Highly specific G-quadruplex recognition covering physiological pH range by a new water-soluble cationic porphyrin with low self-aggregation tendency. (October 2017)

• Record Type: Journal Article
• Authors: Zhang, Li-Na; Zhang, Ran; Cui, Yun-Xi; Liu, Ke-Ke; Kong, De-Ming; Li, Xiao-Zeng; Zhu, Li-Na
• Is Part Of: Dyes and pigments. Volume 145(2017)
• Page Start: 404
• Page End: 417
• Publication Date: 2017-10
• Subjects: Porphyrins -- G-quadruplex -- Optical probe -- Aggregation -- pH; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2017.06.028
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: A new water-soluble cationic porphyrin derivative m -TMPyEOPP (5, 10, 15, 20-tetrakis{4-[2-(O-(N-methylpyridyl)ethoxyl]oxyphenly}porphyrin) has been designed, synthesized, and fully characterized. This porphyrin derivative combines the advantages of two cationic porphyrins used in G-quadruplex recognition and stabilization studies, i.e., the widely investigated G-quadruplex ligand TMPyP4 and TMPipEOPP reported by us. That is to say, the presence of four bulky side-arm substituents endows the m -TMPyEOPP derivative with the capacity for colorimetric and fluorescence-based recognition of G-quadruplexes with high specificity. By virtue of almost negligible pH-dependent self-aggregation, and hence reduced single- and double-stranded DNA-templated aggregation behavior, it can also work well under acidic conditions. By combining the fluorescence signals obtained at different excitation wavelengths (690 or 260 nm), specific G-quadruplex recognition can be achieved by m -TMPyEOPP in the pH range 5.0–7.5, which almost covers the physiological pH range. Ratiometric signal output mode might confer G-quadruplex recognition with high accuracy, reliability and repeatability. This work demonstrates that the aggregation behaviours of water-soluble cationic porphyrins can be controlled by adjusting the nature of the substituents on their side arms, thus endowing them with different G-quadruplex-specific recognition abilities suitable for different pH conditions. Highlights: A water-soluble porphyrin was designed, synthesized and used for optical probing of G-quadruplex. This porphyrin combines the advantages of tworeported cationic porphyrins. The porphyrin can probe G-quadruplex with high specificity in a wide pH range 5.0–7.5. Ratiometric signal output might confer G-quadruplex recognition with high accuracy and reliability. This work paves a way to design G-quadruplex probes suitable for different pH conditions.