Influence of pH and Pyrenyl on the Structural and Morphological Control of Peptide Nanotubes

Martins, Tatiana Duque; Souza, Márcia I.; Cunha, Bruno B.; Takahashi, Pedro Mitsuo; Ferreira, Fábio Furlan; Souza, J. A.; Fileti, Eudes Eterno; Alves, Wendel A.

doi:10.1021/jp1120788

Cited by 24 publications

(31 citation statements)

References 42 publications

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“…The surface of the peptide nanotube was modeled using the same protocol presented in previous works where the generation and equilibration processes of the nanotube surface (and its suitability as a model for interaction with the environment) are also discussed. [ 2,19 ] The only difference concerns the version of the force fi eld; here we use the latest version, CHARMM36. [ 33 ] The cells were equilibrated for 25 ns.…”

Section: Molecular Dynamics Simulationsmentioning

confidence: 99%

“…[ 2,19 ] Since the synthetic routes for such nanocomposites are straightforward, it has motivated us to explore the self-assembly of FF-MNS with conjugated polymers for possible application in organic electronics. In such structures, the charge transport still occurs through the conjugated polymers; the FF-MNS mainly provides a scaffold for the organic semiconductors along with the prospect of obtaining nanostructures for the polymer itself.…”

Section: Introductionmentioning

confidence: 99%

“…[ 19,20 ] The ordering begins at the molecular level with the association of different monomers, as illustrated in Figure 1 . Six FF monomers self-associate into macrocycle structures where amino and carboxyl groups constitute the inner core of the cycle.…”

Section: Introductionmentioning

confidence: 99%

“…They are synthesized by a liquid-vapor phase method. [ 19,26,27 ] The nanocomposites are characterized by electron microscopy and optical spectroscopy. FF:PF8 shows slight changes in the photoluminescence In recent years, enzyme-mediated degradation has been investigated for polymeric biomaterials.…”

Section: Introductionmentioning

confidence: 99%

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Self‐Assembled Peptide–Polyfluorene Nanocomposites for Biodegradable Organic Electronics

Khanra

Cipriano

Lam

et al. 2015

Adv Materials Inter

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Based on self‐assembly and mimicking strategies occurring in nature, peptide nanomaterials play a unique role in a new generation of hybrid materials for the electronics of the 21st century. This report describes the functionalization of diphenylalanine (FF)‐based micro/nanostructures with blue‐emitting conducting polymers of the polyfluorene (PF) family. The FF:PF polymer nanocomposites are synthesized by a liquid‐vapor phase method. Electron microscopy images reveal di‐octyl‐substituted PF (PF8) to bind better to the FF micro/nanotubes in comparison with ethyl‐hexyl PF (PF2/6), which influences its optical properties. Molecular dynamics simulations of FF nanotubes with monomeric units of PFs show that PF8 favors greater proximity to the grooves on the surface of the nanotubes due to a higher van der Waals interaction energy compared to PF2/6. The FF:PF nanocomposites are further utilized in light‐emitting diodes. Biodegradability tests from FF:PF8 nanocomposite films show more than 80% weight loss in 2 h by enzymatic action compared to PF8 pristine films, which do not degrade. Self‐assembly of FF nanostructures with organic semiconductors opens up a new generation of biocompatible and biodegradable materials in organic electronics.

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Section: Molecular Dynamics Simulationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Self‐Assembled Peptide–Polyfluorene Nanocomposites for Biodegradable Organic Electronics

Khanra

Cipriano

Lam

et al. 2015

Adv Materials Inter

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“…Wang et al [12] investigated implicitly the effect of impurities on the morphological evolution of the dipeptide. Han et al [11] and Martins et al [13] considered the effect of pH on the hierarchal assembly of the dipeptide and on the morphological control of the dipeptide nanotubes, respectively. There is no published report, to the best of our knowledge, on the profound effect of supersaturation on the self-assembly of the diphenylalanine dipeptide into various micro/nanostructures.…”

Section: Introductionmentioning

confidence: 99%

Novel method for prediction of micro/nanostructures of diphenylalanine dipeptide based on semiempirical thermodynamic study

Nezammahalleh

Amoabediny

2013

Fluid Phase Equilibria

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The role of water and structure on the generation of reactive oxygen species in peptide/hypericin complexes

Souza

Silva

Jaques

et al. 2014

Journal of Peptide Science

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Hybrid associates formed between peptide assemblies and fluorophores are attractive mainly because of their unique properties for biomedical applications. Recently, we demonstrated that the production of reactive oxygen species (ROS) by hypericin and their stability in excited states are enhanced upon conjugation with l,l-diphenylalanine microtubes (FF-MNTs). Although the detailed mechanisms responsible for improving the photophysical properties of ROS remain unclear, tentative hypotheses have suggested that the driving force is the growth of overall dipolar moments ascribed either to coupling between aligned H2O dipoles within the ordered structures or to the organization of hypericin molecules on peptide interfaces. To provide new insights on ROS activity in hypericin/FF-MNTs hybrids and further explore the role of water in this respect, we present results obtained from investigations on the behavior of these complexes organized into different crystalline arrangements. Specifically, we monitored and compared the photophysical performance of hypericin bound to FF-MNTs with peptides organized in both hexagonal (water-rich) and orthorhombic (water-free) symmetries. From a theoretical perspective, we present the results of new molecular dynamics simulations that highlight the distinct hypericin/peptide interaction at the interface of FF-MNTs for the different symmetries. As a conclusion, we propose that although water enhances photophysical properties, the organization induced by peptide structures and the availability of a hydrophobic environment surrounding the hypericin/peptide interface are paramount to optimizing ROS generation. The findings presented here provide useful basic research insights for designing peptide/fluorophore complexes with outstanding technological potential.

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Influence of pH and Pyrenyl on the Structural and Morphological Control of Peptide Nanotubes

Cited by 24 publications

References 42 publications

Self‐Assembled Peptide–Polyfluorene Nanocomposites for Biodegradable Organic Electronics

Self‐Assembled Peptide–Polyfluorene Nanocomposites for Biodegradable Organic Electronics

Novel method for prediction of micro/nanostructures of diphenylalanine dipeptide based on semiempirical thermodynamic study

The role of water and structure on the generation of reactive oxygen species in peptide/hypericin complexes

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