Synthesis and applications of Rhodamine derivatives as fluorescent probes.
ABSTRACT Rhodamine dyes are widely used as fluorescent probes owing to their high absorption coefficient and broad fluorescence in the visible region of electromagnetic spectrum, high fluorescence quantum yield and photostability. A great interest in the development of new synthetic procedures for preparation of Rhodamine derivatives has arisen in recent years because for most applications the probe must be covalently linked to another (bio)molecule or surface. In this critical review the strategies for modification of Rhodamine dyes and a discussion on the variety of applications of these new derivatives as fluorescent probes are given (108 references).
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ABSTRACT: Conjugates of the photoactivated rhodamine dyes with biopolymers (proteins, polysaccharides, and nucleic acids) are important tools for microscopic investigation of biological tissue. In this study, a precursor of the photoactivated fluorescent dye (PFD) has been successfully used for staining of numerous mammalian cells lines and for conjugate formation with chitosan ("Chitosan-PFD") and histone H1 ("Histone H1.3-PFD"). The intensive fluorescence has been observed after photoactivation of these conjugates inside cells (A431, HaCaT, HEK239, HBL-100, and MDCK). Developed procedures and obtained data are important for further application of novel precursors of fluorescent dyes ("caged" dyes) for microscopic probing of biological objects. Thus, the synthesized "Chitosan-PFD" and "Histone H1-PFD" have been successfully applied in this study for intracellular transport visualization by fluorescent microscopy.TheScientificWorldJournal. 01/2014; 2014:285405.
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ABSTRACT: We have synthesized a novel 2-chloronicotinaldehyde-functionalized rhodamine B derivative (RBCN)that acts as an “OFF–ON” chemosensor. RBCN specifically binds Al3+in the presence of a large excessof competing metal ions (Li+, Na+, K+, Cs+, Mg2+, Ca2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Ag+, Cd2+, Hg2+andPb2+) and exhibits visible changes in its electronic and fluorescent spectral behavior. These spectralchanges are significant in the visible region of the spectrum and thus enable detection with the nakedeye. Upon coordination with Al3+, the promoted ring opening of the rhodamine spirolactam ring in theRBCN chemosensor evokes a fluorescence turn-on response via the chelation-enhanced fluorescence pro-cess. The probe exhibited good brightness and fluorescence enhancement in which the lower detectionlimit for Al3+was 2.86 × 10−8M. The ring-opening mechanism of the rhodamine spirolactam inducedby Al3+binding and the 1:1 stoichiometric structure between RBCN and Al3+were supported by Job’splot evaluation, UV–vis, fluorescence titrations, FT-IR and1H NMR spectroscopic studies. Finally, theo-retical calculations and modeling simulations were conducted using Material Studio 4.3 suite to simulatethe formation of a 1:1 complex between RBCN and Al3+. However, the fluorescence and colorimetricresponse of the RBCN-Al3+complex was quenched by the addition of azide (N3−) anion, which abstractsthe Al3+ion from the complex and turns off the sensor, confirming that the recognition process isreversible.Sensors and Actuators B Chemical 11/2014; 208:75-84. · 3.84 Impact Factor
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ABSTRACT: Ordered mono-amide cross-linked alkyl/siloxane hybrids (mono-amidosils) incorporating a Rhodamine (B) methyl ester perchlorate dye (Rh(B)CH3ClO4) have been synthesized through the sol–gel process and self-directed assembly. The host hybrid matrix m-A(14) is a lamellar bilayer hierarchically structured hybrid composed of short methyl-capped alkyl chains grafted to a siliceous framework through amide groups. At low dye concentration [n = 20, where n is the molar ratio of amide groups per Rh(B)CH3ClO4] a new lamellar structure with higher interlamellar distance than that of m-A(14) is formed, whereas at higher dye content (n = 5) this new lamellar structure coexists with that of m-A(14). The efficient encapsulation of Rh(B)CH3ClO4 provided by m-A(14) via hydrogen bonding interactions ensured the complete dissolution of the dye and induced a blue shift of the emission of the dye with respect to that of the isolated state, leading to an increase in the quantum yield from values below 0.01 % (measured for the isolated dye) to 4 % at n = 20. The formation of non-fluorescent H-type dimers in the sample with n = 5 accounts for the reduction of the quantum yield. The incorporation of Rh(B)CH3ClO4) into m-A(14) was clearly beneficial from the standpoint of the dye’s photostability, allowing to suppress photobleaching during the first 4 h. An intensification of the emission intensity by 50 and 25 % for the emission centered at 600 and 645 nm resulted, respectively, at n = 20.Journal of Sol-Gel Science and Technology 11/2014; 72(2). · 1.66 Impact Factor