skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Bioinspired Peptoid Nanotubes for Targeted Tumor Cell Imaging and Chemo-Photodynamic Therapy

Abstract

Substantial progress has been made in applying nanotubes in biomedical applications such as bioimaging and drug delivery due to their unique architecture, characterized by very large internal surface areas and high aspect ratios. Yet, the biomedical applications of organic nanotubes, especially for those assembled from sequence-defined molecules, are very uncommon. In our work, the synthesis of two new peptoid nanotubes (PepTs1 and PepTs2) is reported by using sequence-defined and ligand-tagged peptoids as building blocks. These nanotubes are highly robust due to sharing a similar structure to those of nontagged ones, and offer great potential to hold guest molecules for biomedical applications. The findings indicate that peptoid nanotubes loaded with doxorubicin drugs are promising candidates for targeted tumor cell imaging and chemo-photodynamic therapy.

Authors:
 [1];  [1];  [2];  [2];  [1];  [2];  [2];  [1];  [1];  [2]; ORCiD logo [1];  [1];  [3]; ORCiD logo [1]
  1. Washington State Univ., Pullman, WA (United States)
  2. Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
  3. Pacific Northwest National Lab. (PNNL), Richland, WA (United States); Univ. of Washington, Seattle, WA (United States)
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). The Center for the Science of Synthesis Across Scales (CSSAS); Univ. of Washington, Seattle, WA (United States); Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1595478
Alternate Identifier(s):
OSTI ID: 1561384; OSTI ID: 1701732
Report Number(s):
PNNL-SA-147458
Journal ID: ISSN 1613-6810
Grant/Contract Number:  
SC0019288; AC02‐05CH11231; AC05‐76RL01830; DE‐AC02‐05CH11231; AC05-76RL01830
Resource Type:
Accepted Manuscript
Journal Name:
Small
Additional Journal Information:
Journal Volume: 15; Journal Issue: 43; Journal ID: ISSN 1613-6810
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
77 NANOSCIENCE AND NANOTECHNOLOGY; 60 APPLIED LIFE SCIENCES; chemo‐/photodynamic therapy; peptoids nanotube; singlet oxygen; targeted drug delivery

Citation Formats

Luo, Yanan, Song, Yang, Wang, Mingming, Jian, Tengyue, Ding, Shichao, Mu, Peng, Liao, Zhihao, Shi, Qiurong, Cai, Xiaoli, Jin, Haibao, Du, Dan, Dong, Wen‐Ji, Chen, Chun‐Long, and Lin, Yuehe. Bioinspired Peptoid Nanotubes for Targeted Tumor Cell Imaging and Chemo-Photodynamic Therapy. United States: N. p., 2019. Web. https://doi.org/10.1002/smll.201902485.
Luo, Yanan, Song, Yang, Wang, Mingming, Jian, Tengyue, Ding, Shichao, Mu, Peng, Liao, Zhihao, Shi, Qiurong, Cai, Xiaoli, Jin, Haibao, Du, Dan, Dong, Wen‐Ji, Chen, Chun‐Long, & Lin, Yuehe. Bioinspired Peptoid Nanotubes for Targeted Tumor Cell Imaging and Chemo-Photodynamic Therapy. United States. https://doi.org/10.1002/smll.201902485
Luo, Yanan, Song, Yang, Wang, Mingming, Jian, Tengyue, Ding, Shichao, Mu, Peng, Liao, Zhihao, Shi, Qiurong, Cai, Xiaoli, Jin, Haibao, Du, Dan, Dong, Wen‐Ji, Chen, Chun‐Long, and Lin, Yuehe. Fri . "Bioinspired Peptoid Nanotubes for Targeted Tumor Cell Imaging and Chemo-Photodynamic Therapy". United States. https://doi.org/10.1002/smll.201902485. https://www.osti.gov/servlets/purl/1595478.
@article{osti_1595478,
title = {Bioinspired Peptoid Nanotubes for Targeted Tumor Cell Imaging and Chemo-Photodynamic Therapy},
author = {Luo, Yanan and Song, Yang and Wang, Mingming and Jian, Tengyue and Ding, Shichao and Mu, Peng and Liao, Zhihao and Shi, Qiurong and Cai, Xiaoli and Jin, Haibao and Du, Dan and Dong, Wen‐Ji and Chen, Chun‐Long and Lin, Yuehe},
abstractNote = {Substantial progress has been made in applying nanotubes in biomedical applications such as bioimaging and drug delivery due to their unique architecture, characterized by very large internal surface areas and high aspect ratios. Yet, the biomedical applications of organic nanotubes, especially for those assembled from sequence-defined molecules, are very uncommon. In our work, the synthesis of two new peptoid nanotubes (PepTs1 and PepTs2) is reported by using sequence-defined and ligand-tagged peptoids as building blocks. These nanotubes are highly robust due to sharing a similar structure to those of nontagged ones, and offer great potential to hold guest molecules for biomedical applications. The findings indicate that peptoid nanotubes loaded with doxorubicin drugs are promising candidates for targeted tumor cell imaging and chemo-photodynamic therapy.},
doi = {10.1002/smll.201902485},
journal = {Small},
number = 43,
volume = 15,
place = {United States},
year = {2019},
month = {8}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 7 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Free-floating ultrathin two-dimensional crystals from sequence-specific peptoid polymers
journal, April 2010

  • Nam, Ki Tae; Shelby, Sarah A.; Choi, Philip H.
  • Nature Materials, Vol. 9, Issue 5
  • DOI: 10.1038/nmat2742

Biological applications of peptides nanotubes: An overview
journal, January 2013


Photosensitized singlet oxygen and its applications
journal, November 2002


Peptide Nanotubes
journal, June 2014


Structural Features of m eso -Tetrakis(4-carboxyphenyl)porphyrin Interacting with Amino-Terminated Poly(propylene oxide)
journal, August 2006

  • Castriciano, Maria Angela; Romeo, Andrea; Angelini, Nicola
  • Macromolecules, Vol. 39, Issue 16
  • DOI: 10.1021/ma060583i

Supramolecular Nanotube Architectures Based on Amphiphilic Molecules
journal, April 2005

  • Shimizu, Toshimi; Masuda, Mitsutoshi; Minamikawa, Hiroyuki
  • Chemical Reviews, Vol. 105, Issue 4
  • DOI: 10.1021/cr030072j

Peptoid Polymers: A Highly Designable Bioinspired Material
journal, May 2013


Self-assembly of crystalline nanotubes from monodisperse amphiphilic diblock copolypeptoid tiles
journal, March 2016

  • Sun, Jing; Jiang, Xi; Lund, Reidar
  • Proceedings of the National Academy of Sciences, Vol. 113, Issue 15
  • DOI: 10.1073/pnas.1517169113

Highly stable and self-repairing membrane-mimetic 2D nanomaterials assembled from lipid-like peptoids
journal, July 2016

  • Jin, Haibao; Jiao, Fang; Daily, Michael D.
  • Nature Communications, Vol. 7, Issue 1
  • DOI: 10.1038/ncomms12252

MnO 2 Nanotube-Based NanoSearchlight for Imaging of Multiple MicroRNAs in Live Cells
journal, July 2017

  • Lu, Qian; Ericson, Daniel; Song, Yang
  • ACS Applied Materials & Interfaces, Vol. 9, Issue 28
  • DOI: 10.1021/acsami.6b15387

Discovery and Development of Folic-Acid-Based Receptor Targeting for Imaging and Therapy of Cancer and Inflammatory Diseases
journal, January 2008

  • Low, Philip S.; Henne, Walter A.; Doorneweerd, Derek D.
  • Accounts of Chemical Research, Vol. 41, Issue 1
  • DOI: 10.1021/ar7000815

Designable and dynamic single-walled stiff nanotubes assembled from sequence-defined peptoids
journal, January 2018


Applications of carbon nanotubes in drug delivery
journal, December 2005

  • Bianco, Alberto; Kostarelos, Kostas; Prato, Maurizio
  • Current Opinion in Chemical Biology, Vol. 9, Issue 6
  • DOI: 10.1016/j.cbpa.2005.10.005

Carrier-Free, Chemophotodynamic Dual Nanodrugs via Self-Assembly for Synergistic Antitumor Therapy
journal, May 2016

  • Zhang, Ruiyun; Xing, Ruirui; Jiao, Tifeng
  • ACS Applied Materials & Interfaces, Vol. 8, Issue 21
  • DOI: 10.1021/acsami.6b02416

Supramolecular peptide constructed by molecular Lego allowing programmable self-assembly for photodynamic therapy
journal, June 2019


Reactive Oxygen-Mediated Protein Oxidation in Aging and Disease
journal, May 1997

  • Stadtman, Earl R.; Berlett, Barbara S.
  • Chemical Research in Toxicology, Vol. 10, Issue 5
  • DOI: 10.1021/tx960133r

Controlling the Physical Dimensions of Peptide Nanotubes by Supramolecular Polymer Coassembly
journal, July 2016


Carbon nanotubes in biology and medicine: In vitro and in vivo detection, imaging and drug delivery
journal, February 2009


Mesoporous Pt Nanotubes as a Novel Sensing Platform for Sensitive Detection of Intracellular Hydrogen Peroxide
journal, October 2015

  • Shi, Qiurong; Song, Yang; Zhu, Chengzhou
  • ACS Applied Materials & Interfaces, Vol. 7, Issue 43
  • DOI: 10.1021/acsami.5b08146

Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis
journal, December 1992

  • Zuckermann, Ronald N.; Kerr, Janice M.; Kent, Stephen B. H.
  • Journal of the American Chemical Society, Vol. 114, Issue 26
  • DOI: 10.1021/ja00052a076

Peptoids: a modular approach to drug discovery.
journal, October 1992

  • Simon, R. J.; Kania, R. S.; Zuckermann, R. N.
  • Proceedings of the National Academy of Sciences, Vol. 89, Issue 20
  • DOI: 10.1073/pnas.89.20.9367

Cyclic peptide-poly(HPMA) nanotubes as drug delivery vectors: In vitro assessment, pharmacokinetics and biodistribution
journal, September 2018


Advancing porphyrin's biomedical utility via supramolecular chemistry
journal, January 2017

  • Rajora, M. A.; Lou, J. W. H.; Zheng, G.
  • Chem. Soc. Rev., Vol. 46, Issue 21
  • DOI: 10.1039/C7CS00525C

Self-assembled peptide-based nanostructures: Smart nanomaterials toward targeted drug delivery
journal, February 2016


Efficient Cytosolic Delivery Using Crystalline Nanoflowers Assembled from Fluorinated Peptoids
journal, November 2018


Label-Free Pathogen Detection with Sensor Chips Assembled from Peptide Nanotubes
journal, December 2008

  • de la Rica, Roberto; Mendoza, Ernest; Lechuga, Laura M.
  • Angewandte Chemie International Edition, Vol. 47, Issue 50
  • DOI: 10.1002/anie.200804299

An Injectable Self-Assembling Collagen-Gold Hybrid Hydrogel for Combinatorial Antitumor Photothermal/Photodynamic Therapy
journal, March 2016


Self-Repair and Patterning of 2D Membrane-Like Peptoid Materials
journal, August 2016

  • Jiao, Fang; Chen, Yulin; Jin, Haibao
  • Advanced Functional Materials, Vol. 26, Issue 48
  • DOI: 10.1002/adfm.201602365

Shape effects of filaments versus spherical particles in flow and drug delivery
journal, March 2007

  • Geng, Yan; Dalhaimer, Paul; Cai, Shenshen
  • Nature Nanotechnology, Vol. 2, Issue 4
  • DOI: 10.1038/nnano.2007.70

Peptoid nanosheets exhibit a new secondary-structure motif
journal, October 2015

  • Mannige, Ranjan V.; Haxton, Thomas K.; Proulx, Caroline
  • Nature, Vol. 526, Issue 7573
  • DOI: 10.1038/nature15363

Self-organized nanotube materials and their application in bioengineering
journal, August 2014

  • Shimizu, Toshimi; Minamikawa, Hiroyuki; Kogiso, Masaki
  • Polymer Journal, Vol. 46, Issue 12
  • DOI: 10.1038/pj.2014.72

Self-Assembling Peptide Nanotubes
journal, January 1996

  • Hartgerink, Jeffrey D.; Granja, Juan R.; Milligan, Ronald A.
  • Journal of the American Chemical Society, Vol. 118, Issue 1
  • DOI: 10.1021/ja953070s

Nanoparticles as vehicles for delivery of photodynamic therapy agents
journal, November 2008


Crystalline Dipeptide Nanobelts Based on Solid–Solid Phase Transformation Self-Assembly and Their Polarization Imaging of Cells
journal, January 2018

  • Song, Jingwen; Xing, Ruirui; Jiao, Tifeng
  • ACS Applied Materials & Interfaces, Vol. 10, Issue 3
  • DOI: 10.1021/acsami.7b17933

Receptor-mediated endocytosis of transferrin and recycling of the transferrin receptor in rat reticulocytes
journal, August 1983


Enzyme-Regulated Supramolecular Assemblies of Cholesterol Conjugates against Drug-Resistant Ovarian Cancer Cells
journal, August 2016

  • Wang, Huaimin; Feng, Zhaoqianqi; Wu, Dongdong
  • Journal of the American Chemical Society, Vol. 138, Issue 34
  • DOI: 10.1021/jacs.6b06075

Nanoparticles in Photodynamic Therapy
journal, January 2015

  • Lucky, Sasidharan Swarnalatha; Soo, Khee Chee; Zhang, Yong
  • Chemical Reviews, Vol. 115, Issue 4
  • DOI: 10.1021/cr5004198

Integrating Enzymatic Self-Assembly and Mitochondria Targeting for Selectively Killing Cancer Cells without Acquired Drug Resistance
journal, December 2016

  • Wang, Huaimin; Feng, Zhaoqianqi; Wang, Youzhi
  • Journal of the American Chemical Society, Vol. 138, Issue 49
  • DOI: 10.1021/jacs.6b09783

Molecular mechanisms of caspase regulation during apoptosis
journal, November 2004

  • Riedl, Stefan J.; Shi, Yigong
  • Nature Reviews Molecular Cell Biology, Vol. 5, Issue 11
  • DOI: 10.1038/nrm1496