Luminescent polymers and methods of use thereof

• US 20040121337A1
• Filed: 12/19/2002
• Published: 06/24/2004
• Est. Priority Date: 12/19/2002
• Status: Abandoned Application

• Current Assignee: Nomadics, Inc. (Teledyne Technologies Incorporated)
• Original Assignee: Nomadics, Inc. (Teledyne Technologies Incorporated)
• Inventors: Deans, Robert, Hancock, Lawrence F., Moon, Joong Ho
• Application Number:
  US10/325,660
• Publication Number:
  US 20040121337A1
• Time in Patent Office: Days
• US Class Current: 435/6
• CPC Class Codes: B01J 2219/00497 Features relating to the solid phase supports
• CPC Class Codes: B01J 2219/00576 fluorophore
• CPC Class Codes: B01J 2219/00605 the compounds being directly bound or immobilised to solid supports
• CPC Class Codes: B01J 2219/0061 The surface being organic
• CPC Class Codes: B01J 2219/00612 the surface being inorganic
• CPC Class Codes: B01J 2219/00621 by physical means, e.g. trenches, raised areas
• CPC Class Codes: B01J 2219/00626 Covalent
• CPC Class Codes: B01J 2219/00628 Ionic
• CPC Class Codes: B01J 2219/0063 Other, e.g. van der Waals forces, hydrogen bonding
• CPC Class Codes: B01J 2219/00637 by coating it with another layer
• CPC Class Codes: B01J 2219/00644 the porous medium being present in discrete locations, e.g. gel pads
• CPC Class Codes: B01J 2219/00648 by the use of solid beads
• CPC Class Codes: B01J 2219/00659 Two-dimensional arrays
• CPC Class Codes: B01J 2219/00677 Ex-situ synthesis followed by deposition on the substrate
• CPC Class Codes: B01J 2219/00722 Nucleotides
• CPC Class Codes: B01J 2219/00729 Peptide nucleic acids [PNA]
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1425 Non-condensed systems
• CPC Class Codes: C12Q 1/37 involving peptidase or proteinase
• CPC Class Codes: G01N 33/6845 Methods of identifying protein-protein interactions in protein mixtures

Abstract

The present invention involves a series of articles, compositions, methods, and kits. Some aspects of the invention include articles such as particles, sols, blends, dispersions, films, or microarrays that comprise luminescent polymers, as well as methods for making and using such articles. In some cases, the luminescent polymer may be characterized in part by having a delocalized π-orbital structure, which can allow the polymer to have a high degree of luminosity. The polymers of this invention may also have, in some embodiments, bulky substituents to prevent intermolecular π-π interactions that can decrease luminosity. Some articles may include more than one luminescent polymer, for example, a first polymer that absorbs energy and directs the energy to a second polymer that releases the energy. The articles of the invention may be used, in certain embodiments, to detect the presence of other compounds such as single molecules, proteins, or specific nucleic acid sequences, as well as cells, bacteria, and viruses. In one set of embodiments, the luminescent polymers are associated with an entity that can interact with, for example, a nucleic acid or a protein. The association may be direct, or through an energy transfer pathway. The entity can be, for example, a nucleic acid, a charged surface, an intercalating agent, or an entity that releases a quenching agent that interacts with the luminescent polymer.

Claims

1. An article, comprising:

a composition comprising a luminescent polymer and a recognition entity, wherein the composition is a sol, a blend, or a film.

2. The article of claim 1, wherein the recognition entity comprises a nucleic acid recognition entity.

3. The article of claim 1, wherein the luminescent polymer comprises an iptycene moiety.

4. The article of claim 3, wherein the iptycene moiety comprises at least three arene planes.

5. The article of claim 3, wherein the iptycene moiety comprises at least five arene planes.

6. The article of claim 3, wherein the iptycene moiety is at least a portion of a repeat unit of the luminescent polymer.

7. The article of claim 1, wherein the luminescent polymer comprises a backbone.

8. The article of claim 7, wherein the backbone comprises a delocalized pi-electron bond.

9. The article of claim 7, wherein the backbone comprises a benzene ring.

10. The article of claim 7, wherein the backbone comprises a triple bond.

11. The article of claim 1, wherein the polymer is a copolymer.

12. The article of claim 1, wherein the polymer has a largest dimension of at least about 10 nm.

13. The article of claim 1, wherein the luminescent polymer comprises a structure:

14. The article of claim 13, wherein the bicyclic ring system comprises an iptycene to moiety.

15. The article of claim 13, wherein at least two of A, B, C, and D are in pi-electron communication.

16. The article of claim 13, wherein n is at least about 100.

17. The article of claim 1, wherein the luminescent polymer is silanated.

18. The article of claim 1, wherein the composition comprises at least two luminescent polymers.

19. The article of claim 1, wherein the composition comprises a non-luminescent polymer.

20. The article of claim 2, wherein the nucleic acid recognition entity comprises a nucleic acid.

21. The article of claim 2, wherein the nucleic acid recognition entity comprises a deoxyribonucleic acid.

22. The article of claim 2, wherein the nucleic acid recognition entity comprises a ribonucleic acid.

23. The article of claim 2, wherein the nucleic acid recognition entity has a stem-loop structure.

24. The article of claim 2, wherein the nucleic acid recognition entity comprises an intercalating agent.

25. The article of claim 2, wherein the nucleic acid recognition entity comprises an endonuclease.

26. The article of claim 2, wherein the nucleic acid recognition entity recognizes a nucleic acid sequence of at least about 10 bases.

27. The article of claim 2, wherein the nucleic acid recognition entity recognizes a nucleic acid sequence of at least about 30 bases.

28. The article of claim 2, wherein the nucleic acid recognition entity recognizes a nucleic acid sequence of at least about 100 bases.

29. The article of claim 2, wherein the nucleic acid recognition entity is charged.

30. The article of claim 2, wherein the nucleic acid recognition entity is positively charged.

31. The article of claim 2, wherein the nucleic acid recognition entity is able to change conformation upon binding of a nucleic acid to a nucleic acid recognition entity.

32. The article of claim 1, wherein the recognition entity comprises an aptamer.

33. The article of claim 1, wherein the recognition entity comprises a protein recognition entity.

34. An article, comprising:

a sol comprising a luminescent polymer.

35. The article of claim 34, wherein the luminescent polymer is silanated.

36. The article of claim 34, wherein the sol comprises at least two luminescent polymers.

37. The article of claim 34, wherein the sol further comprises a non-luminescent polymer.

38. An article, comprising:

a blend comprising a luminescent polymer.

39. The article of claim 38, wherein the blend comprises at least two luminescent polymers.

40. The article of claim 38, wherein the blend further comprises a non-luminescent polymer.

41. An article, comprising:

a mixture comprising a first polymer having a first excitation wavelength and a first emission wavelength;

a second polymer having a second excitation wavelength and a second emission wavelength different from the first emission wavelength; and

an energy migration pathway between the first polymer and the second polymer;

wherein the mixture is able to emit light at substantially the second emission wavelength when incident light at the first excitation wavelength is applied to the composition.

42. A method, comprising:

providing a homogeneous composition comprising a first polymer and a second polymer different from the first polymer;

exposing the composition to energy that is substantially absorbed by the first polymer but is not substantially absorbed by the second polymer; and

detecting light emitted from the composition, wherein the light is emitted substantially by the second polymer.

43. An article, comprising:

a luminescent polymer;

a recognition entity selected from the group consisting of a nucleic acid recognition entity, a protein recognition entity, and an aptamer; and

an energy migration pathway between the luminescent polymer and the recognition entity.

44. The article of claim 43, wherein the luminescent polymer comprises an iptycene moiety.

45. The article of claim 43, wherein the luminescent polymer comprises a backbone.

46. The article of claim 45, wherein the backbone comprises a delocalized pi-electron bond.

47. The article of claim 43, wherein the polymer is a copolymer.

48. The article of claim 43, wherein the polymer has a largest dimension of at least about 10 nm.

49. The article of claim 43, wherein the luminescent polymer comprises a structure:

50. The article of claim 49, wherein n is at least about 100.

51. The article of claim 43, wherein the recognition entity comprises a nucleic acid recognition entity.

52. The article of claim 43, wherein the recognition entity comprises a nucleic acid.

53. The article of claim 43, wherein the recognition entity comprises an intercalating agent.

54. The article of claim 43, wherein the recognition entity comprises an endonuclease.

55. The article of claim 43, wherein the recognition entity recognizes a nucleic acid sequence of at least about 10 bases.

56. The article of claim 43, wherein the recognition entity is charged.

57. The article of claim 43, wherein the recognition entity is positively charged.

58. The article of claim 43, wherein the recognition entity is able to change conformation upon binding of a nucleic acid thereto.

59. The article of claim 43, wherein the recognition entity comprises a protein recognition entity.

60. The article of claim 43, wherein the recognition entity comprises an aptamer.

61. An article, comprising:

a substrate having a surface charge, the substrate comprising a luminescent polymer.

62. The article of claim 61, wherein the substrate comprises a recognition entity.

63. The article of claim 61, wherein the substrate comprises a nucleic acid recognition entity.

64. The article of claim 61, wherein the substrate comprises an aptamer.

65. The article of claim 61, wherein the substrate comprises a protein recognition entity.

66. The article of claim 61, wherein the substrate is a sol.

67. The article of claim 61, wherein the substrate is a blend.

68. The article of claim 61, wherein the substrate is a film.

69. The article of claim 61, wherein the substrate is a microarray.

70. The article of claim 61, wherein the substrate is positively charged.

71. The article of claim 61, wherein the luminescent polymer comprises an iptycene moiety.

72. The article of claim 61, wherein the luminescent polymer comprises a backbone.

73. The article of claim 72, wherein the backbone comprises a delocalized pi-electron bond.

74. The article of claim 61, wherein the polymer is a copolymer.

75. The article of claim 61, wherein the polymer has a largest dimension of at least about 10 nm.

76. The article of claim 61, wherein the luminescent polymer comprises a structure:

77. The article of claim 76, wherein n is at least about 100.

78. A method, comprising:

providing a article comprising a luminescent polymer and a nucleic acid recognition entity, the article having a luminosity;

allowing a nucleic acid molecule to bind to the nucleic acid recognition entity; and

detecting a change in luminosity of the article.

79. The method of claim 78, wherein the change in luminosity is at least by one order-of-magnitude.

80. The method of claim 78, wherein the change in luminosity is at least by two orders-of-magnitude.

81. The method of claim 78, wherein the change in luminosity is at least by three orders-of-magnitude.

82. The method of claim 78, wherein the change in luminosity is at least by four orders-of-magnitude.

83. An article, comprising:

a microarray comprising a luminescent polymeric composition, wherein the composition is a particle, a sol, a blend, or a film.

84. An article, comprising:

a composition comprising a luminescent polymer and an aptamer.

85. The article of claim 84, wherein the luminescent polymer comprises an iptycene moiety.

86. The article of claim 84, wherein the luminescent polymer comprises a backbone.

87. The article of claim 86, wherein the backbone comprises a delocalized pi-electron bond.

88. The article of claim 84, wherein the polymer is a copolymer.

89. The article of claim 84, wherein the polymer has a largest dimension of at least about 10 nm.

90. The article of claim 84, wherein the luminescent polymer comprises a structure:

91. The article of claim 90, wherein n is at least about 100.