Prototropically Allosteric Probe for Superbly Selective DNA Analysis
| Autor: | Yong Shao, Hui Wang, Zhiai Xu, Yufeng Zhou, Benoit Habermeyer, Fan Lin, Xinghua Shi, Qiusha Li, Xiao-Shun Zhou |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Porphyrins
Base Sequence 010405 organic chemistry Guanine Stereochemistry Allosteric regulation Context (language use) DNA 010402 general chemistry 01 natural sciences Porphyrin Tetrapyrrole Polymorphism Single Nucleotide Sensitivity and Specificity 0104 chemical sciences Analytical Chemistry Thymine chemistry.chemical_compound chemistry Nucleic Acid Conformation AP site DNA Probes Cytosine Allosteric Site |
| Zdroj: | Analytical chemistry. 89(17) |
| ISSN: | 1520-6882 |
| Popis: | Selective nucleotide recognition for biosensor evolution requires rational probe design toward the binding-pattern-susceptible readout but without serious poison in selectivity from the context sequences. In this work, we synthesized a dual-function (trihydroxyphenyl)porphyrin (POH3) to target the abasic site (AP site) in ds-DNA using the trihydroxyphenyl substituent and the tetrapyrrole macrocycle as the recognition unit (RU) and the fluorescent signal unit (SU), respectively. RU and SU are separated from each other but are prototropically allosteric. We found that an appropriate pH favors formation of the nonfluorescent quinine/pyrrole (O–NH) conformer of POH3. However, the complementary hydrogen bonding of RU in O–NH with the target cytosine opposite the AP site switches on the SU fluorescence through prototropic allostery toward the phenol/isopyrrole (OH–N) conformer, while the bases thymine, guanine, and adenine totally silence this allostery, suggesting a superb selectivity in single-nucleotide poly... |
| Databáze: | OpenAIRE |
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