New Transmembrane Polyene Bolaamphiphiles as Fluorescent Probes in Lipid Bilayers

Quesada, Ernesto; Acuña, A. Ulises; Amat‐Guerri, F.

doi:10.1002/1521-3773(20010601)40:11<2095::aid-anie2095>3.0.co;2-i

Cited by 34 publications

(18 citation statements)

References 44 publications

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“…The fluorescence quantum yield of 5Bb in lipid vesicles is 0.24, significantly higher than that in EtOH solution (0.15). This effect of the ordered lipid environment on the emission quantum yield has already been observed in other polyene compounds22,23 and is most likely due to the conformational changes that take place on photoexcitation. It is known that the electron reorganization of single and double bonds leads to large conformational variability of the polyene excited states 45.…”

Section: Resultssupporting

confidence: 69%

“…This strategy is more convenient than the use of the Stille33 or Suzuki34–36 reactions particularly when the respective organostannane or ‐borane compound required is either unavailable or too unstable. Several conjugated polyene and polyenyne systems have been prepared in our laboratory by this approach 23,24,28. In this work, the target compounds were obtained similarly, following the sequence shown in Scheme .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups

et al. 2007

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Lipophilic fluorescent groups with a chain-like linear conformation emitting in the visible range and with high photostability are presently unavailable. These structures would be of great interest as labels for long-chain fatty acids and phospholipids lacking intrinsic fluorescent groups. With this aim in mind, we report the synthesis and the spectroscopic characterization of a series of emitting amphiphilic lipids that may approach that ideal fluorescent tag. Each lipid was constructed by attaching a linear, all-(E) conjugated pentaene, tetraenyne, ω-phenyltetraene, or ω-phenyltrienyne chromophore to a hydrophilic head-group through a polymethylene chain spacer. The key steps of the synthesis were the Pd 0 -mediated cross-coupling reaction between bromopolyenes and terminal acetylenic compounds, yielding tetraenynes or ω-phenyltrienynes, and the subsequent triple-bond partial reduction, producing the corresponding pentaenes or ω-

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Section: Resultssupporting

confidence: 69%

Section: Resultsmentioning

confidence: 99%

Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups

et al. 2007

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“… 373 , 374 Click chemistry is a generic term for highly efficient and selective reactions that are generally orthogonal to most biopolymeric chemistries and can be utilized to modularly introduce a broad range of functionalities. 375 …”

Section: Deconstruction and Modification Of Biopolymers And Biocolloidsmentioning

confidence: 99%

Deconstruction and Reassembly of Renewable Polymers and Biocolloids into Next Generation Structured Materials

et al. 2021

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This review considers the most recent developments in supramolecular and supraparticle structures obtained from natural, renewable biopolymers as well as their disassembly and reassembly into engineered materials. We introduce the main interactions that control bottom-up synthesis and top-down design at different length scales, highlighting the promise of natural biopolymers and associated building blocks. The latter have become main actors in the recent surge of the scientific and patent literature related to the subject. Such developments make prominent use of multicomponent and hierarchical polymeric assemblies and structures that contain polysaccharides (cellulose, chitin, and others), polyphenols (lignins, tannins), and proteins (soy, whey, silk, and other proteins). We offer a comprehensive discussion about the interactions that exist in their native architectures (including multicomponent and composite forms), the chemical modification of polysaccharides and their deconstruction into high axial aspect nanofibers and nanorods. We reflect on the availability and suitability of the latter types of building blocks to enable superstructures and colloidal associations. As far as processing, we describe the most relevant transitions, from the solution to the gel state and the routes that can be used to arrive to consolidated materials with prescribed properties. We highlight the implementation of supramolecular and superstructures in different technological fields that exploit the synergies exhibited by renewable polymers and biocolloids integrated in structured materials.

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“…Moreover, these bolaamphiphiles can operate as ligands for lectins17 or form nanodomains 18. Bolaamphiphiles involving molecular rods, such as octaphenylenes,19 naphthalene or perylene diimide arrays,20 and shorter linear biphenyl,21 tolane,22, 23 or polyene units,24 provide useful scaffolds for ion or electron conductance through membranes3 or serve as fluorescent probes 24. Apart from these π‐conjugated rods, nonconjugated linear oligospiroketals have also been incorporated into lipid membranes 25.…”

Section: Introductionmentioning

confidence: 99%

Dendritic Domains with Hexagonal Symmetry Formed by X‐Shaped Bolapolyphiles in Lipid Membranes

Werner

Ebert

Lechner

et al. 2015

Chemistry A European J

101

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A novel class of bolapolyphile (BP) molecules are shown to integrate into phospholipid bilayers and self-assemble into unique sixfold symmetric domains of snowflake-like dendritic shapes. The BPs comprise three philicities: a lipophilic, rigid, π–π stacking core; two flexible lipophilic side chains; and two hydrophilic, hydrogen-bonding head groups. Confocal microscopy, differential scanning calorimetry, XRD, and solid-state NMR spectroscopy confirm BP-rich domains with transmembrane-oriented BPs and three to four lipid molecules per BP. Both species remain well organized even above the main 1,2-dipalmitoyl-sn-glycero-3-phosphocholine transition. The BP molecules only dissolve in the fluid membrane above 70 °C. Structural variations of the BP demonstrate that head-group hydrogen bonding is a prerequisite for domain formation. Independent of the head group, the BPs reduce membrane corrugation. In conclusion, the BPs form nanofilaments by π stacking of aromatic cores, which reduce membrane corrugation and possibly fuse into a hexagonal network in the dendritic domains.

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New Transmembrane Polyene Bolaamphiphiles as Fluorescent Probes in Lipid Bilayers

Cited by 34 publications

References 44 publications

Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups

Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups

Deconstruction and Reassembly of Renewable Polymers and Biocolloids into Next Generation Structured Materials

Dendritic Domains with Hexagonal Symmetry Formed by X‐Shaped Bolapolyphiles in Lipid Membranes

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