Novel Reagents for Directed Biomarker Signal Amplification

• US 20190346450A1
• Filed: 07/31/2019
• Published: 11/14/2019
• Est. Priority Date: 01/19/2010
• Status: Active Grant

• Current Assignee: Sirigen Ii Limited (Becton, Dickinson & Co)
• Original Assignee: Sirigen Ii Limited (Becton, Dickinson & Co)
• Inventors: GAYLORD, Brent S., BARTHOLOMEW, Glenn P., BALDOCCHI, Russell A., HONG, Janice W., HUISMAN, William H., LIANG, Yongchao, NGUYEN, Trung, TRAN, Lan T., WHEELER, Jean M., PALMER, Adrian Charles Vernon, UCKERT, Frank Peter
• Granted Patent: US 10,641,775 B2
• Time in Patent Office: Days
• CPC Class Codes: C07K 16/2812 against CD4
• CPC Class Codes: C07K 16/2815 against CD8
• CPC Class Codes: C08G 2261/1424 containing ether groups, including alkoxy
• CPC Class Codes: C08G 2261/143 Side-chains containing nitrogen
• CPC Class Codes: C08G 2261/1432 containing amide groups
• CPC Class Codes: C08G 2261/146 Side-chains containing halogens
• CPC Class Codes: C08G 2261/148 Side-chains having aromatic units
• CPC Class Codes: C08G 2261/164 comprising organic end groups
• CPC Class Codes: C08G 2261/1642 comprising reactive double bonds or triple bonds
• CPC Class Codes: C08G 2261/3142 fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
• CPC Class Codes: C08G 2261/334 containing heteroatoms
• CPC Class Codes: C08G 2261/3422 conjugated, e.g. PPV-type
• CPC Class Codes: C08G 2261/411 Suzuki reactions
• CPC Class Codes: C08G 2261/94 Applications in sensors, e.g. biosensors
• CPC Class Codes: C08G 61/02 Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
• CPC Class Codes: C08G 61/10 only aromatic carbon atoms, e.g. polyphenylenes
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09B 68/41 Polymers attached to the pigment surface C09B68/444, C09B68/446 take precedence
• CPC Class Codes: C09B 69/00 Dyes not provided for by a single group of this subclass
• CPC Class Codes: C09D 165/00 Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain C09D107/00 - C09D157/00, C09D161/00 take precedence; Coating compositions based on derivatives of such polymers
• CPC Class Codes: C09K 11/06 : containing organic luminescent materials
• CPC Class Codes: C12Q 1/6818 : involving interaction of two or more labels, e.g. resonant energy transfer
• CPC Class Codes: C12Q 1/682 : Signal amplification
• CPC Class Codes: G01N 33/58 : involving labelled substances G01N33/53 takes precedence
• CPC Class Codes: G01N 33/582 : with fluorescent label
• CPC Class Codes: H10K 85/115 : Polyfluorene; Derivatives thereof
• CPC Class Codes: H10K 85/151 : Copolymers

Abstract

Described herein are methods, compositions and articles of manufacture involving neutral conjugated polymers including methods for synthesis of neutral conjugated water-soluble polymers with linkers along the polymer main chain structure and terminal end capping units. Such polymers may serve in the fabrication of novel optoelectronic devices and in the development of highly efficient biosensors. The invention further relates to the application of these polymers in assay methods.

Claims

1-40. -40. (canceled)

41. A water soluble conjugated polymer having a backbone of n-conjugated repeat units and the structure of the formula:

42. The water soluble conjugated polymer according to claim 41, wherein Ar comprises 1 to 5 aromatic rings.

43. The water soluble conjugated polymer according to claim 41, wherein Ar comprises up to 5 fused and/or bridged rings.

44. The water soluble conjugated polymer according to claim 41, wherein Ar comprises a biphenyl.

45. The water soluble conjugated polymer according to claim 44, wherein the biphenyl is bridged.

46. The water soluble conjugated polymer according to claim 41, wherein the ethylene glycol oligomer side group comprises a polyethylene glycol (PEG).

47. The water soluble conjugated polymer according to claim 46, wherein the PEG comprises mPEG5, mPEG8, mPEG11 or mPEG24.

48. The water soluble conjugated polymer according to claim 41, wherein at least one of G₁ and G₂ has the structure:

49. The water soluble conjugated polymer according to claim 41, wherein the biomolecule comprises a sensor protein.

50. The water soluble conjugated polymer according to claim 49, wherein the sensor protein comprises an antibody.

58. The water soluble conjugated polymer according to claim 41, wherein at least one of G₁ and G₂ has the structure:

51. A water soluble conjugated polymer having the structure of the formula:

52. The water soluble conjugated polymer according to claim 51, wherein Ar comprises 1 to 5 aromatic rings.

53. The water soluble conjugated polymer according to claim 51, wherein Ar comprises up to 5 fused and/or bridged rings.

54. The water soluble conjugated polymer according to claim 51, wherein Ar comprises a biphenyl.

55. The water soluble conjugated polymer according to claim 54, wherein the biphenyl is bridged.

56. The water soluble conjugated polymer according to claim 51, wherein the ethylene glycol oligomer side group comprises a polyethylene glycol (PEG).

57. The water soluble conjugated polymer according to claim 56, wherein the PEG comprises mPEG5, mPEG8, mPEG11 or mPEG24.

59. The water soluble conjugated polymer according to claim 51, wherein at least one of G₁ and G₂ is selected from the group consisting of capping units 1-31 having the structures:

wherein;

*=site for covalent attachment to backbone;

k is 2, 4, 8, 12 or 24; and

R15 is selected from the group consisting of 1-t having the structures;

60. The water soluble conjugated polymer according to claim 59, wherein at least one of G1 and G2 is selected from one of the following structures: