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Supramolecular high-aspect ratio assemblies with strong antifungal activity

Author

Listed:
  • Kazuki Fukushima

    (IBM Almaden Research Center, 650 Harry Road
    Yamagata University)

  • 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)

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.

Suggested Citation

  • 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 & J, 2013. "Supramolecular high-aspect ratio assemblies with strong antifungal activity," Nature Communications, Nature, vol. 4(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:4:y:2013:i:1:d:10.1038_ncomms3861
    DOI: 10.1038/ncomms3861
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    Cited by:

    1. Wenping Zhu & Ying Li & Shaoxun Guo & Wu-Jie Guo & Tuokai Peng & Hui Li & Bin Liu & Hui-Qing Peng & Ben Zhong Tang, 2022. "Stereoisomeric engineering of aggregation-induced emission photosensitizers towards fungal killing," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    2. Jiayang Xie & Min Zhou & Yuxin Qian & Zihao Cong & Sheng Chen & Wenjing Zhang & Weinan Jiang & Chengzhi Dai & Ning Shao & Zhemin Ji & Jingcheng Zou & Ximian Xiao & Longqiang Liu & Minzhang Chen & Jin , 2021. "Addressing MRSA infection and antibacterial resistance with peptoid polymers," Nature Communications, Nature, vol. 12(1), pages 1-13, December.

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