Synthesis and photophysical properties of new SNARF derivatives as dual emission pH sensors

We report the synthesis and properties of two new seminaphthorhodafluor (SNARF) derivatives, SNARF-F and SNARF-Cl. Both these derivatives exhibit typical red shifts of absorption and fluorescence, and higher cell permeability as compared to traditional SNARF, while the pH-dependent dual-emission cha...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2011-03, Vol.21 (6), p.1663-1666
Hauptverfasser:	Nakata, Eiji, Nazumi, Yoshijiro, Yukimachi, Yoshihiro, Uto, Yoshihiro, Maezawa, Hiroshi, Hashimoto, Toshihiro, Okamoto, Yasuko, Hori, Hitoshi
Format:	Artikel
Sprache:	eng
Schlagworte:	absorption Analytical biochemistry: general aspects, technics, instrumentation Analytical, structural and metabolic biochemistry Benzopyrans - chemical synthesis Benzopyrans - chemistry Biological and medical sciences Cell permeability fluorescence Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry Fundamental and applied biological sciences. Psychology Hydrogen-Ion Concentration Near infrared permeability pH indicator Photochemistry Ratiometry SNARF Spectrometry, Fluorescence
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Zusammenfassung:	We report the synthesis and properties of two new seminaphthorhodafluor (SNARF) derivatives, SNARF-F and SNARF-Cl. Both these derivatives exhibit typical red shifts of absorption and fluorescence, and higher cell permeability as compared to traditional SNARF, while the pH-dependent dual-emission characteristics are well retained. In particular, the lower p K a (7.38) of SNARF-F makes it more suitable than traditional SNARF derivatives for intracellular applications.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2011.01.105