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

Title: Cytosolic delivery of materials with endosome-disrupting colloids

Abstract

A facile procedure to deliver nanocrystals to the cytosol of live cells that is both rapid and general. The technique employs a unique cationic core-shell polymer colloid that directs nanocrystals to the cytosol of living cells within a few hours of incubation. The present methods and compositions enable a host of advanced applications arising from efficient cytosolic delivery of nanocrystal imaging probes: from single particle tracking experiments to monitoring protein-protein interactions in live cells for extended periods.

Inventors:
;
Issue Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1243071
Patent Number(s):
9,284,188
Application Number:
13/225,199
Assignee:
The Regents of the University of California (Oakland, CA)
DOE Contract Number:  
AC02-05CH11231
Resource Type:
Patent
Resource Relation:
Patent File Date: 2011 Sep 02
Country of Publication:
United States
Language:
English
Subject:
60 APPLIED LIFE SCIENCES; 47 OTHER INSTRUMENTATION; 77 NANOSCIENCE AND NANOTECHNOLOGY

Citation Formats

Helms, Brett A., and Bayles, Andrea R. Cytosolic delivery of materials with endosome-disrupting colloids. United States: N. p., 2016. Web.
Helms, Brett A., & Bayles, Andrea R. Cytosolic delivery of materials with endosome-disrupting colloids. United States.
Helms, Brett A., and Bayles, Andrea R. Tue . "Cytosolic delivery of materials with endosome-disrupting colloids". United States. https://www.osti.gov/servlets/purl/1243071.
@article{osti_1243071,
title = {Cytosolic delivery of materials with endosome-disrupting colloids},
author = {Helms, Brett A. and Bayles, Andrea R.},
abstractNote = {A facile procedure to deliver nanocrystals to the cytosol of live cells that is both rapid and general. The technique employs a unique cationic core-shell polymer colloid that directs nanocrystals to the cytosol of living cells within a few hours of incubation. The present methods and compositions enable a host of advanced applications arising from efficient cytosolic delivery of nanocrystal imaging probes: from single particle tracking experiments to monitoring protein-protein interactions in live cells for extended periods.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2016},
month = {3}
}

Patent:

Save / Share:

Works referenced in this record:

Accelerated Discovery of Synthetic Transfection Vectors:  Parallel Synthesis and Screening of a Degradable Polymer Library
journal, August 2001

  • Lynn, David M.; Anderson, Daniel G.; Putnam, David
  • Journal of the American Chemical Society, Vol. 123, Issue 33
  • DOI: 10.1021/ja016288p

Synthesis of Poly(β-amino ester)s Optimized for Highly Effective Gene Delivery
journal, September 2003

  • Akinc, Akin; Anderson, Daniel G.; Lynn, David M.
  • Bioconjugate Chemistry, Vol. 14, Issue 5
  • DOI: 10.1021/bc034067y

Proton-Sponge Coated Quantum Dots for siRNA Delivery and Intracellular Imaging
journal, July 2008

  • Yezhelyev, Maksym V.; Qi, Lifeng; O’Regan, Ruth M.
  • Journal of the American Chemical Society, Vol. 130, Issue 28
  • DOI: 10.1021/ja800086u

Characterization of nanoparticle uptake by endothelial cells
journal, February 2002


In vitro cytotoxicity testing of polycations: influence of polymer structure on cell viability and hemolysis
journal, March 2003


Interaction of Poly(amidoamine) Dendrimers with Supported Lipid Bilayers and Cells:  Hole Formation and the Relation to Transport
journal, July 2004

  • Hong, Seungpyo; Bielinska, Anna U.; Mecke, Almut
  • Bioconjugate Chemistry, Vol. 15, Issue 4
  • DOI: 10.1021/bc049962b

Endocytosis and Membrane Potential Are Required for HeLa Cell Uptake of R.I.-CKTat9, a Retro-Inverso Tat Cell Penetrating Peptide
journal, April 2009

  • Zhang, Xiaoping; Jin, Yongjiu; Plummer, Mark R.
  • Molecular Pharmaceutics, Vol. 6, Issue 3
  • DOI: 10.1021/mp800121f

Size-Dependent Endocytosis of Nanoparticles
journal, January 2009

  • Zhang, Sulin; Li, Ju; Lykotrafitis, George
  • Advanced Materials, Vol. 21, Issue 4, p. 419-424
  • DOI: 10.1002/adma.200801393

Chemoselective Ligation in the Functionalization of Polysaccharide-Based Particles
journal, August 2009

  • Beaudette, Tristan T.; Cohen, Joel A.; Bachelder, Eric M.
  • Journal of the American Chemical Society, Vol. 131, Issue 30
  • DOI: 10.1021/ja903984s

The endocytic matrix
journal, January 2010


Synthesis and Characterization of Novel pH-Responsive Microgels Based on Tertiary Amine Methacrylates
journal, October 2004

  • Amalvy, J. I.; Wanless, E. J.; Li, Y.
  • Langmuir, Vol. 20, Issue 21
  • DOI: 10.1021/la049156t

Cytosolic Delivery of Membrane-Impermeable Molecules in Dendritic Cells Using pH-Responsive Core−Shell Nanoparticles
journal, October 2007

  • Hu, Yuhua; Litwin, Tamara; Nagaraja, Arpun R.
  • Nano Letters, Vol. 7, Issue 10
  • DOI: 10.1021/nl071542i

Nanocarrier Cross-Linking Density and pH Sensitivity Regulate Intracellular Gene Transfer
journal, December 2009

  • You, Jin-Oh; Auguste, Debra T.
  • Nano Letters, Vol. 9, Issue 12
  • DOI: 10.1021/nl902789s

Cytosolic Delivery Mediated via Electrostatic Surface Binding of Protein, Virus, or siRNA Cargos to pH-Responsive Core−Shell Gel Particles
journal, April 2009

  • Hu, Yuhua; Atukorale, Prabhani U.; Lu, James J.
  • Biomacromolecules, Vol. 10, Issue 4
  • DOI: 10.1021/bm801199z

Probing the Cytotoxicity of Semiconductor Quantum Dots
journal, January 2004

  • Derfus, Austin M.; Chan, Warren C. W.; Bhatia, Sangeeta N.
  • Nano Letters, Vol. 4, Issue 1
  • DOI: 10.1021/nl0347334

Physicochemical Properties and Cellular Toxicity of Nanocrystal Quantum Dots Depend on Their Surface Modification
journal, November 2004

  • Hoshino, Akiyoshi; Fujioka, Kouki; Oku, Taisuke
  • Nano Letters, Vol. 4, Issue 11
  • DOI: 10.1021/nl048715d

Unmodified Cadmium Telluride Quantum Dots Induce Reactive Oxygen Species Formation Leading to Multiple Organelle Damage and Cell Death
journal, November 2005


Cytotoxicity of Colloidal CdSe and CdSe/ZnS Nanoparticles
journal, February 2005

  • Kirchner, Christian; Liedl, Tim; Kudera, Stefan
  • Nano Letters, Vol. 5, Issue 2
  • DOI: 10.1021/nl047996m

Variables Influencing Interactions of Untargeted Quantum Dot Nanoparticles with Skin Cells and Identification of Biochemical Modulators
journal, May 2007

  • Ryman-Rasmussen, Jessica P.; Riviere, Jim E.; Monteiro-Riviere, Nancy A.
  • Nano Letters, Vol. 7, Issue 5
  • DOI: 10.1021/nl070375j

Photopolymerizable degradable polyanhydrides with osteocompatibility
journal, February 1999

  • Anseth, Kristi S.; Shastri, Venkatram R.; Langer, Robert
  • Nature Biotechnology, Vol. 17, Issue 2
  • DOI: 10.1038/6152

In situ forming degradable networks and their application in tissue engineering and drug delivery
journal, January 2002

  • Anseth, Kristi S.; Metters, Andrew T.; Bryant, Stephanie J.
  • Journal of Controlled Release, Vol. 78, Issue 1-3, p. 199-209
  • DOI: 10.1016/S0168-3659(01)00500-4

Role of the Mannose Receptor in the Immune Response
journal, September 2001


Synthesis of in Situ Cross-Linkable Macroporous Biodegradable Poly(propylene fumarate- co -ethylene glycol) Hydrogels
journal, March 2002

  • Behravesh, Esfandiar; Jo, Seongbong; Zygourakis, Kyriacos
  • Biomacromolecules, Vol. 3, Issue 2
  • DOI: 10.1021/bm010158r

Synthesis and Inverse Emulsion Polymerization of Aminated Acrylamidodextran
journal, December 1993


A Tunable Hydrogel for Encapsulation and Controlled Release of Bioactive Proteins
journal, March 2002

  • Delgado, Mercedes; Spanka, Carsten; Kerwin, Lisa D.
  • Biomacromolecules, Vol. 3, Issue 2
  • DOI: 10.1021/bm010147y

Loading of plasmid DNA into PLGA microparticles using TROMS (Total Recirculation One-Machine System): evaluation of its integrity and controlled release properties
journal, January 2003


Hydrogels for Biomedical Applications
journal, November 2001


Release Behavior of High Molecular Weight Solutes from Poly(ethylene glycol)-Based Degradable Networks
journal, April 2000

  • Lu, Sanxiu; Anseth, Kristi S.
  • Macromolecules, Vol. 33, Issue 7
  • DOI: 10.1021/ma9915024

pH-Responsive Polymer Microspheres: Rapid Release of Encapsulated Material within the Range of Intracellular pH
journal, May 2001


A Novel Strategy for Encapsulation and Release of Proteins:  Hydrogels and Microgels with Acid-Labile Acetal Cross-Linkers
journal, October 2002

  • Murthy, Niren; Thng, Yi X.; Schuck, Stephany
  • Journal of the American Chemical Society, Vol. 124, Issue 42
  • DOI: 10.1021/ja026925r

Poly(lactide-co-glycolide) microparticles for the development of single-dose controlled-release vaccines
journal, July 1998


Temperature modulated protein release from pH/temperature-sensitive hydrogels
journal, March 1999


Controlled release of clot-dissolving tissue-type plasminogen activator from a poly(l-glutamic acid) semi-interpenetrating polymer network hydrogel
journal, July 2001

  • Park, Yoon-Jeong; Liang, Junfeng; Yang, Zhiqiang
  • Journal of Controlled Release, Vol. 75, Issue 1-2, p. 37-44
  • DOI: 10.1016/S0168-3659(01)00360-1

A Novel Breakable Cross-Linker and pH-Responsive Star-Shaped and Gel Polymers
journal, June 1999

  • Ruckenstein, Eli; Zhang, Hongmin
  • Macromolecules, Vol. 32, Issue 12
  • DOI: 10.1021/ma990016d

Partitioning of proteins and small biomolecules in temperature- and pH-sensitive hydrogels
journal, May 1996


Bioerodible hydrogels based on photopolymerized poly(ethylene glycol)-co-poly(.alpha.-hydroxy acid) diacrylate macromers
journal, July 1993

  • Sawhney, Amarpreet S.; Pathak, Chandrashekhar P.; Hubbell, Jeffrey A.
  • Macromolecules, Vol. 26, Issue 4
  • DOI: 10.1021/ma00056a005

Quantum Dot−Amphipol Nanocomplex for Intracellular Delivery and Real-Time Imaging of siRNA
journal, June 2008


Candida albicans mannan–protein conjugate as vaccine candidate
journal, February 2003


Conjugation of yeast mannans with protein employing cyanopyridinium agent (CDAP) – an effective route of antifungal vaccine preparation
journal, January 2000

  • Bystrický, Slavomír; Machova´, Eva; Bartek, Peter
  • Glycoconjugate Journal, Vol. 17, Issue 10, p. 677-680
  • DOI: 10.1023/A:1011002118819

Degradation and Release Behavior of Dextran-Based Hydrogels
journal, August 1997

  • van Dijk-Wolthuis, W. N. E.; Hoogeboom, J. A. M.; van Steenbergen, M. J.
  • Macromolecules, Vol. 30, Issue 16, p. 4639-4645
  • DOI: 10.1021/ma9704018

Acetals as pH-Sensitive Linkages for Drug Delivery
journal, November 2004

  • Gillies, Elizabeth R.; Goodwin, Andrew P.; Fréchet, Jean M. J.
  • Bioconjugate Chemistry, Vol. 15, Issue 6, p. 1254-1263
  • DOI: 10.1021/bc049853x

Acetalated dextran is a chemically and biologically tunable material for particulate immunotherapy
journal, March 2009

  • Broaders, K. E.; Cohen, J. A.; Beaudette, T. T.
  • Proceedings of the National Academy of Sciences, Vol. 106, Issue 14, p. 5497-5502
  • DOI: 10.1073/pnas.0901592106

Degradable Poly(β-amino esters):  Synthesis, Characterization, and Self-Assembly with Plasmid DNA
journal, November 2000

  • Lynn, David M.; Langer, Robert
  • Journal of the American Chemical Society, Vol. 122, Issue 44
  • DOI: 10.1021/ja0015388

Parallel Synthesis and Biophysical Characterization of a Degradable Polymer Library for Gene Delivery
journal, May 2003

  • Akinc, Akin; Lynn, David M.; Anderson, Daniel G.
  • Journal of the American Chemical Society, Vol. 125, Issue 18
  • DOI: 10.1021/ja034429c

Acid-Degradable Polyurethane Particles for Protein-Based Vaccines: Biological Evaluation and in Vitro Analysis of Particle Degradation Products
journal, June 2008

  • Bachelder, Eric M.; Beaudette, Tristan T.; Broaders, Kyle E.
  • Molecular Pharmaceutics, Vol. 5, Issue 5
  • DOI: 10.1021/mp800068x

Fully Acid-Degradable Biocompatible Polyacetal Microparticles for Drug Delivery
journal, April 2008

  • Paramonov, Sergey E.; Bachelder, Eric M.; Beaudette, Tristan T.
  • Bioconjugate Chemistry, Vol. 19, Issue 4, p. 911-919
  • DOI: 10.1021/bc7004472

Acetal-Derivatized Dextran: An Acid-Responsive Biodegradable Material for Therapeutic Applications
journal, August 2008

  • Bachelder, Eric M.; Beaudette, Tristan T.; Broaders, Kyle E.
  • Journal of the American Chemical Society, Vol. 130, Issue 32, p. 10494-10495
  • DOI: 10.1021/ja803947s

Creating new fluorescent probes for cell biology
journal, December 2002

  • Zhang, Jin; Campbell, Robert E.; Ting, Alice Y.
  • Nature Reviews Molecular Cell Biology, Vol. 3, Issue 12
  • DOI: 10.1038/nrm976

The versatility and universality of calcium signalling
journal, October 2000

  • Berridge, Michael J.; Lipp, Peter; Bootman, Martin D.
  • Nature Reviews Molecular Cell Biology, Vol. 1, Issue 1
  • DOI: 10.1038/35036035

Signaling mechanisms
journal, June 2005

  • Jan, Lily Yeh; Siegelbaum, Steven A.
  • Current Opinion in Neurobiology, Vol. 15, Issue 3, p. 253-256
  • DOI: 10.1016/j.conb.2005.05.015

Simplistic pathways or complex networks?
journal, February 2010

  • Jørgensen, Claus; Linding, Rune
  • Current Opinion in Genetics & Development, Vol. 20, Issue 1, p. 15-22
  • DOI: 10.1016/j.gde.2009.12.003

Visualizing dynamic interaction between calmodulin and calmodulin-related kinases via a monitoring method in live mammalian cells
journal, February 2010

  • Lee, K. H.; Lee, S.; Lee, W. Y.
  • Proceedings of the National Academy of Sciences, Vol. 107, Issue 8, p. 3412-3417
  • DOI: 10.1073/pnas.0911262107

Untangling the ErbB signalling network
journal, February 2001

  • Yarden, Yosef; Sliwkowski, Mark X.
  • Nature Reviews Molecular Cell Biology, Vol. 2, Issue 2
  • DOI: 10.1038/35052073

Immunofluorescent labeling of cancer marker Her2 and other cellular targets with semiconductor quantum dots
journal, December 2002

  • Wu, Xingyong; Liu, Hongjian; Liu, Jianquan
  • Nature Biotechnology, Vol. 21, Issue 1
  • DOI: 10.1038/nbt764

In vivo cancer targeting and imaging with semiconductor quantum dots
journal, July 2004

  • Gao, Xiaohu; Cui, Yuanyuan; Levenson, Richard M.
  • Nature Biotechnology, Vol. 22, Issue 8
  • DOI: 10.1038/nbt994

Semiconductor Clusters, Nanocrystals, and Quantum Dots
journal, February 1996


Semiconductor Nanocrystals as Fluorescent Biological Labels
patent, September 1998


Quantum Dot Bioconjugates for Ultrasensitive Nonisotopic Detection
journal, September 1998


Properties of Fluorescent Semiconductor Nanocrystals and their Application to Biological Labeling
journal, December 2001


Biological applications of colloidal nanocrystals
journal, June 2003


The use of nanocrystals in biological detection
journal, January 2003

  • Alivisatos, Paul
  • Nature Biotechnology, Vol. 22, Issue 1, p. 47-52
  • DOI: 10.1038/nbt927

Cell-specific targeting of nanoparticles by multivalent attachment of small molecules
journal, October 2005

  • Weissleder, Ralph; Kelly, Kimberly; Sun, Eric Yi
  • Nature Biotechnology, Vol. 23, Issue 11, p. 1418-1423
  • DOI: 10.1038/nbt1159

CdSe nanocrystal based chem-/bio- sensors
journal, January 2007

  • Somers, Rebecca C.; Bawendi, Moungi G.; Nocera, Daniel G.
  • Chemical Society Reviews, Vol. 36, Issue 4
  • DOI: 10.1039/B517613C

Quantum dots versus organic dyes as fluorescent labels
journal, August 2008

  • Resch-Genger, Ute; Grabolle, Markus; Cavaliere-Jaricot, Sara
  • Nature Methods, Vol. 5, Issue 9
  • DOI: 10.1038/nmeth.1248

The many ways to cross the plasma membrane
journal, March 2001

  • Stephens, D. J.; Pepperkok, R.
  • Proceedings of the National Academy of Sciences, Vol. 98, Issue 8, p. 4295-4298
  • DOI: 10.1073/pnas.081065198

Quantum Dots for Live Cells, in Vivo Imaging, and Diagnostics
journal, January 2005


A cell nanoinjector based on carbon nanotubes
journal, May 2007

  • Chen, X.; Kis, A.; Zettl, A.
  • Proceedings of the National Academy of Sciences, Vol. 104, Issue 20, p. 8218-8222
  • DOI: 10.1073/pnas.0700567104

Imaging and Tracking of Tat Peptide-Conjugated Quantum Dots in Living Cells:  New Insights into Nanoparticle Uptake, Intracellular Transport, and Vesicle Shedding
journal, November 2007

  • Ruan, Gang; Agrawal, Amit; Marcus, Adam I.
  • Journal of the American Chemical Society, Vol. 129, Issue 47
  • DOI: 10.1021/ja074936k

Biodegradable Quantum Dot Nanocomposites Enable Live Cell Labeling and Imaging of Cytoplasmic Targets
journal, November 2008

  • Kim, Betty Y. S.; Jiang, Wen; Oreopoulos, John
  • Nano Letters, Vol. 8, Issue 11
  • DOI: 10.1021/nl802311t

Virus trafficking – learning from single-virus tracking
journal, March 2007

  • Brandenburg, Boerries; Zhuang, Xiaowei
  • Nature Reviews Microbiology, Vol. 5, Issue 3
  • DOI: 10.1038/nrmicro1615

Long-term multiple color imaging of live cells using quantum dot bioconjugates
journal, December 2002

  • Jaiswal, Jyoti K.; Mattoussi, Hedi; Mauro, J. Matthew
  • Nature Biotechnology, Vol. 21, Issue 1
  • DOI: 10.1038/nbt767

Intracellular Delivery of Quantum Dots for Live Cell Labeling and Organelle Tracking
journal, June 2004

  • Derfus, A. M.; Chan, W. C. W.; Bhatia, S. N.
  • Advanced Materials, Vol. 16, Issue 12, p. 961-966
  • DOI: 10.1002/adma.200306111

Cellular internalization and targeting of semiconductor quantum dots
journal, January 2005

  • Rozenzhak, Sophie M.; Kadakia, Madhavi P.; Caserta, Tina M.
  • Chemical Communications, Issue 17
  • DOI: 10.1039/B418454H

Self-Assembled Quantum Dot−Peptide Bioconjugates for Selective Intracellular Delivery
journal, July 2006

  • Delehanty, James B.; Medintz, Igor L.; Pons, Thomas
  • Bioconjugate Chemistry, Vol. 17, Issue 4
  • DOI: 10.1021/bc060044i

Cell-Penetrating Quantum Dots Based on Multivalent and Endosome-Disrupting Surface Coatings
journal, March 2007

  • Duan, Hongwei; Nie, Shuming
  • Journal of the American Chemical Society, Vol. 129, Issue 11
  • DOI: 10.1021/ja068158s

Intracellular Delivery of Quantum Dot−Protein Cargos Mediated by Cell Penetrating Peptides
journal, September 2008

  • Medintz, Igor L.; Pons, Thomas; Delehanty, James B.
  • Bioconjugate Chemistry, Vol. 19, Issue 9
  • DOI: 10.1021/bc800089r

Site-Specific Labeling of Enveloped Viruses with Quantum Dots for Single Virus Tracking
journal, August 2008

  • Joo, Kye-Il; Lei, Yuning; Lee, Chi-Lin
  • ACS Nano, Vol. 2, Issue 8
  • DOI: 10.1021/nn8002136

Clathrin-Mediated Endocytosis of Quantum Dot−Peptide Conjugates in Living Cells
journal, August 2009

  • Anas, Abdulaziz; Okuda, Tetsuya; Kawashima, Nagako
  • ACS Nano, Vol. 3, Issue 8
  • DOI: 10.1021/nn900663r

Non-blinking and photostable upconverted luminescence from single lanthanide-doped nanocrystals
journal, June 2009

  • Wu, S.; Han, G.; Milliron, D. J.
  • Proceedings of the National Academy of Sciences, Vol. 106, Issue 27, p. 10917-10921
  • DOI: 10.1073/pnas.0904792106