Self‐Assembly of Tyrosine into Controlled Supramolecular Nanostructures

Ménard‐Moyon, Cécilia; Venkatesh, V.; Krishna, K. Vijaya; Bonachéra, Fanny; Verma, Sandeep; Bianco, Alberto

doi:10.1002/chem.201502076

Cited by 75 publications

(77 citation statements)

References 55 publications

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“…demonstrated that aqueous solutions of free unprotected phenylalanine form amyloid-like fibrillary structures that may contribute to the etiology of phenylketonuria 14 . Tyrosine and tryptophan have also been shown to assemble into nano- and microscale architectures 15 – 17 .…”

Section: Introductionmentioning

confidence: 99%

“Carboranyl-cysteine”—Synthesis, Structure and Self-Assembly Behavior of a Novel α-Amino Acid

Misuraca

Musah

2017

Sci Rep

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Substitution of the thiol proton in cysteine with m-carborane furnished 2-amino-3-(1,7-dicarba-closo-dodecacarboranyl-1-thio)propanoic acid (3), a boron cluster amino acid that exhibits self-assembly to form micron-sized constructs. Field emission scanning electron microscopy revealed that ethanol solutions of 3 form floret-shaped constructs, while fibrillar architectures are formed in water. Furthermore, slow evaporation of methanol solutions of 3 produced crystals whose structure was revealed by X-ray crystallography. The crystal structure shows that the hydrogen bonding interactions between pairs of 3 result in the formation of bilayers of 174 Å in length. The orientation of the clusters is not random in the crystal structure, such that the side-by-side aligned polyhedra are offset by 158 degrees. The material was characterized by FT-IR, NMR, high resolution mass spectrometry and dynamic light scattering. Circular dichroism studies indicated that self-assembly occurs at concentrations as low as 0.01 μM. This represents the first demonstration of self-assembly of a carborane-based molecule in the absence of metals. The amino acid motif provides opportunities for the controlled synthesis of extended multimeric units with tunable properties and the potential for applications in biology, medicine and materials chemistry.

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Section: Introductionmentioning

confidence: 99%

“Carboranyl-cysteine”—Synthesis, Structure and Self-Assembly Behavior of a Novel α-Amino Acid

Misuraca

Musah

2017

Sci Rep

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“…In this context, a number of peptidebased building blocks related to these amino acids have been designed and developed to create supramolecular structures (Zhou et al, 2017;Lee et al, 2018). Moreover, the amino acids Phe and Tyr have been shown to be capable of self-assembling into supramolecular nanostructures (Adler-Abramovich et al, 2012;Singh et al, 2014;Mé nard-Moyon et al, 2015). Even though it is feasible for both Tyr and Phe-based fragments to be part of self-assembly processes, the structural difference associated with the phenolic OH group, as a side-chain functional group in Tyr, seems to be critical for the structural features and properties of the resultant entity.…”

Section: Introductionmentioning

confidence: 99%

Nickel(II) complexes based on L-amino-acid-derived ligands: synthesis, characterization and study of the role of the supramolecular structure in carbon dioxide capture

Marquina¹,

Movilla²,

Montilva³

et al. 2020

Acta Crystallogr Sect B

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The formation of the symmetrical μ3-carbonate-bridged self-assembled trinuclear NiII complex Na2{[Ni(LO)2(H2O)]3(μ3-CO3)} (LO is the carboxylate anion of a L-tyrosine derivative), involves atmospheric CO2 uptake. The asymmetric unit of the complex comprises an octahedral coordination for the NiII with two L-tyrosine-based ligands, a water molecule and one O atom of the carbonate bridge. The Ni3–μ3-CO3 core in this compound is the first reported of this kind according to the Cambridge Structural Database (CSD). The supramolecular structure is mainly sustained by hydrogen bonds developed by the phenolic functionality of the L-tyrosine moiety of one ligand and the carboxylate group of a neighbouring ligand. The crystal packing is then characterized by three interpenetrated supramolecular helices associated with a diastereoisomer of the type R-sup P, which is essential for the assembly process. Magnetic susceptibility and magnetization data support weak ferromagnetic exchange interactions within the novel Ni3–μ3-CO3 core. The NiII complex obtained under the same synthetic conditions but using the analogous ligand derived from the amino acid L-phenylalanine instead of L-tyrosine gives rise to to a mononuclear octahedral system. The results obtained for the different complexes demonstrate the role of the supramolecular structure regarding the CO2 uptake property for these NiII–amino-acid-based systems.

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“…Specifically, the aromatic l -Tyrosine (Tyr) amino acid was found to form amyloid-like fibrils [ 13 , 18 ]. The accumulation of Tyr occurs in three different types of tyrosinemia, all resulting from autosomal recessive mutations in several genes in the phenylalanine (Phe) and Tyr metabolic pathway [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

Antibodies towards Tyrosine Amyloid-Like Fibrils Allow Toxicity Modulation and Cellular Imaging of the Assemblies

et al. 2018

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The amino acid tyrosine forms cytotoxic amyloid-like fibrils by molecular self-assembly. However, the production of antibodies towards tyrosine assemblies, reflecting their presentation to the immune system, was not demonstrated yet. Here, we describe the production of antibodies that specifically recognize tyrosine in its fibrillated form. The antibodies were demonstrated to specifically bind self-assembled tyrosine, in contrast to its non-aggregated form or disintegrated fibrils. The antibodies could be used for immunostaining of tyrosine fibrils in cultured cells. Furthermore, confocal microscopy allowed a demonstration of the intracellular presence of the metabolite amyloids in a neuroblastoma cell model. Finally, pre-incubation of tyrosine fibrils with the antibodies resulted in significant reduction in their cytotoxicity. Taken together, we provide an experimental proof for the immunogenicity of tyrosine amyloid fibrillary assemblies. These specific antibodies against tyrosine structures could be further used as a research tool to study the dynamics, toxicity and cellular localization of the assemblies.

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Self‐Assembly of Tyrosine into Controlled Supramolecular Nanostructures

Cited by 75 publications

References 55 publications

“Carboranyl-cysteine”—Synthesis, Structure and Self-Assembly Behavior of a Novel α-Amino Acid

“Carboranyl-cysteine”—Synthesis, Structure and Self-Assembly Behavior of a Novel α-Amino Acid

Nickel(II) complexes based on L-amino-acid-derived ligands: synthesis, characterization and study of the role of the supramolecular structure in carbon dioxide capture

Antibodies towards Tyrosine Amyloid-Like Fibrils Allow Toxicity Modulation and Cellular Imaging of the Assemblies

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