Fluorophore-linked zinc(II)dipicolylamine coordination complexes as sensors for phosphatidylserine-containing membranes

Lakshmi, C.; Hanshaw, Roger G.; Smith, Bradley D.

doi:10.1016/j.tet.2004.08.052

Cited by 84 publications

(74 citation statements)

References 29 publications

(27 reference statements)

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“…The fluorescein-labeled compound PSS-480 was prepared by coupling the known amine 1 [21] with 5-carboxyfluorescein diacetate. Subsequent deprotection with ammonium hydroxide followed by treatment with Zn(NO 3 ) 2 in aqueous methanol gave PSS-480 as its bis(ammonium) salt.…”

Section: Synthesismentioning

confidence: 99%

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Fluorescent Detection of Apoptotic Cells by Using Zinc Coordination Complexes with a Selective Affinity for Membrane Surfaces Enriched with Phosphatidylserine

et al. 2005

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The appearance of phosphatidylserine on the membrane surface of apoptotic cells (Jurkat, CHO, HeLa) is monitored by using a family of bis(Zn2+-2,2'-dipicolylamine) coordination compounds with appended fluorescein or biotin groups as reporter elements. The phosphatidylserine affinity group is also conjugated directly to a CdSe/CdS quantum dot to produce a probe suitable for prolonged observation without photobleaching. Apoptosis can be detected under a wide variety of conditions, including variations in temperature, incubation time, and binding media. Binding of each probe appears to be restricted to the cell membrane exterior, because no staining of organelles or internal membranes is observed.

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Section: Synthesismentioning

confidence: 99%

“…[20] Our initial studies used fluorophores with nonoptimal properties, [21] but the work produced important structural information that led us to the modular, three-component design shown in Scheme 1. The…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Detection of Apoptotic Cells by Using Zinc Coordination Complexes with a Selective Affinity for Membrane Surfaces Enriched with Phosphatidylserine

et al. 2005

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“…S1 in Supporting Information). 49 Dpa is known to be strongly bound to Zn 2+ with Ka of approximately 10 7 M -1 , 49 and therefore, Zn…”

Section: Resultsmentioning

confidence: 99%

Zinc Ion-immobilized Magnetic Microspheres for Enrichment and Identification of Multi-phosphorylated Peptides by Mass Spectrometry

et al. 2017

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The selective isolation of phosphorylated peptides and subsequent analysis using mass spectrometry is important for understanding how protein kinase and phosphatase signals can precisely modulate the on/off states of signal transduction pathways. However, the isolation and detection of multi-phosphorylated peptides is still limited due to their distinct affinity to various materials and their poor ionization efficiency. Here, we report a highly efficient and selective enrichment of phosphorylated peptides using binuclear Zn 2+ -dipicolylamine complex-coated magnetic microspheres (ZnMMs). ZnMMs can utilize the rapid and selective isolation/enrichment of phosphorylated peptides and the subsequent mass spectrometric analysis, given the intrinsic magnetic property of magnetic microspheres and the highly selective binding ability of the binuclear Zn 2+ -dipicolylamine complex to phosphate groups. α-Casein and β-casein were chosen for a proof-of-concept demonstration. We contemplated that phosphopeptides were selectively isolated and enriched from both the tryptic digests of casein proteins and mixed samples with a high degree of sensitivity by facilitating ZnMMs. Especially, ZnMMs showed high efficiency with multi-phosphopeptides, which are in general difficult to be examined by mass analysis on account of their poor ionization efficiency. For the model protein α, β-casein mixture of the tryptic digest, 17 phosphopeptides were identified with ZnMMs and 82% of the enriched phosphopeptides were multiphosphorylated peptides, indicating that ZnMMs have excellent enrichment efficiency and strong affinity towards multiphosphorylated peptides.

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“…3]. More recently NBD labelled molecules were used as sensors for phosphatidylserine containing membranes [4], cysteine/homocysteine [5] and for selective chemical sensing of hazardous compounds and drugs of abuse [6]. In several hundred papers small percent (0.5 to 1 % typically) NBD labelled lipids were used in a mixture with other lipids to visualize domain structure in Langmuir films with fluorescence microscopy or in FRAP measurements.…”

Section: Introductionmentioning

confidence: 99%

New effects in Langmuir and Langmuir-Blodgett monolayers from fluorescently labelled phospholipids and their possible use for water quality control

Ivanov

Geshev

2016

J. Phys.: Conf. Ser.

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Abstract. Secondary water contamination poses significant challenges to the sensitivity and selectivity of sensors used for its detection and monitoring. Currently only lab tests can detect these contaminants and by the time this happens the contaminated water has entered the city water supply system. Fluorescent chromophore NitroBenzoxaDiazole (NBD) is very suitable and had been successfully used in biosensor applications due to its high sensitivity to close proximity polarity of the medium. Over the years we have discovered 3 new effects in NBDlabelled phospholipids which can significantly improve the performance of biosensors. The phospholipid matrix provides flexible biocompatible environment for immobilization of selectively reacting enzymes, microorganisms, DNA, immunoagents, whole cells. Use of single layer (3.1 nm thickness) films at the air-water interface (Langmuir films) or deposited on solid support as Langmuir-Blodgett (LB) film gives fast response times for real time monitoring (no slow diffusion processes) and precise molecule ordering and orientation. The first new effect was fluorescence self-quenching in Langmuir and LB films. In the liquid phase films exhibit normal fluorescence. Upon transition to solid phase fluorescence intensity is almost completely self-quenched and fluorescence lifetimes in the nanosecond region decrease 2 times. This is easily measured. Usually large heavy metal atoms quench fluorescence. We observed the opposite new effect when LB film is deposited in the solid phase from a subphase containing heavy metals. The third new effect is the obtaining of nanosized cylinders with bilayer thickness, which remain stable at least for months, when LB monolayer is deposited in the phase coexistence region at thermodynamic equilibrium. This greatly increases reacting surface and sensitivity of possible sensors. Almost all possible optical experimental methods were used for this research. This includes polarized ATR FTIR and polarized UV-VIS spectroscopies, Fluorescence Lifetime Imaging Microscopy (FLIM), Scanning Near-field Optical Microscopy (SNOM).

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Fluorophore-linked zinc(II)dipicolylamine coordination complexes as sensors for phosphatidylserine-containing membranes

Cited by 84 publications

References 29 publications

Fluorescent Detection of Apoptotic Cells by Using Zinc Coordination Complexes with a Selective Affinity for Membrane Surfaces Enriched with Phosphatidylserine

Fluorescent Detection of Apoptotic Cells by Using Zinc Coordination Complexes with a Selective Affinity for Membrane Surfaces Enriched with Phosphatidylserine

Zinc Ion-immobilized Magnetic Microspheres for Enrichment and Identification of Multi-phosphorylated Peptides by Mass Spectrometry

New effects in Langmuir and Langmuir-Blodgett monolayers from fluorescently labelled phospholipids and their possible use for water quality control

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