C-Linked 8-aryl guanine nucleobase adducts: biological outcomes and utility as fluorescent probes

Chemical Science
Richard A Manderville, Stacey D Wetmore

Abstract

Aryl radical species derived from enzymatic transformations of aromatic mutagens preferentially react at the 8-site of the guanine (G) nucleobase to afford carbon-linked 8arylG adducts. The resulting lesions possess altered biophysical and genetic coding properties compared to the precursor G nucleoside in B-form DNA. Unlike other adducts, these lesions also possess useful fluorescent properties, since direct attachment of the 8aryl ring extends the purine π-system to afford G mimics with red-shifted excitation maxima and emission that can be sensitive to the microenvironment of the 8arylG base within nucleic acid structures. In B-form DNA, 8arylG adducts are disruptive to duplex formation because they prefer to adopt the syn-conformation about the bond connecting the nucleobase to the deoxyribose backbone, which perturbs Watson-Crick (WC) H-bonding with the opposing cytosine (C). Thus, in a B-form duplex, the emissive properties of 8arylG adducts can be employed as a tool to provide insight into adduct conformation, which can be related to their biological outcomes. However, since Gs preferentially adopt the syn-conformation in left-handed Z-DNA and antiparallel G-quadruplex (GQ) structures, 8arylG lesions can be inserted into...Continue Reading

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Citations

May 21, 2019·Nucleic Acids Research·Ashok NuthanakantiSeergazhi G Srivatsan
Dec 21, 2016·Organic & Biomolecular Chemistry·Diana Silva-BrenesJosé M Rivera
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May 11, 2018·Organic & Biomolecular Chemistry·Abigail J Van RiesenStacey D Wetmore
Jul 5, 2019·Analytical Chemistry·Shanfang HuShouzhuo Yao
Jul 23, 2016·ACS Chemical Biology·Thomas Z CservenyiRichard A Manderville

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Methods Mentioned

BETA
biosensors
NMR
circular dichroism
FRET

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