CA2490413A1 - Nanoparticle polyanion conjugates and methods of use thereof in detecting analytes - Google Patents

Nanoparticle polyanion conjugates and methods of use thereof in detecting analytes Download PDF

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CA2490413A1
CA2490413A1 CA002490413A CA2490413A CA2490413A1 CA 2490413 A1 CA2490413 A1 CA 2490413A1 CA 002490413 A CA002490413 A CA 002490413A CA 2490413 A CA2490413 A CA 2490413A CA 2490413 A1 CA2490413 A1 CA 2490413A1
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nucleic acid
polyanionic polymer
protein
nanoparticle
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CA2490413C (en
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James J. Storhoff
Robert L. Letsinger
Susan R. Hetzel
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Nanosphere LLC
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    • 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
    • G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/588—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with semiconductor nanocrystal label, e.g. quantum dots
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y15/00—Nanotechnology for interacting, sensing or actuating, e.g. quantum dots as markers in protein assays or molecular motors
    • 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
    • G01N33/54313—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals the carrier being characterised by its particulate form
    • G01N33/54346—Nanoparticles
    • 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
    • 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
    • G01N33/544—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals the carrier being organic
    • G01N33/545—Synthetic resin
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
    • G01N2333/435—Assays involving biological materials from specific organisms or of a specific nature from animals; from humans
    • G01N2333/705—Assays involving receptors, cell surface antigens or cell surface determinants
    • G01N2333/72—Assays involving receptors, cell surface antigens or cell surface determinants for hormones
    • G01N2333/726—G protein coupled receptor, e.g. TSHR-thyrotropin-receptor, LH/hCG receptor, FSH
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/70—Nanostructure
    • Y10S977/701—Integrated with dissimilar structures on a common substrate
    • Y10S977/702—Integrated with dissimilar structures on a common substrate having biological material component
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]

Abstract

This invention provides polyanionic polymer conjugates containing non-nucleotide polyanionic polymers that are useful in detecting target analytes such as proteins or small molecules. The invention also provides nanoparticle bound to polyanionic polymer conjugates and methods of preparation and use thereof. The polyanionic polymer conjugates have the formula: L-O~PO2-O-Z-O~n-PO2-O-X wherein n ranges from 1 to 200; L represents a moiety comprising a functional group for attaching the polyanion polymer to the nanoparticle surface; Z represents a bridging group, and X represents Q, X~ or -Q-X~, wherein Q represents a functional group for attaching a recognition probe to the polyanion polymer, and X~ represents a recognition probe.

Claims (50)

1. A polyanionic polymer conjugate of the formula:
L-O-[PO2-O-Z-O]n-PO2-O-X
wherein n ranges from 1 to 200; L represents a moiety comprising a functional group for attaching the polyanion polymer to a nanoparticle surface; Z represents a bridging group, and X
represents Q, X' or -Q-X', wherein Q represents a functional group for attaching a recognition probe to the polyanion polymer, and X' represents a recognition probe.
2. The polyanionic polymer conjugate of claim 1, wherein the polyanion polymer further comprises a detection label bound thereto.
3. The polyanionic polymer conjugate of claim 2, wherein the detection label comprises a chromophore, a fluorescent label, a UV label, a radioisotope, a Raman label or a SERS (surface enhanced raman spectroscopy) label, or an enzyme.
4. The polyanionic polymer conjugate of claim 1, wherein the functional group for attaching a recognition probe to the polyanion polymer comprises a carboxylic acid or an amino group.
5. The polyanionic polymer conjugate of claim 1, wherein the recognition probe comprises a protein, a peptide, a nucleic acid, a peptide nucleic acid, a linked nucleic acid, a nucleoside triphosphate, a carbohydrate, a lipid, a lipid bound protein, an aptamer, a virus, a cell fragment, or a whole cell.
6. The polyanionic polymer conjugate of claim 5, wherein the lipid bound protein comprises a G-protein coupled receptor.
7. The polyanionic polymer conjugate of claim 1, wherein the recognition probe comprises an antibody, an antigen, a receptor, or a ligand.
8. The polyanionic polymer conjugate of claim 1 wherein L comprises an alkanethiol contaning group, a phosphorothioate contaning group, a substituted alkylsiloxane containing, a polythiol containing group, or a cyclic disulfide containing group.
9. The polyanionic polymer conjugate of claim 1 wherein Z comprises a polymer, -C1-C10-alkyl-, -COO-, -CH2(CH2)v COO-, -OCO-, R1NCH2)v NR1-, -OC(CH2)v-,-(CH2) v-, -O-(CH2)v-O-, -R1N-(CH2)v-, v is 0-30 and R1 is H or is G(CH2)v, wherein G is -CH3, -CHCH3, -COOH, -CO2(CH2)v CH3, -OH, or -CH2OH.
10. A nanoparticle having a plurality of polyanionic polymer conjugates of claim 1 attached thereto.
11. The nanoparticle of claim 10, wherein the polyanionic polymer conjugate further comprises a detection label bound thereto.
12. The nanoparticle of claim 11, wherein the detection label comprises a chromophore, a fluorescent label, a UV label, a radioisotope, a Raman label or a SERS (surface enhanced raman spectroscopy) label, or an enzyme.
13. The nanoparticle of claim 10, wherein the functional group for attaching a probe to the polyanionic polymer conjugate comprises a carboxylic acid or an amino group.
14. The nanoparticle of claim 10, wherein the recognition probe comprises a protein, a peptide, a nucleic acid, a peptide nucleic acid, a linked nucleic acid, a nucleoside triphosphate, a carbohydrate, a lipid, a lipid bound protein, an aptamer, a virus, a cell fragment, or a whole cell.
15. The nanoparticle of claim 14, wherein the lipid bound protein comprises a G-protein coupled receptor.
16. The nanoparticle of claim 10, wherein the recognition probe comprises an antibody, an antigen, a receptor, or a ligand.
17. The nanoparticle of claim 10 wherein L comprises an alkanethiol containing group, a phosphorothioate containing group, a substituted alkylsiloxane containing, a polythiol containing group, or a cyclic disulfide containing group.
18. The nanoparticle of claim 10 wherein Z comprises a polymer, -C1-C10-alkyl-, -COO-, -CH2(CH2)v COO-, -OCO-, R1N(CH2)v-NR1-, -OC(CH2)v-, -(CH2)v-, -O-(CH2)v-O-, -R1N-(CH2)v-, v is 0-30 and R1 is H or is G(CH2)v, wherein G is -CH3, -CHCH3, -COOH, -CO2(CH2)v CH3, -OH, or -CH2OH.
19. A method for detecting the presence or absence of a target analyte in a sample comprising:
providing nanoparticles having a plurality of polyanionic polymer conjugates of claim 1 attached thereto, wherein the recognition probes bound to the polyanionic polymer conjugates selectively bind to the target analyte;
contacting the nanoparticles with the sample under conditions effective to allow for binding of the recognition probes with the target analyte; and observing a detectable change brought by the binding of the recognition probes with the target analyte.
20. The method according to claim 19 wherein the recognition probe bound to the polyanionic polymer conjugate comprises a protein, a peptide, a nucleic acid, a peptide nucleic acid, a linked nucleic acid, a nucleoside triphosphate, a carbohydrate, a lipid, a lipid bound protein, an aptamer, a virus, a cell fragment, or a whole cell.
21. The method according to claim 19 wherein the lipid bound protein comprises a G-protein coupled receptor.
22. The method according to claim 19 wherein the recognition probe comprises an antibody, an antigen, a receptor, or a ligand.
23. The method according to claim 19 wherein detection label comprises a chromophore, a fluorescent label, a UV label, a radioisotope, a Raman label or a SERS (surface enhanced raman spectroscopy) label, or an enzyme.
24. The method according to claim 19 wherein the detectable change is a change in color.
25. The method according to claim 19 wherein the detectable change is an optical change associated with nanoparticle binding of the target.
26. A method for detecting the presence or absence of one or more target analytes in a sample comprising:
providing one or more types of nanoparticles having a plurality of polyanionic polymer conjugates of claim 1 attached thereto, wherein the polyanionic polymer conjugate attached to each type of nanoparticles has bound thereto a recognition probe specific for a target analyte and a detection label that serves as an identifer for a specific target analyte;
contacting the nanoparticles with the sample under conditions effective to allow for binding of the recognition probes and the target analytes; and observing detectable changes for each analyte brought by the binding of the recognition probe with the target analyte.
27. The method according to claim 26 wherein the recognition probe bound to the polyanionic polymer conjugate comprises a protein, a peptide, a nucleic acid, a peptide nucleic acid, a linked nucleic acid, a nucleoside triphosphate, a carbohydrate, a lipid, a lipid bound protein, an aptamer, a virus, a cell fragment, or a whole cell.
28. The method according to claim 26 wherein the lipid bound protein comprises a G-protein coupled receptor.
29. The method according to claim 26 wherein the recognition probe comprises an antibody, an antigen,a receptor, or a ligand.
30. The method according to claim 26 wherein detection label comprises a chromophore, a fluorescent label, a UV label, a radioisotope, a Raman label or a SERS (surface enhanced raman spectroscopy) label, or an enzyme.
31. The method according to claim 26 wherein the detectable change is a change in color.
32. The method according to claim 26 wherein the detectable change is an optical change associated with nanoparticle binding of the target.
33. A method for detecting for the presence or absence of one or more target analytes in a sample, the target analyte having at least two binding sites, said method comprising:
providing a substrate having bound thereto one or more types of capture probes for immobilizing the target analyte onto said substrate, each capture probe specific for a target analyte;
providing one or more types of nanoparticles having a plurality of polyanionic polymer conjugates attached thereto, wherein the polyanionic polymer conjugates attached to each type of nanoparticles has bound thereto (i) a recognition probe specific for a target analyte and (ii) a detection label that serves as an identifer for a specific target analyte;
contacting the nanoparticles, the sample, and the substrate under conditions effective for specific binding interactions between the target analyte, the capture probe, and the nanoparticle so as to form a detection substrate having nanoparticles complexed thereto in the presence of one or more target analytes in the sample; and determining for the presence of said complexes on said detection substrate as an indication of the presence of one or more target analytes in the sample.
34. The method of claim 33, wherein the substrate has a plurality of different capture probes attached thereto in an array to allow for the detection of multiple types of target analytes.
35. The method of claim 33, wherein the substrate comprises a glass slide, a microplate well, or glass beads.
36. The method according to claim 33 wherein the recognition probe bound to the polymer comprises a protein, a peptide, a nucleic acid, a peptide nucleic acid, a linked nucleic acid, a nucleoside triphosphate, a carbohydrate, a lipid, a lipid bound protein, an aptamer, a virus, a cell fragment, or a whole cell.
37. The method according to claim 33 wherein the recognition probe bound to the polyanionic polymer conjugate comprises a protein, a peptide, a nucleic acid, a peptide nucleic acid, a linked nucleic acid, a nucleoside triphosphate, a carbohydrate, a lipid, a lipid bound protein, an aptamer, a virus, a cell fragment, or a whole cell.
38. The method according to claim 33 wherein the lipid bound protein comprises a G-protein coupled receptor.
39. The method according to claim 33 wherein the recognition probe comprises an antibody, an antigen, a receptor, or a ligand.
40. The method according to claim 33 wherein detection label comprises a chromophore, a fluorescent label, a UV label, a radioisotope, a Raman label or a SERS (surface enhanced raman spectroscopy) label, or an enzyme.
41. The method according to claim 33 wherein the detectable change is a change in color.
42. The method according to claim 33 wherein the detectable change is an optical change associated with nanoparticle binding of the target.
43. A kit for detecting the presence or absence of a target analyte in a sample comprising:
(a) nanoparticles having polyanionic polymer conjugates bound thereto, wherein the polyanion polymers have the formula:

L-O-[PO2-O-Z-O]n-PO2-O-X

wherein n ranges from 1 to 200; L represents a moiety comprising a functional group for attaching the polyanion polymer to a nanoparticle surface; Z represents a bridging group, and X
represents Q, X' or -Q-X', wherein Q represents a functional group for attaching a probe to the polyanion polymer, and X' represents a probe; and (b) an optional substrate for observing a detectable change.
44. The kit of claim 43, wherein the polyanionic polymer conjugate further comprises a detection label bound thereto.
45. The kit of claim 44, wherein the detection label comprises a chromophore, a fluorescent label, a UV label, a radioisotope, a Raman label or a SERS
(surface enhanced raman spectroscopy) label, or an enzyme.
46. The kit of claim 43, wherein the functional group for attaching a probe to the polyanionic polymer conjugate comprises a carboxylic acid or an amino group.
47. The kit of claim 43, wherein the probe comprises a protein, a peptide, a nucleic acid, a peptide nucleic acid, a linked nucleic acid, a nucleoside triphosphate, a carbohydrate, a lipid, a lipid bound protein, an aptamer, a virus, a cell fragment, or a whole cell.
48. The kit of claim 47, wherein the lipid bound protein comprises a G-protein coupled receptor.
49. The kit of claim 43, wherein the probe comprises an antibody, an antigen, a receptor, or a ligand.
50. The kit of claim 43 wherein the substrate is a transparent substrate or an opaque white substrate.
CA2490413A 2002-07-02 2003-07-02 Nanoparticle polyanion conjugates and methods of use thereof in detecting analytes Expired - Lifetime CA2490413C (en)

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US39325502P 2002-07-02 2002-07-02
US60/393,255 2002-07-02
PCT/US2003/021021 WO2004004647A2 (en) 2002-07-02 2003-07-02 Nanoparticle polyanion conjugates and methods of use thereof in detecting analytes

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EP (1) EP1540006B1 (en)
JP (1) JP2005532456A (en)
AT (1) ATE420357T1 (en)
AU (1) AU2003247788B2 (en)
CA (1) CA2490413C (en)
DE (1) DE60325743D1 (en)
WO (1) WO2004004647A2 (en)

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