Flavonoid compounds of low toxicity for biological imaging applications

Patent metadata

Field	Value
Publication number	US-9636021-B2
Application number	US-201514740914-A
Country	US
Kind code	B2
Filing date	Jun 16, 2015
Priority date	Jun 16, 2014
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

Flavonoid compounds that are selective for a protein, a portion or a living cell, or a portion of an organism may be used as biological imaging agents. The flavonoid compounds are useful for methods of imaging organisms such as zebrafish embryos and zebra fish. Flavonoid compounds may also be used to detect protein. Advantageously, flavonoids that selectively bind protein, a portion of a living cell, or a portion of an organism may exhibit a florescence “turn-on” mechanism, where the flavonoids that are selectively bound exhibit a florescence response when excited.

First claim

What is claimed is:

1. A flavonoid compound for imaging zebrafish embryos, zebrafish larva, and/or zebrafish blood vessels, where the flavonoid compound is defined by the formula

where each R 1 -R 4 is individually an organic group or a hydrogen atom and X is a halogen atom.

2. The flavonoid of claim 1 , where the flavonoid compound is defined by the formula

where X is a halogen atom.

3. The flavonoid of claim 1 , where the flavonoid compound is defined by the formula

4. The flavonoid of claim 1 , where each of R 1 -R 4 is individually an alkyl group or a hydrogen atom.

5. A method of imaging a zebrafish comprising:
providing an embryo media;
adding a flavonoid compound to the embryo media, where the flavonoid compound is defined by the formula

where each R 1 -R 4 is individually an organic group or a hydrogen atom and X is a halogen atom;
adding a zebrafish embryo to the embryo media;
allowing the flavonoid compound to permeate into the zebrafish embryo;
optionally allowing the zebrafish embryo to develop into a zebrafish larva;
exciting the zebrafish embryo and/or zebrafish larva with an excitation wavelength that excites the flavonoid compound and induces a fluorescence response; and
capturing an image of the zebrafish embryo, the zebrafish larva, or both the zebrafish embryo and the zebrafish larva.

6. The method of claim 5 , where the zebrafish embryo is at from about 4 to about 170 hours post fertilization when it is added to the embryo media.

7. The method of claim 5 , where the embryo media is E3 media.

8. The method of claim 5 , where the zebrafish embryo includes a yolk syncytial layer and the flavonoid compound selectively stains the yolk syncytial layer.

9. The method of claim 5 , where the excitation wavelength is from about 550 nm to about 570 nm or from about 400 nm to about 460 nm.

10. The method of claim 5 , where the zebrafish embryo develops into a zebrafish larva.

11. The method of claim 5 , where each of R 1 -R 4 is individually an alkyl group or a hydrogen atom.

12. The method of claim 5 , where the flavonoid compound is defined by the formula

where X is a halogen atom.

13. The method of claim 5 , where the flavonoid compound is defined by the formula

14. A method of imaging zebrafish blood vessels comprising:
providing an embryo media;
adding a flavonoid compound to the embryo media, where the flavonoid compound is defined by the formula

where each R 1 -R 4 is individually an organic group or a hydrogen atom and X is a halogen atom;
adding a zebrafish of about 72 to about 108 hours post fertilization to the embryo media;
allowing the flavonoid compound to permeate into the zebrafish;
exciting the zebrafish with an excitation wavelength that excites the flavonoid compound and induces a fluorescence response; and
capturing an image of the zebrafish.

15. The method of claim 14 , where the step of allowing the flavonoid compound to permeate into the zebrafish takes from about 6 to about 8 hours.

Assignees

• Pang Yi
• Liu Bin
• Univ Akron

Inventors

• Pang Yi
• Liu Bin

Classifications

• G01N33/582

  with fluorescent label · CPC title

• G01N2333/4603

  from fish · CPC title

• C07D311/30

  not hydrogenated in the hetero ring, e.g. flavones · CPC title

• A61B2503/40

  Animals · CPC title

• A61B5/02007

  Evaluating blood vessel condition, e.g. elasticity, compliance · CPC title