Self-Assembly of a Cyclobutane β-Tetrapeptide To Form Nanosized Structures

F, Rúa; Boussert, Stéphanie; Parella, Teodor; Díez‐Pérez, Ismael; Branchadell, Vicenç; Giralt, Ernest; Rm, Ortuno

doi:10.1021/ol701521k

Cited by 81 publications

(15 citation statements)

References 15 publications

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“…The challenge to generate and perfect nano and micro level stable molecular architectures through self-assembly lies in two mutually fulfilling exercises; i) synthesis of individual building blocks with the right composition and ii) design and fabrication of assembled architectures 36 , 37 . The single crystal organic compound we report here assembles to a flower- like morphology, by means of a supra-molecular interaction network, thus becoming one among the rare organic nanoflowers reported so far.…”

Section: Discussionmentioning

confidence: 99%

Single Crystal Organic Nanoflowers

Sasidharan

Shyni

Chaudhary

et al. 2017

Sci Rep

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Nano-flowers reported so far were mostly constituted of inorganic or hybrid materials. We have synthesized and crystallized a new organic compound, 1, 2-bis(tritylthio)ethane forming an organic nano-flower consisting of single crystalline petals. Crystal structure at nano and micro level indicates that π-π stacking interactions between aromatic systems is the principal factor governing molecular recognition and assembly. Single crystal X-ray Diffraction (S-XRD) supported by Selective Area Electron Diffraction (SAED) experiments indicate the single crystalline nature of the flower-like assembly even at the nanoscale. In order to fabricate the nanoflower as a potential stimulus responsive material; the ‘petals’ were coated with magnetite nanoparticles, verified by Energy-dispersive X-ray spectroscopic (EDX) analysis. Herein, we have further tested the potential utility of the hybrid material in water remediation as a nano-based adsorbent for removal of heavy metals like chromium.

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Section: Discussionmentioning

confidence: 99%

Single Crystal Organic Nanoflowers

Sasidharan

Shyni

Chaudhary

et al. 2017

Sci Rep

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“…In earlier studies of other LMWOGs, we used IR and 1 H-NMR spectroscopies to gain information about the aggregation process [21,22,23]. Nevertheless, in the present case in which different groups can contribute to the gel formation, we thought that the combined results from computational calculations and CD spectroscopy would be better to provide an overall view and a more reliable interpretation.…”

Section: Resultsmentioning

confidence: 97%

“…Amides have been reported as functional groups present in some of the simplest LMWOGs that have been described [20]. We have previously developed good LMWOGs of peptide nature based on chiral β-cyclobutane amino acids [21,22], or hybrid peptides presenting a cyclobutane β-amino acid joined in alternation with linear residues [23]. In both cases, a model to explain the self-assembly of the individual molecules to produce the gel was suggested by means of computational calculations.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Gelling Abilities of Polyfunctional Cyclohexane-1,2-dicarboxylic Acid Bisamides: Influence of the Hydroxyl Groups

et al. 2019

Self Cite

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New enantiomerically pure C16-alkyl diamides derived from trihydroxy cyclohexane-1,2-dicarboxylic acid have been synthesized from (−)-shikimic acid. The hydroxyl groups in these compounds are free or, alternatively, they present full or partial protection. Their gelling abilities towards several solvents have been tested and rationalized by means of the combined use of Hansen solubility parameters, scanning electron microscopy (SEM), and circular dichroism (CD), as well as computational calculations. All the results allowed us to account for the capability of each type of organogelator to interact with different solvents and for the main mode of aggregation. Thus, compounds with fully protected hydroxyl groups are good organogelators for methanol and ethanol. In contrast, a related compound bearing three free hydroxyl groups is insoluble in water and polar solvents including alcohols but it is able to gelate some low-polarity solvents. This last behavior can be justified by strong hydrogen bonding between molecules of organogelator, which competes advantageously with polar solvent interactions. As an intermediate case, an organogelator with two free hydroxyl groups presents an ambivalent ability to gelate both apolar and polar solvents by means of two aggregation patterns. These involve hydrogen bonding interactions of the unprotected hydroxyl groups in apolar solvents and intermolecular interactions between amide groups in polar ones.

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“…Plenty of shapes of amyloid structures were reported in many previous studies, including globular, -hairpin, -sheet, disk-like, worm-like, rod-like, honeycomb, parallel, and braided structures [1]. The variety of these assembled structures is attributed to the intermolecular interactions including hydrogen bonds, electrostatic interaction, and hydrophobic interactions [32,38,[86][87][88][89]. The globular structures formed at the beginning of the incubation process are easily observed in AFM (Figure 2(a)).…”

Section: Self-assembled Structuresmentioning

confidence: 99%

Characterization of Inter- and Intramolecular Interactions of Amyloid Fibrils by AFM-Based Single-Molecule Force Spectroscopy

Liang

Zhao

et al. 2016

Journal of Nanomaterials

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Amyloids are fibrous protein aggregates defined by shared specific structural features. Abnormal accumulation of amyloid in organs leads to amyloidosis, which results in various neurodegenerative diseases. Atomic force microscopy (AFM) has proven to be an excellent tool investigating amyloids; it has been extensively utilized to characterize its morphology, assembly process, and mechanical properties. This review summarizes studies which applied AFM to detect the inter- and intramolecular interactions of amyloid fibrils and classified the influencing factors of amyloid’s nanomechanics in detail. The characteristics of amyloid fibrils driven by inter- and intramolecular interactions, including various morphologies of amyloid fibrils, self-assembly process, and the aggregating pathway, are described. Successful examples where AFM provided abundant information about inter- and intramolecular interactions of amyloid fibrils in different environments are presented. Direct force measurement of intra- or intermolecular interactions utilizing an AFM-based tool, single-molecular force spectroscopy (SMFS), is introduced. Some mechanical information such as elasticity, adhesiveness, and strength was obtained by stretching amyloid fibrils. This review helps researchers in understanding the mechanism of amyloidogenesis and exploring the properties of amyloid using AFM techniques.

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Self-Assembly of a Cyclobutane β-Tetrapeptide To Form Nanosized Structures

Cited by 81 publications

References 15 publications

Single Crystal Organic Nanoflowers

Single Crystal Organic Nanoflowers

Synthesis and Gelling Abilities of Polyfunctional Cyclohexane-1,2-dicarboxylic Acid Bisamides: Influence of the Hydroxyl Groups

Characterization of Inter- and Intramolecular Interactions of Amyloid Fibrils by AFM-Based Single-Molecule Force Spectroscopy

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