Fluorescent Xanthenes and White Light Fluorophores

• US 20100051826A1
• Filed: 07/19/2007
• Published: 03/04/2010
• Est. Priority Date: 07/21/2006
• Status: Active Grant

• Current Assignee: Board of Supervisors of Louisiana State University Agricultural & Mechanical College (Louisiana State University System)
• Original Assignee: Board of Supervisors of Louisiana State University Agricultural & Mechanical College (Louisiana State University System)
• Inventors: Fakayode, Sayo O., Escobedo Cordova, Jorge O., Strongin, Robert M., Lowry, Mark, Yang, Youjun, Xu, Xiangyang, Warner, Isiah M.
• Granted Patent: US 8,350,064 B2
• Time in Patent Office: Days
• US Class Current: 250/459.100
• CPC Class Codes: C07D 311/78 Ring systems having three or more relevant rings
• CPC Class Codes: C09B 11/06 Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
• CPC Class Codes: C09B 11/22 containing OH groups bound to an aryl nucleus and their ethers and esters
• CPC Class Codes: G01N 1/30 Staining; Impregnating ; Fixation; Dehydration; Multistep processes for preparing samples of tissue, cell or nucleic acid material and the like for analysis

Abstract

Xanthene compounds are disclosed having fluorescence at multiple wavelengths. Also disclosed are methods for their synthesis and use. Some of the compounds fluoresce at three wavelengths, emitting white light. Uses include the imaging of biological tissues, illumination, and display technologies. Many of the compounds have large Stokes shifts, and are resistant to photobleaching. The fluorescence may be readily distinguished from that of endogenous fluorophores, and from that of most existing, commercially-available fluorescent probes. The compounds are well suited for use in “multiplexing” techniques. They exhibit clear isosbestic and isoemissive points, and have broad absorption and emission ranges.

Claims

1. A compound having a structure selected from the group consisting of:

wherein;

R1, R2, R3, R4, R6, and R7 are each independently selected from the group consisting of H, C₁ to C₄ substituted or unsubstituted alkyl, C₆ to C₁₀ aryl, C₁ to C₄ alkenyl, C₁ to C₄ alkynyl, substituted or unsubstituted amino, halide, hydroxyl, C₁ to C₄ alkoxy, thio, nitro, C₁ to C₄ aldehyde, acetyl, C₁ to C₄ carboxyl, C₁ to C₄ alkoxycarbonyl, and C₁ to C₄ alkylaminocarbonyl;

R5 is selected from the group consisting of H, C₁ to C₄ alkyl, C₁ to C₄ carboxyl, C₁ to C₄ alkoxycarbonyl, and C₁ to C₄ alkylaminocarbonyl;

R8 and R9 are each independently selected from the group consisting of H, and C₁ to C₄ alkyl; and

X is selected from the group consisting of F, Cl, Br, I, CF₃COO, and PF₆.

2. A compound as recited in claim 1, wherein said compound is selected from the group consisting of

4. A compound as recited in claim 2, wherein said compound is SNAFR-1.

5. A compound as recited in claim 2, wherein said compound is SNAFR-3.

6. A compound as recited in claim 2, wherein said compound is SNAFR-4.

7. A compound as recited in claim 2, wherein said compound is SNAFR-5.

8. A compound as recited in claim 2, wherein said compound is SNAFR-6.

9. A compound as recited in claim 2, wherein said compound is SNAFR-2.

10. A process comprising irradiating with ultraviolet light a solution of the compound SNAFR-2, as recited in claim 9;

and allowing the SNAFR-2 to emit light in three distinct regions;

one such region having a maximum emission at a wavelength of about 390 nm, one such region having a maximum emission at a wavelength of about 540 nm, and one such region having a maximum emission at a wavelength of about 620 nm;

so that the combined emissions are perceived by most humans having normal eyesight as being white light or as being nearly white light.

11. A process comprising irradiating with ultraviolet light a solution of a compound as recited in claim 1;

and allowing the compound to emit light in three distinct regions;

one such region having a maximum emission at a violet or blue wavelength, one such region having a maximum emission at a green wavelength, and one such region having a maximum emission at a red or orange wavelength;

so that the combined emissions are perceived by most humans having normal eyesight as being white light or as being nearly white light.

3. (canceled)