Supramolecular amplification of amyloid self-assembly by iodination

Arianna Bertolani, Lisa Pirrie, Loic Stefan, Nikolay Houbenov, Johannes S. Haataja, Luca Catalano, Giancarlo Terraneo, Gabriele Giancane, Ludovico Valli, Roberto Milani, Olli Ikkala, Giuseppe Resnati, Pierangelo Metrangolo

    Research output: Contribution to journalArticleScientificpeer-review

    37 Citations (Scopus)

    Abstract

    Amyloid supramolecular assemblies have found widespread exploitation as ordered nanomaterials in a range of applications from materials science to biotechnology. New strategies are, however, required for understanding and promoting mature fibril formation from simple monomer motifs through easy and scalable processes. Noncovalent interactions are key to forming and holding the amyloid structure together. On the other hand, the halogen bond has never been used purposefully to achieve control over amyloid self-assembly. Here we show that single atom replacement of hydrogen with iodine, a halogen-bond donor, in the human calcitonin-derived amyloidogenic fragment DFNKF results in a super-gelator peptide, which forms a strong and shape-persistent hydrogel at 30-fold lower concentration than the wild-type pentapeptide. This is remarkable for such a modest perturbation in structure. Iodination of aromatic amino acids may thus develop as a general strategy for the design of new hydrogels from unprotected peptides and without using organic solvents.
    Original languageEnglish
    Article number7574
    JournalNature Communications
    Volume6
    DOIs
    Publication statusPublished - 2015
    MoE publication typeA1 Journal article-refereed

    Fingerprint

    Halogenation
    Amyloid
    halogens
    Self assembly
    peptides
    Amplification
    self assembly
    Halogens
    biotechnology
    materials science
    exploitation
    assemblies
    iodine
    amino acids
    low concentrations
    Aromatic Amino Acids
    Peptides
    Hydrogels
    Nanostructures
    monomers

    Keywords

    • chemical modification
    • Organic chemistry
    • self-assembly

    Cite this

    Bertolani, A., Pirrie, L., Stefan, L., Houbenov, N., Haataja, J. S., Catalano, L., ... Metrangolo, P. (2015). Supramolecular amplification of amyloid self-assembly by iodination. Nature Communications, 6, [7574]. https://doi.org/10.1038/ncomms8574
    Bertolani, Arianna ; Pirrie, Lisa ; Stefan, Loic ; Houbenov, Nikolay ; Haataja, Johannes S. ; Catalano, Luca ; Terraneo, Giancarlo ; Giancane, Gabriele ; Valli, Ludovico ; Milani, Roberto ; Ikkala, Olli ; Resnati, Giuseppe ; Metrangolo, Pierangelo. / Supramolecular amplification of amyloid self-assembly by iodination. In: Nature Communications. 2015 ; Vol. 6.
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    abstract = "Amyloid supramolecular assemblies have found widespread exploitation as ordered nanomaterials in a range of applications from materials science to biotechnology. New strategies are, however, required for understanding and promoting mature fibril formation from simple monomer motifs through easy and scalable processes. Noncovalent interactions are key to forming and holding the amyloid structure together. On the other hand, the halogen bond has never been used purposefully to achieve control over amyloid self-assembly. Here we show that single atom replacement of hydrogen with iodine, a halogen-bond donor, in the human calcitonin-derived amyloidogenic fragment DFNKF results in a super-gelator peptide, which forms a strong and shape-persistent hydrogel at 30-fold lower concentration than the wild-type pentapeptide. This is remarkable for such a modest perturbation in structure. Iodination of aromatic amino acids may thus develop as a general strategy for the design of new hydrogels from unprotected peptides and without using organic solvents.",
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    author = "Arianna Bertolani and Lisa Pirrie and Loic Stefan and Nikolay Houbenov and Haataja, {Johannes S.} and Luca Catalano and Giancarlo Terraneo and Gabriele Giancane and Ludovico Valli and Roberto Milani and Olli Ikkala and Giuseppe Resnati and Pierangelo Metrangolo",
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    Bertolani, A, Pirrie, L, Stefan, L, Houbenov, N, Haataja, JS, Catalano, L, Terraneo, G, Giancane, G, Valli, L, Milani, R, Ikkala, O, Resnati, G & Metrangolo, P 2015, 'Supramolecular amplification of amyloid self-assembly by iodination', Nature Communications, vol. 6, 7574. https://doi.org/10.1038/ncomms8574

    Supramolecular amplification of amyloid self-assembly by iodination. / Bertolani, Arianna; Pirrie, Lisa; Stefan, Loic; Houbenov, Nikolay; Haataja, Johannes S.; Catalano, Luca; Terraneo, Giancarlo; Giancane, Gabriele; Valli, Ludovico; Milani, Roberto; Ikkala, Olli; Resnati, Giuseppe; Metrangolo, Pierangelo.

    In: Nature Communications, Vol. 6, 7574, 2015.

    Research output: Contribution to journalArticleScientificpeer-review

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    T1 - Supramolecular amplification of amyloid self-assembly by iodination

    AU - Bertolani, Arianna

    AU - Pirrie, Lisa

    AU - Stefan, Loic

    AU - Houbenov, Nikolay

    AU - Haataja, Johannes S.

    AU - Catalano, Luca

    AU - Terraneo, Giancarlo

    AU - Giancane, Gabriele

    AU - Valli, Ludovico

    AU - Milani, Roberto

    AU - Ikkala, Olli

    AU - Resnati, Giuseppe

    AU - Metrangolo, Pierangelo

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    PY - 2015

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    AB - Amyloid supramolecular assemblies have found widespread exploitation as ordered nanomaterials in a range of applications from materials science to biotechnology. New strategies are, however, required for understanding and promoting mature fibril formation from simple monomer motifs through easy and scalable processes. Noncovalent interactions are key to forming and holding the amyloid structure together. On the other hand, the halogen bond has never been used purposefully to achieve control over amyloid self-assembly. Here we show that single atom replacement of hydrogen with iodine, a halogen-bond donor, in the human calcitonin-derived amyloidogenic fragment DFNKF results in a super-gelator peptide, which forms a strong and shape-persistent hydrogel at 30-fold lower concentration than the wild-type pentapeptide. This is remarkable for such a modest perturbation in structure. Iodination of aromatic amino acids may thus develop as a general strategy for the design of new hydrogels from unprotected peptides and without using organic solvents.

    KW - chemical modification

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    Bertolani A, Pirrie L, Stefan L, Houbenov N, Haataja JS, Catalano L et al. Supramolecular amplification of amyloid self-assembly by iodination. Nature Communications. 2015;6. 7574. https://doi.org/10.1038/ncomms8574