Light harvesting multichromophore compositions and methods of using the same

• US 10,365,271 B2
• Filed: 05/24/2016
• Issued: 07/30/2019
• Est. Priority Date: 06/20/2002
• Status: Active Grant

• Current Assignee: Regents of the University of California (University of California)
• Original Assignee: Regents of the University of California (University of California)
• Inventors: Bazan, Guillermo C., Gaylord, Brent S., Wang, Shu, Liu, Bin
• Primary Examiner(s): Riley, Jezia
• Application Number:
  US15/163,525
• Publication Number:
  US 20160341720A1
• Time in Patent Office: 1,162 Days
• Field of Search: 536 266, 435 61
• CPC Class Codes: B82Y 15/00 Nanotechnology for interacting, sensing or actuating, e.g. quantum dots as markers in protein assays or molecular motors
• CPC Class Codes: C09B 11/02 derived from diarylmethanes
• CPC Class Codes: C09B 69/103 containing a diaryl- or triarylmethane dye
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1416 Condensed systems
• CPC Class Codes: C09K 2211/1425 Non-condensed systems
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials
• CPC Class Codes: C12Q 1/6818 involving interaction of two or more labels, e.g. resonant energy transfer
• CPC Class Codes: C12Q 2525/107 incorporating a peptide nucleic acid
• CPC Class Codes: C12Q 2527/125 Specific component of sample, medium or buffer
• CPC Class Codes: C12Q 2565/107 Alteration in the property of hybridised versus free label oligonucleotides
• CPC Class Codes: G01N 33/52 Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements immunological elements G01N33/54386; involving labelled immunochemicals G01N33/58; for haemoglobin or occult blood G01N33/72
• CPC Class Codes: G01N 33/542 with steric inhibition or signal modification, e.g. fluorescent quenching
• CPC Class Codes: G01N 33/582 with fluorescent label

Abstract

Light harvesting luminescent multichromophores that are configured upon excitation to transfer energy to, and amplify the emission from, an acceptor signaling chromophore in energy-receiving proximity therewith are provided. Also provided are compositions for labelling a target. The labelling composition may include a donor light harvesting multichromophore and an acceptor signaling chromophore in energy-receiving proximity to the donor light harvesting multichromophore. Also provided is an aqueous composition for labelling a target, including: a donor light harvesting multichromophore; an acceptor signaling chromophore in energy-receiving proximity therewith; and a sensor biomolecule. Methods for using the subject compositions are also provided.

Claims

1. An aqueous composition comprising an aggregate of light harvesting multichromophore conjugated polymers in an aqueous solution that are configured upon excitation to transfer energy to, and amplify the emission from, an acceptor signaling chromophore in energy-receiving proximity therewith in the aqueous solution, wherein the light harvesting multichromophore conjugated polymers comprise water soluble groups and are linked to a sensor biomolecule that specifically binds a target.

2. The aqueous composition according to claim 1, wherein the aqueous solution comprises water-solvated aggregates of the light harvesting multichromophore conjugated polymers.

3. The aqueous composition according to claim 1, wherein the multichromophore has a luminescent emission spectrum.

4. The aqueous composition according to claim 1, wherein the conjugated polymers are neutral.

5. The aqueous composition according to claim 1, wherein the multichromophore is linked to a fluorophore.

6. The aqueous composition according to claim 1, wherein the multichromophore is in energy-receiving proximity to an acceptor signaling chromophore.

7. The aqueous composition according to claim 1, wherein the conjugated polymers comprise a conjugated segment having the structure:

8. The aqueous composition according to claim 7, wherein R³ and R⁴ are alkyl, each optionally substituted, which may contain one or more heteroatoms.

9. The aqueous composition according to claim 7, wherein E and R⁵ are not present.

10. An aqueous labelling composition comprising:

a donor light harvesting multichromophore system comprising an aggregate of conjugated polymers in an aqueous solution that upon excitation are capable of transferring energy to an acceptor signaling chromophore, wherein the conjugated polymers comprise water soluble groups; and

the acceptor signaling chromophore in energy-receiving proximity to the donor light harvesting multichromophore in the aqueous solution;

wherein the donor light harvesting multichromophore system comprises conjugated polymers of aromatic repeat units and the ratio of the number of repeat units to the acceptor signaling chromophore is 100;

1 or more.

11. The labelling composition according to claim 10, wherein the acceptor signaling chromophore is a fluorophore.

12. The labelling composition according to claim 10, wherein amplification of the emission from the acceptor signaling chromophore occurs when incident light is at a wavelength absorbed by the donor light harvesting multichromophore system than when the acceptor signaling chromophore is directly excited by incident light.

13. The labelling composition according to claim 12, wherein the amplification of the emission from the acceptor signaling chromophore is 2-fold greater or more.

14. The labelling composition according to claim 10, wherein the ratio of the donor light harvesting multichromophore system to the acceptor signaling chromophore is 1:

1.

15. The labelling composition according to claim 10, wherein the donor light harvesting multichromophore system is directly conjugated to the acceptor signaling chromophore.

16. The labelling composition according to claim 10, wherein the donor light harvesting multichromophore system is indirectly conjugated to the acceptor signaling chromophore.

17. The labelling composition according to claim 10, further comprising a sensor biomolecule.

18. The labelling composition according to claim 10, wherein the conjugated polymers comprise a neutral conjugated segment having the structure:

19. An aqueous composition for labelling a target, the composition comprising:

a donor light harvesting multichromophore system comprising an aggregate of conjugated polymers in an aqueous solution that upon excitation are capable of transferring energy to an acceptor signaling chromophore, wherein the conjugated polymers comprise water soluble groups;

the acceptor signaling chromophore in energy-receiving proximity to the donor light harvesting multichromophore in the aqueous solution; and

a sensor biomolecule.

20. The composition according to claim 19, wherein the acceptor signaling chromophore is a fluorophore.

21. The composition according to claim 19, wherein amplification of the emission from the acceptor signaling chromophore occurs when incident light is at a wavelength absorbed by the donor light harvesting multichromophore system than when the acceptor signaling chromophore is directly excited by incident light.

22. The composition according to claim 21, wherein the amplification of the emission from the acceptor signaling chromophore is 2-fold greater or more.

23. The composition according to claim 19, wherein the ratio of the donor light harvesting multichromophore system to the acceptor signaling chromophore is 1:

1.

24. The composition according to claim 19, wherein the donor light harvesting multichromophore system comprises conjugated polymers of aromatic repeat units and the ratio of the number of repeat units to the acceptor signaling chromophore is 100:

1 or more.

25. The composition according to claim 19, wherein the donor light harvesting multichromophore system is directly conjugated to the acceptor signaling chromophore.

26. The composition according to claim 19, wherein the donor light harvesting multichromophore system is directly conjugated to the sensor biomolecule.

27. The composition according to claim 19, wherein the sensor biomolecule is a target binding protein.

28. The composition according to claim 19, wherein the sensor biomolecule is an antibody.

29. The composition according to claim 19, wherein the conjugated polymers comprise a neutral conjugated segment having the structure: