Cationic porphyrins with large side arm substituents as resonance light scattering ratiometric probes for specific recognition of nucleic acid G-quadruplexes

Abstract Specific G-quadruplex-probing is crucial for both biological sciences and biosensing applications. Most reported probes are focused on fluorescent or colorimetric recognition of G-quadruplexes. Herein, for the first time, we reported a new specific G-quadruplex-probing technique—resonance l...

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Bibliographic Details
Published in:Nucleic acids research 2019-04, Vol.47 (6), p.2727-2738
Main Authors: Zhang, Li-Ming, Cui, Yun-Xi, Zhu, Li-Na, Chu, Jun-Qing, Kong, De-Ming
Format: Article
Language:English
Subjects:
Binding Sites
Biosensing Techniques - methods
Calorimetry - methods
Cations - chemical synthesis
Cations - chemistry
Cations - metabolism
Chemical Biology and Nucleic Acid Chemistry
Circular Dichroism
G-Quadruplexes
Light
Molecular Probes - chemical synthesis
Molecular Probes - chemistry
Molecular Probes - metabolism
Nuclear Magnetic Resonance, Biomolecular - methods
Nucleic Acids - analysis
Nucleic Acids - isolation & purification
Nucleic Acids - metabolism
Optical Imaging - methods
Porphyrins - chemical synthesis
Porphyrins - chemistry
Porphyrins - metabolism
Protein Structure, Secondary
Scattering, Radiation
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Summary:Abstract Specific G-quadruplex-probing is crucial for both biological sciences and biosensing applications. Most reported probes are focused on fluorescent or colorimetric recognition of G-quadruplexes. Herein, for the first time, we reported a new specific G-quadruplex-probing technique—resonance light scattering (RLS)-based ratiometric recognition. To achieve the RLS probing of G-quadruplexes in the important physiological pH range of 7.4-6.0, four water soluble cationic porphyrin derivatives, including an unreported octa-cationic porphyrin, with large side arm substituents were synthesized and developed as RLS probes. These RLS probes were demonstrated to work well for ratiometric recognition of G-quadruplexes with high specificity against single- and double-stranded DNAs, including long double-stranded ones. The working mechanism was speculated to be based on the RLS signal changes caused by porphyrin protonation that was promoted by the end-stacking of porphyrins on G-quadruplexes. This work adds an important member in G-quadruplex probe family, thus providing a useful tool for studies on G-quadruplex-related events concerning G-quadruplex formation, destruction and changes in size, shape and aggregation. As a proof-of-concept example of applications, the RLS probes were demonstrated to work well for label-free and sequence-specific sensing of microRNA. This work also provides a simple and useful way for the preparation of cationic porphyrins with high charges.
ISSN:0305-1048
1362-4962
DOI:10.1093/nar/gkz064