Intracellular guest exchange between dynamic supramolecular hosts

S. Swaminathan, Colin Fowley, Bridgeen McCaughan, J. Cusido, J Callan, F.M. Raymo

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Decyl and oligo(ethylene glycol) chains were appended to the same poly(methacrylate) backbone to generate an amphiphilic polymer with a ratio between hydrophobic and hydrophilic segments of 2.5. At concentrations greater than 10 μg mL-1 in neutral buffer, multiple copies of this particular macromolecule assemble into nanoparticles with a hydrodynamic diameter of 15 nm. In the process of assembling, these nanoparticles can capture anthracene donors and borondipyrromethene acceptors within their hydrophobic interior and permit the transfer of excitation energy with an efficiency of 95. Energy transfer is observed also if nanocarriers containing exclusively the donors are mixed with nanoparticles preloaded separately with the acceptors in aqueous media. The two sets of supramolecular assemblies exchange their guests with fast kinetics upon mixing to co-localize complementary chromophores within the same nanostructured container and enable energy transfer. After guest exchange, the nanoparticles can cross the membrane of cervical cancer cells and bring the co-entrapped donors and acceptors within the intracellular environment. Alternatively, intracellular energy transfer is also established after sequential cell incubation with nanoparticles containing the donors first and then with nanocarriers preloaded with the acceptors or vice versa. Under these conditions, the nanoparticles exchange their cargo only after internalization and allow energy transfer exclusively within the cell interior. Thus, the dynamic character of such supramolecular containers offers the opportunity to transport independently complementary species inside cells and permit their interaction only within the intracellular space. © 2014 American Chemical Society.
LanguageEnglish
Pages7907-7913
JournalJOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume136
Issue number22
DOIs
Publication statusE-pub ahead of print - 9 May 2014

Fingerprint

Nanoparticles
Energy transfer
Containers
Ethylene Glycol
Methacrylates
Excitation energy
Chromophores
Macromolecules
Buffers
Polymers
Hydrodynamics
Cells
Membranes
Kinetics

Keywords

  • Chromophores
  • Containers
  • Energy transfer
  • Ethylene glycol
  • Hydrophobicity
  • Supramolecular chemistry
  • Amphiphilic polymers
  • Cervical cancer cells
  • Hydrodynamic diameter
  • Hydrophobic and hydrophilic
  • Intracellular spaces
  • Oligo(ethylene glycol)
  • Supramolecular assemblies
  • Supramolecular host
  • Nanoparticles
  • anthracene
  • anthracene derivative
  • dipyrromethene
  • macrogol derivative
  • nanoparticle
  • polymethacrylic acid
  • polymethacrylic acid derivative
  • porphobilinogen
  • article
  • cancer cell
  • chromatophore
  • dynamics
  • energy transfer
  • excitation
  • hydrophobicity
  • internalization
  • intracellular space
  • supramolecular chemistry
  • uterine cervix cancer
  • analogs and derivatives
  • cell membrane
  • chemistry
  • HeLa cell line
  • human
  • metabolism
  • Anthracenes
  • Cell Membrane
  • Energy Transfer
  • HeLa Cells
  • Humans
  • Polyethylene Glycols
  • Polymethacrylic Acids
  • Porphobilinogen

Cite this

Swaminathan, S. ; Fowley, Colin ; McCaughan, Bridgeen ; Cusido, J. ; Callan, J ; Raymo, F.M. / Intracellular guest exchange between dynamic supramolecular hosts. In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. 2014 ; Vol. 136, No. 22. pp. 7907-7913.
@article{1d7b9f3c78564a238cef02a16eba5a96,
title = "Intracellular guest exchange between dynamic supramolecular hosts",
abstract = "Decyl and oligo(ethylene glycol) chains were appended to the same poly(methacrylate) backbone to generate an amphiphilic polymer with a ratio between hydrophobic and hydrophilic segments of 2.5. At concentrations greater than 10 μg mL-1 in neutral buffer, multiple copies of this particular macromolecule assemble into nanoparticles with a hydrodynamic diameter of 15 nm. In the process of assembling, these nanoparticles can capture anthracene donors and borondipyrromethene acceptors within their hydrophobic interior and permit the transfer of excitation energy with an efficiency of 95. Energy transfer is observed also if nanocarriers containing exclusively the donors are mixed with nanoparticles preloaded separately with the acceptors in aqueous media. The two sets of supramolecular assemblies exchange their guests with fast kinetics upon mixing to co-localize complementary chromophores within the same nanostructured container and enable energy transfer. After guest exchange, the nanoparticles can cross the membrane of cervical cancer cells and bring the co-entrapped donors and acceptors within the intracellular environment. Alternatively, intracellular energy transfer is also established after sequential cell incubation with nanoparticles containing the donors first and then with nanocarriers preloaded with the acceptors or vice versa. Under these conditions, the nanoparticles exchange their cargo only after internalization and allow energy transfer exclusively within the cell interior. Thus, the dynamic character of such supramolecular containers offers the opportunity to transport independently complementary species inside cells and permit their interaction only within the intracellular space. {\circledC} 2014 American Chemical Society.",
keywords = "Chromophores, Containers, Energy transfer, Ethylene glycol, Hydrophobicity, Supramolecular chemistry, Amphiphilic polymers, Cervical cancer cells, Hydrodynamic diameter, Hydrophobic and hydrophilic, Intracellular spaces, Oligo(ethylene glycol), Supramolecular assemblies, Supramolecular host, Nanoparticles, anthracene, anthracene derivative, dipyrromethene, macrogol derivative, nanoparticle, polymethacrylic acid, polymethacrylic acid derivative, porphobilinogen, article, cancer cell, chromatophore, dynamics, energy transfer, excitation, hydrophobicity, internalization, intracellular space, supramolecular chemistry, uterine cervix cancer, analogs and derivatives, cell membrane, chemistry, HeLa cell line, human, metabolism, Anthracenes, Cell Membrane, Energy Transfer, HeLa Cells, Humans, Polyethylene Glycols, Polymethacrylic Acids, Porphobilinogen",
author = "S. Swaminathan and Colin Fowley and Bridgeen McCaughan and J. Cusido and J Callan and F.M. Raymo",
note = "cited By 10",
year = "2014",
month = "5",
day = "9",
doi = "10.1021/ja500285p",
language = "English",
volume = "136",
pages = "7907--7913",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
number = "22",

}

Intracellular guest exchange between dynamic supramolecular hosts. / Swaminathan, S.; Fowley, Colin; McCaughan, Bridgeen; Cusido, J.; Callan, J; Raymo, F.M.

In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Vol. 136, No. 22, 09.05.2014, p. 7907-7913.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Intracellular guest exchange between dynamic supramolecular hosts

AU - Swaminathan, S.

AU - Fowley, Colin

AU - McCaughan, Bridgeen

AU - Cusido, J.

AU - Callan, J

AU - Raymo, F.M.

N1 - cited By 10

PY - 2014/5/9

Y1 - 2014/5/9

N2 - Decyl and oligo(ethylene glycol) chains were appended to the same poly(methacrylate) backbone to generate an amphiphilic polymer with a ratio between hydrophobic and hydrophilic segments of 2.5. At concentrations greater than 10 μg mL-1 in neutral buffer, multiple copies of this particular macromolecule assemble into nanoparticles with a hydrodynamic diameter of 15 nm. In the process of assembling, these nanoparticles can capture anthracene donors and borondipyrromethene acceptors within their hydrophobic interior and permit the transfer of excitation energy with an efficiency of 95. Energy transfer is observed also if nanocarriers containing exclusively the donors are mixed with nanoparticles preloaded separately with the acceptors in aqueous media. The two sets of supramolecular assemblies exchange their guests with fast kinetics upon mixing to co-localize complementary chromophores within the same nanostructured container and enable energy transfer. After guest exchange, the nanoparticles can cross the membrane of cervical cancer cells and bring the co-entrapped donors and acceptors within the intracellular environment. Alternatively, intracellular energy transfer is also established after sequential cell incubation with nanoparticles containing the donors first and then with nanocarriers preloaded with the acceptors or vice versa. Under these conditions, the nanoparticles exchange their cargo only after internalization and allow energy transfer exclusively within the cell interior. Thus, the dynamic character of such supramolecular containers offers the opportunity to transport independently complementary species inside cells and permit their interaction only within the intracellular space. © 2014 American Chemical Society.

AB - Decyl and oligo(ethylene glycol) chains were appended to the same poly(methacrylate) backbone to generate an amphiphilic polymer with a ratio between hydrophobic and hydrophilic segments of 2.5. At concentrations greater than 10 μg mL-1 in neutral buffer, multiple copies of this particular macromolecule assemble into nanoparticles with a hydrodynamic diameter of 15 nm. In the process of assembling, these nanoparticles can capture anthracene donors and borondipyrromethene acceptors within their hydrophobic interior and permit the transfer of excitation energy with an efficiency of 95. Energy transfer is observed also if nanocarriers containing exclusively the donors are mixed with nanoparticles preloaded separately with the acceptors in aqueous media. The two sets of supramolecular assemblies exchange their guests with fast kinetics upon mixing to co-localize complementary chromophores within the same nanostructured container and enable energy transfer. After guest exchange, the nanoparticles can cross the membrane of cervical cancer cells and bring the co-entrapped donors and acceptors within the intracellular environment. Alternatively, intracellular energy transfer is also established after sequential cell incubation with nanoparticles containing the donors first and then with nanocarriers preloaded with the acceptors or vice versa. Under these conditions, the nanoparticles exchange their cargo only after internalization and allow energy transfer exclusively within the cell interior. Thus, the dynamic character of such supramolecular containers offers the opportunity to transport independently complementary species inside cells and permit their interaction only within the intracellular space. © 2014 American Chemical Society.

KW - Chromophores

KW - Containers

KW - Energy transfer

KW - Ethylene glycol

KW - Hydrophobicity

KW - Supramolecular chemistry

KW - Amphiphilic polymers

KW - Cervical cancer cells

KW - Hydrodynamic diameter

KW - Hydrophobic and hydrophilic

KW - Intracellular spaces

KW - Oligo(ethylene glycol)

KW - Supramolecular assemblies

KW - Supramolecular host

KW - Nanoparticles

KW - anthracene

KW - anthracene derivative

KW - dipyrromethene

KW - macrogol derivative

KW - nanoparticle

KW - polymethacrylic acid

KW - polymethacrylic acid derivative

KW - porphobilinogen

KW - article

KW - cancer cell

KW - chromatophore

KW - dynamics

KW - energy transfer

KW - excitation

KW - hydrophobicity

KW - internalization

KW - intracellular space

KW - supramolecular chemistry

KW - uterine cervix cancer

KW - analogs and derivatives

KW - cell membrane

KW - chemistry

KW - HeLa cell line

KW - human

KW - metabolism

KW - Anthracenes

KW - Cell Membrane

KW - Energy Transfer

KW - HeLa Cells

KW - Humans

KW - Polyethylene Glycols

KW - Polymethacrylic Acids

KW - Porphobilinogen

U2 - 10.1021/ja500285p

DO - 10.1021/ja500285p

M3 - Article

VL - 136

SP - 7907

EP - 7913

JO - Journal of the American Chemical Society

T2 - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 22

ER -