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• W2742045722 abstract "Even though many fluorescent sensors for various metal ions or anions have been reported, there has been no precedent example which can sense Au so far. A more rational basis for the therapeutic use of gold, especially as an antirheumatic drug, has been studied for more than 50 years, while the scientific explanation for the beneficial effects is still lacking. For example, it is known that gold ions are known as inhibitors of macrophages and polymorphonuclear leucocytes and to suppress inflammation in rheumatic joints, although information on the effect of gold ion on the cellular immune response is currently sparse. Accordingly, Au selective sensing would be very useful for the development of cellular imaging probes and other purposes. Recently, rhodamine derivatives have been utilized for sensing metal ions and oxidative species, in which the spirolactam (nonfluorescent) to ring opened amide (fluorescent) process was utilized. These changes can be due to the reversible ring-opening process, while there are a few examples of chemodosimeters. On the other hand, there are recent reports of utilizing the alkyne moiety for sensing mercury. Herein, we report the first fluorescent and colorimetric chemodosimeter for Au, which works at pH 7.4. Rhodamine– alkyne derivative 1 displayed a highly selective fluorescence enhancement (over 100 fold) and colorless to pink colorimetric change with Au among the various metal ions examined. This was an irreversible change and the product was characterized by NMR and mass spectroscopy. For the synthesis of sensor 1, as shown in Scheme 1, rhodamine B was first reacted with POCl3 and then with excess prop-2-yn-1-amine to give 1 in 92% yield after column chromatography using hexane–EtOAc (7 : 3, v/v) as an eluent. The detailed experimental procedure and characterization data are explained in the ESI (Fig. S1 and S2).w Ag, Al, Au, Au, Ca, Cd, Co, Cr, Cu, Cu, Fe, Fe, Hg, K, Li, Mg, Mn, Na, Ni, Pb, Pd, Pt and Zn ions were used to evaluate the metal ion selectivity of 1 (5 mM) in EtOH–HEPES buffer (0.01 M, pH 7.4) (1 : 1, v/v). For Cu, Pd, Pt and Au due to the solubility problem, DMSO–HEPES buffer (0.01 M, pH 7.4) (1 : 1, v/v) was used. Among these metal ions (10 equiv.), probe 1 showed large fluorescence enhancement only with Au (Fig. 1). All the fluorescence data for Fig. 1 and 2 were taken after 10 min. As large as 250-fold ‘‘Off–On’’ type fluorescence enhancement was observed upon the addition of Au. The addition of Au also induced a colorimetric change. Colorless to pink color change was observed as naked eye detection of Au (Fig. S3, ESIw). There was also a large enhancement (B6-fold) in the UV absorption (lmax = 562 nm) of probe 1 upon the addition of Au (Fig. S4, ESIw). Fig. 2 shows the fluorescence changes with increasing amounts of Au in EtOH–HEPES buffer (0.01 M, pH 7.4) (1 : 1, v/v). The fluorescence intensity of probe 1 with Au was also checked in the presence of other metal ions (including Ag, Al, Ca, Cd, Co, Cu, Cu, Fe, Fe, Hg, K, Mg, Mn, Na, Ni, Pb, Zn, Au, Cu, Pd, Pt). Similar fluorescence enhancements were observed in the presence of various metal ions, which suggests that other metal ions have little effect on the fluorescence induced by Au (Fig. S5 and S6, ESIw). As shown in Fig. 3, chemodosimeter 1 can detect Au as low as 0.50 mM. From these data, we have estimated a limit of detection of 1 to be 100 ppb. Furthermore, the fluorescence responses of 1 (1 mM) in EtOH–water (1 : 1, v/v) toward various amounts of Au was examined. It was increased linearly, with a limit of detection of 63 ppb of Au (Fig. S7, ESIw) The color change from colorless to pink and fluorescence enhancement were attributed to Au-induced ring-opening of the spirolactam followed by intramolecular cyclization forming oxazolecarbaldehyde 2 (Scheme 2). Through reversephase column chromatography, the product 2 with strong" @default.
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• W2742045722 date "2009-01-01" @default.
• W2742045722 modified "2023-09-24" @default.
• W2742045722 title "Highly selective fluorescent probe for Au 3+ based on cyclization of propargylamidew" @default.
• W2742045722 hasPublicationYear "2009" @default.
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