Superior Fluorescent Probe for Detection of Cardiolipin

Leung, Chris W. T.; Hong, Yuning; Hanske, Jonas; Zhao, Engui; Chen, Sijie; Pletneva, Ekaterina V.; Tang, Ben Zhong

doi:10.1021/ac403616c

Cited by 61 publications

(68 citation statements)

References 36 publications

(83 reference statements)

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“…Among those are recently reported improved fluorescent probes for CL. 37 Recently, a powerful approach based on the employment of caged lipids, membrane-permeable photoactivatable derivatives of different PLs has been developed to specifically probe signaling pathways at the single cell level. 3839,40 Caged lipids are designed to contain a photocleavable group attached to a position that is crucial for their function, thus rendering lipid analogs inactive.…”

Section: Resultsmentioning

confidence: 99%

Mitochondrial Redox Opto-Lipidomics Reveals Mono-Oxygenated Cardiolipins as Pro-Apoptotic Death Signals

Mao¹,

Qu²,

Croix³

et al. 2016

ACS Chem. Biol.

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While opto-genetics has proven to have tremendous value in revealing the functions of the macromolecular machinery in cells, it is not amenable to exploration of small molecules such as phospholipids (PLs). Here, we describe a redox opto-lipidomics approach based on a combination of high affinity light-sensitive ligands to specific PLs in mitochondria with LC-MS based redox lipidomics/bioinformatics analysis for the characterization of pro-apoptotic lipid signals. We identified the formation of mono-oxygenated derivatives of C18:2-containing cardiolipins (CLs) in mitochondria after the exposure of 10-nonylacridine orange bromide (NAO)-loaded cells to light. We ascertained that these signals emerge as an immediate opto-lipidomics response, but they decay long before the commencement of apoptotic cell death. We found that a protonophoric uncoupler caused depolarization of mitochondria and prevented the mitochondrial accumulation of NAO, inhibited the formation of C18:2-CL oxidation product,s and protected cells from death. Redox opto-lipidomics extends the power of opto-biologic protocols to studies of small PL molecules resilient to opto-genetic manipulations.

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Section: Resultsmentioning

confidence: 99%

Mitochondrial Redox Opto-Lipidomics Reveals Mono-Oxygenated Cardiolipins as Pro-Apoptotic Death Signals

Mao¹,

Qu²,

Croix³

et al. 2016

ACS Chem. Biol.

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“…15 For example, a water-soluble AIE dye was used for cardiolipin phospholipid sensing and quantitative analysis. 16 …”

Section: Introductionmentioning

confidence: 99%

Multi-stimuli responsive luminescent azepane-substituted β-diketones and difluoroboron complexes

Wang

DeRosa

Daly

et al. 2017

Mater. Chem. Front.

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Difluoroboron β-diketonate (BF2bdk) compounds show environment-sensitive optical properties in solution, aggregation-induced emission (AIE) and multi-stimuli responsive fluorescence switching in the solid state. Here, a series of 4-azepane-substituted β-diketone (bdk) ligands (L-H, L-OMe, L-Br) and their corresponding difluoroboron dyes (D-H, D-OMe, D-Br) were synthesized, and various responsive fluorescence properties of the compounds were studied, including solvatochromism, viscochromism, AIE, mechanochromic luminescence (ML) and halochromism. Compared to the β-diketones, the boron complexes exhibited higher extinction coefficients but lower quantum yields, and red-shifted absorption and emission in CH2Cl2. Computational studies showed that intramolecular charge transfer (ICT) dominated rather than π–π* transitions in all the compounds regardless of boron coordination. In solution, all the bdk ligands and boron dyes showed red-shifted emission in more polar solvents and increased fluorescence intensity in more viscous media. Upon aggregation, the emission of the β-diketones was quenched, however, the boronated dyes showed increased emission, indicative of AIE. Solid-state emission properties, ML and halochromism, were investigated on spin cast films. For ML, smearing caused a bathochromic emission shift for L-Br, and powder X-ray diffraction (XRD) patterns showed that the “as spun” and thermally annealed states were more crystalline and the smeared state was amorphous. No obvious ML emission shift was observed for L-H or L-OMe, and the boronated dyes were not mechano-active. Trifluoroacetic acid (TFA) and triethylamine (TEA) vapors were used to study halochromism. Large hypsochromic emission shifts were observed for all the compounds after TFA vapor was applied, and reversible fluorescence switching was achieved using the acid/base pair.

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“…Therefore, the LC-based design may offer a facile approach for the detection of CL in addition to other past studies reported earlier [40][41][42][43][44][45][46][47][48]. …”

mentioning

confidence: 99%

pH-Driven Ordering Transitions in Liquid Crystal Induced by Conformational Changes of Cardiolipin

2015

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We report an investigation of interfacial phenomena occurring at aqueous-liquid crystal (LC) interfaces that triggers an orientational ordering transition of the LC in the presence of cardiolipin (CL) by varying pH, salt concentration and valence. In particular, the effects of three different conformational isomeric forms of the CL are observed to cause the response of the LC ordering to vary significantly from one to another at those interfaces. An ordering transition of the LC was observed when the CL is mostly in undissociated (at pH 2) and/or in bicyclic (at pH 4) conformation in which LC shows changes in the optical appearance from bright to dark. By contrast, no change in the optical appearance of the LC was observed when the pH of the system increases to 8 or higher in which the CL mostly exists in the open conformation. Fluorescence microscopy measurements further suggest that pH-dependent conformational forms of the CL have different ability to self-assemble (thus different packing efficiency) at aqueous-LC interfaces leading to dissimilar orientational behavior of the LC. Specifically, we found that change in headgroup-headgroup repulsion of the central phosphatidyl groups of the CL plays a key role in tuning the lipid packing efficiency and thus responses to interfacial phenomena. Orientational ordering transition of the LC was also observed as a function of increasing the ionic strength (buffer capacity) and strongly influenced in the presence of mono and divalent cations. Langmuir-Blodgett (LB) and polarization modulation infrared reflection absorption spectroscopy (PM-IRRAS) measurements provide further insight in modulation of the lipid packing efficiency and alkyl chain conformation of the CL at different pH and ionic conditions. Overall, the results presented in this paper establish that LCs offer a promising approach to differentiate different conformations (label free detection) of the CL through ordering transition of the LC at aqueous-LC interfaces.

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Superior Fluorescent Probe for Detection of Cardiolipin

Cited by 61 publications

References 36 publications

Mitochondrial Redox Opto-Lipidomics Reveals Mono-Oxygenated Cardiolipins as Pro-Apoptotic Death Signals

Mitochondrial Redox Opto-Lipidomics Reveals Mono-Oxygenated Cardiolipins as Pro-Apoptotic Death Signals

Multi-stimuli responsive luminescent azepane-substituted β-diketones and difluoroboron complexes

pH-Driven Ordering Transitions in Liquid Crystal Induced by Conformational Changes of Cardiolipin

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