Triggering DNAzymes with light: a photoactive C8 thioether-linked adenosine.

Richard Ting; Leonard Lermer; David M Perrin

doi:10.1021/ja046964y

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Triggering DNAzymes with light: a photoactive C8 thioether-linked adenosine.

Richard Ting·Leonard Lermer·David M Perrin

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Abstract

Herein we report evidence for a light-inducible DNAzyme. In so doing, we also disclose the synthesis and photochemical properties of a novel nucleoside: 8-(2-(4-imidazolyl)ethyl-1-thio)-2'-deoxyriboadenosine (d1). The light sensitivity of (d1) was evaluated via an examination of the photoinduced reactivation of DNAzyme 8-17E from an inactive form that contained a single nucleotide (d1) modification. Restoration of DNAzyme activity results from a photoinduced reversion of (d1) to unmodified deoxyadenosine. Deuterium studies indicate that water is the source of hydrogen in the C8-H product and not the alkylthio group, suggesting that reversion of (1) to adenosine is not a consequence of simple homolysis of the C8-S bond but of an unprecedented photochemical conversion. This adenosine, which affords significant control of catalytic reactivation of a DNAzyme, may find general use in photodecaging other biological systems.

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Adenosine Base Sequence DNA, Catalytic Light Nucleic Acid Conformation Photochemistry RNA Spectrophotometry, Ultraviolet Sulfides Journal Article Research Support, Non-U.S. Gov't

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Richard Ting, Leonard Lermer, David M Perrin. 2004-10-13. Triggering DNAzymes with light: a photoactive C8 thioether-linked adenosine.. https://doi.org/10.1021/ja046964y

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