Interactions between amino acid-tagged naphthalenediimide and single walled carbon nanotubes for the design and construction of new bioimaging probes

Zhiyuan Hu, G Dan Pantoș, Navaratnarajah Kuganathan, Rory Arrowsmith, Robert M J Jacobs, Gabriele Kociok-Köhn, Justin O'Byrne, Kerstin Jurkschat, Pierre Burgos, Rex M Tyrrell, Stan W Botchway, Jeremy K M Sanders, Sofia I Pascu

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

A new synthetic route to functionalized single walled carbon nanotubes (SWNTs) via supramolecular interactions using a specifically designed naphthalenediimide (NDI) nanoreceptor is demonstrated. The tendency of the NDI to spontaneously form composites with carbon nanomaterials leads to fluorescent amino acid tagged SWNTs, which are dispersible in widely accessible organic solvents (CHCl3, DMSO) as well as in biocompatible cell medium (EMEM, Eagle's modified essential medium). The X-ray crystal structure of the first iodine-tagged and amino acid-functionalized NDI molecule, designed especially to facilitate the high resolution transmission electron microscopy (HR TEM) imaging whilst retaining its ability to self-assemble into a nanodimensional receptor in weakly polar solvents, is also described. A new hybrid material, NDI@SWNT, was prepared and characterized as dispersed in organic solvents and aqueous media and in the solid state by HR TEM, tapping mode atomic force microscopy (TM AFM), scanning electron microscopy (SEM), circular dichroism, Raman and fluorescence spectroscopies (steady-state single and two-photon techniques). Combined microscopy techniques, density functional theory (DFT) calculations using the Spanish Initiative for Electronic Simulations with Thousands of Atoms (SIESTA) program and spectroscopic measurements in solution indicate that amino acid-functionalized NDI interacts strongly with SWNTs and forms a donor-acceptor complex. Density functional theory (DFT) calculations predicted the geometry and the binding energies of an NDI molecule loaded onto a SWNT strand and the possibility of charge transfer interactions within the hybrid. The NDI@SWNT composite translocates into cells (e.g. FEK-4, HeLa, MCF-7) as an intact object and localizes in the cells' cytoplasm and partially in the nucleus. The NDI coating enhances the biocompatibility of SWNTs and mediates its intracellular localization as shown by confocal fluorescence imaging and fluorescence lifetime imaging (FLIM) techniques. The excited state fluorescence lifetime of the probes in cells versus solution phase indicates that the probes remain unaffected by the change in their chemical environment within the experimental timescale (2 h).
Original languageEnglish
Pages (from-to)503-518
Number of pages16
JournalAdvanced Functional Materials
Volume22
Issue number3
Early online date8 Dec 2011
DOIs
Publication statusPublished - 8 Feb 2012

Fingerprint

Single-walled carbon nanotubes (SWCN)
Amino acids
Amino Acids
Fluorescence
High resolution transmission electron microscopy
Imaging techniques
Organic solvents
Density functional theory
Circular dichroism spectroscopy
Molecules
Hybrid materials
Fluorescence spectroscopy
Composite materials
naphthalenediimide
Binding energy
Iodine
Biocompatibility
Excited states
Nanostructured materials
Dimethyl Sulfoxide

Cite this

Interactions between amino acid-tagged naphthalenediimide and single walled carbon nanotubes for the design and construction of new bioimaging probes. / Hu, Zhiyuan; Pantoș, G Dan; Kuganathan, Navaratnarajah; Arrowsmith, Rory; Jacobs, Robert M J; Kociok-Köhn, Gabriele; O'Byrne, Justin; Jurkschat, Kerstin; Burgos, Pierre; Tyrrell, Rex M; Botchway, Stan W; Sanders, Jeremy K M; Pascu, Sofia I.

In: Advanced Functional Materials, Vol. 22, No. 3, 08.02.2012, p. 503-518.

Research output: Contribution to journalArticle

Hu, Zhiyuan ; Pantoș, G Dan ; Kuganathan, Navaratnarajah ; Arrowsmith, Rory ; Jacobs, Robert M J ; Kociok-Köhn, Gabriele ; O'Byrne, Justin ; Jurkschat, Kerstin ; Burgos, Pierre ; Tyrrell, Rex M ; Botchway, Stan W ; Sanders, Jeremy K M ; Pascu, Sofia I. / Interactions between amino acid-tagged naphthalenediimide and single walled carbon nanotubes for the design and construction of new bioimaging probes. In: Advanced Functional Materials. 2012 ; Vol. 22, No. 3. pp. 503-518.
@article{021c763358a047088a4f607539d9233a,
title = "Interactions between amino acid-tagged naphthalenediimide and single walled carbon nanotubes for the design and construction of new bioimaging probes",
abstract = "A new synthetic route to functionalized single walled carbon nanotubes (SWNTs) via supramolecular interactions using a specifically designed naphthalenediimide (NDI) nanoreceptor is demonstrated. The tendency of the NDI to spontaneously form composites with carbon nanomaterials leads to fluorescent amino acid tagged SWNTs, which are dispersible in widely accessible organic solvents (CHCl3, DMSO) as well as in biocompatible cell medium (EMEM, Eagle's modified essential medium). The X-ray crystal structure of the first iodine-tagged and amino acid-functionalized NDI molecule, designed especially to facilitate the high resolution transmission electron microscopy (HR TEM) imaging whilst retaining its ability to self-assemble into a nanodimensional receptor in weakly polar solvents, is also described. A new hybrid material, NDI@SWNT, was prepared and characterized as dispersed in organic solvents and aqueous media and in the solid state by HR TEM, tapping mode atomic force microscopy (TM AFM), scanning electron microscopy (SEM), circular dichroism, Raman and fluorescence spectroscopies (steady-state single and two-photon techniques). Combined microscopy techniques, density functional theory (DFT) calculations using the Spanish Initiative for Electronic Simulations with Thousands of Atoms (SIESTA) program and spectroscopic measurements in solution indicate that amino acid-functionalized NDI interacts strongly with SWNTs and forms a donor-acceptor complex. Density functional theory (DFT) calculations predicted the geometry and the binding energies of an NDI molecule loaded onto a SWNT strand and the possibility of charge transfer interactions within the hybrid. The NDI@SWNT composite translocates into cells (e.g. FEK-4, HeLa, MCF-7) as an intact object and localizes in the cells' cytoplasm and partially in the nucleus. The NDI coating enhances the biocompatibility of SWNTs and mediates its intracellular localization as shown by confocal fluorescence imaging and fluorescence lifetime imaging (FLIM) techniques. The excited state fluorescence lifetime of the probes in cells versus solution phase indicates that the probes remain unaffected by the change in their chemical environment within the experimental timescale (2 h).",
author = "Zhiyuan Hu and Pantoș, {G Dan} and Navaratnarajah Kuganathan and Rory Arrowsmith and Jacobs, {Robert M J} and Gabriele Kociok-K{\"o}hn and Justin O'Byrne and Kerstin Jurkschat and Pierre Burgos and Tyrrell, {Rex M} and Botchway, {Stan W} and Sanders, {Jeremy K M} and Pascu, {Sofia I}",
year = "2012",
month = "2",
day = "8",
doi = "10.1002/adfm.201101932",
language = "English",
volume = "22",
pages = "503--518",
journal = "Advanced Functional Materials",
issn = "1616-301X",
publisher = "Wiley-VCH Verlag",
number = "3",

}

TY - JOUR

T1 - Interactions between amino acid-tagged naphthalenediimide and single walled carbon nanotubes for the design and construction of new bioimaging probes

AU - Hu, Zhiyuan

AU - Pantoș, G Dan

AU - Kuganathan, Navaratnarajah

AU - Arrowsmith, Rory

AU - Jacobs, Robert M J

AU - Kociok-Köhn, Gabriele

AU - O'Byrne, Justin

AU - Jurkschat, Kerstin

AU - Burgos, Pierre

AU - Tyrrell, Rex M

AU - Botchway, Stan W

AU - Sanders, Jeremy K M

AU - Pascu, Sofia I

PY - 2012/2/8

Y1 - 2012/2/8

N2 - A new synthetic route to functionalized single walled carbon nanotubes (SWNTs) via supramolecular interactions using a specifically designed naphthalenediimide (NDI) nanoreceptor is demonstrated. The tendency of the NDI to spontaneously form composites with carbon nanomaterials leads to fluorescent amino acid tagged SWNTs, which are dispersible in widely accessible organic solvents (CHCl3, DMSO) as well as in biocompatible cell medium (EMEM, Eagle's modified essential medium). The X-ray crystal structure of the first iodine-tagged and amino acid-functionalized NDI molecule, designed especially to facilitate the high resolution transmission electron microscopy (HR TEM) imaging whilst retaining its ability to self-assemble into a nanodimensional receptor in weakly polar solvents, is also described. A new hybrid material, NDI@SWNT, was prepared and characterized as dispersed in organic solvents and aqueous media and in the solid state by HR TEM, tapping mode atomic force microscopy (TM AFM), scanning electron microscopy (SEM), circular dichroism, Raman and fluorescence spectroscopies (steady-state single and two-photon techniques). Combined microscopy techniques, density functional theory (DFT) calculations using the Spanish Initiative for Electronic Simulations with Thousands of Atoms (SIESTA) program and spectroscopic measurements in solution indicate that amino acid-functionalized NDI interacts strongly with SWNTs and forms a donor-acceptor complex. Density functional theory (DFT) calculations predicted the geometry and the binding energies of an NDI molecule loaded onto a SWNT strand and the possibility of charge transfer interactions within the hybrid. The NDI@SWNT composite translocates into cells (e.g. FEK-4, HeLa, MCF-7) as an intact object and localizes in the cells' cytoplasm and partially in the nucleus. The NDI coating enhances the biocompatibility of SWNTs and mediates its intracellular localization as shown by confocal fluorescence imaging and fluorescence lifetime imaging (FLIM) techniques. The excited state fluorescence lifetime of the probes in cells versus solution phase indicates that the probes remain unaffected by the change in their chemical environment within the experimental timescale (2 h).

AB - A new synthetic route to functionalized single walled carbon nanotubes (SWNTs) via supramolecular interactions using a specifically designed naphthalenediimide (NDI) nanoreceptor is demonstrated. The tendency of the NDI to spontaneously form composites with carbon nanomaterials leads to fluorescent amino acid tagged SWNTs, which are dispersible in widely accessible organic solvents (CHCl3, DMSO) as well as in biocompatible cell medium (EMEM, Eagle's modified essential medium). The X-ray crystal structure of the first iodine-tagged and amino acid-functionalized NDI molecule, designed especially to facilitate the high resolution transmission electron microscopy (HR TEM) imaging whilst retaining its ability to self-assemble into a nanodimensional receptor in weakly polar solvents, is also described. A new hybrid material, NDI@SWNT, was prepared and characterized as dispersed in organic solvents and aqueous media and in the solid state by HR TEM, tapping mode atomic force microscopy (TM AFM), scanning electron microscopy (SEM), circular dichroism, Raman and fluorescence spectroscopies (steady-state single and two-photon techniques). Combined microscopy techniques, density functional theory (DFT) calculations using the Spanish Initiative for Electronic Simulations with Thousands of Atoms (SIESTA) program and spectroscopic measurements in solution indicate that amino acid-functionalized NDI interacts strongly with SWNTs and forms a donor-acceptor complex. Density functional theory (DFT) calculations predicted the geometry and the binding energies of an NDI molecule loaded onto a SWNT strand and the possibility of charge transfer interactions within the hybrid. The NDI@SWNT composite translocates into cells (e.g. FEK-4, HeLa, MCF-7) as an intact object and localizes in the cells' cytoplasm and partially in the nucleus. The NDI coating enhances the biocompatibility of SWNTs and mediates its intracellular localization as shown by confocal fluorescence imaging and fluorescence lifetime imaging (FLIM) techniques. The excited state fluorescence lifetime of the probes in cells versus solution phase indicates that the probes remain unaffected by the change in their chemical environment within the experimental timescale (2 h).

UR - http://www.scopus.com/inward/record.url?scp=84856728132&partnerID=8YFLogxK

UR - http://dx.doi.org/10.1002/adfm.201101932

U2 - 10.1002/adfm.201101932

DO - 10.1002/adfm.201101932

M3 - Article

VL - 22

SP - 503

EP - 518

JO - Advanced Functional Materials

JF - Advanced Functional Materials

SN - 1616-301X

IS - 3

ER -