Light harvesting multichromophore compositions and methods of using the same

• US 10,001,473 B2
• Filed: 03/16/2017
• Issued: 06/19/2018
• Est. Priority Date: 06/20/2002
• Status: Expired due to Term

• 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:
  US15/461,426
• Publication Number:
  US 20170184571A1
• Time in Patent Office: 460 Days
• Field of Search: 435 61, 536 266
• 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. A solution comprising:

a light harvesting multichromophore that is a conjugated polymer configured upon excitation to transfer energy to, and amplify the emission from, an acceptor signaling chromophore; and

the acceptor signaling chromophore that is a fluorescent dye in energy-receiving proximity to the donor light harvesting multichromophore.

2. The solution according to claim 1, wherein the multichromophore has a luminescent emission spectrum.

3. The solution according to claim 1, wherein the conjugated polymer is neutral.

4. The solution according to claim 1, wherein the multichromophore is directly linked to the acceptor signaling chromophore.

5. The solution according to claim 1, wherein the multichromophore is linked to a sensor biomolecule that specifically binds to a target.

6. The solution according to claim 1, wherein the multichromophore is linked to a substrate.

7. The solution according to claim 1, wherein the conjugated polymer comprises a conjugated segment having the structure:

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

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

10. A solution for labelling a target, comprising:

a donor light harvesting multichromophore that is a conjugated polymer that upon excitation is capable of transferring energy to, and amplifying the emission from, an acceptor signaling chromophore;

the acceptor signaling chromophore that is a fluorescent dye in energy-receiving proximity to the donor light harvesting multichromophore; and

a sensor biomolecule.

11. The solution 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.

12. The solution according to claim 11, wherein the amplification of the emission from the acceptor signaling chromophore is 2-fold greater or more.

13. The solution according to claim 10, wherein the ratio of the donor light harvesting multichromophore to the acceptor signaling chromophore is 1:

1.

14. The solution according to claim 10, wherein the donor light harvesting multichromophore comprises a conjugated polymer of aromatic repeat units and the ratio of the number of repeat units to the acceptor signaling chromophore is 100:

1 or more.

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

16. The solution according to claim 10, wherein the donor light harvesting multichromophore is directly conjugated to the sensor biomolecule.

17. The solution according to claim 10, wherein the sensor biomolecule is a target binding protein.

18. The solution according to claim 17, wherein the sensor biomolecule is an antibody.

19. The solution according to claim 10, wherein the donor light harvesting multichromophore comprises an aggregate of conjugated molecules.

20. The solution according to claim 10, wherein the light harvesting multichromophore is a conjugated polymer comprising a neutral conjugated segment having the structure:

21. The solution according to claim 20, wherein R³ and R⁴ are alkyl, each optionally substituted;

which may contain one or more heteroatoms.

22. The solution according to claim 20, wherein E and R⁵ are not present.