π -π Stacking Mediated Chirality in Functional Supramolecular Filaments

Macromolecules
Myungshim KangSharon M Loverde

Abstract

While a great diversity of peptide-based supra-molecular filaments have been reported, the impact of an auxiliary segment on the chiral assembly of peptides remains poorly understood. Herein we report on the formation of chiral filaments by the self-assembly of a peptide-drug conjugate containing an aromatic drug camptothecin (CPT) in a computational study. We find that the chirality of the filament is mediated by the π‒π stacking between CPTs, not only by the well-expected intermolecular hydrogen bonding between peptide segments. Our simulations show that π‒π stacking of CPTs governs the early stages of the self-assembly process, while a hydrogen bonding network starts at a relatively later stage to contribute to the eventual morphology of the filament. Our results also show the possible presence of water within the core of the CPT filament. These results provide very useful guiding principles for the rational design of supramolecular assemblies of peptide conjugates with aromatic segments.

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Citations

Aug 31, 2017·Organic & Biomolecular Chemistry·Anjela ManandharSharon M Loverde
Oct 12, 2017·Chemical Society Reviews·Andrew G CheethamHonggang Cui
Dec 8, 2017·Biomaterials Science·Yi-An LinHonggang Cui
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Mar 7, 2017·Acta Pharmacologica Sinica·Andrew G CheethamHonggang Cui
Jul 7, 2018·Chemistry : a European Journal·Alexander E CloutGareth R Williams
Jul 3, 2016·Advanced Drug Delivery Reviews·Yin WangHonggang Cui
Mar 12, 2021·Advanced Drug Delivery Reviews·Julie MouginPatrick Couvreur
Mar 25, 2021·Computational and Structural Biotechnology Journal·Ettore Lo CascioAlessandro Arcovito
Oct 1, 2019·Langmuir : the ACS Journal of Surfaces and Colloids·Sayak Subhra PandaJohn D Tovar
Jun 2, 2018·Journal of Chemical Information and Modeling·Myungshim KangSharon M Loverde
Nov 22, 2019·The Journal of Physical Chemistry. B·Anjela ManandharSharon M Loverde
Mar 4, 2020·Journal of Chemical Theory and Computation·Phu K TangSharon M Loverde
Oct 14, 2021·Soft Matter·Jahnu SaikiaVibin Ramakrishnan

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