable of Real-Time Reporting of Drug Release

Tian

You

Xiong

et al. 2023

ACS Med. Chem. Lett.

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A novel photocaged PI3K inhibitor 2 was designed and synthesized by introducing a cascade photocaging group to block its key interaction with the kinase. Upon UV light irradiation, the photocaged compound released a highly potent PI3K inhibitor to recover its anticancer properties and a fluorescent dye for real-time reporting of drug release, providing a new approach for studying the PI3K signaling transduction pathway as well as developing precisely controlled cancer therapeutics.

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Photo-controllable biochemistry: Exploiting the photocages in phototherapeutic window

Xiong

Kim

et al. 2023

Chem

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Two-photon uncaging of bioactive thiols in live cells at wavelengths above 800 nm

Abstract: Photoactivatable protecting groups (PPGs) are useful for a broad range of applications ranging from biology to materials science. In chemical biology, induction of biological processes via photoactivation is a powerful...

Cited by 7 publications

References 51 publications

Visible-Light-Mediated Modification and Manipulation of Biomacromolecules

Visible-Light-Mediated Modification and Manipulation of Biomacromolecules

Discovery of a Novel Photocaged PI3K Inhibitor Capable of Real-Time Reporting of Drug Release

Photo-controllable biochemistry: Exploiting the photocages in phototherapeutic window

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