Chelation-enhanced fluorescence of anthrylazamacrocycle conjugate probes in aqueous solution

Akkaya, Engin U.; Huston, Michael E.; Czarnik, Anthony W.

doi:10.1021/ja00165a051

Cited by 292 publications

(171 citation statements)

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“…We also observed complexation with fluorescence enhancement interaction in above mentioned Co(II) and Cu(II) complexes in DMF and DMSO solutions [37]. Where as in Ni(II) complex (6) we could observed fluorescence quenching quite effectively [38].…”

Section: Chemistrysupporting

confidence: 54%

Synthesis, spectral characterization and microbiological studies of Co(II), Ni(II) and Cu(II) complexes with some novel 20-membered macrocyclic hydrazino-1,2,4-triazole Schiff bases

Avaji

Patil

2009

Journal of Enzyme Inhibition and Medicinal Chemistry

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Section: Chemistrysupporting

confidence: 54%

Synthesis, spectral characterization and microbiological studies of Co(II), Ni(II) and Cu(II) complexes with some novel 20-membered macrocyclic hydrazino-1,2,4-triazole Schiff bases

Avaji

Patil

2009

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In addition, there was a significant increase in emission intensity upon addition of Zn 2 + ions. These results are consistent with other studies on these types of anthracenefunctionalised macrocycles, such as bis-azamacrocycles, [15] azamacrocycles, [16] azathia crown ethers [17] and aza cages. [18] The enhancement of emission intensity is attributable to a decrease in the photoinduced electron transfer effect.…”

Section: Luminescence Spectroscopysupporting

confidence: 93%

Evaluation of a Fluorescent Derivative of AMD3100 and its Interaction with the CXCR4 Chemokine Receptor

et al. 2011

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AMD3100 is a potent and selective antagonist of the CXCR4 receptor; it has been shown to block the route of entry of HIV into host T-cells. This compound and its analogues have since been found to act as haematopoietic stem cell mobilisation agents and, more recently, as anti-cancer agents. Here, we have examined a fluorescent derivative of AMD3100, L(1), which offered the potential to assess the behaviour of AMD3100 at the cell surface by using optical imaging modalities. The binuclear Zn(II) , Cu(II) and Ni(II) complexes of L(1) have also been investigated as these metals have been previously shown to enhance the binding properties of AMD3100. Furthermore, Zn(II) and Cu(II) are known to enhance and quench, respectively, the fluorescence of similar anthracenyl-based ligands. Whilst L(1) demonstrates an ability to inhibit the binding of the anti-CXCR4 monoclonal antibody 12G5 (IC(50) =0.25-0.9 μM), the incorporation of an anthracenyl moiety resulted in a significantly reduced affinity for CXCR4 compared to AMD3100 (IC(50) =10 nM). We observed no significant increase in fluorescence intensity following incubation with murine pre-B cells overexpressing CXCR4 compared to a control cell line. This limits the usefulness of L(1) as a fluorescent imaging probe. Interestingly, the Zn(II) complex, which carries an overall +4 charge, revealed marginally higher specificity and reduced toxicity in vitro compared to the free ligand, albeit with reduced affinity for CXCR4 (IC(50) =1.8-5 μM). We suggest that the incorporation of an anthracenyl group contributes to the lipophilic character of the free ligand, thereby resulting in transport across the plasma membrane. This effect is seemingly diminished when the ligand is complexed to charged metal ions.

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“…There are three main strategies to approach the design of fluorescent molecular indicators for chemical sensing in solution. The first results in intrinsic fluorescent probes, 30,31 which are fluorescent molecules where the mechanism for signal transduction involves interaction of the analyte with a ligand that is part of the p-system of the fluorophore. The second are extrinsic fluorescent probes, in which the receptor moiety and the fluorophore are covalently linked but are electronically independent.…”

Section: Classical Design Of Fluorescent Indicatorsmentioning

confidence: 99%

Design of Fluorescent Materials for Chemical Sensing

2007

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There is an enormous demand for chemical sensors for many areas and disciplines. High sensitivity and ease of operation are two main issues for sensor development. Fluorescence techniques can easily fulfill these requirements and therefore fluorescent-based sensors appear as one of the most promising candidates for chemical sensing. However, the development of sensors is not trivial; material science, molecular recognition and device implementation are some of the aspects that play a role in the design of sensors. The development of fluorescent sensing materials is increasingly captivating the attention of the scientists because its implementation as a truly sensory system is straightforward. This critical review shows the use of polymers, sol-gels, mesoporous materials, surfactant aggregates, quantum dots, and glass or gold surfaces, combined with different chemical approaches for the development of fluorescent sensing materials. Representative examples have been selected and they are commented here.

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Chelation-enhanced fluorescence of anthrylazamacrocycle conjugate probes in aqueous solution

Cited by 292 publications

References 0 publications

Synthesis, spectral characterization and microbiological studies of Co(II), Ni(II) and Cu(II) complexes with some novel 20-membered macrocyclic hydrazino-1,2,4-triazole Schiff bases

Synthesis, spectral characterization and microbiological studies of Co(II), Ni(II) and Cu(II) complexes with some novel 20-membered macrocyclic hydrazino-1,2,4-triazole Schiff bases

Evaluation of a Fluorescent Derivative of AMD3100 and its Interaction with the CXCR4 Chemokine Receptor

Design of Fluorescent Materials for Chemical Sensing

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