WO2008044896A1 - Composite nanotube de carbone-dendron et biocapteur comprenant ce composite - Google Patents

Composite nanotube de carbone-dendron et biocapteur comprenant ce composite Download PDF

Info

Publication number
WO2008044896A1
WO2008044896A1 PCT/KR2007/005006 KR2007005006W WO2008044896A1 WO 2008044896 A1 WO2008044896 A1 WO 2008044896A1 KR 2007005006 W KR2007005006 W KR 2007005006W WO 2008044896 A1 WO2008044896 A1 WO 2008044896A1
Authority
WO
WIPO (PCT)
Prior art keywords
dendron
cnt
cnts
composite
dendrons
Prior art date
Application number
PCT/KR2007/005006
Other languages
English (en)
Inventor
Joon-Won Park
Hee-Cheul Choi
Sung-Wook Woo
Original Assignee
Postech Academy-Industry Foundation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Postech Academy-Industry Foundation filed Critical Postech Academy-Industry Foundation
Publication of WO2008044896A1 publication Critical patent/WO2008044896A1/fr

Links

Classifications

    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
    • G01N33/54353—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals with ligand attached to the carrier via a chemical coupling agent
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/15—Nano-sized carbon materials
    • C01B32/158—Carbon nanotubes
    • C01B32/168—After-treatment
    • C01B32/174—Derivatisation; Solubilisation; Dispersion in solvents
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2202/00—Structure or properties of carbon nanotubes
    • C01B2202/02—Single-walled nanotubes
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2202/00—Structure or properties of carbon nanotubes
    • C01B2202/06—Multi-walled nanotubes
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2202/00—Structure or properties of carbon nanotubes
    • C01B2202/20—Nanotubes characterized by their properties
    • C01B2202/28—Solid content in solvents
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2202/00—Structure or properties of carbon nanotubes
    • C01B2202/20—Nanotubes characterized by their properties
    • C01B2202/36—Diameter

Definitions

  • the present invention relates to a carbon nanotube (CNT)-Dendron composite and a biosensor for detecting a biomolecule comprising the CNT-Dendron composite. More specifically, the present invention relates to CNT-Dendron composite where a plurality of termini of a branched region of at least a Dendron comprising a branched region and a linear region are bound non-covalently to the sidewall of CNT.
  • the noncovalent functionalization of CNT by a Dendron is a new approach toward sensible nanobio-devices, not only by introducing biomolecular probes on CNTs without disruption of the electronic network of the tubes, but also by providing the immobilized probe molecules with an ample space enough to minimize steric hindrance for the unhindered interaction with their target species.
  • CNTs comprising multiple concentric shells and termed multi-wall carbon nanotubes (MWNTs)
  • MWNTs multi-wall carbon nanotubes
  • SWNTs single-wall carbon nanotubes
  • Nanotubes modified by such destructive methods are not therefore suitable for adsorption and/or immobilization at their outer surface of synthetic products or of biological macromolecules.
  • the nanotubes have in particular so-called MWNT or single- SWNT. They can be completely, partially or not at all oxidized.
  • high density packing might seem to be desirable to achieve enhanced binding probability and capacity.
  • Jiang et al suggested in their report that changing the reaction conditions for surface oxidation would control the immobilization density, but the control of spacing seems to be challenging yet.
  • the present inventors can provide the noncovalent functionalization of CNTs with selected dendrons.
  • the dendrons on CNTs generate a certain distance between adjacent functionalities, further attached biomolecules at the apex are given proper space without unwanted aggregation.
  • the Dendron lpproach can be utilized for enhancing the performance of various CNT-based nanobiosystems.
  • An object of the invention is to provide a CNT-Dendron composite where a plurality of termini of a branched region of at least a Dendron comprising a branched region and a linear region are bound non-covalently to the sidewall of CNT.
  • Another object of the present invention is to provide a biosensor for detecting a biomolecule comprising a CNT-Dendron composite where a plurality of termini of a branched region of at least a Dendron comprising a branched region and a linear region are bound non-covalently to the sidewall of CNT.
  • Fig. 1 shows three types of dendrons used for Example 1 in (a), and is a schematic illustration of the immobilization of gold nanoparticles and streptavidin on CNT surfaces through the fingertip-guided functionalization by dendrons (b).
  • Fig. 2 is an AFM image of a CNT functional ized by Dendron 1 , to which gold nanoparticles are attached, with the height values of three representative parts in (a), section profiles (b), and (c) is a corresponding model of the parts designated in (a),
  • the height values without brackets in (a) indicate the heights from the bottom of the substrate, and the values with brackets are the differences from the point A.
  • Fig. 3 shows (a) visual comparison of CNTs without (left) and with (right) the Dendron 1 after sonication and centrifugation in DMF, and (b) Raman spectra of CNTs before (left) and after (right) the dendron treatment.
  • Fig. 4 is AFM images of CNTs functionalized by dendrons, to which gold nanoparticles are applied, showing discriminative binding efficiency of Dendrons 1, 2 and 3.
  • CNTs were treated with (a) Dendron 1, (b) Dendron 2, and (c) Dendron 3, respectively.
  • Fig. 5 is spacing realized by the dendrons.
  • Fig. 6 shows tapping mode AFM images of a CNT obtained before (top) and after (bottom) the treatment of Dendron 1.
  • Fig. 7 shows AFM images obtained before and after applying gold nanoparticles to (a) CNTs functionalized with the Dendron 1 , (b) bare CNTs, and (c) Tween20-treated CNTs. There is no observable binding in cases of (b) and (c).
  • Fig. 8 represents control experiments with streptavidin on (a) bare CNTs and (b) Tween20-coated CNTs. (a) The image shows considerable nonspecific binding of streptavidin onto CNTs. (b) The image reveals that Tween20 repels streptavidin.
  • Fig. 9 is (a) t-Boc protected Dendron 1 analog (Dendron 1 '). (b) The Dendron 1 ' showed a similar binding affinity toward the sidewalls of CNTs.
  • dendrimer is characterized by a core, at least one interior branched layer, and a surface branched layer (see Petar et al, Pages 641-645, In Chem. in England, August 1994).
  • a "dendron” is a species of dendrimer having branches emanating from a focal point, which is or can be joined to a core, either directly or through a linking moiety to form a dendrimer.
  • Many dendrimers include two or more dendrons joined to a common core. However, the term “dendrimer” may be used broadly to encompass a single dendron.
  • branched as it is used to describe a macromolecule or a dendron structure is meant to refer to a plurality of polymers having a plurality of termini which are able to bind covalently or ionically to a substrate.
  • the macromolecule containing the branched structure is "pre-made” and is then attached to a substrate.
  • regular intervals refers to the spacing between the tips of the size-controlled macromolecules, which is a distance from about 1 nm to about 100 nm so as to allow room for interaction between the target-specific ligand and the target substantially without steric hindrance.
  • the layer of macromolecules on a substrate is not too dense for specific molecular interactions to occur.
  • the CNT can be prepared: the nanotubes have in particular so-called MWNT or SWNT. They can be completely, partially or not at all oxidized.
  • the present inventors provide the noncovalent functional ization of the sidewalls of CNTs by dendrons.
  • a CNT-Dendron composite where a plurality of termini of a branched region of at least a Dendron comprising a branched region and a linear region are bound non-covalently to the sidewall of CNT.
  • the CNT-Dendron composite is a chemical compound having the following chemical structures.
  • Chemical formula 1
  • Rl is OH, or ⁇ ⁇ V . /
  • R2 is a protecting group of tert-butyloxycarbonyl (t-BOC) or
  • the examples of the dendrons includes a compound of chemical formula I wherein Rl is OH and R2 is anthracene group, a compound of chemical formula wherein Rl is OH and R2 is t-BOC, a compound of chemical formula 1 wherein Rl is and R2 is anthracene group, and a compound of Chemical formula 1
  • the CNT-Dendron composite wherein the dendrons are spaced at regular intervals between about 0.1 nm and about 100 nm, preferably IOnm and 30 nm, and more preferably 10 nm and 25 nm among the linear regions.
  • the the CNT of the composite maintains its ⁇ -configuration without disruption of the electronic network of the CNTs.
  • a dendron which denotes a subunit of a dendrimer, inherits the superior properties of the macromolecule, such as monodispersity, a well-defined structure, and an easy tunability in their functionalities(Newkome 5 G. R.; Moorefield, C. N.; V ⁇ gtle, F.
  • Dendrons have a unique anisotropic shape and an orthogonal functional group at their apex, and thus can generate a certain spacing between the functional groups upon the immobilization on surfaces.
  • Atomic force microscope (AFM) imaging, dispersion experiments, and micro-Raman spectroscopy were employed for the characterization of the functional ization.
  • the binding was found to be governed by the chemical nature of the terminal groups, namely, the "fingertips", through the comparison study on the adsorption efficiency of the Dendron lnalogs.
  • Functional groups such as carboxylic acid group and benzyl amide group were effective for the cooperative binding.
  • the present invention represents the first demonstration of the noncovalent binding of dendrons to CNT sidewalls. Further, the inventors propose fingertip-guided binding as the adsorption mode, where the "fingertips" represent the terminal groups of a dendron that appear to govern the binding efficiency of the molecule to CNT surfaces. The binding mode was revealed by comparing the adsorption efficiency of three types of dendrons that differed only in their terminal groups, Finally, the present inventors demonstrate the spacing ensured by the dendrons and discuss the applicability of the present system to controlled immobilization of biomolecules. The streptavidin-biotin system was used for this investigation.
  • the present invention selects a dendron having benzyl groups as their termini (Dendron 1 in Fig.1), of which the aromatic benzene rings are expected to bind the sidewalls of CNTs via the ⁇ - ⁇ interaction.
  • the use of the ⁇ - ⁇ interaction has been a common approach for the noncovalent functionalization of CNTs.
  • the Dendron 1 was synthesized by amide-coupling of a dendron having carboxylic acid groups with benzylamine.
  • CNTs used in the experiments of the present invention are single-walled CNTs with diameters of 1-2 nm and were grown on SiO 2 ZSi wafers by the chemical vapor deposition method as previously reported.
  • Tween20 After removal of the amine-protecting anthracene group of the dendron molecules attached to the CNT surfaces by treatment with an acid, Tween20 was applied to protect unoccupied (dendron-free) sites of the CNTs from potential nonspecific binding.
  • Tween20 is a surfactant molecule composed of a linear aliphatic chain and three polyethylene oxide (PEO) branches, and is known to bind to CNT surfaces and prevent nonspecific binding.
  • PEO polyethylene oxide
  • DSC N,N'-disuccinimidyl carbonate
  • Fig. 2 showed a tapping mode AFM height image, a section profile, and a simplified model of a Dendron 1-treated CNT after applying gold nanoparticles.
  • the AFM section analyses give the height values of the nanoparticles attached to the dendrons consistent with the predicted values.
  • Nanoparticles that appear to be standing upright (point B in Fig. 2) in AFM images have a height value 3.23 ⁇ 0.49 nm higher than the base CNT surface (point A) which is coated only by Tween20.
  • the predicted value is ⁇ 3 nm, which is obtained by adding 2.7 nm (the diameter of a nanoparticle) and -1 .3 nm (the estimated height of a dendron when bound to a CNT surface) and subtracting -0.9 ⁇ 0.3 nm (the average height of Tween20 coated on CNTs obtained from independent experiments).
  • control experiments were carried out with bare CNTs and Tween20-treated CNTs (Fig, 7). It is certain that no significant binding occurred in either case.
  • Tween20 does not replace the existing dendrons on the sidewalls of the CNTs, which indicates that the binding of Dendron 1 is more favored than that of Tween20 - a surfactant known to bind to CNTs through the hydrophobic interaction - at least in terms of kinetics.
  • Dendron 1 The binding mechanism of Dendron 1 can be explained as a "multiple" ⁇ - ⁇ interaction. Although previously reported theoretical and experimental studies suggest that the interaction between a single benzene moiety and the sidewall of a CNT is relatively weak, the cooperative action of the multiple benzyl moieties of Dendron 1 is believed to have synergistically enhanced the driving force for the effective binding.
  • the binding of Dendron 2 shows comparable efficiency and this seems to involve the multiple interactions between the carboxylic acids and CNTs.
  • the capability of carboxylic acid groups to hold CNTs through multiple attractions has been studied and utilized for controlled alignment of CNTs on surfaces. Especially in a recent work, the strong attraction was demonstrated both experimentally and theoretically, and depicted as a strong van der Waals interaction.
  • Dendron 3 exhibited weak affinity to the sidewalls of CNTs, which indicates weaker interactions of the methyl ester group with CNTs.
  • the present inventors believe that the weak affinity is due to the relatively weak polarity of the methyl ester group compared to the carboxylic acid group, which is consistent with the previous SAM (self-assembled monolayer) studies, where CNTs favored surfaces having higher polarity.
  • the present invention investigated the spacing between functionalities provided by the dendrons, by measuring horizontal distances between the highest points of nanoparticles.
  • the smallest spacing was measured to be ⁇ 6 nm (Fig. 5) while the average spacing between adjacent nanoparticles (within the distance less than 30 nm) was 14.4 ⁇ 4.9 nm for Dendron 1 and 14.6 ⁇ 5.4 nm for Dendron 2.
  • the present inventors also found that the spacing can be controlled by regulating the number of dendrons immobilized on the nanotube surface.
  • dendron-treated CNTs hold streptavidins in a fairly regulated fashion (average spacing of 14.2 ⁇ 6.1 nm), more importantly with no serious aggregation (Fig. 5, C).
  • the average spacing measured is consistent with the spacing observed for gold nanoparticles, from which the present inventors presume that each streptavidin molecule is linked to a Dendron l nd aggregation was prevented due to the spacing secured by the dendrons.
  • the average spacing is bigger than that measured for a same-generation dendron that is covalently bound to flat surfaces, in which the strong driving force accompanied by the formation of multiple covalent bonds resulted in compact packing of the dendrons on surfaces.
  • the covalent approach requires the use of higher-generation dendrons to achieve larger spacing, which involves cumbersome synthetic procedures and generates undesirably large vertical distance of the active functionalities from surfaces.
  • the noncovalent approach which renders relatively small binding energy, generates the larger spacing at the similar concentration and reaction time without relying on a dendron of higher generations.
  • the average spacing of 14-15 nm has a significant meaning because this value is no smaller than the sizes of most protein molecules commonly found in cells, and at the same time the spacing provides a reasonably high immobilization density on surfaces.
  • the space ensured by the dendrons would be able to accommodate virtually most kinds of proteins, while avoiding steric hindrance and thus facilitating their specific and selective interactions.
  • CNTs are arranged on a substrate, and an electric field of an opposite polarity to a net charge of the receptors is applied to some or all of the CNTs to selectively move receptors for diagnostic target biomolecules to a desired CNTs and to bind them there to a desired position at a high-density.
  • suitable materials for the substrate include a variety of polymeric substances, such as silicon, glass, molten silica, plastics, and polydimethylsiloxane (PDMS), and CNTs of several to hundreds of nanometers are arranged on the substrate.
  • polymeric substances such as silicon, glass, molten silica, plastics, and polydimethylsiloxane (PDMS), and CNTs of several to hundreds of nanometers are arranged on the substrate.
  • the receptors are biological substances capable of acting as probes that are detectable when bound to the target biomolecules.
  • Suitable receptors include nucleic acids, proteins, peptides, amino acids, ligands, enzyme substrates, cofactors, and oligosaccharides.
  • a target biomolecule which binds to a receptor, is a biomolecule of interest to be analyzed.
  • the target biomolecule may be proteins, nucleic acids, enzymes, or other boimolecules capable of binding to the receptor.
  • Fig.l (a) Three types of dendrons used for this study, (b) Schematic illustration of the immobilization of gold nanoparticles and streptavidin on CNT surfaces through the fingertip-guided functionalization by dendrons. Chemical identity of the fingertips
  • Dendron 1 was synthesized by amide-coupling of Dendron 2 with benzylamine.
  • Substrates were immersed in a 0.20 mM N,N-dimethylformamide (DMF) solution of each type of the dendrons for 13 h, followed by rinsing with DMF for 1 min, sonication in DMF, deionized water and methanol each for 30 sec, rinsing with methanol for 1 min, and drying with N 2 stream.
  • DMF N,N-dimethylformamide
  • Atomic force microscope (AFM) imaging, dispersion experiments, and micro- Raman spectroscopy were employed for the characterization of the functionalization.
  • AFM Atomic force microscope
  • Raman spectra were analyzed to examine the effect of the functionalization on CNTs.
  • Micro-Raman spectroscopy is one of the most widely used tools to characterize CNTs and their surface modifications.
  • the G-band ( ⁇ 1590 cm “ '), the most intensive high-energy modes of single-walled CNTs, represents the tangential modes which originate from the in-plane stretching modes in graphite.
  • An appearance of the D-band (-1340 cm '1 ) in the Raman spectra of CNTs is an indication that the tube surface contains defects, and thus the D-band intensity or the D/G intensity ratio is often used to estimate the degree of covalent functionalization.
  • (b) of Fig.3 shows the Raman spectra obtained before and after the functionalization by the Dendron 1.
  • Fig 3 was (a) Visual comparison of CNTs without (left) and with (right) the Dendron 1 after sonication and centrifugation in DMF. (b) Raman spectra of CNTs before (left) and after (right) the dendron treatment.
  • Example 3 AFM images of gold NPs attached to dendrons on CNTs
  • a gold nanoparticle was introduced to each immobilized Dendron 2y covalent linkage.
  • surfactant Tween20 (1 % in a 50:50 deionized water and DMF mixture) was treated to protect unoccupied (dendron-free) sites of CNTs from potential nonspecific binding.
  • Counting the number of NPs on different nanotubes with various lengths gives the average number per length: 16.8 particles/ ⁇ m, 24.8 particles/ ⁇ m, and 5.0 particles/ ⁇ m for Dendron 1 , Dendron 2, and Dendron 3, respectively.
  • the NPs attached to the dendrons were verified by AFM section analyses (Fig. 7). NPs that appear to be standing upright in AFM images have a height value 3.23 ⁇ 0.49 nm higher than the base CNT surface which is coated only by Tween20.
  • the predicted value is ⁇ 3 nm, which was obtained by adding 2.7 nm (the diameter of an NP) and ⁇ 1 ,3 nm (the estimated height of a dendron when bound to a CNT surface) and subtracting -0,9 ⁇ 0.3 nm (the average height of Tween20 coated on CNTs obtained from independent experiments).
  • Fig 2 represented (a) An AFM image of a CNT functionalized by Dendron 1 , to which gold nanoparticles are attached, with the height values of three representative parts (see text), (b) Section profiles and (c) the corresponding model of the parts designated in (a). Height values in white color (and without brackets) in (a) indicate the heights from the bottom of the substrate, and the values in orange color (and with brackets) are the differences from the point A.
  • the substrates were immersed into a dichloromethane solution of 1.0 M trifluoroacetic acid (TFA). After 3 h, they were transferred into a dichloromethane solution of 20 % (v/v) diisopropylethylamine (DIPEA) and left for 10 min. The substrates were then sonicated in dichloromethane and methanol each for 30 sec, in fresh methanol again for 30 sec, rinsed with methanol for 1 min, and dried with N 2 stream.
  • TFA trifluoroacetic acid
  • DIPEA diisopropylethylamine
  • the substrates were soaked in a 1 % (v/v) solution of Tween20 in a 50:50 mixture of deionized water and DMF for 3 h.
  • the substrates were then sonicated in deionized water, dichloromethane, and methanol each for 30 sec, rinsed with methanol for 1 min, and dried with N 2 stream.
  • the result was shown in Fig. 7 3.3.
  • the substrates were placed in an acetonitrile solution of DSC (25 mM) and diisopropylethylamine (DlPEA, 1 mM) for 4 h under N2 atmosphere. The substrates were then washed with DMF for 1 min and methanol for 30 sec, and dried with N 2 stream.
  • DSC 25 mM
  • DlPEA diisopropylethylamine
  • a NaHCO 3 (20 1, 50 mM, pH 8.5, 10 % dimethyl surfoxide (DMSO)) solution of gold nanoparticles (6 ⁇ M) was dropped onto each substrate kept in a saturated humidity chamber, and 8 h was allowed for the reaction.
  • the substrates were washed with deionized water and DMSO each for 1 min, then placed in stirred DMSO for 2 h, rinsed with DMSO and methanol each for 1 min, and dried with N 2 stream.
  • AFM for a sample, and several tubes that appear in the area were investigated. Images of l ⁇ m ⁇ l ⁇ m or often 500 nni x 500 nm along each tube were subsequently obtained and used for counting the number. The analysis was carried out for multiple samples from independent batches. The numbers of particles used for the spacing analyses were 68 and 84 for Dendron 1 and Dendron 2, respectively. Heights of nine vertically standing particles were taken to obtain the average height value. Because measuring the height of particles at the specific orientation (such as point B in Fig. 2) is desirable, a limited number of particles were taken into the calculation.
  • Fig. 2 shows (a) an AFM image of a CNT functional ized by Dendron 1 , to which gold nanoparticles are attached, with the height values of three representative parts (see text), (b) Section profiles and (c) the corresponding model of the parts designated in (a). Height values without brackets in (a) indicate the heights from the bottom of the substrate, and the values with brackets are the differences from the point A.
  • Fig. 4 showed AFM images of CNTs functionalized by dendrons, to which gold nanoparticles are applied, showing discriminative binding efficiency of Dendron 1 , Dendron 2 and Dendron 3.
  • CNTs were treated with (a) Dendron 1, (b) Dendron 2, and (c) Dendron 3, respectively.
  • Fig. 5 was spacing realized by the dendrons.
  • Example 5 A control test with t-Boc protected Dendron 1 analog
  • a Dendron 3ontaining a t-Boc moiety as the protecting group instead of the anthryl group was tested to investigate the influence of the latter protecting group on the binding event. While the anthryl group might interact with CNTs through ⁇ - ⁇ interaction, the t-Boc group is not the case.
  • a dendron having the same terminal groups as those of Dendron 1 and a t-Boc group as the protecting group (Fig. 9, a) was employed for this investigation, and showed a similar binding probability or density (18.1 particles/ ⁇ m).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nanotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Physics & Mathematics (AREA)
  • Molecular Biology (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Hematology (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Biomedical Technology (AREA)
  • Urology & Nephrology (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Biotechnology (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Food Science & Technology (AREA)
  • Pathology (AREA)
  • Microbiology (AREA)
  • Manufacturing & Machinery (AREA)
  • Cell Biology (AREA)
  • Composite Materials (AREA)
  • Carbon And Carbon Compounds (AREA)

Abstract

La présente invention concerne un composite nanotube de carbone (CNT)-Dendron et un bio capteur permettant de détecter une biomolécule comprenant ce composite CNT-Dendron. La fonctionnalisation non covalente des CNT par un Dendron peut être une nouvelle approche pour des dispositifs nanobio sensibles, non seulement par l'introduction de sondes biomoléculaire sur les CNT sans interruption du réseau électronique de ces tubes, mais aussi par l'apport des molécules de sondes immobilisées avec un espace suffisamment important pour minimiser l'empêchement stérique pour l'interaction empêchée avec leurs espèces chimiques cible.
PCT/KR2007/005006 2006-10-12 2007-10-12 Composite nanotube de carbone-dendron et biocapteur comprenant ce composite WO2008044896A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US82926206P 2006-10-12 2006-10-12
US60/829,262 2006-10-12

Publications (1)

Publication Number Publication Date
WO2008044896A1 true WO2008044896A1 (fr) 2008-04-17

Family

ID=39283059

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2007/005006 WO2008044896A1 (fr) 2006-10-12 2007-10-12 Composite nanotube de carbone-dendron et biocapteur comprenant ce composite

Country Status (1)

Country Link
WO (1) WO2008044896A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2333545A2 (fr) * 2008-08-22 2011-06-15 Sungkyunkwan University Foundation for Corporate Collaboration Procédé permettant d'augmenter la sensibilité au moyen d'un agent de liaison et d'un espaceur dans un biocapteur fondé sur un nanotube de carbone
WO2011158068A1 (fr) 2010-06-18 2011-12-22 Centre National De La Recherche Scientifique (Cnrs) Structure moléculaire non covalente, dispositif la comprenant et son utilisation pour la détection d'une lectine
WO2013008062A1 (fr) 2011-07-12 2013-01-17 Centre National De La Recherche Scientifique (Cnrs) Structure moléculaire non covalente, comprenant un glycoconjugué à base de pyrène, dispositif la comprenant et son utilisation pour la détection d'une lectine
WO2013025736A2 (fr) * 2011-08-15 2013-02-21 Seta Biomedicals, Llc Molécules rapporteurs de type dendrons
WO2020089678A1 (fr) * 2018-11-01 2020-05-07 Nb Postech Membrane de nitrocellulose comprenant une molécule nanostructurée organique liée par liaison non covalente

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6806223B2 (en) * 2002-04-19 2004-10-19 Central Michigan University Board Of Trustees Single oxygen catalysts including condensed carbon molecules
US6890654B2 (en) * 2002-04-18 2005-05-10 Northwestern University Encapsulation of nanotubes via self-assembled nanostructures
US7098056B2 (en) * 2002-08-09 2006-08-29 Nanoink, Inc. Apparatus, materials, and methods for fabrication and catalysis

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6890654B2 (en) * 2002-04-18 2005-05-10 Northwestern University Encapsulation of nanotubes via self-assembled nanostructures
US6806223B2 (en) * 2002-04-19 2004-10-19 Central Michigan University Board Of Trustees Single oxygen catalysts including condensed carbon molecules
US7098056B2 (en) * 2002-08-09 2006-08-29 Nanoink, Inc. Apparatus, materials, and methods for fabrication and catalysis

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2333545A2 (fr) * 2008-08-22 2011-06-15 Sungkyunkwan University Foundation for Corporate Collaboration Procédé permettant d'augmenter la sensibilité au moyen d'un agent de liaison et d'un espaceur dans un biocapteur fondé sur un nanotube de carbone
CN102317776A (zh) * 2008-08-22 2012-01-11 成均馆大学产业协力团 利用连接基团与间隔基团提高碳纳米管基生物传感器灵敏度的方法
EP2333545A4 (fr) * 2008-08-22 2012-01-25 Univ Sungkyunkwan Found Procédé permettant d'augmenter la sensibilité au moyen d'un agent de liaison et d'un espaceur dans un biocapteur fondé sur un nanotube de carbone
WO2011158068A1 (fr) 2010-06-18 2011-12-22 Centre National De La Recherche Scientifique (Cnrs) Structure moléculaire non covalente, dispositif la comprenant et son utilisation pour la détection d'une lectine
WO2011158200A1 (fr) 2010-06-18 2011-12-22 Centre National De La Recherche Scientifique (Cnrs) Structure moléculaire non covalente, dispositif comprenant celle-ci et son utilisation pour la détection d'une lectine
WO2013008062A1 (fr) 2011-07-12 2013-01-17 Centre National De La Recherche Scientifique (Cnrs) Structure moléculaire non covalente, comprenant un glycoconjugué à base de pyrène, dispositif la comprenant et son utilisation pour la détection d'une lectine
WO2013025736A2 (fr) * 2011-08-15 2013-02-21 Seta Biomedicals, Llc Molécules rapporteurs de type dendrons
WO2013025736A3 (fr) * 2011-08-15 2013-05-10 Seta Biomedicals, Llc Molécules rapporteurs de type dendrons
WO2020089678A1 (fr) * 2018-11-01 2020-05-07 Nb Postech Membrane de nitrocellulose comprenant une molécule nanostructurée organique liée par liaison non covalente
US20210230399A1 (en) * 2018-11-01 2021-07-29 Nb Postech Nitrocellulose membrane comprising non-covalently attached organic nanostructured molecule
US11795304B2 (en) 2018-11-01 2023-10-24 Nb Postech Nitrocellulose membrane comprising non-covalently attached organic nanostructured molecule

Similar Documents

Publication Publication Date Title
Erol et al. Recent advances in bioactive 1D and 2D carbon nanomaterials for biomedical applications
US6890654B2 (en) Encapsulation of nanotubes via self-assembled nanostructures
Capek Dispersions, novel nanomaterial sensors and nanoconjugates based on carbon nanotubes
Fu et al. Dispersion and solubilization of carbon nanotubes
Kharisov et al. Recent advances on the soluble carbon nanotubes
Lin et al. Advances toward bioapplications of carbon nanotubes
Pan et al. Growth of multi-amine terminated poly (amidoamine) dendrimers on the surface of carbon nanotubes
US6896864B2 (en) Spatial localization of dispersed single walled carbon nanotubes into useful structures
JP4927319B2 (ja) 高密度カーボンナノチューブフィルムまたはパターンを用いたバイオチップの製造方法
Kohli et al. Smart nanotubes for biotechnology
Singh et al. Carbon nanotube–nucleobase hybrids: nanorings from uracil‐modified single‐walled carbon nanotubes
Mehra et al. Challenges in the use of carbon nanotubes for biomedical applications
Liao et al. Applications of carbon nanotubes in biomedical studies
WO2008044896A1 (fr) Composite nanotube de carbone-dendron et biocapteur comprenant ce composite
WO2007139244A1 (fr) Nanotube de carbone dont la surface est modifiée par la coordination de métal de transition, et son procédé de modification
Gheybi et al. Graphene-dendritic polymer hybrids: synthesis, properties, and applications
Teker et al. Applications of carbon nanotubes for cancer research
Prajapati et al. Surface modification strategies for the carbon nanotubes
Shuster et al. Comparison of Oligo (ethylene glycol) alkanethiols versus n-Alkanethiols: Self-Assembly, Insertion, and Functionalization
Yang et al. Polydiacetylene single-walled carbon nanotubes nano-hybrid for cellular imaging applications
Porwal An overview of current developments in the synthesis of carbon nanotubes and their use in medicinal applications
Hasnain et al. Functionalization of carbon nanotubes
Fletcher et al. Biochemical functionalization of vertically aligned carbon nanofibres
KR100864422B1 (ko) 플러렌 나노구조체에 생체물질을 고정화하는 방법
Bhoi et al. Surface immobilization of carbon nanotubes by β-cyclodextrins and their inclusion ability

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07833317

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 07833317

Country of ref document: EP

Kind code of ref document: A1