1D Self-Assembly and Ice Recrystallization Inhibition Activity of Antifreeze Glycopeptide-Functionalized Perylene Bisimides

Madeleine K. Adam; Charles Jarrett-Wilkins; Michael Beards; Emiliyan Staykov; Liam R. MacFarlane; Toby D.M. Bell; Jacqueline M. Matthews; Ian Manners; Charl F.J. Faul; Pierre D.J. Moens; Robert N. Ben; Brendan L. Wilkinson

doi:10.1002/chem.201800857

1D Self-Assembly and Ice Recrystallization Inhibition Activity of Antifreeze Glycopeptide-Functionalized Perylene Bisimides

Madeleine K. Adam, Charles Jarrett-Wilkins, Michael Beards, Emiliyan Staykov, Liam R. MacFarlane, Toby D.M. Bell, Jacqueline M. Matthews, Ian Manners, Charl F.J. Faul, Pierre D.J. Moens, Robert N. Ben, Brendan L. Wilkinson^*

^*Corresponding author for this work

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Abstract

Antifreeze glycoproteins (AFGPs) are polymeric natural products that have drawn considerable interest in diverse research fields owing to their potent ice recrystallization inhibition (IRI) activity. Self-assembled materials have emerged as a promising class of biomimetic ice growth inhibitor, yet the development of AFGP-based supramolecular materials that emulate the aggregative behavior of AFGPs have not yet been reported. This work reports the first example of the 1D self-assembly and IRI activity of AFGP-functionalized perylene bisimides (AFGP-PBIs). Glycopeptide-functionalized PBIs underwent 1D self-assembly in water and showed modest IRI activity, which could be tuned through substitution of the PBI core. This work presents essential proof-of-principle for the development of novel IRIs as potential supramolecular cryoprotectants and glycoprotein mimics.

Original language	English
Pages (from-to)	7834-7839
Number of pages	6
Journal	Chemistry - A European Journal
Volume	24
Issue number	31
Early online date	12 Apr 2018
DOIs	https://doi.org/10.1002/chem.201800857
Publication status	Published - 4 Jun 2018

Structured keywords

BCS and TECS CDTs

Keywords

1D self-assembly
antifreeze glycopeptides
perylene bisimides
pi interactions
soft matter

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10.1002/chem.201800857

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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via WILEY at https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201800857. Please refer to any applicable terms of use of the publisher.
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Adam, M. K., Jarrett-Wilkins, C., Beards, M., Staykov, E., MacFarlane, L. R., Bell, T. D. M., Matthews, J. M., Manners, I., Faul, C. F. J., Moens, P. D. J., Ben, R. N., & Wilkinson, B. L. (2018). 1D Self-Assembly and Ice Recrystallization Inhibition Activity of Antifreeze Glycopeptide-Functionalized Perylene Bisimides. Chemistry - A European Journal, 24(31), 7834-7839. https://doi.org/10.1002/chem.201800857

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title = "1D Self-Assembly and Ice Recrystallization Inhibition Activity of Antifreeze Glycopeptide-Functionalized Perylene Bisimides",

abstract = "Antifreeze glycoproteins (AFGPs) are polymeric natural products that have drawn considerable interest in diverse research fields owing to their potent ice recrystallization inhibition (IRI) activity. Self-assembled materials have emerged as a promising class of biomimetic ice growth inhibitor, yet the development of AFGP-based supramolecular materials that emulate the aggregative behavior of AFGPs have not yet been reported. This work reports the first example of the 1D self-assembly and IRI activity of AFGP-functionalized perylene bisimides (AFGP-PBIs). Glycopeptide-functionalized PBIs underwent 1D self-assembly in water and showed modest IRI activity, which could be tuned through substitution of the PBI core. This work presents essential proof-of-principle for the development of novel IRIs as potential supramolecular cryoprotectants and glycoprotein mimics.",

keywords = "1D self-assembly, antifreeze glycopeptides, perylene bisimides, pi interactions, soft matter",

author = "Adam, {Madeleine K.} and Charles Jarrett-Wilkins and Michael Beards and Emiliyan Staykov and MacFarlane, {Liam R.} and Bell, {Toby D.M.} and Matthews, {Jacqueline M.} and Ian Manners and Faul, {Charl F.J.} and Moens, {Pierre D.J.} and Ben, {Robert N.} and Wilkinson, {Brendan L.}",

year = "2018",

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doi = "10.1002/chem.201800857",

language = "English",

volume = "24",

pages = "7834--7839",

journal = "Chemistry - A European Journal",

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Adam, MK, Jarrett-Wilkins, C, Beards, M, Staykov, E, MacFarlane, LR, Bell, TDM, Matthews, JM, Manners, I, Faul, CFJ, Moens, PDJ, Ben, RN & Wilkinson, BL 2018, '1D Self-Assembly and Ice Recrystallization Inhibition Activity of Antifreeze Glycopeptide-Functionalized Perylene Bisimides', Chemistry - A European Journal, vol. 24, no. 31, pp. 7834-7839. https://doi.org/10.1002/chem.201800857

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T1 - 1D Self-Assembly and Ice Recrystallization Inhibition Activity of Antifreeze Glycopeptide-Functionalized Perylene Bisimides

AU - Adam, Madeleine K.

AU - Jarrett-Wilkins, Charles

AU - Beards, Michael

AU - Staykov, Emiliyan

AU - MacFarlane, Liam R.

AU - Bell, Toby D.M.

AU - Matthews, Jacqueline M.

AU - Manners, Ian

AU - Faul, Charl F.J.

AU - Moens, Pierre D.J.

AU - Ben, Robert N.

AU - Wilkinson, Brendan L.

PY - 2018/6/4

Y1 - 2018/6/4

N2 - Antifreeze glycoproteins (AFGPs) are polymeric natural products that have drawn considerable interest in diverse research fields owing to their potent ice recrystallization inhibition (IRI) activity. Self-assembled materials have emerged as a promising class of biomimetic ice growth inhibitor, yet the development of AFGP-based supramolecular materials that emulate the aggregative behavior of AFGPs have not yet been reported. This work reports the first example of the 1D self-assembly and IRI activity of AFGP-functionalized perylene bisimides (AFGP-PBIs). Glycopeptide-functionalized PBIs underwent 1D self-assembly in water and showed modest IRI activity, which could be tuned through substitution of the PBI core. This work presents essential proof-of-principle for the development of novel IRIs as potential supramolecular cryoprotectants and glycoprotein mimics.

AB - Antifreeze glycoproteins (AFGPs) are polymeric natural products that have drawn considerable interest in diverse research fields owing to their potent ice recrystallization inhibition (IRI) activity. Self-assembled materials have emerged as a promising class of biomimetic ice growth inhibitor, yet the development of AFGP-based supramolecular materials that emulate the aggregative behavior of AFGPs have not yet been reported. This work reports the first example of the 1D self-assembly and IRI activity of AFGP-functionalized perylene bisimides (AFGP-PBIs). Glycopeptide-functionalized PBIs underwent 1D self-assembly in water and showed modest IRI activity, which could be tuned through substitution of the PBI core. This work presents essential proof-of-principle for the development of novel IRIs as potential supramolecular cryoprotectants and glycoprotein mimics.

KW - 1D self-assembly

KW - antifreeze glycopeptides

KW - perylene bisimides

KW - pi interactions

KW - soft matter

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U2 - 10.1002/chem.201800857

DO - 10.1002/chem.201800857

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C2 - 29644728

AN - SCOPUS:85046535469

VL - 24

SP - 7834

EP - 7839

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 31

ER -

1D Self-Assembly and Ice Recrystallization Inhibition Activity of Antifreeze Glycopeptide-Functionalized Perylene Bisimides

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