Emission quenching via intramolecular electron transfer for fluorescein conjugates. Dependences on driving force and medium

Jones, Guilford; Qian, Xiaohua

doi:10.1016/s1010-6030(97)00326-2

Cited by 11 publications

(3 citation statements)

References 38 publications

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“…All of these results are in agreement with the occurrence of two processes, which involve the fluorescein units in the nanoparticles. The first one causes the complete quenching of about 50% of the fluorophoric units and is known to be due to the short-range interactions between the fluorescein molecules. , The second one leads to fluorescence depolarization and implies the excitation energy transfer between the different dye units in the nanoparticles. , These two situations are schematically depicted in Scheme . The possibility of having different kinds of interactions depending on the intermolecular distance makes fluorescein a good probe to test the structure of the fluorophore network.…”

mentioning

confidence: 99%

Energy Transfer in Fluorescent Silica Nanoparticles

et al. 2004

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confidence: 99%

Energy Transfer in Fluorescent Silica Nanoparticles

et al. 2004

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“…The conversion of the amine to an amide restores the fluorescence due to the electron‐withdrawing effects of the carbonyl oxygen. However, the presence of additional electron‐donating substituents on the amide can overcome this effect so that quenching is reestablished and electron transfer occurs with the chromophore acting as an electron donor (24,25). In these cases, the monoanion and dianion forms exhibit different sensitivities to quenching, which reflects their ability to act as electron donors, and they exhibit biexponential emission decays (25).…”

Section: Discussionmentioning

confidence: 99%

“…The distribution model and sulfur quenching can account for many of the observed properties of fluorescein‐conjugated molecules. However, fluorescein‐conjugated molecules can still show multiple lifetimes even when the conjugation does not occur through a sulfur group (25,30,31). As demonstrated in the present study, the presence of proximal sulfhydryl groups, such as cysteine residues in proteins, can cause quenching of fluorescein.…”

Section: Discussionmentioning

confidence: 99%

The Thiourea Group Modulates the Fluorescence Emission Decay of Fluorescein-labeled Molecules ¶

Klonis¹,

Sawyer²

2007

Photochemistry and Photobiology

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We have investigated the spectral properties and emission characteristics of fluorescein-5-thiocarbamoyl-N,N9-caproate (FITC-ACA) to examine the origin of the complex emission decay often observed in fluorescein-labeled molecules. The covalent attachment of fluorescein to e-amino-n-caproic acid does not perturb the prototropic transitions of the chromophore or the general fluorescence characteristics of the various prototropic forms. However, both the monoanion and dianion forms of FITC-ACA are quenched relative to free fluorescein and exhibit a complex emission decay that is described by two discrete lifetimes. The thiourea group that links the chromophore to the caproic acid is shown to modulate the emission properties of the FITC-ACA. We show that the emission decay can also be analyzed using the asymmetric distribution model of Alcala et al. In this analysis, the s L and s u parameters that represent the lower and upper lifetime limits of the distribution reflect the quenched (0 ns) and unquenched lifetimes, respectively. The b parameter that describes the distribution of lifetimes between the two limiting states can be related to the quenching efficiency of the thiourea group and to the structure and dynamics of the FITC-ACA molecule.

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Preparation and photophysical behaviors of fluorescent chitosan bearing fluorescein: Potential biomaterial as temperature/pH probes

Guan

Liu

2007

J of Applied Polymer Sci

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A novel method for attaching fluorescein (via its epoxy derivative) to water-soluble chitosan, and the temperature/pH-sensitive qualities of fluorescence were investigated. 3-Epoxypropoxy fluorescein (EPF) was firstly synthesized by the reaction between fluorescein and epichlorohydrin, and then water-soluble chitosan bearing fluorescein (CS-EPF) was prepared via ring-opening reaction with EPF. They were characterized by the methods of 1 H NMR, MS, IR, UV-Vis, and luminescence spectra, respectively. The chemiluminescent and photophysical behaviors of EPF and CS-EPF were studied in detail. The results showed that the fluorescent chitosan could still provide temperature and pH sensitivities similar to that of fluorescein, achieving better long-term stability and fast equilibrium response. CS-EPF had an excellent linear response between relative fluorescence intensity and temperature in the range of 0-608C and two linear relationships between relative fluorescence intensity and pH in 0.0-4.14 and 8.15-13.20, respectively. This investigation may provide a convenient way to prepare low-cost and multifunctional macromolecule biomaterial to probe pH and temperature in biological systems.

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Emission quenching via intramolecular electron transfer for fluorescein conjugates. Dependences on driving force and medium

Cited by 11 publications

References 38 publications

Energy Transfer in Fluorescent Silica Nanoparticles

Energy Transfer in Fluorescent Silica Nanoparticles

The Thiourea Group Modulates the Fluorescence Emission Decay of Fluorescein-labeled Molecules ¶

Preparation and photophysical behaviors of fluorescent chitosan bearing fluorescein: Potential biomaterial as temperature/pH probes

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