EP0910340A1 - Nanotubes fonctionnalises - Google Patents

Nanotubes fonctionnalises

Info

Publication number
EP0910340A1
EP0910340A1 EP97914892A EP97914892A EP0910340A1 EP 0910340 A1 EP0910340 A1 EP 0910340A1 EP 97914892 A EP97914892 A EP 97914892A EP 97914892 A EP97914892 A EP 97914892A EP 0910340 A1 EP0910340 A1 EP 0910340A1
Authority
EP
European Patent Office
Prior art keywords
less
fibrils
sir
integer
enzyme
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP97914892A
Other languages
German (de)
English (en)
Other versions
EP0910340A4 (fr
Inventor
Alan Fischer
Robert Hoch
David Moy
Ming Lu
Mark Martin
Chun Ming Niu
Naoya Sophia University OGATA
Howard Tennent
Liwen Dong
Ji Sun
Larry Helms
Fabian Jameison
Pam Liang
David Simpson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hyperion Catalysis International Inc
Original Assignee
Hyperion Catalysis International Inc
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 Hyperion Catalysis International Inc filed Critical Hyperion Catalysis International Inc
Publication of EP0910340A1 publication Critical patent/EP0910340A1/fr
Publication of EP0910340A4 publication Critical patent/EP0910340A4/fr
Withdrawn legal-status Critical Current

Links

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    • 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
    • G01N33/54313—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals the carrier being characterised by its particulate form
    • G01N33/54346—Nanoparticles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01D15/08—Selective adsorption, e.g. chromatography
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Definitions

  • the invention relates broadly to graphitic nanotubes, which includes tubular fullerenes (commonly called "buckytubes") and fibrils, which are functionalized by chemical substitution or by adsorption of functional moieties. More specifically the invention relates to graphitic nanotubes which are uniformly or non-uniformly substituted with chemical moieties or upon which certain cyclic compounds are adsorbed and to complex structures comprised of such functionalized fibrils linked to one another. The invention also relates to methods of introducing functional groups onto the surface of such fibrils. BACKGROUND OF THE INVENTION
  • continuous carbon fibers In contrast to fibrils, which have, desirably large, but unavoidably finite aspect ratios, continuous carbon fibers have aspect ratios (L/D) of at least 10 4 and often 10 6 or more.
  • the diameter of continuous fibers is also far larger than that of fibrils, being always >1.0 ⁇ and typically 5 to 7 ⁇ .
  • Continuous carbon fibers are made by the pyrolysis of organic precursor fibers, usually rayon, polyacrylonitrile (PAN) and pitch. Thus, they may include heteroatoms within their structure.
  • PAN polyacrylonitrile
  • the graphitic nature of "as made" continuous carbon fibers varies, but they may be subjected to a subsequent graphitization step. Differences in degree of graphitization, orientation and crystallinity of graphite planes, if they are present, the potential presence of heteroatoms and even the absolute difference in substrate diameter make experience with continuous fibers poor predictors of nanofiber chemistry.
  • the carbon atoms, C n are surface carbons of a substantially cylindrical, graphitic nanotube of substantially constant diameter.
  • the nanotubes have a length to diameter ratio of greater than 5 and a diameter of less than 0.5 ⁇ , preferably less than O.l ⁇ .
  • the nanotubes may be nanotubes which are substantially free of pyrolytically deposited carbon. More preferably, the nanotubes are those in which the projection of the graphite layers on the fibril axes extends for a distance of at least two fibril diameters and/or those having cylindrical graphitic sheets whose c-axes are substantially perpendicular to their cylindrical axis.
  • Y is an appropriate functional group of a protein, a peptide, an amino acid, an enzyme, an antibody, a nucleotide, an oligonucleotide, an antigen, or an enzyme substrate, enzyme inhibitor or the transition state analog of an enzyme substrate or is selected from R'-OH, R'-NR' 2 , R'SH, R'CHO, R'CN, R'X, R'N + (R') 3 X ⁇ , R'SiR' 3 , R'Si-fOR'-)- y R' 3 _ y , R'Si-fO-SiR' 2 -K>R' ,
  • More preferred cyclic compounds for adsorption are porphyrins and phthalocyanines.
  • a composition having the formula [C n H L -H-CH(R')OH] m is formed by reacting R'CH 2 OH with the surface carbons of a nanotube in the presence of a free radical initiator such as benzoyl peroxide.
  • Activated C-H (including aromatic C-H) bonds can be sulfonated using fuming sulfuric acid (oleum) , which is a solution of cone, sulfuric acid containing up to 20% S0 3 .
  • the conventional method is via liquid phase at T-80°C using oleum; however, activated C-H bonds can also be sulfonated using S0 3 in inert, aprotic solvents, or S0 3 in the vapor phase.
  • the reaction is:
  • the reaction may require additionally, a strong base, such as potassium t-butoxide or chelating diamines.
  • Aprotic solvents are necessary (paraffins, benzene) .
  • RADICAL INITIATOR The high degree of stability of carbon nanotubes, while allowing them to be used in harsh environments, makes them difficult to activate for further modification. Previous methods have involved the use of harsh oxidants and acids. It has now been surprisingly found that terminal alcohols can be attached to carbon nanotubes using a free radical initiator such as benzoyl peroxide (BPO) . Carbon nanotubes are added to an alcohol having the formula RCH 2 OH, wherein R is hydrogen, alkyl, aryl, cycloalkyl, aralkyl, cycloaryl, or poly(alkylether) along with a free radical initiator and heated to from about 60°C to about 90°C. Preferred alcohols include ethanol and methanol.
  • H 2 N-R R same as above R- Amines, anilines, fluorinated amines, silylamines, amine terminated polyamides, proteins
  • Trypsin can react with substrate L-BAPNA (N ⁇ - benzoyl-L-arginine p-nitroanilide) and release a colored compound that absorbs light at 410 nm.
  • the assay buffer for this reaction was 0.05 M Tris, 0.02 M CaCl 2 , pH 8.2.
  • the reaction was performed in 1 ml cuvette by mixing 5 ⁇ l of L-BAPNA stock solution (50 mM in 37% DMSO in H 2 0) and 10-25 ⁇ g of trypsin fibrils in a 1 ml of assay buffer.
  • the absorbance increase at 410 nm was monitored over 10 minutes.
  • the enzyme activity ( ⁇ M/min) was then calculated from the initial slope.
  • the activity was 5.24 ⁇ M/min per 13 ⁇ g fibrils. This result can be converted to the amount of active trypsin on fibrils by dividing the activity of a known concentration of trypsin solution, which was measured to be 46 ⁇ M/min per 1 ⁇ M trypsin under the same assay conditions. Therefore the amount of active trypsin per gram of fibrils was 8.3 ⁇ moles (or 195 mg) .
  • the resulting material was filtered onto a polycarbonate membrane filter, washed 2X with buffer, IX with DI water and 2X with absolute EtOH, all under an argon blanket.
  • EXAMPLE 25 Preparation of Maleimide Fibrils From Amino Fibrils
  • Amino fibrils were prepared according to Example 13. The amino fibrils (62.2 mg) were then sonicated in sodium phosphate buffer (5 ml, 5 mM at pH 7.2) . Sulfosuccinmidyl-4-(N-maleimidomethyl)cyclohexane- 1-carboxylate (SMCC; 28.8 mg, 0.66 mmols; Pierce, Cat. No.22360) was added to the fibril suspension. The reaction mixture was stirred overnight at room temperature. The fibrils were washed with water and methanol, and the product fibrils were dried under vacuum. Antibody immobilization on the product confirmed the presence of maleimide fibrils.
  • SMCC Sulfosuccinmidyl-4-(N-maleimidomethyl)cyclohexane- 1-carboxylate
  • Tertiary and quaternary amine functional groups can be attached to the surface of carbon nanotubes via an amide or ester bond via a carboxyl group on the nanotube and either an amine or hydroxyl group of the tertiary or quaternary amine precursor.
  • Such tertiary or quaternary amine fibrils are useful as chromatographic matrices for the separation of biomolecules.
  • the tertiary or quaternary amine fibrils can be fabricated into disk- shaped mats or mixed with conventional chromatographic media (such as agarose) for separation purposes.
  • the column was eluted with 5 mM sodium phosphate at a flow rate of 0.2 ml/min and 0.6ml fractions were collected.
  • the elution profile was monitored using a UV- visible detector, and is shown in Fig 3. Once the detector indicated that no more protein was eluting from the column, bound BSA was eluted by adding 1 M KC1 in 5 mM sodium phosphate (pH 7.3). The presence of the protein in each fraction was identified by micro BCA assay (Pierce, Rockford, II) .
  • Carboxyl dendrimeric fibrils can be prepared by the same method by using aspartic or glutamic acid with carboxyl fibrils.
  • CN/NTA was first converted to the NHS active ester. 0.396 grams of CN/NTA was dried in an oven at 90°C for 30 minutes and then placed in a 100 ml RB flask with 30 mis of anhydrous dioxane and purged with argon. 0.4 g of N-hydroxysuccinimide added with stirring followed by 0.67 grams of EDC with continued stirring for an additional hour. The CN tended to agglomerate together during this time. The dioxane was decanted off and the solids were washed 2X with 20 mis of anhydrous dioxane. The solids were washed with 20 mis of anhydrous MeOH during which the agglomerates broke up.
  • N ⁇ -CBZ-N e - (tert-butoxycarbony1)-L-lysine was treated with 0.2 M calcium carbonate (4 ml) and the aqueous layer was removed to obtain a white solid.
  • the solid was resuspended in N,N- dimethylformamide(40 ml) and benzyl bromide (1.16 ml). The reaction mixture was stirred overnight at room temperature. The reaction mixture was worked up with ethyl acetate and water, and the organic layer was dried over magnesium sulphate.
  • phenyl-alkyl nanotubes which are alkyl nanotubes with the addition of a phenyl group on the end of the alkyl chain, have also been prepared.
  • This modification introduced an aromatic structure that interacts with the amino acids phenylalanine, tyrosine, and tryptophan in proteins through ⁇ - ⁇ interactions.
  • the adsorption of alkaline phosphatase and lipase on phenyl- alkyl nanotubes was comparable to the adsorption on C 8 - alkyl nanotubes.
  • Alkaline phosphatase was immobilized on C 8 -fibrils and C 6 OH-fibrils; trypsin on C 6 - , C 8 -, C 10 - and C 18 -fibrils, lipase on C 6 OH-, C 8 -, C 10 - and C 18 -fibrils, and avidin on C 8 -fibrils.
  • the results are shown in the following table: 1 Enzyme ⁇ mol/g fibril mg/g fibril lipase 6.8 816 trypsin 1.7 40 alkaline phosphatase 0.66 56
  • phenyl-alkyl fibrils were suspended in 50 ⁇ l of 5 mM sodium phosphate buffer (pH 7.1) and sonicated for 20 minutes.
  • 5 mM sodium phosphate buffer pH 7.1
  • lipase solution 0.2 mM in 5 mM sodium phosphate buffer, pH 7.1
  • the fibrils were then washed with 600 ⁇ l of 5 mM sodium phosphate buffer (pH 7.1) three times and suspended in 200 ⁇ l of the same buffer.
  • a 10.0 g sample of graphitic fibrils was slurried in 450 mL concentrated H 2 S0 4 by mixing with a spatula, then transferred to a reactor flask fitted with inlet/outlets and an overhead stirrer. With stirring and under a slow flow of argon, a charge of 8.68 g of NaCl ⁇ 3 was added in portions at room temperature over a 24 hour period. Chlorine vapors, which were generated during the entire course of the run, were swept out of the reactor into an aqueous NaOH trap. At the end of the run, the fibril slurry was poured over cracked ice and vacuum filtered.
  • Carboxylated fibrils were used to prepare NHS ester fibrils as described in Example 50 above.
  • NHS ester fibrils 114 mg
  • 10 equivalents based on the estimation of 0.7 meq NHS ester per gram of fibrils
  • Dry triethylamine (10 equiv.) was added and the mixture was stirred for 3 hours at room temperature.
  • the tyraminyl fibrils were washed under vacuum in a scintered glass funnel first with acetone, then extensively with deionized water.
  • 4-(p-Aminophenylazo)-phenylarsonic acid (66 mg) was suspended in 4 mL of 1 N HCl. The suspension was cooled to 4°C and mixed slowly with 0.36 mL of 0.5 M NaN0 2 . After 15 minutes, the arsonic acid/NaN0 2 mixture was added to the tyraminyl fibrils, which were suspended in 10 mL of 0.1 M NaC0 3 (pH 10.0). The reaction mixture (pH « 10) was stirred overnight at 4°C. The fibrils were then treated with successive washes of 0.1 M Na 2 C0 3 (pH 10.0), 8 M guanidine HCl, 25 mM NaOH, and water until the effluent became clear.
  • alkaline phosphatase from E. coli , Type III; Sigma Chemical Co., St. Louis, MO
  • BG B- galactosidase
  • Covalent immobilization was accomplished by various methods; including reductive amination of antibody carbohydrate groups, NHS ester activation of carboxylated fibrils (see Example 27, supra), and reaction of thiolated or maleimido fibrils with reduced or maleimido-modified antibodies (see Examples 23 and 25 supra) .
  • the NAD + immobilized fibrils (0.26 mg) and plain fibrils (0.37 mg) were sonicated with 0.1% polyethylene glycol (PEG, MW 1000) in sodium phosphate (1 ml, 0.1 M, at pH 7.1) for 30 minutes at 40°C, then incubated for 30 minutes at 40°c.
  • the fibril suspension was centrifuged and the supernatant were removed.
  • the fibrils were incubated with the mixture of L-lactate dehydrogenase (LDH) in 0.1% PEG (1000) sodium phosphate buffer (250 ⁇ l, the ratio of the LDH solution and the 0.1% PEG buffer was 1:1) for 90 minutes at 4 ⁇ C. Then the mixtures were equilibrated for 30 minutes at room temperature.
  • LDH L-lactate dehydrogenase
  • the fibrils were washed with 0.1% PEG (1000) in sodium phosphate buffer (5 X 1000 ⁇ l) and every washing took 15 minutes with rotation.
  • the LDH was eluted with a 5 mM solution of NADH in 0.1% PEG (1000) sodium phosphate buffer (5 mM 3X1000 ⁇ l) .
  • the LDH activity in the eluents was assayed by measuring the absorbance change at 340 nm during reduction of pyruvate.
  • Fibrils offer great advantages as solid carriers because of their high surface area. Beads, which can be made strongly magnetic, are extremely useful in separation assays.
  • the biotinylated fibrils described herein combine the advantages of both the fibrils and the beads.
  • the biotinylated alkyl fibrils are an extension of the same concept but exhibit the additional protein adsorption property of alkyl fibrils.
  • Biotinylated alkyl fibrils were prepared by a two step reaction. First, 4.25 mg of bifunctional fibrils (containing both amino and carboxyl) and 25 mg of NHS ester long chain biotin were mixed. The fibrils were washed and dried under vacuum.
  • the second reaction was carried out by mixing 4 mg of biotinylated bifunctional fibrils with 11 mg of EDC (l-ethyl-3-3-dimethylaminopropyl)carbodiimide) , 7.5 mg of DMAP (4-dimethylaminopyridine) and 10 ⁇ l of NH 2 (CH 2 ) 7 CH 3 in 0.5 ml of DMF. The mixture was stirred at room temperature overnight. The final biotinylated alkyl fibrils were washed by CH 2 C1 2 , MeOH, and dH 2 0.
  • FBS fibril-biotin-streptavidin
  • a biotinylated anti-analyte antibody could be captured on the FBS support (either before or after the antibody has complexed to an analyte) .
  • Assays using biotinylated anti-analyte antibodies are well established. Such assays include competitive assays where the analyte of interest competes with a labeled analyte for binding to the anti-analyte antibody. Free (unbound) analyte and free (unbound) labeled analyte can be washed from the fibril immobilized antibody. The washing step depends on the fibrils being physically separated from the solution phase by common practices involving centrifugation, filtration, or by attraction to a magnet.
  • Sandwich immunoassays are well known in the field of diagnostics. Such assays involve an analyte being bound simultaneously by two antibodies; a first "primary” antibody which is captured on a solid surface by for example being labeled with biotin, and a "secondary” antibody which is not captured by a solid surface but is labeled with a reporter group.
  • a sandwich assay could be carried out using fibrils as a solid capture support whereby the fibrils are captured as described in the previous paragraph.
  • fibrils can be dispersed on an individualized basis, a well-dispersed sample which is stabilized by cross-links allows one to construct such a support.
  • Functionalized fibrils are ideal for this application since they are easily dispersed in aqueous or polar media and the functionality provides cross-link points. Additionally, the functionality provides points to support the catalytic or chromatographic sites. The end result is a rigid, 3-dimensional structure with its total surface area accessible with functional sites on which to support the active agent.

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Abstract

L'invention concerne les nanotubes graphitiques, incluant les fullerènes tubulaires (souvent appelés 'buckytubes' en anglais) et les fibrilles, qui sont fonctionnalisés par substitution chimique ou par adsorption de fractions fonctionnelles. L'invention est plus particulièrement applicable aux nanotubes graphitiques qui sont uniformément ou non uniformément remplacés par des fractions chimiques ou sur lesquels certains composés cycliques sont adsorbés. La présente invention s'applique également aux structures complexes comprenant de tels nanotubes fonctionnalisés reliés entre eux. L'invention concerne aussi les méthodes permettant d'introduire des groupes fonctionnels dans la surface de tels nanotubes. L'invention se rapporte en outre aux utilisations des nanotubes fonctionnalisés.
EP97914892A 1996-03-06 1997-03-05 Nanotubes fonctionnalises Withdrawn EP0910340A4 (fr)

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US3723896P 1996-03-06 1996-03-06
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PCT/US1997/003553 WO1997032571A1 (fr) 1996-03-06 1997-03-05 Nanotubes fonctionnalises

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