An indicator displacement system for fluorescent detection of phosphate oxyanions under physiological conditions

Hanshaw, Roger G.; Hilkert, Sarah M.; Jiang, Hua; Smith, Bradley D.

doi:10.1016/j.tetlet.2004.09.133

Cited by 84 publications

(54 citation statements)

References 25 publications

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“…We attribute this decrease to competitive binding of phosphate anions to the ZnBDPA units in 1 , thus reducing the affinity of 1 for the anionic liposome surface. 29 This result led us to determine if alternative ZnBDPA structures, with higher affinity for PS-rich membranes, would perform better as chemical triggers in physiologically relevant media. We speculated that dimeric ZnBDPA structures might facilitate leakage by strongly sequestering the PS and promoting lateral phase separation.…”

Section: Resultsmentioning

confidence: 99%

Chemically triggered release of 5-aminolevulinic acid from liposomes

et al. 2014

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5-Aminolevulinic acid (5-ALA), a prodrug of Protoporphyrin IX (PpIX), is used for photodynamic therapy of several medical conditions, and as an adjunct for fluorescence guided surgery. The clinical problem of patient photosensitivity after systemic administration could likely be ameliorated if the 5-ALA was delivered more selectivity to the treatment site. Liposomal formulations are inherently attractive as targeted delivery vehicles but it is hard to regulate the spatiotemporal release of aqueous contents from a liposome. Here, we demonstrate chemically triggered leakage of 5-ALA from stealth liposomes in the presence of cell culture. The chemical trigger is a zinc(II)-dipicolylamine (ZnBDPA) coordination complex that selectively targets liposome membranes containing a small amount of anionic phosphatidylserine. Systematic screening of several ZnBDPA complexes uncovered a compound with excellent performance in biological media. Cell culture studies showed triggered release of 5-ALA from stealth liposomes followed by uptake into neighboring mammalian cells and intracellular biosynthesis to form fluorescent PpIX.

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Section: Resultsmentioning

confidence: 99%

Chemically triggered release of 5-aminolevulinic acid from liposomes

et al. 2014

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“…616 Two Zn(Dpa) receptors described previously (i.e. 544b and 563 ) were incorporated into displacement assays that were based on the use of a coumarin (565 ) as the indicator in aqueous media at pH 7.4.…”

Section: Major Phosphate-binding Functionalitiesmentioning

confidence: 99%

Artificial Receptors for the Recognition of Phosphorylated Molecules

et al. 2011

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“…[51] It is notable that although PP i is bound equally well by both dizinc species, Zn 2 L2 binds P i three times less strongly than does Zn 2 L1. The reduced affinity of Zn 2 L2 for P i presumably stems from the larger ZnZn separation accessible using the m-terphenyl scaffold vs. that provided by the m-xylylene spacer and anchoring of zinc centers by the µ-phenolate in L1.…”

Section: Resultsmentioning

confidence: 94%

Dizinc Phosphohydrolase Model Built on a m‐Terphenyl Scaffold and Its Use in Indicator Displacement Assays for Pyrophosphate Under Physiological Conditions

et al. 2009

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A dinucleating ligand {1,3-bis[2-(di-2-picolylaminomethyl)-phenyl]benzene, L2} built on a m-terphenyl scaffold was prepared. The dissociation constants for the dizinc complex of L2 (Zn 2 L2) binding to phosphate, pyrophosphate and commercially available complexometric indicators were determined under physiological pH [10 mM N-(2-hydroxyethyl)piperazine-NЈ-2-ethanesulfonic acid (HEPES) buffer at pH 7.4]. Colorimetric and fluorescence-based indicator displacement

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An indicator displacement system for fluorescent detection of phosphate oxyanions under physiological conditions

Cited by 84 publications

References 25 publications

Chemically triggered release of 5-aminolevulinic acid from liposomes

Chemically triggered release of 5-aminolevulinic acid from liposomes

Artificial Receptors for the Recognition of Phosphorylated Molecules

Dizinc Phosphohydrolase Model Built on a m‐Terphenyl Scaffold and Its Use in Indicator Displacement Assays for Pyrophosphate Under Physiological Conditions

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