Supramolecular high-aspect ratio assemblies with strong antifungal activity

Kazuki Fukushima, Shaoqiong Liu, Hong Wu, Amanda C. Engler, Daniel J. Coady, Hareem Maune, Jed Pitera, Alshakim Nelson, Nikken Wiradharma, Shrinivas Venkataraman, Yuan Huang, Weimin Fan, Jackie Y. Ying, Yi Yan Yang () and James L. Hedrick ()
Additional contact information
Kazuki Fukushima: IBM Almaden Research Center, 650 Harry Road
Shaoqiong Liu: Institute of Bioengineering and Nanotechnology
Hong Wu: Institute of Bioengineering and Nanotechnology
Amanda C. Engler: IBM Almaden Research Center, 650 Harry Road
Daniel J. Coady: IBM Almaden Research Center, 650 Harry Road
Hareem Maune: IBM Almaden Research Center, 650 Harry Road
Jed Pitera: IBM Almaden Research Center, 650 Harry Road
Alshakim Nelson: IBM Almaden Research Center, 650 Harry Road
Nikken Wiradharma: Institute of Bioengineering and Nanotechnology
Shrinivas Venkataraman: Institute of Bioengineering and Nanotechnology
Yuan Huang: State Key Laboratory for Diagnosis and Treatment of Infectious Diseases, First Affiliated Hospital, College of Medicine, Zhejiang University
Weimin Fan: State Key Laboratory for Diagnosis and Treatment of Infectious Diseases, First Affiliated Hospital, College of Medicine, Zhejiang University
Jackie Y. Ying: Institute of Bioengineering and Nanotechnology
Yi Yan Yang: Institute of Bioengineering and Nanotechnology
James L. Hedrick: IBM Almaden Research Center, 650 Harry Road

Nature Communications, 2013, vol. 4, issue 1, 1-9

Abstract: Abstract Efficient and pathogen-specific antifungal agents are required to mitigate drug resistance problems. Here we present cationic small molecules that exhibit excellent microbial selectivity with minimal host toxicity. Unlike typical cationic polymers possessing molecular weight distributions, these compounds have an absolute molecular weight aiding in isolation and characterization. However, their specific molecular recognition motif (terephthalamide-bisurea) facilitates spontaneous supramolecular self-assembly manifesting in several polymer-like properties. Computational modelling of the terephthalamide-bisurea structures predicts zig-zag or bent arrangements where distal benzyl urea groups stabilize the high-aspect ratio aqueous supramolecular assemblies. These nanostructures are confirmed by transmission electron microscopy and atomic force microscopy. Antifungal activity against drug-sensitive and drug-resistant strains with in vitro and in vivo biocompatibility is observed. Additionally, despite repeated sub-lethal exposures, drug resistance is not induced. Comparison with clinically used amphotericin B shows similar antifungal behaviour without any significant toxicity in a C. albicans biofilm-induced mouse keratitis model.

Date: 2013
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DOI: 10.1038/ncomms3861

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