Light-induced functions in DNA

Reisacher, Ulrike; Antusch, Linda; Hofsäß, Robert; Schwechheimer, Christian; Lehmann, Benjamin; Wagenknecht, Hans‐Achim

doi:10.1016/j.cbpa.2017.07.011

Cited by 6 publications

(3 citation statements)

References 47 publications

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“…It should be noted that photoclick reactions on DNA are also known, 449 but all of the examples reported to date operate under UV irradiation and thus are not discussed here.…”

Section: Photoclick Reactions For Protein Functionalizationmentioning

confidence: 99%

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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“…It should be noted that photoclick reactions on DNA are also known, 449 but all of the examples reported to date operate under UV irradiation and thus are not discussed here.…”

Section: Photoclick Reactions For Protein Functionalizationmentioning

confidence: 99%

Visible-Light-Mediated Modification and Manipulation of Biomacromolecules

et al. 2021

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“…Commonly used bioorthogonal cycloaddition reactions, including Cu(I)-catalyzed or strain-promoted azide–alkyne cycloaddition, Staudinger ligation, or the cycloaddition of alkenes with tetrazines, have greatly facilitated the labeling of various biomacromolecules, but not in a temporally and spatially resolved manner. Light irradiation is an ideal way to realize temporal and spatial control. , Photoclick chemistry using UV light to in situ generate reactive nitrile imine, quinonemethide or strained alkyne has provided the possibility to control the following cycloaddition reaction with temporal or spatial resolution. However, nucleophilic thiol or water additions to the highly reactive nitrile imine or quinomethide intermediates can be quite competitive with the cycloaddition reaction in complex biological environments .…”

mentioning

confidence: 99%

Visible Light-Initiated Bioorthogonal Photoclick Cycloaddition

et al. 2018

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Here we report a visible light-triggered, catalyst free bioorthogonal reaction that proceeds via a distinct pathway from reported bioorthogonal reactions. The prototype of this bioorthogonal reaction was the photocycloaddition of 9,10-phenanthrenequinone with electron-rich alkenes to form fluorogenic [4+2] cycloadducts. The bioorthogonal photoclick cycloaddition was readily initiated using a conventional visible light source such as a hand-held LED lamp. The reaction proceeded rapidly under biocompatible conditions, without observable competition from side reactions such as nucleophilic additions by water or common nucleophilic species. The bioorthogonal functionality in this reaction did not cross react with various alkynes and electron-deficient alkenes such as monomethyl fumarate. We demonstrated orthogonal labeling of two proteins using this reaction together with a strain promoting azide−alkyne click reaction or the UV-triggered reaction of tetrazole with monomethyl fumarate. The application of this reaction in the temporal and spatial labeling of live cells was also demonstrated.Communication pubs.acs.org/JACS

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“…[21][22][23][24] TO is especially useful to design quencher-free fluorescent probes. [25][26][27][28][29][30][31][32][33][34][35] Several groups have focused on the excellent photophysical properties of the TO dyes and synthesized TO-modified nucleic acids to create fluorogenic hybridization probes. [20-22,36À 39] TO-conjugated probes have been developed based on the structural basis of DNA, RNA, PNA and peptides, [40,41] used for biosensing and live cell imaging [25,[42][43][44] and the probe for the structural diversity of nucleic acids such as the i-motif and quadruplex.…”

Section: Introductionmentioning

confidence: 99%

Stacked Thiazole Orange Dyes in DNA Capable of Switching Emissive Behavior in Response to Structural Transitions

et al. 2021

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Functional nucleic acids with the capability of generating fluorescence in response to hybridization events, microenvironment or structural changes are valuable as structural probes and chemical sensors. We now demonstrate the enzymeassisted preparation of nucleic acids possessing multiple thiazole orange (TO) dyes and their fluorescent behavior, that show a spectral change from the typical monomer emission to the excimer-type red-shifted emission. We found that the fluorescent response and emission wavelength of the TO dyes were dependent on both the state of the DNA structure (singleor double-stranded DNA) and the arrangement of the TO dyes. We showed that the fluorescent behavior of the TO dyes can be applied for the detection of RNA molecules, suggesting that our approach for preparing the fluorescent nucleic acids functionalized with multiple TO dyes could be useful to design a fluorescence bioimaging and detection technique of biomolecules.

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Light-induced functions in DNA

Cited by 6 publications

References 47 publications

Visible-Light-Mediated Modification and Manipulation of Biomacromolecules

Visible-Light-Mediated Modification and Manipulation of Biomacromolecules

Visible Light-Initiated Bioorthogonal Photoclick Cycloaddition

Stacked Thiazole Orange Dyes in DNA Capable of Switching Emissive Behavior in Response to Structural Transitions

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