Investigating the possible use of a tetra (hydroxyphenyl) porphyrin as a fluorescence probe for the supramolecular detection of phospholipids

Ibrahim, Hanadi; Kasselouri, Athéna; Raynal, Bertrand; Pansu, Robert; Prognon, Patrice

doi:10.1016/j.jlumin.2011.06.016

Cited by 9 publications

(7 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…37 In addition, it was shown that DPH can transfer its excitation energy to nearby acceptor molecule (chromophore). 38 All the above criteria support DPH being an excellent candidate as a matrix for the detection of fatty acids and phospholipids by MALDI-MS. To the best of our knowledge, this is the first report of applying DPH as a matrix for MALDI MS and MSI analyses. Experiments will be presented in this paper to demonstrate that DPH is a suitable and effective matrix to facilitate the MALDI MS imaging of lipids in rat and mouse brain tissues, including a variety of lipids: fatty acids (FAs), lyso-phospholipids (L-PLs), phospholipids (PLs), and sulfatides (STs).…”

Section: Introductionmentioning

confidence: 94%

“…DPH was also generally used in lipid detection for its emission enhancement in the presence of phospholipids and triglycerides compounds in aqueous media . In addition, it was shown that DPH can transfer its excitation energy to nearby acceptor molecule (chromophore) . All the above criteria support DPH being an excellent candidate as a matrix for the detection of fatty acids and phospholipids by MALDI-MS. To the best of our knowledge, this is the first report of applying DPH as a matrix for MALDI MS and MSI analyses.…”

mentioning

confidence: 99%

See 1 more Smart Citation

1,6-Diphenyl-1,3,5-hexatriene (DPH) as a Novel Matrix for MALDI MS Imaging of Fatty Acids, Phospholipids, and Sulfatides in Brain Tissues

et al. 2017

Self Cite

View full text Add to dashboard Cite

1,6-Diphenyl-1,3,5-hexatriene (DPH) is a commonly used fluorescence probe for studying cell membrane-lipids due to its affinity toward the acyl chains in the phospholipid bilayers. In this work, we investigated its use in matrix-assisted laser desorption/ionization (MALDI) as a new matrix for mass spectrometry imaging (MSI) of mouse and rat brain tissue. DPH exhibits very minimal matrix-induced background signals for the analysis of small molecules (below m/z of 1000). In the negative ion mode, DPH permits the highly sensitive detection of small fatty acids (m/z 200-350) as well as a variety of large lipids up to m/z of 1000, including lyso-phospholipid, phosphatidic acid (PA), phosphoethanolamine (PE), phosphatidylserine (PS), phosphatidylglycerol (PG), phosphatidylinositol (PI), and sulfatides (ST). The analytes were mostly detected as the deprotonated ion [M - H]. Our results also demonstrate that sublimated DPH is stable for at least 24 h under the vacuum of our MALDI mass spectrometer. The ability to apply DPH via sublimation coupled with its low volatility allows us to perform tissue imaging of the above analytes at high spatial resolution. The degree of lipid fragmentation was determined experimentally at varying laser intensities. The results illustrated that the use of relatively low laser energy is important to minimize the artificially generated fatty acid signals. On the other hand, the lipid fragmentation obtained at higher laser energies provided tandem MS information useful for lipid structure elucidation.

show abstract

Section: Introductionmentioning

confidence: 94%

mentioning

confidence: 99%

1,6-Diphenyl-1,3,5-hexatriene (DPH) as a Novel Matrix for MALDI MS Imaging of Fatty Acids, Phospholipids, and Sulfatides in Brain Tissues

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…Numerous analytical methods for determination of organic compounds were developed by utilization of porphyrins: e.g. for nucleic acids [28,42,57,58,59] (porphyrin exciton coupled circular dichroism [57] for other chiral agents too), aminoacids and proteins [48,60,61], carbohydrates [28,62,63], phenols and chlorophenols [64], phenolic endocrine compounds [65], hormones [66], non-ionic surfactants [67], phospholipids [68], sulphur-containing hydrocarbons [48,69], and explosives [70]. Most of these analytical methods are based on the spectrophotometric properties (absorption, light scattering and fluorescence) of porphyrins, therefore in this work we would like to summarize and complement the knowledge in this area of porphyrin-chemistry from analytical aspects.…”

Section: Analytical Applications Of Porphyrinsmentioning

confidence: 99%

Application of the electronic spectra of porphyrins for analytical purposes: The effects of metal ions and structural distortions

Valicsek

Horváth

2013

Microchemical Journal

121

118

View full text Add to dashboard Cite

We investigated the UV-Vis absorption, singlet-1 and singlet-2 fluorescence, as well as the formation of several metalloporphyrins from equilibrial and kinetic aspects in aqueous solution. Among these complexes were numerous typical out-of-plane and several in-plane metalloporphyrins, and between the two categories, a few border-line cases. On the basis of our results, we have complemented the categorization introduced by Barnes and Dorough for the metalloporphyrins. According to our observations, also in metalloporphyrins, the distortion, i.e., the planarity or nonplanarity of the macrocycle, is basically responsible for the spectral characteristics, while the electronic structure of metal center is a secondary factor, with a considerable importance mainly in the in-plane complexes. The type of complexes can be spectrophotometrically determined on the basis of their UV-Vis absorption and fluorescence spectra. Beside the spectral and photophysical effects of metalation, also those of the structural distortions were studied, which can originate also from metalation, protonation or overcrowded peripheral substitution of the free-base porphyrins, as well as from the axial ligation of metalloporphyrins. Our observation may be useful for different spectrophotometric analytical detection and determination methods, e.g. size-selective metal detection using free-base porphyrins (or other ringed chelate ligands), as well as the determination of Lewis bases as potential axial ligands, using metalloporphyrins.

show abstract

“…18 Numerous studies demonstrate that porphyrin-based molecules tend to arrange themselves in well-defined long-range ordered lateral structures. [19][20][21][22][23] The combination of both functionality and structure makes them ideal candidates for molecular devices with applications, such as for electronics, spintronics 24 , data storage 25 , non-linear optics 26 , sensors 27 , solar cells 28 , catalysts 29 , as well as for tumor photosensitizers and photodynamic therapy [30][31][32] . In this study, we use hydroxyphenyl functional groups at the meso positions of a porphyrin molecule to enhance the intermolecular interaction and self-assembly properties via hydrogen bonding [33][34][35][36][37] .…”

Section: Introductionmentioning

confidence: 99%

Interplay of hydrogen bonding and molecule–substrate interaction in self-assembled adlayer structures of a hydroxyphenyl-substituted porphyrin

et al. 2014

View full text Add to dashboard Cite

The formation of hydrogen-bonded organic nano-structures and the role of the substrate lattice thereby were investigated by scanning tunneling microscopy. The self-organization of 5,10,15,20-tetra(p-hydroxyphenyl)porphyrin (H 2 THPP) molecules leads to two molecular arrangements on Au(111). One of these is characterized by pair-wise hydrogen bonding between hydroxyl groups and a low packing density which enables a rotation of individual molecules in the structure. A different interaction with stronger chain-like hydrogen bonding and additional interactions of phenyl groups was observed for the second structure. The influence of the substrate on the epitaxial behavior is demonstrated by the adsorption of H 2 THPP on the highly anisotropic Ag(110) substrate. There, several balances between the occupation of favorable adsorption positions and the number of hydrogen bonds per molecule were found. The molecules form molecular chains on Ag(110) and also assemble into two-dimensional periodic arrangements of differently sized close-packed blocks similar to the second type of supramolecular ordering found on Au(111). Dispersion corrected Density Functional Theory calculations were applied to understand the adsorption and complex epitaxy of these molecules. It is shown that the azimuthal orientation of the saddle-shape deformed molecule plays an important role not only for the intermolecular but also for the molecule-substrate interaction.

show abstract

Investigating the possible use of a tetra (hydroxyphenyl) porphyrin as a fluorescence probe for the supramolecular detection of phospholipids

Cited by 9 publications

References 23 publications

1,6-Diphenyl-1,3,5-hexatriene (DPH) as a Novel Matrix for MALDI MS Imaging of Fatty Acids, Phospholipids, and Sulfatides in Brain Tissues

1,6-Diphenyl-1,3,5-hexatriene (DPH) as a Novel Matrix for MALDI MS Imaging of Fatty Acids, Phospholipids, and Sulfatides in Brain Tissues

Application of the electronic spectra of porphyrins for analytical purposes: The effects of metal ions and structural distortions

Interplay of hydrogen bonding and molecule–substrate interaction in self-assembled adlayer structures of a hydroxyphenyl-substituted porphyrin

Contact Info

Product

Resources

About